How I Invest with David Weisburd
- Episodes
- 446
- Released
- several times a week
- Latest episode
- Oct 23, 2026
About the podcast
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
Episodes 446
E446: Vista Equity President: The Death of SaaS? AI Agents and the $3 Trillion Opportunity
Is AI destroying the software industry, or creating its biggest investment opportunity yet? David Breach is President of Vista Equity Partners, a firm managing approximately $100 billion in assets. In this …
Show notes
Is AI destroying the software industry, or creating its biggest investment opportunity yet? David Breach is President of Vista Equity Partners, a firm managing approximately $100 billion in assets. In this episode, David explains why the recent selloff in software stocks may be missing a much larger opportunity: AI-powered digital workers. We explore Vista's repeatable playbook for creating value in enterprise software, why mission-critical products and proprietary data remain competitive advantages, and how AI could expand software's addressable market into trillions of dollars in services. David also shares how Vista evaluates software companies amid AI disruption, why incumbents may be better positioned than startups to deploy AI agents, and the career lessons that took him from selling juice to leading one of the world's largest software-focused private equity firms.Highlights:
(0:00) Why David Left Kirkland & Ellis to Join Vista Equity Partners (3:41) The Vista Playbook for Creating Value in Software Companies (7:12) Is AI Making Software Uninvestable? (11:08) Why AI Could Trigger a Major Revaluation of SaaS Companies (14:00) Will OpenAI and Anthropic Replace Enterprise Software? (20:03) The Three Things Vista Looks for in Software Investments (26:23) How AI Is Changing Software Investment Due Diligence (35:20) Why Data Security Could Determine the Winners in AI (41:13) How Vista Constructs Its Private Equity Portfolios (49:34) From Selling Juice to Leading Vista Equity Partners
- Why David left Kirkland & Ellis to help build Vista Equity Partners
- How Vista grew from $13 billion to approximately $100 billion in AUM
- The four pillars of Vista's repeatable software value creation playbook
- Why David believes the SaaS selloff doesn't reflect software's long-term opportunity
- How AI agents could unlock a $3 trillion services market
- Why existing software companies may have an advantage over AI-native startups
- The three characteristics Vista looks for in mission-critical software
- Why recent customer retention data matters more than historical performance
- How proprietary data and industry expertise create defensible competitive advantages
- Why cybersecurity and data protection are central to enterprise AI adoption
- How Vista approaches diversification and portfolio construction
- The career lesson David believes matters more than intelligence or talent
Guest Bio:
David A. Breach is President of Vista Equity Partners. He serves on the investment committees for Vista's Flagship, Foundation, Endeavor and Perennial Funds and is Co-CEO of VistaOne, the firm's evergreen private equity vehicle.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with David Breach:
LinkedIn:https://www.linkedin.com/in/david-breach/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.E445: AngelList: Why Picking Winners Is the Wrong Way to Invest in Startups
What if the biggest advantage in venture capital isn't picking winners, but getting access to them? Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on …
Show notes
What if the biggest advantage in venture capital isn't picking winners, but getting access to them? Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. Drawing on AngelList's extensive venture investment data, Erik explains why seed and growth investing operate like two different asset classes, why the best startups often command higher valuations from the beginning, and how access drives venture returns. We explore the power law, why doubling down on winners matters, the two strategies for building successful venture portfolios, and the challenges of selling investments in breakout companies. Erik also discusses how USVC aims to expand access to private markets as companies like OpenAI, Anthropic, and SpaceX create enormous value before going public.Highlights:
(0:00) Why Venture Capital Is Actually Two Different Asset Classes (2:32) What AngelList's Data Reveals About Startup Valuations (5:21) Why Access Matters More Than Picking Winners (12:50) The Power Law Behind Venture Capital Returns (17:33) The Cathedral and Bazaar Model of Venture Investing (24:59) How to Find Emerging Managers With an Access Advantage (28:08) How Many Startup Investments Does It Take to Find a Winner? (32:15) The Anthropic Investment Erik Wishes He Had Held (38:08) Why Retail Investors Are Missing Private-Market Wealth Creation (52:54) How USVC Plans to Expand Access to Venture Capital
- Why Erik believes venture capital is actually two different asset classes
- Why access may matter more than picking winners at the seed stage
- What AngelList's data reveals about startup valuations and future returns
- Why venture's power law makes portfolio concentration so important
- How the "Cathedral and Bazaar" framework explains winning VC -strategies
- Why the middle market of venture capital may face structural challenges
- How LPs can identify emerging managers with a genuine access advantage
- Why investing across vintages matters more than timing the market
- What Erik learned from an investment in Anthropic that was sold too early
- Why selling shares can damage a VC's relationship with founders
- Why individual investors struggle to access private-market value creation
Guest Bio:
Erik Syvertsen is GM of Asset Management and Chief Legal Officer at AngelList and Chairman of USVC. With more than eight years at AngelList, Erik works at the intersection of venture capital, investment management, and private-market access.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Erik Syvertsen:
LinkedIn:https://www.linkedin.com/in/erik-syvertsen-334b1138/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.E444: NEPC President on AI Portfolio Risk, Finding Top Funds, and Preparing for a Downturn
What if the biggest advantage in institutional investing isn’t finding better managers, but building an organization that can make better decisions over decades? In this episode, I sit down with Tim McCusker …
Show notes
What if the biggest advantage in institutional investing isn’t finding better managers, but building an organization that can make better decisions over decades? In this episode, I sit down with Tim McCusker, President of NEPC, which advises on approximately $2 trillion in assets, to discuss what separates the best institutional investors from everyone else. Tim explains why even sophisticated endowments and pension funds fall into peer-driven investing, how governance and incentives shape long-term returns, and why the strongest allocators are willing to invest when others are retreating.Highlights:
(0:00) What Advising on $2 Trillion Reveals About Investing (3:07) The Biggest Mistake Sophisticated Institutional Investors Make (7:15) Why the Best CIOs Stay in Their Seats for Decades (10:10) What Separates the Top Institutional Investors? (16:00) How the Best Endowments Construct Their Portfolios (20:14) The Biggest Mistake LPs Make in Co-Investments (25:48) How NEPC Finds the Next Generation of Venture Managers (31:22) Why Venture Capital Belongs in Institutional Portfolios (36:33) Is Portable Alpha Worth the Risk? (43:34) Why AI Concentration Keeps Tim Up at Night
- What advising on nearly $2 trillion reveals about institutional investing
- Why sophisticated investors still fall into herd behavior
- How governance and investment committee support can determine long-term returns
- Why the best LPs stay committed to managers during market downturns
- How endowments and pension funds construct portfolios differently
- Why the best co-investment programs focus on manager selection rather than re-underwriting every deal
- Why venture capital deserves a place in portfolios beyond its return potential
- How AI concentration, changing correlations, and portable alpha are reshaping portfolio risk
Guest Bio:
Tim McCusker is President of NEPC, an institutional investment consulting firm advising on approximately $2 trillion in assets across more than 400 clients, including pension funds, endowments, foundations, and healthcare organizations.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Tim McCusker:
LinkedIn:https://www.linkedin.com/in/tim-mccusker-76174278/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.E443: Why the Next Trillion-Dollar Startup Won’t Be a Software Company
What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world? Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across …
Show notes
What if AI makes software abundant and shifts venture capital’s biggest opportunities into the physical world? Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing across robotics, defense, energy, manufacturing, and other physical industries. Leo explains why AI is commoditizing software, why hardware may capture more value as a result, and why some of the best opportunities are hiding in industries with almost no startup competition. We also discuss how to underwrite deep tech before revenue, what separates exceptional founders, the infrastructure bottlenecks created by AI, and why the biggest risk to deep tech may be its dependence on continued funding.Highlights:
(0:00) Why the Best Investors Need Their Own Lane (2:05) Why More Meetings Can Make You a Better Investor (6:14) What Separates the Best Venture Capitalists? (10:03) Why Leo Is So Bullish on Hardware (12:31) How Do You Underwrite a Deep Tech Startup? (16:08) Is Hardware Really More Capital Intensive? (22:38) Where Are Deep Tech’s Most Underrated Opportunities? (33:28) What Separates the Top 0.1% of Founders? (41:28) Why Leo Is Cautious on Humanoid Robotics (56:26) The Investing Lesson Leo Learned the Hard Way
- Why the best companies and investors need a lane uniquely their own
