Not Another CEO Podcast
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- 122
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- Último episodio
- 10 Nov 2026
Sobre el podcast
Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and hard lessons. Our exclusive content showcases unfiltered stories and practical guidance from those who’ve crawled through the trenches. Our platform offers the largest library of CEO insights and how-to guides, sourced directly from a diverse community of leaders. Find our full video library, detailed playbooks, deep dives, and lessons learned on our Substack here ➡️ https://notanotherceo.substack.com/
Episodios 122
AI Agents Now Read 80% of the Internet’s Docs - Han Wang - Mintlify - EP#121
Agents are now viewing docs more than humans. They make up roughly 80% of the traffic to Mintlify's docs, even as those docs reach over 100 million people a month. In January, it was the reverse.In under a …
Notas del episodio
Agents are now viewing docs more than humans. They make up roughly 80% of the traffic to Mintlify's docs, even as those docs reach over 100 million people a month. In January, it was the reverse.
In under a year, the main readers of developer docs went from people to AI agents. The company behind that shift is Mintlify, which powers docs and knowledge bases for more than 20,000 companies, including Anthropic, Microsoft and Amazon.
On this episode of Not Another CEO, David Politis talks with Han Wang, co-founder and CEO of Mintlify. Mintlify raised a $45 million Series B at a $500 million valuation, co-led by a16z and Salesforce Ventures. Han walks through the pivots that came before it, including the sleepless week that led to the idea, and how he runs and hires for a company that keeps changing.
Takeaways:
1. Keep the problem, change the solution. Han pivoted about three times during YC and about twice more after, but every idea circled the same problem: helping developers learn to build with a product. Each failure fed the next attempt, unlike founders who jump from fintech to construction tech to logistics.
2. Customers will hand you the answer. At pivot number seven, Han was lying awake wondering what to tell his investors. Customers had been asking why he didn’t just power their docs. He kept not wanting to, then built a prototype in a weekend.
3. Investors are guessing too. Han says investors are acting on their best guesses and know it. The one thing he’d look for is former operating experience, ideally a founder, because they talk about how to hit the number, not just the number itself.
4. Hire for slope, then talk candidates out of the job. Startup roles change fast, so Han hires for growth. He runs an anti-sell on finalists, explaining why they shouldn’t join and what it will take to grow into the role.
5. AI made coding obsolete, not judgment. Han says product sense, system design and collaboration still matter. His interviews now lean on those, and LeetCode-style rounds and simple take-homes are gone.
6. Your job resets every few months. Scaling from two people to 100+ meant handing off what he used to do himself. Han says every few months he looks at his job and thinks he was bad at it, and the founder can’t easily be swapped out.
Quote of the show
The one living constant is to constantly trust your instincts and know how to rightly prioritize what really matters in front of you. - Han Wang, CEO & Co-Founder, Mintlify
Guest Featured in this Episode: Han Wang, CEO & Co-Founder, Mintlify
LinkedIn: https://www.linkedin.com/in/handotdev/
Mintlify: https://mintlify.com/
We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00 Trailer
00:56 Meet Han Wang, CEO of Mintlify
02:11 The Sunday habit: what really matters right now
04:57 What Mintlify does and why agents are now 80% of docs traffic
07:17 Eight pivots: how Mintlify found the "obvious" business
11:43 Pivot seven: the sleepless week and the docs idea
14:06 Founder-market fit and why pivots should compound
16:50 Why investors are guessing too
22:09 The one thing to look for in an investor
25:27 Mintlify's culture: top-down, in-office and relocating to SF
32:49 Hiring for growth over experience
37:06 The anti-sell: talking candidates out of the job
39:37 How AI changed the engineering interview
42:46 The hardest part: growing as a CEO
49:07 Why the founders you look up to are struggling too
53:38 What Mintlify looks like in 2030
54:48 Han's immigrant upbringing, the dropout and his parents
57:52 Han's support system
59:35 Advice to his younger self: dream biggerNo Strategy When He Joined, Still Took Them to $1.6B - Scott Staples - First Advantage - EP #120
Scott Staples asked one question when he became CEO of First Advantage: can someone show me the strategy document?The answer was no. There wasn't one. The company was 15 years old, doing $400 million in …
Notas del episodio
Scott Staples asked one question when he became CEO of First Advantage: can someone show me the strategy document?
The answer was no. There wasn't one. The company was 15 years old, doing $400 million in revenue, and had just lost some of its biggest customers. Ten years later, revenue is at $1.6 billion. Four times the revenue, same company, same industry.
Scott is the CEO of First Advantage, a background screening company that runs more than 200 million screens a year for over 80,000 customers worldwide, including roughly two thirds of the Fortune 100, across 200 countries and territories. He inherited First Advantage in 2017, when it was losing revenue and clients, and turned it into the fastest growing player in the industry within a year.
Here were my biggest takeaways.
- Fix the culture before anything else. When Scott arrived, the real problem wasn't go to market or product. It was silos. Finance doing its own thing, sales doing its own thing, nobody talking to each other. He rebuilt the culture around teamwork first. As he put it, when you're trying to turn a ship in an ocean, you need teamwork.
- Find the core problem first. Scott asked for the company's strategy document on day one. There wasn't one. Instead of guessing at fixes, he got every leader in a room and diagnosed the real issue from zero.
- Show up, even without the answers. Scott personally visited 20 to 30 of the company's biggest customers in his first weeks. Over and over he heard the same thing: no one's been here in over a year.
- Match your pitch to your buyer. First Advantage had one sales rep calling on a bank in the morning, a retailer at lunch, and a hospital network in the afternoon, same pitch, three completely different buyers. Scott did a massive reorg of the company around verticals instead.
- The next fraud fight is AI versus AI. Candidates are using AI to fake resumes, credentials, and now entire job interviews. Scott says about 300 US companies have already reported that they inadvertently hired North Korean agents.
Quote of the Show:
"When you're trying to change a company, when you're trying to turn a ship in an ocean, you need teamwork. So I think the biggest thing that I focused on, which is the most important thing, was addressing culture and fixing culture."
Scott Staples, CEO, First Advantage.Guests Featured in this episode:
LinkedIn: https://www.linkedin.com/in/scottdavidstaples/
First Advantage: https://fadv.com/We also break this episode down into a full write-up on Substack, with the exact playbook Scott used to fix the culture and rebuild the strategy from scratch, we're building out a full library of playbooks and lessons from every episode on Substack.