- Why quantity of meetings can improve venture investment quality
- How AI growth is changing the definition of exceptional traction
- Why deep tech companies have a completely different revenue curve
- What separates the best venture capitalists from average investors
- Why Leo believes hardware investing is becoming more attractive
- How to evaluate deep tech companies years before meaningful revenue
- Why hardware may not be as capital intensive as investors assume
- The founder traits that matter most when building physical products
- Why Leo is cautious on investing directly in humanoid robotics
Guest Bio:
Leo Polovets is a General Partner at Humba Ventures, an early-stage deep tech fund investing 500K–1M in companies across robotics, bio, defense, energy, manufacturing, and other physical industries. He previously co-founded Susa Ventures, an early investor in companies including Robinhood, Flexport, and Stord.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Leo Polovets:
LinkedIn:https://www.linkedin.com/in/lpolovets
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.E442: Nelson Mills on Building a $100 Billion Company, the China Threat, and the Future of War
What happens when autonomous underwater vehicles become cheap enough to manufacture at scale? Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles …
Show notes
What happens when autonomous underwater vehicles become cheap enough to manufacture at scale? Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. Nelson explains why undersea autonomy has lagged aerial drones, how advances in AI, navigation, manufacturing, and autonomy are changing the economics, and why Vatn is building lower-cost systems designed to operate at scale. We also discuss raising $85 million for a hardware startup, the rise of asymmetric warfare, lessons from Anduril, and what it takes to build a new defense prime.Highlights:
- Why Nelson left venture capital to become a founder
- Why undersea autonomy is finally reaching an inflection point
- The navigation and communications problems that make underwater technology so difficult
- How Vatn raised its first $2 million pre-seed round in just 30 days
- Why hardware founders should start with the smallest viable version of their product
- Vatn’s plan to become a focused defense prime for the undersea market
- What Anduril proved about building defense technology differently
- How lower-cost underwater vehicles could change deterrence for smaller countries
- The biggest hiring lesson Nelson learned as a founder
- Why founders should always be building relationships for their next round
Guest Bio:
Nelson Mills is the Founder of Vatn Systems, a defense technology company building autonomous underwater vehicles. After growing up on the water and spending roughly nine years operating at startups, Nelson moved into venture capital before leaving to build Vatn.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
**Stay Connected with David Weisburd: **
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Nelson Mills:
LinkedIn:https://www.linkedin.com/in/millsn/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) How Growing Up on a Sailboat Led to Vatn Systems (1:18) Why Nelson Left Venture Capital to Become a Founder (6:08) Why Undersea Autonomy Is Finally Having Its Moment (8:20) What Needs to Happen for Underwater Drones to Scale? (11:13) How Do You Build a Company Everyone Says Is Impossible? (12:41) How Vatn Raised $2 Million on a Dream (20:53) How Vatn Went From Pre-Seed to $85 Million Raised (21:48) Can Vatn Become the Next Defense Prime? (27:42) How Defense Technology Could Change Global Deterrence (45:21) The Advice Nelson Would Give Himself as a First-Time FounderE441: Startup Investing When the Cost of Building Goes to Zero
What if AI makes the founder more important, not less? John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with …
Show notes
What if AI makes the founder more important, not less? John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented. John Borthwick is the Founder of betaworks, the startup studio and venture firm behind companies including Giphy, Dots, bitly, and TweetDeck, with investments in companies including Twitter, Tumblr, Kickstarter, and Hugging Face. We break down why John now puts more weight on founders than products, how betaworks identified Hugging Face before transformers reshaped AI, and why he believes the biggest opportunity is moving toward the AI application layer. We also discuss open-source AI, AI security, the changing nature of work, and why John believes AI was discovered rather than invented.Highlights:
(0:00) Why John Now Believes Founders Matter More Than Ever (1:36) The Question John Uses to Identify Exceptional Founders (7:34) Why Betaworks Chose a Venture Studio Over a Traditional Fund (13:42) How John Finds 100x Venture Investments (15:45) Why AI Is Making Founders More Important (21:30) How Betaworks Found Hugging Face Before the AI Boom (29:03) Why Open-Source AI Still Matters (40:14) Why John Believes AI Was Discovered, Not Invented (56:13) Where the Biggest AI Opportunities Are Emerging (1:01:10) How to Make Your Career Antifragile to AI
- Why John now believes the founder matters more than ever
- The unusual question he uses to understand a founder’s emotional connection to their company
- Why betaworks chose the venture studio model instead of a traditional fund
- How betaworks combines accelerator programs with pre-seed investing
- Why John focuses on proximity to products instead of traditional pattern matching
- How AI is changing founders from builders into “steerers”
- What betaworks saw in Hugging Face before transformers changed AI
- Why John believes open and closed AI models need to coexist
- The AI risks John thinks deserve more attention than existential risk
Guest Bio:
John Borthwick is the Founder of betaworks, which he founded in 2008 as a startup studio for building and investing in early-stage consumer technology companies.
Sponsors:
Juniper Square:
Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with John Borthwick:
LinkedIn:https://www.linkedin.com/in/jborthwick/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.E440: What Steve Jobs Taught Me About Great Founders
What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on …
Show notes
What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on more than two decades as an operator and investor, including his time at Apple and Foursquare, Steven shares what he learned working directly with Steve Jobs, how he separates ambitious founders from delusional ones, what drew Oceans to Etched, and why AI is creating a technology cycle unlike anything he has seen before. Highlights:- Why great technology companies always start with exceptional people
- How Steven separates founder ambition from delusion
- What great founders understand about attracting world-class talent
- What Steven learned from working directly with Steve Jobs
- Why Steve Jobs obsessed over details most CEOs would ignore
- How Apple sold $60 million of advertising before the product was live
- Why the founders of Etched immediately stood out
- The founder traits that remain constant across every technology cycle
- Why AI is moving faster than previous technology revolutions
- Why Steven believes both enormous winners and failures are coming
- What Foursquare taught him about valuations and paper gains
Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm headquartered in New York City. Previously, he held senior operating roles at Foursquare and Apple, joining Apple after its acquisition of Quattro Wireless.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Steven Rosenblatt:LinkedIn:https://www.linkedin.com/in/stevenrosenblatt/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) What Great Technology Companies Have in Common (2:47) How to Separate Ambition From Delusion (6:57) What Steven Learned Working With Steve Jobs (16:10) What Steve Jobs Understood About Building Companies (27:26) How Apple Changed Steven as a Leader (37:30) What Made the Founders of Etched Stand Out (42:18) Do the Rules for Great Founders Change With AI? (47:39) Why This AI Boom Is Different From Every Previous Cycle (51:45) The Timeless Career Lesson Steven Would Give His Younger Self (55:30) Why New York Took Decades to Become a Tech HubE439: Ethan Thornton: The 22-Year-Old Building a $3.7 Billion Defense Company
What if the future of warfare is determined by who can innovate faster, not who can spend more? Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping …
Show notes
What if the future of warfare is determined by who can innovate faster, not who can spend more? Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company he started after dropping out of MIT. We break down how Mach went from experimenting with roughly 20 technologies to becoming a multibillion-dollar company, why Ethan believes asymmetric technology is reshaping modern warfare, and how Pentagon procurement is evolving. We also discuss China and Taiwan, lessons from Ukraine, autonomous warfare, recruiting exceptional talent, taking risk, and why Ethan believes great founders should empower their teams rather than make every decision themselves. Highlights:- Why Ethan dropped out of MIT to build a defense company
- How Mach experimented with roughly 20 technologies before narrowing its focus
- Why building prototypes created an advantage over presenting slide decks
- How Pentagon procurement is changing for defense startups
- Why Ethan believes cost-plus contracting can create the wrong incentives
- Why venture capital matters for asymmetric technology
- How Mach recruits people around mission rather than persuasion
- Why Ethan doesn’t view Anduril as a zero-sum competitor
- How media fits into the strategy of a defense company
- Why Ethan believes founders should find people they trust and empower them
- What he misunderstood about “founder mode”
Guest Bio: Ethan Thornton is the Founder and CEO of Mach Industries, a defense technology company focused on developing and manufacturing next-generation systems. Thornton began working on ideas for asymmetric technology as a teenager and started Mach after leaving MIT.
Sponsors:Juniper Square: Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Ethan Thornton:LinkedIn:https://www.linkedin.com/in/ethan-thornton-74417024a/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Ethan Thornton Dropped Out of MIT to Build Mach Industries (2:50) How an MIT Dropout Built a Multibillion-Dollar Defense Company (5:00) Why Mach Started by Building 20 Different Technologies (6:41) How the Pentagon Is Changing Defense Procurement (12:24) Could the U.S. Deter a Conflict Over Taiwan? (25:00) How Mach Chooses Which Defense Technologies to Build (32:47) How Mach Competes for the Best Engineering Talent (39:03) Why Ethan Believes Staying at MIT Was the Bigger Risk (43:55) The Leadership Lesson Ethan Wishes He Learned Earlier (46:02) What Ethan Misunderstood About “Founder Mode”E438: Will Robbins on Elon Musk, AI & the Future of Silicon Valley
What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does? Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs …
Show notes
What if the biggest edge in venture capital is identifying an exceptional founder before everyone else does? Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at formation. Previously, Will joined Contrary as its first employee and helped grow the firm to more than $250 million in AUM. In this episode, Will explains why traditional VC brands may matter less in an AI-driven world, how he identifies exceptional founders before they have traction, why the best startups often pivot, and why reputation with founders may be the most important asset a venture investor can build. Highlights:- Why traditional VC brands may be losing their edge
- How AI could fundamentally change the economics of seed rounds
- Why founders may need dramatically less capital to reach product-market fit
- How two 17-year-old founders built Zepto into a massive retailer
- Why college dropouts can produce disproportionately large venture outcomes
- The elusive “X factor” Will looks for in exceptional founders
- Why a founder’s social graph can reveal signals a pitch meeting cannot
- Why extreme focus may be one of the most important founder traits
- The small group of business models behind many of venture’s biggest outcomes
- Why Will remains optimistic about software despite AI disruption
- Why 50% of Will’s successful early-stage investments pivoted
- The one asset Will believes matters most for a long-term venture career
Will Robbins is a technology-focused venture investor and founder of Robbins Capital, where he backs companies starting at company formation. Prior to investing under his own name, Will joined Contrary as its first employee and helped grow the firm from the ground up to more than $250 million in AUM. Early-stage companies Will was responsible for backing now have a combined market capitalization of over $10 billion.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Will Robbins:LinkedIn:https://www.linkedin.com/in/whrobbins/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why VC Brands May No Longer Matter (5:05) What Happens to Seed Rounds When Software Gets Cheap? (10:40) How Two 17-Year-Olds Built Zepto (16:00) Why College Dropout Founders Keep Producing Outliers (21:53) What Will Looks for in Exceptional Founders (23:52) Can You Actually Identify the Founder “X Factor”? (29:20) The Founder Signal That’s Almost Impossible to Fake (41:11) Which Business Models Create Venture’s Biggest Outcomes? (54:41) Why So Many Great Startups PivotE437: Doug Beyer on Raising Capital, LP Psychology & GP Stakes
What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms? In this episode, I sit down with Douglas Beyer, managing partner and founder of …
Show notes
What if the biggest opportunity in private markets isn’t backing companies—but backing the next generation of investment firms? In this episode, I sit down with Douglas Beyer, managing partner and founder of Roaring Brook Holdings, to discuss why emerging managers remain one of the most undercapitalized opportunities in alternative assets. Douglas explains how anchor capital changes fundraising dynamics, why LP relationships determine whether firms survive, and how the best emerging managers build trust through transparency and execution. We also explore GP seeding, organizational durability, and why fundraising momentum matters more than most managers realize. Highlights:- Why emerging managers face a structural capital gap
- How anchor investors solve the “cold start” problem
- Why LP relationships are built years before capital is deployed
- The hidden importance of communication and transparency
- How fundraising momentum determines fund survival
- Why many great investors fail at building firms
- The difference between raising capital and building a franchise
- How secondary markets are reshaping private equity liquidity
Douglas Beyer is managing partner and founder of Roaring Brook Holdings, a firm providing seed, acceleration, and GP solutions to the next generation of private market investment firms. He spends his days evaluating opportunities where their capital, relationships, and strategic involvement can catalyze and improve the success of a firm.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Douglas Beyer:LinkedIn:https://www.linkedin.com/in/douglas-beyer-2944bb1a/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why He Left a Prestigious Family Office to Back Emerging GPs (2:00) The Hidden Value Most Investors Miss in Asset Management Firms (5:27) Why LP Relationships Matter More Than Most GPs Realize (9:10) The Gold Standard for Managing LP Communication (14:08) The Anchor Investor Problem Breaking Emerging Managers (17:23) The Silent Risk LPs Fear Most in New Funds (22:26) Why the Best GPs Add Value Before Asking for Capital (29:26) Why Emerging Managers Still Matter in a Mega-Fund World (34:17) The One Thing Every New Fund Needs to SurviveE436: Nnamdi Okike on Billionaires, Founder Psychology & the Venture Capital Bubble
Can venture capital really be turned from instinct into science? Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled …
Show notes
Can venture capital really be turned from instinct into science? Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he leads Seed and Series A investments in software and software-enabled companies. We discuss why Nnamdi believes venture investing is driven by the totality of an investor’s experiences rather than pure instinct, how 645 quantifies founder qualities, and why missionary and “non-central casting” founders can become exceptional investments. We also explore why startups need the right market inflections, how stablecoins and agentic commerce are reshaping fintech, what Nnamdi has learned across five fund vintages, and why raising too much capital at Seed can actually hurt a company. Highlights:- Why venture investing may be more science than instinct
- How 645 Ventures quantifies founder potential
- Why Nnamdi prefers missionaries over mercenaries
- What separates “non-central casting” founders
- Why great founders still need the right market inflection
- Why VCs can mistake themselves for the customer
- How to tell whether founder confidence is actually justified
- Why stablecoins could transform global financial infrastructure
- How AI and programmable money could enable agentic commerce
- Why market cycles should influence venture deployment
- Why patience and truth-seeking are core values at 645 Ventures
- Why massive Seed rounds can damage startup culture
Nnamdi Okike is Co-Founder and Managing Partner of 645 Ventures, where he partners with founders building vertical and horizontal software and software-enabled companies. 645 Ventures leads Seed and Series A rounds and works closely with exceptional teams as they scale toward the growth stage.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Nnamdi Okike:LinkedIn:https://www.linkedin.com/in/nnamdiokike/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Venture Investing Isn’t About Instinct (3:36) How 645 Quantifies Founder Potential (5:41) Why the Best Founders Think Differently (9:14) What Really Predicts an Exceptional Founder (13:29) The Inflection Points Behind Great Startups (17:35) The Hidden Failure Mode in Early-Stage Investing (23:51) Why Harder Markets Require Different Founders (31:53) Where Fintech’s Next Opportunities Are Emerging (44:38) The Biggest Lessons From Four Venture Funds (57:03) Why Too Much Seed Capital Can Hurt StartupsE435: Why Most Companies Aren’t Ready for AI
Which competitive moats will actually survive the AI era? SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 …
Show notes
Which competitive moats will actually survive the AI era? SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. We break down what Mighty Capital learned from mapping 550 companies by defensibility, why traditional SaaS advantages like switching costs and data moats may be weakening, and why network effects and counter-positioning are emerging as powerful AI-era moats. We also discuss why SC disagrees with the conventional power-law approach to venture, how AI is transforming M&A and corporate innovation, the Product Alpha Effect behind Mighty Capital’s investment strategy, and what venture firms must change to survive the AI transition. Highlights:- What Mighty Capital learned from analyzing 550 companies
- Why traditional SaaS moats may no longer work in AI
- Why network effects and counter-positioning are gaining importance
- Why the IPO threshold may now be closer to $30–50 billion
- Why SC disagrees with the conventional power-law approach to venture
- How AI is shifting M&A from financial engineering to product innovation
- Why the best companies treat leaders like resource allocators
- How the Product Alpha Effect turns product innovation into investment alpha
- How Mighty Capital uses signals from 600,000 product builders
- The two metrics SC believes investors should watch in AI companies
- Why AI could force companies to reinvent distribution
- Which venture capital firms could survive the AI transition
SC Moatti is Managing Partner at Mighty Capital and Board Chair at Products That Count. She co-founded Mighty Capital around the Product Alpha Effect, a data-backed framework for investment outperformance, and has invested in companies including Amplitude, Netskope, and Groq. Earlier in her career, SC built products at Meta and Siebel Systems and authored an award-winning book on what makes a great product. She is a Stanford GSB alum, Kauffman Fellow, YPO member, and graduate of CentraleSupélec.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with SC Moatti:LinkedIn:https://www.linkedin.com/in/scmoatti/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Which Moats Actually Survive AI? (1:37) How SC Stays Disciplined on Valuation (4:55) Why Power-Law Investing Can Become a Constraint (6:32) How AI Is Rewriting the M&A Playbook (14:11) The Product Alpha Effect Behind Mighty Capital (17:47) The Two AI Metrics Investors Should Watch (21:43) Why AI Could Reinvent Distribution (24:11) What Makes a Great Product in the AI Era? (30:30) Which Venture Firms Will Survive AI? (36:20) The Advice SC Would Give Her Younger SelfE434: Warren Gibbon on How AI is Changing the Private Markets
Are private markets still positioned to outperform public markets? Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio …
Show notes
Are private markets still positioned to outperform public markets? Warren Gibbon is a Multi-Family Office Chief Investment Officer with deep experience across asset allocation, equity research, and portfolio management. We discuss why investors may need to re-underwrite their assumptions about private markets, how higher rates and growing competition have changed private equity, and why public-market earnings growth may be underappreciated. Warren also explains why he is more constructive on venture, what he looks for in emerging managers, the risks created by passive investing, and how he would deploy $100 million of fresh capital today. Highlights:- Why investors should re-underwrite the case for private markets.