Sources:
- ClearanceJobs (May 17, 2024) – “U.S. Companies Tricked by North Korean IT Workers: DOJ Unveils Complex Fraud Network”
https://news.clearancejobs.com/2024/05/17/doj-reveals-u-s-companies-unwittingly-hired-north-korean-it-workers/ - Gartner (July 31, 2025) – “Gartner Survey Shows Just 26% of Job Applicants Trust AI Will Fairly Evaluate Them”
https://www.gartner.com/en/newsroom/press-releases/2025-07-31-gartner-survey-shows-just-26-percent-of-job-applicants-trust-ai-will-fairly-evaluate-them
Chapters:
00:00 - Trailer
01:05 - Intro
02:22 - Fixing Culture First: The One Thing He'd Do Again
04:53 - Finding the Core Problem
08:14 - The Listening Tour: Buying Time with Customers
22:59 - Matching the Pitch to the Buyer
33:28 - The Bad AI Epidemic in Hiring
47:17 - The Biggest Challenge Faced as CEO
54:10 - Where First Advantage Will Be in 3 Years
57:05 - Advice to His Younger SelfThis VC Admitted He Was Wrong for Passing on the Seed - Jake Fingert, Camber Creek - EP#119
He rejected a founder’s seed round. When that founder went out to raise his Series A, Jake’s firm was the first call he made.Jake is the Managing Partner at Camber Creek, a venture firm that invests in proptech …
Notas del episodio
He rejected a founder’s seed round. When that founder went out to raise his Series A, Jake’s firm was the first call he made.
Jake is the Managing Partner at Camber Creek, a venture firm that invests in proptech and fintech, has nearly $1 billion under management and has backed more than 50 companies, including Bilt Rewards. Before venture, he worked in consulting at Deloitte and BCG, then in government, first at GSA and then as a senior policy advisor on the National Economic Council in the Obama White House.
He and David have known each other for over 25 years. In this episode of Not Another CEO, he explains how he decides whether to back a founder, what founders get wrong about his side of the table, and what the White House taught him about building companies.
Here are the best takeaways from the episode:
1. Resilience beats everything: Jake backs founders who found a problem with no good solution and will do whatever it takes to solve it, not people drawn to the Silicon Valley or YC image. Very few companies become multibillion dollar successes overnight, so he wants the founder who can keep going through the hard stretches.
2. A no can be a request for proof: Jake passed on Bilt’s seed round but told the founder to stay in touch. Over the next 12 months the founder did what he said he would, including partnerships with banks, airlines and hotels, and Camber Creek was the first call for the next round.
3. Self-awareness is a filter: Jake would rather hear what you got wrong than hear that everything is perfect. A founder who can’t name what keeps them up at night is a quick pass, because it shows a lack of self-awareness and empathy for customers, employees and investors.
4. He decides fast, then verifies: About 30 minutes tells Jake whether he wants to partner with someone for ten years. Customers, other investors and even a college roommate then tell him whether that person will build a big company.
5. Bring your board questions you can’t answer yourself: The most common pitfall Jake sees is founders asking questions they already know the answer to. Send the financials in advance and spend the meeting on real strategic choices, with board members who bring different backgrounds.
Quote of the Show
“To me, one of the biggest turn offs is when I meet a founder and I say, you know, what keeps you up at night? And they say nothing.” - Jake Fingert, Managing Partner, Camber Creek
Guest featured in this episode: Jake Fingert, Managing Partner, Camber Creek
LinkedIn: https://www.linkedin.com/in/jake-broder-fingert-a4388b3/
Camber Creek: https://cambercreek.com/
We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00 Introduction
02:07 The one trait Jake looks for in founders
03:53 Passing on Bilt's seed round
08:23 The red flag: "nothing keeps me up at night"
10:21 How fast a VC decides
15:25 How to run a board meeting
22:53 From GSA to the White House
27:23 What founders don't understand about VCs
33:13 How Jake has changed in ten years
38:00 Is this 2021 again?
42:53 Moats and founder-led sales in the AI era
55:15 What to teach your kids: AI tools and finding truthBig VCs Don’t Care Unless You’re in Their Top 5% - Michal Rokosz, Inovo Venture Partners - EP#118
Big funds may not fight for you unless you’re in their top 5% of companies, and Michal Rokosz explains how to tell which kind of investor you’re talking to.Michal is a partner at Inovo Venture Partners, a …
Notas del episodio
Big funds may not fight for you unless you’re in their top 5% of companies, and Michal Rokosz explains how to tell which kind of investor you’re talking to.
Michal is a partner at Inovo Venture Partners, a Warsaw-based seed fund and one of the leading early-stage investors in Central and Eastern Europe. Before investing he was an operator, as managing director at foodpanda and COO at Booksy, and he has backed more than 25 companies.
In this conversation with David Politis, he breaks down how fast VCs decide, why capital can beat operational excellence, and how his region went from copying proven startups to building frontier AI companies.
Key takeaways
1. Investors decide faster than you think: Michal can often tell within the first five minutes whether a founder is an outlier, and the full decision takes about two weeks. His fund found that its fastest investments tended to perform best.2. Your backstory is part of the pitch: From an Olympiad win to an overnight drive for a missing part, the stories founders skip are often what set them apart. Michal says a founder who can’t explain why they’re exceptional will lose to one who can.
3. More money can beat better operations: At foodpanda, his team was less efficient than several competitors but had more funding, and that was enough to win. In AI, the same logic means a company that grabs the market while losing money can beat one that gets the economics right first.
4. A VC isn’t grading your business: Michal says his job is to find the anomalies. A fund needs one or two companies to return the whole fund, so a founder with a lower ceiling shouldn’t expect the same valuation as one with a higher ceiling.
5. Big funds may not fight for you: Outside a large fund’s top 5% of companies, you may get little attention, while a smaller fund may treat you as one of its most important bets. Talk to a few of an investor’s founders before you sign.
6. Not every founder should raise venture capital: Michal argues that some founders are better off bootstrapping to a profitable business, and that VC only makes sense if you’re aiming to build something huge.