- What the endowment model’s historical returns may be hiding.
- Why Warren believes public-market value creation is underestimated.
- The risk behind today’s massive AI infrastructure spending boom.
- Why private equity faces a much harder environment going forward.
- How passive investing may be changing the behavior of public markets.
- Why “boring and hard” investments can remain structurally underfunded.
- How Warren would deploy $100 million of fresh liquidity today.
Warren Gibbon is a Multi-Family Office Chief Investment Officer with 14 years of investment management experience and a focus on U.S. and global equities. His expertise spans asset allocation, equity research, portfolio management, investment analysis, and valuation, with additional interests in behavioral finance and the construction of diversified portfolios across public and private markets.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Warren Gibbon:LinkedIn:https://www.linkedin.com/in/warren-gibbon-cfa/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Will Private Markets Still Outperform? (4:00) Is the AI Spending Boom Sustainable? (7:00) Why Warren Is Cautious on Private Equity (13:00) Why Venture May Be More Attractive Today (18:00) Why “Boring and Hard” Can Be a Great Investment (21:00) Is Passive Investing Breaking the Market? (27:00) Why Liquidity Could Become Your Biggest Advantage (31:00) The Problem With Portable Alpha (34:00) How Warren Thinks About Venture’s Top Firms (40:00) How He Would Invest $100 Million TodayE433: AlphaSense’s Chris Ackerson on AI, the Future of Finance & Finding Alpha
What happens to financial analysts when AI can do the work they used to spend all night doing? Chris Ackerson is SVP of Product at AlphaSense, where he focuses on applying information retrieval, natural …
Show notes
What happens to financial analysts when AI can do the work they used to spend all night doing? Chris Ackerson is SVP of Product at AlphaSense, where he focuses on applying information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery. We discuss how AI is changing the analyst role, why vertical AI can outperform general-purpose models in financial research, and why proprietary data may become one of the most important competitive advantages in AI. Chris also explains why LLMs hallucinate, how AlphaSense is using AI to conduct expert interviews, where humans still create investment alpha, and why the future of financial research may look less like software and more like an AI teammate that never sleeps. Highlights:- How AI is changing the role of financial analysts
- How AlphaSense increased banker coverage by up to 15% in one case study
- Why vertical AI can outperform general-purpose models in financial research
- Why hallucinations remain a barrier to professional AI adoption
- Why proprietary data could become a defining AI advantage
- How AI agents are conducting expert interviews and channel checks
- What investment bankers and hedge fund analysts may do in five years
- Why human judgment becomes more valuable as AI improves
- Where investment alpha comes from if everyone has access to similar AI
- Why frontier AI models are becoming more specialized, not less
- How AI agents could become teammates that work 24/7
- Why AI companies must constantly be willing to disrupt themselves
Chris Ackerson is SVP of Product at AlphaSense and an experienced product leader focused on applying innovations in information retrieval, natural language processing, deep learning, and recommendation systems to search and discovery.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Chris Ackerson:LinkedIn:https://www.linkedin.com/in/chris-ackerson-965b1313/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Will AI Replace Financial Analysts? (3:00) Why Vertical AI Could Beat General-Purpose Models (6:28) Why Do LLMs Hallucinate? (7:50) Why Proprietary Data Matters More in AI (10:58) How AI Can Interview Human Experts (14:11) What Finance Jobs Could Look Like in Five Years (17:23) If Everyone Has AI, Where Does Alpha Come From? (20:32) Why AI Models Are Becoming More Specialized (27:16) What Happens When AI Agents Work With Other Agents? (30:57) The AI Lesson Chris Wishes He Learned EarlierE432: $24 Billion Investor on Private Credit, the Psychology of Winning & Fear of Failure
Is private credit really in a bubble, or are investors looking for risk in the wrong place? Theodore “Ted” Koenig is Chairman and CEO of Monroe Capital, a $24 billion private credit firm. We break down how …
Show notes
Is private credit really in a bubble, or are investors looking for risk in the wrong place? Theodore “Ted” Koenig is Chairman and CEO of Monroe Capital, a $24 billion private credit firm. We break down how private credit grew from a niche alternative to a $2 trillion asset class, why financing shifted from banks to private credit after the financial crisis, and the two ways Ted believes lenders can generate alpha. We also discuss the flood of retail capital into private credit, why Monroe focuses on the lower middle market, the dangers of prioritizing AUM growth over investor returns, and the personal drive and tradeoffs behind building Monroe. Highlights:- How Ted spotted the opportunity in private credit before it became an asset class.
- Why the financial crisis permanently shifted lending away from banks.
- The two ways Ted believes private credit managers can generate alpha.
- Why Monroe built its moat around lower middle-market companies.
- Why Ted expects private credit to grow from $2 trillion to $5 trillion.
- What the surge of retail capital means for the future of private credit.
- Why Ted believes the greater risk today may actually sit in private equity.
- The personal tradeoff Ted made while building Monroe Capital.
Theodore L. “Ted” Koenig is Chairman and CEO of Monroe Capital LLC. He founded Monroe in 2004 after previously serving as President and CEO of Hilco Capital LP. Ted also co-founded HOPE Chicago and has received lifetime achievement recognition from the Association for Corporate Growth Midwest and SFNet, as well as recognition from Private Debt Investor as one of the top changemakers in private credit. He earned a B.S. in accounting with high honors from Indiana University’s Kelley School of Business and a J.D. with honors from Chicago-Kent College of Law.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Ted Koenig:LinkedIn:http://linkedin.com/in/theodore-koenig
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) How Ted Saw Private Credit Before Everyone Else (3:18) What Keeps Him Building After $24 Billion (5:30) Why the Best Entrepreneurs Never Stop Competing (9:09) The Story Behind Ted’s Relentless Drive (13:36) How Private Credit Became a $2 Trillion Market (20:50) The Only Two Ways to Generate Alpha in Private Credit (24:16) Is Private Credit Actually in a Bubble? (30:30) Why Retail Investors Are Flooding Into Private Credit (35:13) The Problem With Chasing AUM Instead of Returns (42:46) The Personal Cost of Building a $24 Billion FirmE431: Marty Kausas on AI, Trillion Dollar Startups & Founder Psychology
What if the best reason to start a company isn’t to change the world, but simply because you love the game? In this episode, I sit down with Marty Kausas, CEO of Pylon, to unpack how he thinks about building an …
Show notes
What if the best reason to start a company isn’t to change the world, but simply because you love the game? In this episode, I sit down with Marty Kausas, CEO of Pylon, to unpack how he thinks about building an ambitious company from first principles. Marty explains why Pylon started with a goal of reaching $1 billion in revenue, why market size can matter more than the quality of the founding team, and why the rise of AI has pushed his definition of a generational company even higher. Highlights:- Why Marty started Pylon for “fun and adventure.”