Quote of the Show :
“If I have like five times more money and I'm 20% less efficient, I'm still going to win” - Michal Rokosz, Partner at Inovo Venture PartnersGuest Featured in this Episode: Michal Rokosz, Partner at Inovo Venture Partners
LinkedIn : https://www.linkedin.com/in/mrokosz/
Inovo Venture Partners : https://www.linkedin.com/company/inovovc/home/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00 Meet Michal Rokosz
02:07 What Inovo looks for in a founder
04:07 Why your backstory is the pitch
09:23 How fast Inovo decides to invest
11:10 Viktor and the founder who killed his own project
16:40 Why big VCs won't fight for you
19:56 How Central and Eastern Europe has changed
28:00 Are we in an AI bubble?
31:21 Why VCs need a company that can return the fund
36:21 Two founders, one wins by losing money
41:15 What founders get wrong about VCs
43:04 Why Michal loves being an investorWhy Founders Feel Lost After a Successful Exit - Barak Kaufman - Post-Exit Founders - EP#117
When you sell your company and hit the milestone most founders only dream of, why does it feel so lonely?Barak Kaufman has met around 2,000 exited founders, and almost all of them describe the same thing.In …
Notas del episodio
When you sell your company and hit the milestone most founders only dream of, why does it feel so lonely?
Barak Kaufman has met around 2,000 exited founders, and almost all of them describe the same thing.
In this episode of Not Another CEO Podcast, I sat down with Barak Kaufman, an investor, operator, exited founder and community builder.
Barak started his career at Insight Partners, co-founded Intello (Which competed with my company, BetterCloud), and sold it to SailPoint in 2021. He then started Post-Exit Founders, now more than 7,000 members across 12 countries. Today he is a partner at Vine Ventures and Chief Strategy Officer at Wonderful, an applied AI company.
We cover identity loss after an exit, building in the AI era, startup life in New York and Israel, and what founders get wrong about investors.
Takeaways
1. The hardest part of an exit is identity, not money: Barak says most exited founders feel lost and lonely, and many end up with a boss for the first time in years.
2. Take a year off and commit to nothing: His advice is 12 months, not six and not 24. The biggest mistake he sees is jumping into the next company because the in-between phase is uncomfortable.
3. Luck and agency both matter: Exited founders split on whether they got lucky or slaved for it. Barak believes in agency and says the founders he respects most don’t blame the situation.
4. Building in the AI era is faster, but the fundamentals haven’t changed: Wonderful’s deals are mostly over $1M a year, versus about $30K at Intello. A-plus talent, enablement and enterprise trust still decide who wins.
5. Believe your pitch: Barak admits he’s not sure he truly believed his own billion-dollar story at Intello. His standard for founders is believing that you will get there, not that you can.
6. Run your fundraise like a process: Most VCs have less figured out than founders think, and FOMO drives a lot of decisions. Be tactical, not passive.
Quote of the Show
“When you build a company and you sell that company and you reach the milestone that many would only dream of, it ends up feeling very weird and very lonely.” - Barak Kaufman, Chief Strategy Officer, Wonderful
Guest Featured in this Episode: Barak Kaufman, Chief Strategy Officer, Wonderful
LinkedIn: https://www.linkedin.com/in/barakk/
Post-Exit Founders: https://pef.co/
Vine Ventures: https://vineventures.com/
Wonderful: https://www.wonderful.ai/
We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00 Trailer & Introduction
02:47 From investor to founder to Wonderful's Chief Strategy Officer
04:46 What Wonderful does and how it started
07:37 Building in the SaaS era vs. the AI era
11:07 What stays the same: talent, enablement and enterprise sales
17:44 Inside Post-Exit Founders: the identity loss after an exit
22:30 Take a year off, and the paths after an exit
30:28 Why everyone wants to be a founder
34:06 Luck, skill and what sets exited founders apart
38:05 Agency over timing: Airtable, Miro and COVID
44:29 New York vs. Israel startup ecosystems
48:01 Inside Israel's talent war
51:14 What founders don't understand about investors
57:53 FOMO, hot rounds and the flight to quality
1:00:02 The advice he'd give his younger selfWhy He Left a Decade at Forbes to Build Upstarts From Scratch - Alex Konrad - Upstarts - EP#116
Most founders think the best story wins. Alex Konrad has spent 15 years watching what happens when the story is all there is.In this episode, Alex Konrad, Founder of Upstarts Media, joins me to share what he's …
Notas del episodio
Most founders think the best story wins. Alex Konrad has spent 15 years watching what happens when the story is all there is.
In this episode, Alex Konrad, Founder of Upstarts Media, joins me to share what he's learned from covering the biggest names in tech. He spent more than a decade at Forbes writing cover stories on people like Marc Benioff and the Collison brothers, ran the Midas List for ten years, and co-created the Cloud 100. In February 2025, he left to build Upstarts Media on his own.
From the one trait he sees in the most successful founders to why great storytelling can make or break a company, Alex unpacks what he's learned from watching thousands of founders and investors up close. We also get into the loneliness of being a solo founder, the customer stories that stay with you, and what it takes to build a bootstrapped media company.
If you're building a company, raising capital, or wondering whether you're built for the founder journey, this conversation will change how you think about obsession, storytelling, and what actually lasts.
Key Takeaways:
- The Obsession Is the Real Qualifier: The most successful founders Alex has interviewed aren't building for wealth or Twitter popularity. They're almost sick in the head about the work, and they couldn't live with themselves doing anything else. Alex explains why the founders chasing the lifestyle, the YC badge, or the title tend to burn out faster.
- Find Your One Superpower: Early on, a founder should be able to do one thing better than anyone they could hire. For Alex, it's storytelling. For me, it turned out to be motivating people.
- Storytelling Should Accelerate the Story, Not Be the Story: If you're a great salesperson selling magic beans, it catches up to you eventually.
- What Great Investors Actually Do: After a decade on the Midas List, Alex says the number one thing CEOs want is an investor who feels like part of the team.
- Great Founders Find Great Markets: Silicon Valley says a great founder can't fix a bad market. Alex isn't so sure. With how many companies pivot in the AI era, he believes a great founder will evolve into the market, or prove everyone wrong about how big it was.
- Online Can Build a Brand or Eat Your Day: Alex recently wrote about CEOs and investors who are highly online to terminally online. We talk about the real advantage of a public brand, the risk of the doom scroll, and why he suggests putting your time on social media on the calendar.
Quote of the Show:
"Storytelling should accelerate your story, for good and bad. It shouldn't be the entire story." – Alex Konrad, Founder, Upstarts Media
Guest Featured in This Episode: Alex Konrad, Founder, Upstarts Media
LinkedIn: https://www.linkedin.com/in/alexrkonrad/
Upstarts Media: https://www.linkedin.com/company/upstarts-media/
We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00 - Intro
02:01 - How Alex decides who to cover
11:37 - Why Alex left Forbes to build Upstarts
17:52 - The number one trait of successful founders
19:56 - Founder cycles and finding your one superpower
27:05 - The Midas List and what makes a great investor
34:35 - Storytelling and the trillion-dollar outcome
40:23 - Building Upstarts solo and bootstrapped
42:14 - The loneliness of being a solo founder
44:26 - Crazy customer stories and "Elon-level" security
49:16 - Terminally online founders
54:59 - Where Upstarts is in three yearsHe Blew Up His Own Winning Product Before AI Could - Eoin Hinchy - Tines - EP#115
Eoin Hinchy spent 15 years living the exact problem he'd eventually build a company to solve. First at Deloitte, then eBay, then as Director of Information Security at DocuSign, he watched security teams burn …
Notas del episodio
Eoin Hinchy spent 15 years living the exact problem he'd eventually build a company to solve. First at Deloitte, then eBay, then as Director of Information Security at DocuSign, he watched security teams burn hours gluing broken tools together by hand. So in 2018, he and his co-founder Thomas left to build the product they wished they'd had, out of a small office in Dublin.
That company is Tines. Today it's 450 people across Dublin, Boston, San Francisco and Sydney, has raised over $270 million from Goldman Sachs, SoftBank, Accel and others, is valued at over a billion dollars, and is approaching $100 million in ARR. In this episode, we talk about the moment Tines decided to blow up its own winning product to get ahead of AI, why he's never built a pitch deck in his life, and the piece of advice he'd give himself before his very first job.
Key Takeaways:
Why founders beat sales teams from $60B companies: Eoin explains the difference between a missionary and a mercenary, and why buyers can feel it immediately.
Refounding the company at its best quarter ever: The "falling off a building" analogy Eoin uses for why Tines rebuilt its core product around AI before the market forced their hand, and how he broke the news to his team and board.
Why no customer was ever forced to migrate: The promise Eoin made to protect the people who got Tines to where it is today.
Raising $270M without a single pitch deck: How Tines picked investors the way you'd pick a co-founder, and why Eoin never went looking for capital.
"Nobody cares" : The reframe that Eoin says makes the hardest parts of the job easier, not harder.
The Wizard of Oz moment: What happened the first time Eoin worked inside a company he used to think was run by geniuses.
Quote of the Show:
"The failures aren't going to be these dramatic explosions. They're going to be this kind of like quiet, unrequited effort where you put in all this hard work and like, everybody's kind of like, yeah, cool and moves on."
— Eoin Hinchy, Co-Founder & CEO, TinesGuest Featured in This Episode: Eoin Hinchy, Co-Founder & CEO, Tines
LinkedIn: https://www.linkedin.com/in/eoinhinchy/
Tines: https://www.tines.com/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.
Chapters:
00:00:00 - Introduction
00:02:35 - Best Decision at Tines: Picking a Problem He Lived
00:06:26 - Why Founders Beat Sales Teams
00:11:18 - Spending 30–50% of His Week With Customers
00:12:58 - The Refounding Moment Begins
00:17:22 - The "Falling Off a Building" Analogy
00:21:13 - Telling the Team and the Board
00:24:38 - No Existing Customer Was Ever Forced to Migrate
00:33:13 - Bootstrapping and the First Raise
00:33:33 - Blossom Capital Shows Up at Their Office
00:36:33 - How He Actually Picked Investors
00:38:27 - Board as an Extension of the Team
00:41:27 - Building a Fully Remote, Global Team
00:43:18 - Biggest Challenge: "Nobody Cares"
00:55:48 - The Wizard of Oz Moment
00:58:38 - What Actually Drives Him
00:59:48 - Advice to His Younger SelfHow Paw Patrol saved Spin Master - Ronnen Harary - Spin Master - EP#114
Most people think experience is your greatest advantage. Ronnen Harary believes it can become your biggest blind spot.In this episode, Ronnen Harary, Co-Founder of Spin Master, shares the lessons behind …
Notas del episodio
Most people think experience is your greatest advantage. Ronnen Harary believes it can become your biggest blind spot.
In this episode, Ronnen Harary, Co-Founder of Spin Master, shares the lessons behind building one of the world's most successful toy and entertainment companies, the creator of global brands like Paw Patrol, Bakugan, Air Hogs, Rubik's Cube, and Etch A Sketch.
From turning down a $100 million Hollywood deal he now regrets, to explaining why it's riskier not to bet on yourself, Ronnen unpacks the mindset that helped Spin Master grow from three friends with an idea into a multi-billion-dollar public company.
Key Takeaways:
1. The Power of Not Knowing: Sometimes experience becomes a limitation. Ronnen explains why the lack of conventional wisdom helped Spin Master create products that industry veterans had already dismissed, and why trusting your instincts matters more than following what everyone else believes.
2. Bet on Yourself Early: Your 20s are a unique window to take meaningful risks. As responsibilities grow, so does the cost of leaving a stable career. Ronnen argues that waiting until you feel "ready" often means you never start at all.
3. Create Your Own Luck: Luck isn't something that happens to you. It's something you earn by staying in motion, building relationships, and consistently putting yourself in situations where unexpected opportunities can find you.
4. Trust Your Instincts: The same experience that helps you build a successful company can eventually cause you to overthink. Ronnen shares why he believes your intuition is often a better guide than your intellect when making the biggest decisions.
5. Build a Culture of Ideas: Some of Spin Master's best ideas came from meetings that everyone else wanted to cancel. Ronnen explains why protecting time for open discussion and pulling the right people into the room fuels creativity and better decision-making.