- Why market selection can matter more than the founding team.
- How Pylon’s ambition grew from $1B in revenue to a $1T valuation.
- Why Marty believes AI replacement is the wrong startup thesis.
- What it really means for a support team to “go agentic.”
- Why great founders may be overestimating incumbent software companies.
- How category creation can become a company’s biggest marketing advantage.
- Marty’s biggest mistake transitioning from engineer to CEO.
Marty Kausas is CEO and Co-Founder of Pylon, where he is building a next-generation customer support platform for B2B companies and helping support teams transition toward agentic workflows. Before founding Pylon, Marty held an engineering role at Airbnb, invested through Andreessen Horowitz’s scout fund, and completed software engineering internships at Yelp and Qualcomm.
Sponsors: Juniper Square:Juniper Square is trusted as the operations partner by more than 2,300 private markets GPs worldwide, connecting technology, data, and fund administration services to help GPs fundraise efficiently, streamline operations, and improve the investor experience. Their unified platform centralizes data and connects LPs and GPs across every workflow, including fundraising, investor onboarding, compliance, treasury, and reporting. Today, more than $1 trillion in LP capital is managed through Juniper Square. For more information, please visit https://www.junipersquare.com/howiinvest.
AlphaSense:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest to learn more.
AlphaSummit Discount Code: AS26HII50
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Marty Kausas:LinkedIn:https://www.linkedin.com/in/martykausas/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Marty Started Pylon for “Fun and Adventure” (4:00) Why Market Matters More Than the Founding Team (8:00) The Greatest Gift a Founder Can Give Their Company (12:00) Why Building a Huge Company Can Actually Be Easier (16:00) Pylon’s New Goal: Build a Trillion-Dollar Company (20:00) Why Marty Thinks AI Won’t Replace Humans (24:00) What It Really Means to “Go Agentic” (31:00) Why the Best Startup Ideas Don’t Sound Serious (36:00) The Underrated Trait Marty Looks for When Hiring (44:00) Marty’s Biggest Mistake as a First-Time CEOE430: Goldman Sachs’ Michael Bruun on AI, Private Equity & The War for Talent
What if AI makes talent, not technology, the biggest competitive advantage in private equity? Michael Bruun is Partner and Global Co-Head of Private Equity within Goldman Sachs Asset Management. We break down …
Show notes
What if AI makes talent, not technology, the biggest competitive advantage in private equity? Michael Bruun is Partner and Global Co-Head of Private Equity within Goldman Sachs Asset Management. We break down how Goldman Sachs competes for the best middle-market assets, why Michael believes talent can move the needle more than almost anything else, and how higher rates have forced private equity back to the fundamentals of EBITDA and cash-flow growth. We also discuss how Goldman is implementing AI across portfolio companies, why transformation must start with the CEO, and why the war for exceptional talent may become even more important as every employee becomes AI-enabled. Highlights:- How Goldman Sachs competes for the best middle-market assets.
- Why more than 110 operating partners can create a talent advantage.
- Why private equity’s value-creation playbook works best during volatility.
- How higher rates forced private equity to return to fundamentals.
- Why the best exits may depend on what never appears in the financial statements.
- How Goldman thinks about continuation vehicles versus strategic exits.
- The two outcomes Michael wants from every AI initiative.
- Why AI transformation has to start with the CEO.
Michael Bruun is Partner and Global Co-Head of Private Equity within Goldman Sachs Asset Management, which he joined in 2004. He is a member of several investment committees across Asset Management and previously served as Head of EMEA Private Equity and Head of Private Equity and Growth Equity investing for India. Michael earned bachelor’s and master’s degrees in economics from the University of Copenhagen, with studies at Cornell University. He currently serves on the Boards of Directors of Advania, GS Wyvern, LRQA, and Norgine and previously served on the Board of Directors of Northvolt
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Michael Bruun:LinkedIn: https://www.linkedin.com/in/michael-bruun-486883/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why AI Transformation Has to Start With the CEO (1:39) Why Goldman Sachs Believes in “Skin in the Game” (3:38) How Goldman Competes for the Best Private Equity Deals (7:17) Why Talent Compounds Better Than Ideas (9:17) Why Volatility Creates an Operating Advantage (13:20) What Higher Rates Changed in Private Equity (15:36) The Value That Never Shows Up in a Spreadsheet (18:14) Should Great PE Assets Ever Be Sold? (22:09) How AI Is Actually Changing Portfolio Companies (28:32) The AI Implementation Playbook That Starts at the TopE429: Dr. V on AI, Market Bubbles & Finding the Next Anthropic
What if the biggest mistake in venture capital is investing in what already looks like a great venture investment? In this episode, I sit down with Dr. V (Vaibhav Agrawal), Founder ODDBIRD VC, is a San …
Show notes
What if the biggest mistake in venture capital is investing in what already looks like a great venture investment? In this episode, I sit down with Dr. V (Vaibhav Agrawal), Founder ODDBIRD VC, is a San Francisco-based venture investor who spent nearly a decade at Lightspeed, to explore why he believes the traditional venture playbook is changing. Sourcing has become a media and distribution business, companies are staying private longer, and investors increasingly need to think proactively about liquidity rather than simply waiting for their winners to go public. Highlights:- Why the old venture capital playbook no longer works.
- How sourcing became a media and distribution business.
- Why liquidity management is becoming a core skill for venture firms.
- How fund growth can quietly create strategy drift.
- Why markups can turn venture investors into momentum traders.
- Why Dr. V believes early-stage investing requires finding “pattern breakers.”
- Why consumer and fintech may be systematically oversold today.
- The overlooked opportunity in “fresh off the boat” founders.
Dr. V (Vaibhav Agrawal) Founder ODDBIRD VC, is a San Francisco-based venture investor who spent nearly a decade at Lightspeed before spinning out to build his own venture firm. Originally trained in medicine, he has developed an investing philosophy centered on finding exceptional founders and opportunities before they fit established patterns.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected withDr.V (Vaibhav Agrawal):LinkedIn:https://www.linkedin.com/in/drvaibhavagrawal/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Venture May Still Be Undervalued (3:13) Why the Old VC Playbook No Longer Works (6:57) Who Will Buy Venture’s Illiquid Assets? (10:51) Why Dr. V Refuses to Invest Outside Venture (14:38) When Bigger Funds Lose Their Edge (16:21) The Hidden Bias Driving Venture Investors (20:58) Why Early-Stage Investors Need Pattern Breakers (21:44) Why Dr. V “Chases Chaos” (27:18) The Venture Categories Everyone May Be Underestimating (30:30) Why “Fresh Off the Boat” Founders May Be MispricedE428: Michael Green on Peter Thiel, SpaceX, and Inefficient Markets
What if passive investing is actually one of the biggest active forces shaping markets today? In this episode, I sit down with Michael Green, Founder and CIO at Tier1 Alpha Asset Management. Michael challenges …
Show notes
What if passive investing is actually one of the biggest active forces shaping markets today? In this episode, I sit down with Michael Green, Founder and CIO at Tier1 Alpha Asset Management. Michael challenges the conventional view that stock prices primarily reflect fundamentals, arguing that the transaction itself moves prices and that the rise of passive investing has fundamentally changed who trades, why they trade, and how markets respond to capital flows. Highlights:- Why Michael believes passive investing isn’t actually passive.
- The Peter Thiel question that changed how Michael evaluates consensus.
- Why transactions and flows may matter more to prices than fundamentals.
- How index inclusion can create powerful self-reinforcing feedback loops.
- Why passive investing may be making the biggest companies even bigger.
- How leveraged ETFs can amplify both rallies and selloffs.
- Why Michael believes traditional value factors are fighting against passive flows.
- What happens when automatic retirement inflows eventually become outflows.
Michael Green is Founder and CIO at Tier1 Alpha Asset Management. He founded and ran Canyon Capital Advisors’ New York office, where he built global macro strategies covering more than $5 billion of exposure across equities, credit, FX, and commodities. He later founded Ice Farm Capital, a discretionary global macro hedge fund seeded by Soros Fund Management, and managed macro strategies at Thiel Macro.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Michael Green:LinkedIn:https://www.linkedin.com/in/michael-green-9a15142/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) What Peter Thiel Taught Michael About Being Contrarian (4:18) Why Stock Prices May Have Less to Do With Fundamentals (9:18) The $1 Flow That Could Create $22 of Market Value (14:37) How Leveraged ETFs Can Amplify the Market (20:01) Why Passive Investing May Be a Systemic Risk (25:46) The Market Signal Michael Says Everyone Is Missing (31:34) Why Passive Flows Keep Making the Biggest Stocks Bigger (36:36) Why Traditional Factor Investing May Be Breaking (42:05) How Market Makers Became the New Alpha Winners (44:04) What Happens When Passive Inflows ReverseE427: AQR's Peter Hecht on AI, Market Bubbles & How the Best Investors Build Portfolios
Peter Hecht, Managing Director at AQR Capital Management, explains why diversification has to be measured by underlying risk rather than the number of investments you own. At AQR, diversification is a core …
Show notes
Peter Hecht, Managing Director at AQR Capital Management, explains why diversification has to be measured by underlying risk rather than the number of investments you own. At AQR, diversification is a core principle: thousands of relatively small, uncorrelated investment decisions can collectively create an attractive return for a given level of risk. Highlights:- Why tracking error is necessary if you actually want to beat a benchmark.
- How AQR thinks about diversification like a casino playing thousands of independent hands.
- Why “alpha” has no single universal definition.
- What Eugene Fama taught Pete about separating alpha from compensated risk.
- Why AQR uses AI differently from simply asking ChatGPT or Claude which stocks to buy.
- How a systematic investor can succeed while being wrong roughly 45% of the time.
- Why 90% of a seemingly diversified portfolio’s risk can still come from equities.
- What 2022 revealed about the hidden weakness of the traditional 60/40 portfolio.
- Why trend following can provide protection without requiring a permanently negative correlation to stocks.
- How portable alpha separates where investors get their market exposure from where they seek alpha.
Peter Hecht is a Managing Director at AQR Capital Management, where he advises institutional and other sophisticated investors on portfolio construction, investment strategies, and some of the most challenging questions in asset allocation.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Peter Hecht:LinkedIn: https://www.linkedin.com/in/peter-hecht-ba850215/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Tracking Error Isn’t Necessarily Bad (3:00) How AQR Thinks About Diversification (7:00) What Alpha Actually Means (12:00) Eugene Fama, Value and Factor Investing (17:00) How AQR Uses AI and Machine Learning (24:00) What Makes a Great Systematic Investor (30:00) Why Being Right 55% of the Time Is Enough (35:00) The Case for Trend Following (42:00) Why Most Portfolios Are Still Equity BetsE426: American Securities CEO on Warren Buffett, Private Equity & Playing the Long Game
What happens when a private equity firm refuses to chase every new opportunity and spends 30 years getting better at one thing? David sits down with Michael Fisch, co-founder and CEO of American Securities, to …
Show notes
What happens when a private equity firm refuses to chase every new opportunity and spends 30 years getting better at one thing? David sits down with Michael Fisch, co-founder and CEO of American Securities, to unpack how the firm grew from a $71.4 million first fund to $23 billion in AUM without abandoning the investment discipline that got it there. Michael explains how private equity evolved from a sub-$1 billion institutional market into a multi-trillion-dollar industry, why American Securities resisted the temptation to expand into every adjacent asset class, and why seeing more deals matters almost as much as knowing which ones to reject. Highlights:- How private equity evolved from a niche strategy into a multi-trillion-dollar industry.
- Why cash flow changed the way Michael thought about buying companies.
- The discipline that helped American Securities scale without chasing adjacent strategies.
- Why the best investors need both a massive deal funnel and a narrow investment filter.
- What Michael learned from knowing Warren Buffett for decades.
- The hiring framework American Securities uses to reduce judgment errors.
- How an 80%+ CEO “win rate” reflects a different approach to private equity ownership.
- Why retail capital could create a new wave of demand for private equity.
- How AI could collapse finance’s traditional analyst pyramid.
- Why “make the call” remains one of Michael’s most important career lessons.
Michael Fisch is the co-founder and CEO of American Securities, where he is a member of the Investment Committee and has helped build the firm into a leading private equity platform. American Securities launched its first fund in 1994 with $71.4 million and today manages approximately $23 billion in AUM.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Michael Fisch:LinkedIn: https://www.linkedin.com/in/michaelfisch-americansecurities/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Private Equity Barely Existed When Michael Started (4:27) Why He Took the Risk of Starting His Own Fund (9:04) Why Private Equity Is Really a People Business (15:20) The Hiring Mistake Most Leaders Still Make (19:27) What Warren Buffett Taught Him About Staying in Your Lane (22:00) How Saying “No” Helped Build a $23B Firm (31:22) The Operating Advantage Most PE Firms Didn’t Have (35:23) The Secret Behind an 80%+ CEO Win Rate (42:06) The Retail Capital “Tsunami” Coming to Private Equity (47:29) Why AI Makes “Make the Call” More Important Than EverE425: What 30,000 Founders Taught Me About AI, Judgment & Top Founders
David sits down with Byron Ling of Twelve Below to unpack the judgment required to invest at the earliest stages of technology. After roughly 30,000 founder meetings over the past decade, Byron believes the …
Show notes
David sits down with Byron Ling of Twelve Below to unpack the judgment required to invest at the earliest stages of technology. After roughly 30,000 founder meetings over the past decade, Byron believes the strongest signals rarely appear on a résumé. He looks for an almost biological drive to win, second-level thinking, exceptional learning velocity, clear communication, authenticity, and a sense of urgency that makes a founder difficult to compete against. Highlights:- The founder traits that matter more than pedigree or early traction.
- Why a chip on your shoulder can become a competitive advantage.
- How second-level thinking separates exceptional founders from consensus thinkers.
- Why the best founders are learning machines.
- What 30,000 founder meetings taught Byron about pattern recognition.
- Why AI can improve VC sourcing without replacing investment judgment.
- The mistake of underwriting $100B outcomes instead of studying their original inputs.
- Why Byron would tell his younger self to take more risk.
Byron Ling is a Partner at Twelve Below, a New York-based venture firm focused on pre-seed and seed technology investing. He began his startup career working with Kevin Ryan at Gilt Groupe before joining the then-first-time fund Primary Venture Partners. He later became a General Partner at multi-stage venture firm Canaan before co-founding Twelve Below with longtime investing collaborator Taylor Greene.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Byron Ling:LinkedIn: https://www.linkedin.com/in/byron-ling-10b7474/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) The Founder Trait You Can’t See on a Résumé (4:18) Why the Most Obsessive Founders Think Differently (9:05) What Zoom Hides About Great Founders (12:50) What 30,000 Founder Meetings Revealed (19:30) Why Young AI Founders Have an Unfair Advantage (27:10) The Strange Opportunity Hidden in Today’s VC Market (33:00) Why Vibe Coding Is Creating a New Investing Problem (44:45) How AI Can Find Great Founders Before Everyone ElseE424: 32-Year Notre Dame CIO on Sequoia, Venture Capital & Concentration
What can 32 years as a university CIO teach you about identifying exceptional investors before everyone else does? David sits down with Scott Malpass, Co-Founder and Managing Partner of Grafton Street Partners …
Show notes
What can 32 years as a university CIO teach you about identifying exceptional investors before everyone else does? David sits down with Scott Malpass, Co-Founder and Managing Partner of Grafton Street Partners and former Chief Investment Officer of the University of Notre Dame, to discuss the patterns he learned from evaluating thousands of investment firms and building decades-long relationships with some of the world’s leading managers. Highlights:- Why investing is ultimately a people business.
- The patterns Scott learned from evaluating thousands of investment firms.
- Why the best GPs combine confidence with humility.
- How Scott recognized exceptional managers before their track records made them obvious.
- The story behind Notre Dame’s decades-long relationship with Sequoia Capital.
- Why Scott was willing to pay premium carry for exceptional performance.
- Why capacity rights can be more valuable than lower fees.
- The number one mistake Scott believes ruins investment firms.
- Why many institutional portfolios are more diversified than they need to be.
- How experience makes great investors faster decision-makers.