Quote of the Show:
"The power isn't in not knowing. It's in not letting your intellect override what you know internally." – Ronnen Harary, Co-Founder, Spin Master
Guest Featured in This Episode: Ronnen Harary, Co-Founder, Spin Master
LinkedIn: https://www.linkedin.com/in/ronnen-harary-99b13370/
Spin Master: https://www.spinmaster.com/en-US/
No Experience Necessary: https://www.penguinrandomhouse.com/books/789812/no-experience-necessary-by-ronnen-harary/
Chapters:
00:00:00 — Trailer & Introduction
00:02:05 — The 32-Year Tri-Founder Partnership
00:05:34 — "The Power of Not Knowing" & The Air Hogs Story
00:09:00 — The $100M Bakugan Regret
00:10:26 — Betting on Yourself in Your 20s & Inverse Risk
00:16:44 — Early Parent Support
00:18:47 — Becoming a "Grinder"
00:22:46 — Operational Discipline
00:27:14 — Making Your Own Luck: The Flick Tricks Story
00:33:40 — "Tethered Freedom" & Owning Your Culture
00:35:20 — Seeking Micro-Mentors & Writing "No Experience Required"
00:38:46 — The Decision to Take Spin Master Public
00:41:28 — The Origin Story of Paw Patrol
00:47:08 — Evolution of the Toy Industry
00:49:45 — Future Outlook for Spin Master
00:50:37 — Ronen’s Background
00:53:39 — Early Hustles
00:58:03 — Core Drive
00:59:13 — Workaholism, Burnout, and Health Sacrifices
01:04:03 — Advice to Younger SelfThe Provocative Statement That Built Knox - Irina Denisenko - Knox Systems - #EP113
Most companies that start the FedRAMP process never finish it. Irina Denisenko built a business on getting you through it in 90 days, and said so, loudly, when everyone told her not to.Irina is the founder and …
Notas del episodio
Most companies that start the FedRAMP process never finish it.
Irina Denisenko built a business on getting you through it in 90 days, and said so, loudly, when everyone told her not to.
Irina is the founder and CEO of Knox Systems, a company that gets software companies FedRAMP certified — the federal government's exhaustive cybersecurity authorization required to sell to agencies like the Pentagon — in 90 days instead of the usual multi-year process.
Two years in, Knox has raised over $30 million, crossed 100 customers, and counts Adobe among them. Before this, Irina was COO of Class Technologies, where she had to get her own company FedRAMP certified and ended up acquiring an already, authorized company just to get through the process. She later spun that capability out as Knox.
Here were my biggest takeaways:
1. Trust that you know your market better than the room does: When advisors pushed Irina to soften her tagline, she refused. "I know my market. I've lived this problem," she told me.
2. Turn a cost center into a revenue unlock: Irina assumed her first customers would come through CISOs. Instead, her first ten came from calling friends who ran companies. The real unlock was reframing FedRAMP: it's not a compliance expense, it's access to a market a company was previously shut out of entirely.
3. Make your investors work for you, even when you're not raising: Irina stays close to her investor network specifically because boardrooms are where FedRAMP tends to get dismissed as too slow to bother with. She's built a habit of asking investors to correct that in the room on her behalf.
4. Kill a bad bet before you defend it: Knox made an early bet on a specific AI approach to auto-remediate security vulnerabilities. The technology wasn't ready yet, and by the time that was undeniable, they'd already sunk real time and money into it.
5. Never underpay your best people: Irina calls her hiring approach "Delta Force" — senior only, nobody walking in without years of reps elsewhere. Her rule on comp: she's never once regretted overpaying for the right person, and calls the opposite mindset "pennywise, pound foolish."
Quote of the Show:
"If you know your market, you should know how to talk to them. And if you don't know your market, you go figure out your market first.” - Irina Denisenko, Founder & CEO, Knox Systems
Guest Featured in this Episode:
Irina Denisenko: https://www.linkedin.com/in/irinadenisenko/
Knox Systems: https://knoxsystems.com/
If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network.
We also break this episode down into a full write-up on Substack, with the exact playbook Irina used to build a go-to-market motion around a tagline everyone told her to drop, we're building out a full library of playbooks and lessons from every episode on Substack.
Chapters:
00:00:00 — Intro: Irina Denisenko & Knox Systems
00:02:13 — The "FedRAMP in 90 Days" Tagline
00:06:34 — Building In-Person Across 3 Cities
00:08:52 — Hiring Only "Delta Force" Talent
00:11:41 — Revenue Per Employee in the Age of AI
00:17:10 — How She Vets a Delta Force Hire
00:25:57 — Never Regretting Overpaying for Talent
00:31:26 — Landing the First 10 Customers
00:42:41 — Investors as Her Best Referral Channel
00:47:43 — "Who Cares About This Market"
00:52:31 — The Valuation Hangover
01:02:16 — Scrapping a Year of AI Work
01:05:29 — From the Soviet Union to Founder
01:16:41 — Closing Advice: Integrity Above AllBack to School Special with Sammy & Noah Politis #EP112
I've interviewed over 100 founders and CEOs on Not Another CEO. I've asked them about their hardest days, their biggest regrets, and the sacrifices they made to build what they built. I never thought I'd be the …
Notas del episodio
I've interviewed over 100 founders and CEOs on Not Another CEO. I've asked them about their hardest days, their biggest regrets, and the sacrifices they made to build what they built. I never thought I'd be the one in that seat.
This week, my own kids flipped the mic on me. Sammy and Noah wrote their own questions and interviewed me for the show, and I had no idea what was coming. We covered the worst week of my career, firing people I actually liked, the sacrifices I made that I'd still make again, and the moment my son stumped two successful CEOs on a live stage with a single question.
Here's what we got into:
Where it started: My father, their grandfather, built companies my whole life, and he put me on the BCC of every email he ever sent so I could learn the business before I had a job in it. My actual first paycheck came from a summer carrying furniture up four story walk ups for a moving company in New York.
The worst week of my career: one week in 2019 where we lost our biggest customer, our incoming CRO backed out the day before he was supposed to start, I found out I wasn't winning an award I really wanted, I tore my Achilles, and I missed a family trip to Israel, all in the span of five days.
Firing people I liked: I've fired hundreds of people over 20 years, including good friends. My kids asked how I could do that, and we talked about why it's actually the kinder move when it's done right.
The sacrifice question: I missed my son's first steps building BetterCloud, and I left the hospital right after my younger son was born to go straight to a VC meeting. My kids wanted to know if I'd still make that call today.
Comparing myself to other CEOs: yes, I still get jealous scrolling LinkedIn. It was worse when I was actually running BetterCloud and too deep in the weeds to see anything but my own world.