Scott Malpass is Co-Founder and Managing Partner of Grafton Street Partners. Previously, he spent 32 years as Chief Investment Officer of the University of Notre Dame, where he built one of the country’s most respected institutional investment programs and also served as an Adjunct Professor of Finance at the Mendoza College of Business.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Scott Malpass:LinkedIn:https://www.linkedin.com/in/scott-malpass-301545144/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) The #1 Lesson From 32 Years as a CIO (3:18) What the Best Investment Managers Have in Common (8:24) How Notre Dame Helped Build 35% of the Nasdaq (12:05) The Signals That Reveal a Great GP Early (22:11) How a Chance Meeting Led to Sequoia Capital (30:13) Why Great LPs Don’t Obsess Over Fees (33:47) The #1 Thing That Ruins Investment Firms (41:06) Why Notre Dame Made Him CIO at Just 26 (47:49) How Scott Finds Emerging Managers Before Everyone Else (1:01:00) The Investing Lesson He Wishes He Learned EarlierE423: Castelion CEO on Elon Musk, Hypersonic Missiles & the Future of Defense
David sits down with Bryon Hargis, co-founder of Castelion, to unpack why rebuilding America’s defense manufacturing capacity has become a national security imperative. Bryon explains why decades of …
Show notes
David sits down with Bryon Hargis, co-founder of Castelion, to unpack why rebuilding America’s defense manufacturing capacity has become a national security imperative. Bryon explains why decades of consolidation and outsourcing weakened the defense industrial base, why America could struggle against an adversary with significantly greater manufacturing capacity, and why Castelion is betting that deterrence ultimately requires weapons that can be produced affordably by the thousands. Highlights:- Why America’s defense problem is increasingly a manufacturing problem.
- How the defense industry’s “Last Supper” reshaped the industrial base.
- What Bryon learned about speed and iteration at SpaceX.
- Why “the best part is no part” is more than an Elon Musk catchphrase.
- Why Castelion combines product and sales instead of separating them.
- How mission-driven hiring helps protect culture as a startup scales.
- Why Bryon left SpaceX even when defense hardware was considered nearly uninvestable.
- How Castelion survived almost 100 VC rejections.
- Why one major investor can completely change a startup’s access to capital.
- Inside Castelion’s plan to manufacture hypersonic weapons at massive scale.
Bryon Hargis is the co-founder of Castelion, a defense technology company focused on developing and manufacturing advanced hypersonic weapon systems in the United States. Before founding Castelion, Bryon worked at SpaceX, including on the Starshield program and in government satellite sales. His work focused on applying SpaceX capabilities to national security problems, an experience that helped shape Castelion’s hardware-first and customer-driven approach.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Bryon Hargis:LinkedIn:https://www.linkedin.com/in/hargsb/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why America Needs Hypersonic Missiles (3:00) How Defense Manufacturing Lost Its Edge (5:30) What SpaceX Taught Bryon About Building Hardware (10:00) Why Product and Sales Should Be the Same Team (15:30) The Traits Bryon Looks for When Hiring (20:00) SpaceX’s Responsible Engineer Culture (25:00) Why Aerospace Became Too Risk-Averse (30:00) The Danger of Too Much Process (37:00) Nearly 100 VC Rejections to $1B (44:00) Building Hypersonic Missiles at Massive ScaleE422: Founding CIO of Berkeley Endowment on Track Records, Contrarian Investing & First-Time Funds
Why do so many GPs misunderstand what institutional LPs actually care about? David sits down with John-Austin Saviano, an Backing & Building Challenger Investment Firms and Former Endowment CIO, argues that one …
Show notes
Why do so many GPs misunderstand what institutional LPs actually care about? David sits down with John-Austin Saviano, an Backing & Building Challenger Investment Firms and Former Endowment CIO, argues that one of the biggest mistakes GPs make is overemphasizing track record. Great LPs care less about the headline returns than how those returns were generated. They want to understand the investment process, whether it is repeatable, and whether the people and market conditions that produced past performance still exist today. Highlights:- Why track record is less predictive than most GPs believe.
- What LPs actually want to understand about an investment firm.
- How great allocators separate good decisions from good outcomes.
- Why being different is necessary to generate differentiated returns.
- What investors misunderstood about David Swensen’s endowment model.
- Why Fund I may actually be more knowable than Fund XIV.
- How challenger firms become the R&D of an institutional portfolio.
- The hunt, farm, and fish framework for raising institutional capital.
John-Austin Saviano is Backing & Building Challenger Investment Firms and Former Endowment CIO. Over more than 20 years as an institutional allocator, he helped launch two ten-figure endowments, served as the founding CIO of UC Berkeley’s endowment, was part of the founding investment team at the Gordon & Betty Moore Foundation, and worked on the private capital team at Cambridge Associates. Today, he draws on his experience backing dozens of challenger firms and reviewing billions of dollars of fund commitments to help investment firm founders navigate fundraising, firm building, and the transition from talented investor to enduring investment organization.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with John-Austin Saviano:LinkedIn: https://www.linkedin.com/in/john-austin-saviano/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Track Record Is Overrated (8:20) Why Private Markets Got So Much Harder (18:22) What the Best Fund Managers Have in Common (25:08) The Danger of a Great Track Record (29:51) What Everyone Got Wrong About the Yale Model (36:34) Why First-Time Funds May Be Less Risky (43:18) How a Former CIO Would Build an Endowment Today (47:50) The Mistake That Kills Most GP Pitches (56:27) The Fundraising Strategy Most GPs IgnoreE421: Jack Purcell — Building an $11B Private Equity Firm
What if the biggest edge in private equity isn’t finding better deals, but designing better incentives? In this episode, I sit down with Jack Purcell, Managing Partner at Ridgemont Equity Partners, to unpack …
Show notes
What if the biggest edge in private equity isn’t finding better deals, but designing better incentives? In this episode, I sit down with Jack Purcell, Managing Partner at Ridgemont Equity Partners, to unpack how alignment helped turn a Bank of America spinout with fewer than 15 people into a private equity firm managing more than $11 billion. Jack explains why Ridgemont invests significant GP capital alongside its LPs, why more than two-thirds of the team participates economically in its funds, and how a nine-person unanimous investment committee uses a proprietary 40-point scorecard to evaluate deals. Highlights:- Why traditional GP economics can create the wrong incentives.
- How Ridgemont grew from fewer than 15 people to nearly 70.
- Why more than two-thirds of the team invests in the funds and participates in carry.
- The nine-person investment committee where every member has a veto.
- Why Ridgemont spends an average of three years with companies before investing.
- How one founder relationship took 10.5 years before becoming an investment.
- Why Ridgemont generated more than $2 of DPI for every $1 generated by the industry in recent years.
- How a $4 billion Fund V stays focused on three core sectors instead of chasing novelty.
- Why Jack personally visits every institutional investor partner each year.
- The lesson Jack learned from being too conservative after the Global Financial Crisis.
Jack Purcell is Managing Partner at Ridgemont Equity Partners, where he helps lead the firm and focuses on investments across business and technology services and industrial growth. Ridgemont traces its history to 1993 and has managed third-party institutional capital since its 2010 spinout from Bank of America.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Jack Purcell:Website: https://www.ridgemontep.com/team/jack-purcell/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Incentives Matter More Than Great Investments (3:25) How Ridgemont Built an $11B Private Equity Firm (7:57) Why Most Firms Get Succession Wrong (12:29) The Incentive Model Most PE Firms Won’t Copy (17:50) Why Ridgemont Waits Years Before Investing (24:22) The Hidden Advantage That Wins Competitive Deals (30:58) The Communication Mistake GPs Make in a Crisis (34:21) Why Chasing the Hottest Sector Usually Backfires (38:48) Inside a Nine-Person Investment Committee With Veto Power (45:43) The Investing Mistake Jack Would Fix From 2010E420: Why Infrastructure Is a $40 Trillion Opportunity
What if the biggest AI investment opportunity isn’t AI companies, but the infrastructure required to make AI possible? David sits down with Stuart Waugh, Managing Partner of Northleaf Capital Partners, to …
Show notes
What if the biggest AI investment opportunity isn’t AI companies, but the infrastructure required to make AI possible? David sits down with Stuart Waugh, Managing Partner of Northleaf Capital Partners, to explore why the AI boom is creating massive demand for power, data centers, communications networks, and other essential infrastructure. Stuart explains why Northleaf estimates roughly $40 trillion of infrastructure investment will be needed across its addressable markets over the next decade, and why governments increasingly need private capital to help fund it. Highlights:- Why AI’s biggest bottleneck may be infrastructure, not computing.
- The investment opportunity behind AI’s enormous demand for power.
- Why Northleaf sees roughly $40 trillion of addressable infrastructure investment.
- How infrastructure can provide long-term cash flows, inflation protection, and lower correlation.
- Why the middle market becomes more attractive as mega-funds get bigger.
- How secondaries became a mainstream portfolio management tool.
- Why relationships and proprietary information still create an edge in secondaries.
- How institutional investors are approaching today’s private credit uncertainty.
- Why Stuart believes “boring” can be an investing advantage.
- The lessons behind scaling Northleaf from five people to more than 300.
Stuart Waugh is the Managing Partner of Northleaf Capital Partners and a member of the firm’s Executive Committee. He oversees the direction and development of Northleaf’s private markets investment strategies and fund management capabilities and chairs its Investment Committees. Stuart joined Northleaf’s predecessor, TD Capital, in 2002. Earlier in his career, he worked at McKinsey & Company, BPI Financial Corporation, and McCarthy Tétrault. He holds a B.A. from Trinity College at the University of Toronto and an LL.B. from the University of Toronto Faculty of Law.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Stuart Waugh:Website:https://www.northleafcapital.com/person/stuart-waugh
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why AI’s Biggest Opportunity Isn’t AI (8:56) The $40 Trillion Infrastructure Opportunity (15:36) Why Deglobalization Could Make Infrastructure More Valuable (23:18) Why the Traditional 60/40 Portfolio Is Disappearing (27:54) The Private Markets Liquidity Engine Most Investors Miss (33:14) The Hidden Advantage in Buying Secondaries (42:47) Is the Private Credit Fear Creating a Buying Opportunity? (50:08) What Most GPs Get Wrong About Their LPs (56:14) Why “Boring” May Be the Best Investment StrategyE419: Venture Capital Has a Liquidity Crisis
Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO. David sits down with Benjamin Black Powerlaw Corp. (Nasdaq …
Show notes
Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO. David sits down with Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, Ben invests in growth-stage technology companies while providing alternative liquidity to founders, employees, angel investors, and venture funds. In this episode, Ben and David unpack the evolution of the venture secondary market, why great companies staying private longer creates an entirely different opportunity set, how sophisticated investors price illiquid private-company shares, and why liquidity itself is becoming a critical piece of venture capital infrastructure. The result is a different way to think about private markets: the investment opportunity doesn't end after the primary financing round. Highlights:- Why venture secondaries have become a major private-market opportunity
- What happens when great companies stay private for much longer
- How Akkadian approaches growth-stage technology investing
- Why founders and employees increasingly need pre-IPO liquidity
- How investors price private-company secondary transactions
- The difference between primary and secondary venture investing
- Why venture funds themselves can become secondary sellers
- How liquidity can strengthen rather than weaken a cap table
Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, an investment firm focused on growth-stage technology companies and private-company secondary transactions.
Akkadian provides alternative liquidity solutions for entrepreneurs, employees, angel investors, and venture capital funds, giving Ben a distinctive perspective at the intersection of venture capital, growth investing, and the rapidly evolving private secondary market.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Ben Black:LinkedIn:https://www.linkedin.com/in/benblack/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Venture Capital Is Finally Going Public (7:51) Why the 10-Year VC Fund Model Is Broken (11:41) Why Late-Stage Secondaries Are Getting Overcrowded (14:47) The Information Advantage in Private Markets (17:01) Why Ben Black Built a Public Venture Fund (22:38) What He Learned After Taking Venture Capital Public (26:52) Who Is Actually Investing in Public Venture Funds? (31:49) Why Startups Are Warming Up to Public VC Funds (38:17) How to Get Access to the Hottest Private CompaniesE418: AI, Venture Capital & the Future of Investing
Most venture firms think AI is another productivity tool. David sits down with John Melas-Kyriazi co-founder and CEO of Standard Metrics—the AI-native portfolio management platform used by leading venture …
Show notes
Most venture firms think AI is another productivity tool. David sits down with John Melas-Kyriazi co-founder and CEO of Standard Metrics—the AI-native portfolio management platform used by leading venture capital and private equity firms—to discuss how AI is transforming every stage of investing, from sourcing and diligence to portfolio management, follow-on decisions, and firm operations. John explains why the best venture firms are becoming AI-native organizations, how investors are using large language models today, why every investment memo should be "red teamed" by AI, the rise of MCPs, when firms should build software versus buy it, what Standard Metrics is seeing across more than 12,000 portfolio companies, and why human judgment will become even more valuable as AI automates everything else. Highlights:- How AI is changing every stage of venture investing.
- The AI workflows top VC firms already use every day.
- Why every investment memo should be "red teamed."
- MCPs explained and why they'll reshape enterprise software.
- Build vs. buy: what VC firms should develop internally.
- The surprising data behind today's fastest-growing AI companies.
- Why judgment—not research—becomes the scarce resource.
- How Standard Metrics analyzes thousands of private companies.
- Hiring lessons from building an AI-native company.
- Why culture matters more than tools in the AI era.
John Melas-Kyriazi is the co-founder and CEO of Standard Metrics, an AI-powered portfolio management platform trusted by many of the world's leading venture capital and private equity firms. Before founding Standard Metrics, he was an investor at Spark Capital and previously worked as a research scientist at Stanford University. Today, he works with thousands of investors and portfolio companies, giving him a unique perspective on how AI is transforming the future of venture capital.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with John Melas-Kyriazi:LinkedIn:https://www.linkedin.com/in/johnmk/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why AI Will Transform Venture Capital (8:04) The AI Workflows Top VC Firms Use Today (18:31) Build vs. Buy: Where AI Should Replace Software (30:15) What Actually Creates Alpha in the AI Era (43:11) Why the Best Investors Double Down on Winners (53:02) The Future of AI-Native Services BusinessesE417: $20B Investor on Risk, Uncertainty & Adaptability
Most investors spend their careers trying to eliminate risk. David sits down with Alec Litowitz the founder of Qstar Capital, founder and former CEO of Magnetar Capital, and one of Citadel's earliest partners …
Show notes
Most investors spend their careers trying to eliminate risk. David sits down with Alec Litowitz the founder of Qstar Capital, founder and former CEO of Magnetar Capital, and one of Citadel's earliest partners to explore the difference between risk and uncertainty, why adaptability is becoming the world's most valuable skill, how elite investors make decisions when there is no model to follow, and the cultural principles behind building one of the world's leading hedge funds. Alec also shares lessons from building Magnetar, working alongside Ken Griffin during Citadel's early years, hiring exceptional talent, creating organizations that continuously learn, why ego destroys great investing, and the core ideas behind his upcoming book The Adaptability Quotient. Highlights:- Why uncertainty creates bigger opportunities than risk.
- The investing framework that built Magnetar Capital.
- Lessons from working with Ken Griffin during Citadel's early years.
- Why adaptability matters more than IQ in the AI era.
- How elite investors update their beliefs without ego.
- Building organizations that learn faster than competitors.
- Why the best decision-makers embrace feedback loops.
- How to identify uncertainty that can actually be resolved.
- The hidden cost of certainty in investing and business.
- Why great investors think in systems, not predictions.
Alec Litowitz is the founder of Qstar Capital and founder and former CEO of Magnetar Capital, one of the world's leading alternative asset managers. Previously, he was one of the four original partners at Citadel Investment Group, where he led Global Equities. He is the author of the forthcoming book The Adaptability Quotient, which argues that adaptability—not IQ or EQ—will become the defining competitive advantage in an increasingly uncertain world. He also founded Magnetar Academy, serves on multiple educational initiatives, and holds degrees from MIT and the University of Chicago.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/
Stay Connected with Alec Litowitz:LinkedIn:https://www.linkedin.com/in/aleclitowitz/ Book: https://www.theaqbook.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
Disclaimer:This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) Why Most Investors Misunderstand Risk (6:58) How to Profit From Uncertainty Before Everyone Else (15:04) The Adaptability Mindset That Built Magnetar (24:36) Why Great Investors Change Their Minds Faster (34:02) Building a Culture of Excellence Without Ego (44:21) The Hiring Traits That Matter More Than IQ (54:47) Can You Teach Drive or Is It Innate?
These are the latest 100 of 446 episodes. You’ll find older episodes in the podcast’s feed.
Similar podcasts
More Business podcasts