How I define success: the same answer my son got out of me at our first ever live show, the one that stumped Kass and Mike Lazarow in front of a packed room.
This is a different kind of episode for the show, and it might be one of my favorites. Thanks for listening, and thanks to Sammy and Noah for the toughest interview I've ever done.
Quote of the Show:
"The way that I define success is being able to meaningfully impact other people's lives while significantly benefiting your own life." — David Politis, Host, Not Another CEO Podcast
Chapters:
00:00:00 - Trailer
00:02:22 - BetterCloud's Biggest Lesson
00:04:52 - What Inspired Me to Want to Be a CEO
00:07:12 - My First Job
00:10:14 - Pitching BetterCloud to My Own Kids
00:15:21 - What 100+ Interviews Taught Me About Building a Company 00:20:31 - AI and the Skills That Won't Get Replaced
00:23:37 - The Hardest Days
00:29:35 - Still Bad At It, Jealous of Other CEOs
00:33:13 - How I Define Success
00:41:29 - The Sacrifice Question
00:46:47 - Trust Your GutThe Loneliness Every Leader Feels| Loneliness Compilation - Episode#111
Most founders assume the loneliness fades once the company succeeds.It doesn't. If anything, it gets quieter and harder to name.In this special compilation episode of Not Another CEO, David brings together …
Notas del episodio
Most founders assume the loneliness fades once the company succeeds.
It doesn't. If anything, it gets quieter and harder to name.In this special compilation episode of Not Another CEO, David brings together lessons from nine founders, CEOs, and investors who have built, scaled, sold, and advised some of the most recognizable companies in tech.
The conversation moves through why the seat is lonely in the first place, the false belief that you are the only one carrying it, and what the best CEOs actually build around themselves once they stop trying to carry it alone.
Key Takeaways:- Loneliness at the top isn't a personal failing, it's baked into the structure of the job: unpopular decisions, imperfect information, and a team that only ever sees half the picture.
- The belief that you are uniquely alone in your struggles is common and almost always wrong.
- Even the most people-first, culture-driven CEOs cannot fully escape the isolation of being the one who stays in the seat while everyone else eventually moves on.
- Founder loneliness is a default, not a fixed destiny. A co-founder, a coach, or a peer group can change the default entirely.
- The most effective support comes from someone with independent context on your business and your team.
- Support systems show up in real outcomes, not just in how someone feels.
- The founders who say they never felt the loneliness usually point to the same thing: a spouse, a family member, or a peer they could call and be fully honest with.
Quote of the Episode
"Your team has no conception of how lonely it is to be the CEO."
— Adam Dell, Founder & CEO, Domain Money
Guests Featured in This Episode:- Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn
- Adam Dell, Founder & CEO, Domain Money — LinkedIn
- Chieh Huang, Co-Founder & Former CEO, Boxed — LinkedIn
- Nick Mehta, Co-Founder & Former CEO, Gainsight — LinkedIn
- Nadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedIn
- Chip Hazard, General Partner & Co-Founder, Flybridge — LinkedIn
- Kathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedIn
- Mike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedIn
- Kyle Porter, Founder & Board Chair, Salesloft — LinkedIn
Chapters:
00:00 – Trailer00:48 – Intro
02:20 – Marcus Ryu
03:34 – Adam Dell
04:57 – Chieh Huang05:59 – Nick Mehta
07:26 – Nadia Boujarwah
08:43 – Chip Hazard10:10 – Kathryn Minshew
12:34 – Mike Grossman
15:38 – Kyle Porter
16:38 – Closing Thoughts
Lessons From The Coach of Silicon Valley - Mike Grossman - EP#110
Everything you think you know about why startups succeed might be wrongIn this episode, Mike Grossman, six-time CEO and mentor to first-time founders across Silicon Valley, breaks down what thirty years of …
Notas del episodio
Everything you think you know about why startups succeed might be wrong
In this episode, Mike Grossman, six-time CEO and mentor to first-time founders across Silicon Valley, breaks down what thirty years of running companies actually taught him.From the $200 million counteroffer that blew up his first company, to why he believes luck accounts for 80 to 90 percent of every outcome, Mike pulls back the curtain on what nobody tells you before you take the job.
If you think success is mostly about hard work and good decisions, this conversation will make you rethink how you handle risk, pivots, and your own sense of control.
Key Takeaways:Build a System to Find the Truth: Your direct reports won't always tell you what's really happening, whether they're afraid to or simply don't know themselves. Cut through the management chain and find the people who will tell you the truth.
Hold Your Plans Loosely: A plan is obsolete the moment you make it. The goal isn't a perfect plan, it's a planning mindset flexible enough to adjust without losing the team.
Stop Whiplashing Your Team: What feels like velocity to a founder can feel like chaos to everyone else. Pivot too often and even your own board will stop trusting your judgment.
Beware Your Own Kool-Aid: Believing your company is destined for outsized value can cost you the deal in front of you. Mike turned down a $40 million offer and countered at $200 million. He got neither.
Luck Runs the Table: Mike believes 80 to 90 percent of a company's outcome comes down to luck, not execution. Focus on what you can control and let go of the rest.
Watch Out for the Debilitating Win: Founders who succeed once often can't understand why the second company isn't working the same way. It usually wasn't the formula. It was luck.
Nobody Talks About the Loneliness: Nearly every first-time CEO Mike coaches struggles with anxiety and isolation, and most feel they can't show it to their own investors.
Quote of the Show: Plans are useless because whatever plan you make is immediately out of date and you have to make adjustments to it. But if you don't make any plan and you just do it on a seat of the pants basis, everything is kind of ad hoc, you end up jerking the company around and people get frustrated.- Mike Grossman, Entrepreneur and Author
Connect with Mike:
LinkedIn: https://www.linkedin.com/in/migrossman/
Book Failure is an Option: https://share.google/9DUEHB6596Eb1uXAa
Chapters:
00:00 — Intro02:21 — The One Thing Mike Would Do Again At Every Company
08:39 — Bill Campbell's Rule
20:13 — Plans Are Useless, Planning Is Indispensable
25:19 — The Pivot His Board Rejected
26:58 — All Of Them Struggle With Their Mental Health
30:47 — The $200 Million Deal He Blew Up
38:58 — Luck Accounts For 80 To 90 Percent
44:17 — The Debilitating Win
54:16 — Remembering The Coach Of Silicon Valley
How to get your first 10 customers - July Pulse Episode - EP#109
"You cannot outsource acquiring those first ten customers. You can't do it."In this episode of Not Another CEO, David breaks down the six tactical ways he's used, three separate times now, to land his first …
Notas del episodio
"You cannot outsource acquiring those first ten customers. You can't do it."
In this episode of Not Another CEO, David breaks down the six tactical ways he's used, three separate times now, to land his first customers from zero. From holding a pizza party for international students to handing out fliers at the Atlanta airport taxi stand to asking his own uncle to buy a phone system, David gets specific about what actually works when you're starting from nothing.
What's covered:
-Why getting your first customers is harder now than ever, even though building product has never been easier
-Reconnecting with former employers and coworkers who already trust you
-How to actually use your investor network, even at the angel stage
-Why showing up in person at trade shows and meetups still beats almost everything else
-Building in public on social media, even when almost nobody engages at first
-The one BCC email that got David a customer and an important hire at the same time
-How to do cold outreach that people actually respond to
-Why none of these six tactics scale, and why that's exactly the point
If you're a founder still chasing your first ten customers, this one's for you.
We cover more topics like this in full playbooks on our Substack. Subscribe to get the tactical deep dives, not just the highlights: notanotherceo.substack.com
Chapters:
00:00 - Trailer
00:44 - Why Finding Your First Customers Is Harder Than Ever
05:20 - Tactic 1: Reconnect with Former Employers & Coworkers
06:28 - Tactic 2: Tap Into Your Investor Network
08:14 - Tactic 3: Show Up in Person (Trade Shows & Meetups)
09:42 - Tactic 4: Build in Public on Social Media
11:02 - Tactic 5: Tell Your Friends and Family
12:02 - Tactic 6: Cold Outreach Done Right
13:53 - Why Doing Things That Don't Scale Is the Entire PointBacking Maniacs at Inception - What Investors Actually Look For | Jeff Becker - Antler - Episode#108
Everything you think you know about venture capital might be wrong. In this episode, Jeff Becker, General Partner at Antler New York, breaks down the brutal, hidden realities of the startup world. From why …
Notas del episodio
Everything you think you know about venture capital might be wrong.
In this episode, Jeff Becker, General Partner at Antler New York, breaks down the brutal, hidden realities of the startup world.
From why investors care more about your childhood psychology than your pitch deck, to why a $500 million exit can actually be a massive disappointment to a fund, Jeff pulls back the curtain on how venture capitalists actually math out risk.
If you are operating with a broken mental model of how fundraising works, this conversation will completely reshape how you build, pitch, and scale your business.
Key Takeaways:
Pitch Yourself, Not the Product: Early-stage investors bet on the person first. Master your personal story of resilience before you even open your slide deck.
Understand Fund Math: A $500 million exit does not return a large fund. You must build toward a multi-billion-dollar scale to make your investor's job a success.
Expect the Volume Game: Firms like Antler build "engineered serendipity" by backing 200 early-stage founders at once, relying on massive diversification to find a breakout winner.
Take Money Off the Table: Luck and market shifts rule the startup graveyard. When liquidity windows open, secure your personal financial safety.
Storytellers Win the Cash: Being a great operator is not enough. You must be able to compress the gap between reality and future potential to get funded.
Give Investors Specific Homework: Investors want to work for you, but vague asks get vague results. Give them transparent, direct tasks so they can help you win.
Quote of the Show:
"If I'm not working as hard as the founders, none of them are going to want me on their cap table." - Jeff Becker, General Partner, Antler
Guest Featured in This Episode:
Jeff Becker, General Partner, Antler (New York)
LinkedIn: https://www.linkedin.com/in/jeffreylbecker/
Antler: https://www.antler.co/We also break this episode down into a full write-up on Substack, with the exact playbook Scott used to fix the culture and rebuild the strategy from scratch, we're building out a full library of playbooks and lessons from every episode on Substack.
Chapters
00:00 — Intro
02:00 — The Maniac Framework
09:00 — Why Childhood Matters
15:00 — Jeff's Origin Story
20:00 — Angel Investing Days
26:00 — The Role of Luck
33:00 — AI & One-Person Companies
41:00 — Fund Math & Dilution
46:00 — Storytellers vs. Operators
51:00 — "I Work For You"Backing the outsiders most VCs ignore | Nick Moran - New Stack Ventures - Episode#107
Majority founders only start thinking seriously about their next round when they’re already running low on cash. By then, you’re not really raising; you’re begging.On this week’s episode of Not Another CEO, we …
Notas del episodio
Majority founders only start thinking seriously about their next round when they’re already running low on cash. By then, you’re not really raising; you’re begging.
On this week’s episode of Not Another CEO, we sit down with Nick Moran, Co-Founder and General Partner at New Stack Ventures. Founded in 2015, New Stack manages close to $100 million and leads pre-seed and seed rounds with a unique mission: backing "The Outsiders," who are ambitious founders building category-defining companies outside the Bay Area and outside the obvious networks. Nick also hosts Full Ratchet, one of the first venture capital podcasts ever made, now closing in on 1,000 episodes. I know how hard it is to stay consistent with a podcast. Doing it for over a decade is a different level.
Nick shares his brutal honesty on what it actually takes to build a venture-backed business, why he tells founders to build their next pitch deck the day they close their current round, and how he evaluates the intangibles that traditional VCs completely miss.
Key Takeaways:- The Next Round Plan (NRP): Why fundraising is a continuous narrative, not a sporadic event. Nick breaks down how to align on business models, track leading indicators over lagging revenue, and build a highly targeted investor list early.
- Desire Beats Talent: Most VCs look for the "Peyton Mannings" of tech, meaning those who are obvious, expensive, and pedigreed. Nick hunts for the "Tom Bradys," founders with a chip on their shoulder, undeniable ambition, and the drive to beat long odds.
- Bad News Travels Fast: The ultimate trust-builder between a founder and a VC. Going dark creates anxiety; transparency during a brutal quarter is exactly what inspires an investor to throw you a lifeline.
- The Power of Being an "Outsider": Building in cities like Charlotte, Nashville, Dallas, or Chicago isn't a disadvantage. When the herd concentrates in the Bay Area, the best, most capital-efficient opportunities are often found where others aren't looking.
- Where the Smart Money is in AI: The shift from infrastructure to proprietary data. Nick explains why the next massive wave of AI value belongs to domain experts who control the data locked behind enterprise firewalls.
Quote of the Show:
“Do you want to be great or do you want to be happy?… You better be ready for the big game here because this is not an easy path. We're not going to be happy for the next ten years.” — Nick Moran
Connect with Nick:- LinkedIn: https://www.linkedin.com/in/nick-moran-a738503/
- New Stack Ventures: https://www.newstack.com/
- The Full Ratchet: https://www.youtube.com/@nicholasmoran3095/featured
Chapters :
00:00 Trailer01:30 Welcome Nick Moran, New Stack Ventures
03:54 Why desire is the ultimate founder trait
10:02 First impressions and the dating phase of investing
15:34 Founder-VC fit is like marriage
20:56 The Outsiders thesis and building a national network
27:48 Inside the Next Round Plan (NRP)
32:20 Communication, bad news should travel fast
39:00 What founders misunderstand about the VC side of the table
42:10 Where the smart money is moving in AI & Closing thoughts
The Customer Segments Hiding in Your Own Data | ICP Compilation - Episode#106
Most founders know they need an Ideal Customer Profile. Fewer realize how much growth depends on getting it right.In this special compilation episode of Not Another CEO, David brings together lessons from seven …
Notas del episodio
Most founders know they need an Ideal Customer Profile. Fewer realize how much growth depends on getting it right.
In this special compilation episode of Not Another CEO, David brings together lessons from seven founders, CEOs, and investors who all reached the same conclusion: growth accelerates when you're crystal clear about who you serve.
The episode explores why broad ICPs slow companies down, leading to weaker messaging, scattered product roadmaps, and unfocused sales efforts. Guests share how they identified their ideal customers, the mistakes they made, and the tough decisions required to stay focused as they scaled.
Key Takeaways
- An ICP that only exists in your head isn't an ICP. Write it down and you'll often discover you're targeting multiple markets at once.
- Segment until it hurts. The best companies define their market so specifically that they can name every company that fits their profile.
- Your users are not always your customers. Understanding the difference can prevent years of wasted effort.
- Focus requires sacrifice. Sometimes the right decision is walking away from paying customers who don't fit your long-term vision.
- The best teams use data, not assumptions, to refine their ICP and identify their highest-value customers.
- Micro-segmentation is becoming increasingly important. The strongest go-to-market teams don't just define an ICP, they segment within it.
- Your ICP should influence every part of the company, from product decisions to marketing strategy to hiring plans.
Quote of the Episode
"If you try to sell to everyone, you really end up selling to no one effectively." - David Politis, Host of Not Another CEO Podcast
Guests Featured in This Episode:
- Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn
- Tom Buiocchi, Former CEO, ServiceChannel — LinkedIn
- Craig Rosenberg, Chief Platform Officer, Scale Venture Partners — LinkedIn
- Zach Smith, Co-Founder & Former CEO, Packet — LinkedIn
- Melanie Fellay, Co-Founder & CEO, Spekit — LinkedIn
- Sean Henry, Co-Founder & CEO, Stord — LinkedIn
- Rohyt Belani, Co-Founder & Former CEO, PhishMe — LinkedIn
Chapters:
00:00 - Trailer
00:55 - Why your ICP is probably too broad
05:55 - The exercise that exposes a fake ICP
08:59 - "Segment until it hurts"
14:00 - Why your ICP is actually several smaller ones
17:22 - Your users aren't always your customers
20:08 - The real cost of firing the wrong customers
23:36 - Champions aren't customers
24:59 - Your ICP will change, and that's not failureWhy Fast-Growing Companies Slow Down | Dan O’Connell - Front - Episode#105
Most people assume starting a company is the hardest job in business. Dan O'Connell has learned that taking over one can be even harder.Dan's career has taken him from Google, where he joined when the company …
Notas del episodio
Most people assume starting a company is the hardest job in business.
Dan O'Connell has learned that taking over one can be even harder.
Dan's career has taken him from Google, where he joined when the company was 300 people, to founding TalkIQ before AI was cool, to helping scale Dialpad past $200M in revenue, and now to leading Front as CEO.
Not many people have been an executive at a big tech company, a founder, a high growth operator, and a hired CEO. Dan has done all four.Front is a customer operations platform used by more than 9,000 companies to manage customer conversations across support, customer success, account management, and sales.
When Dan joined, the company had strong talent, a strong product, and strong customers. But growth had slowed. This episode is about what he did next and what he learned along the way.
Takeaways:
- Focus reaccelerates growth:
When Dan joined Front, his first move wasn't a product change or a new hire. It was getting brutally clear on who they serve, where they win, and explicitly what they were not going to do. That intentionality alone reaccelerated growth. - Speed is a competitive advantage:
Dan introduced speed as a formal company value at Front and it remains polarizing two and a half years later. It doesn't mean reckless. It means faster decision-making, strong opinionated leaders, and fighting friction when it shows up. Any decision is better than no decision. - Taking over is harder than starting:
You're inheriting history, culture, and legacy inertia and you can't take six months to build trust before making changes. You have to do both at the same time. As Dan puts it, you're flying the plane while rebuilding it. - Great leaders stay close to customers:
In his first week as CEO, Dan got on customer calls, visited every office, and jumped in the support queue to answer tickets. The same thing he now requires of every executive he hires. The team is always judging you and nothing builds credibility faster than showing you're willing to do the work. - Platforms will outlast pure agents:
After attending OpenAI's Frontiers Conference, Dan's contrarian take is that pure agent companies solving one workflow may get commoditized by OpenAI and Anthropic over time. His bet is on platforms and Front's position as the entry point for all customer conversations across channels, regardless of how the AI landscape evolves.
If you are a founder, operator, or CEO this episode is worth your time.
Quote of the Show:
"Taking over has been much harder than I thought. And it's usually from the behaviors and people side." — Dan O'Connell, CEO, FrontLinks:
LinkedIn: https://www.linkedin.com/in/danoconnell/
Front: https://front.com
Chapters:
00:00 Trailer
01:15 Introduction
02:15 The One Thing That Had the Biggest Impact: Focus
05:00 Narrowing the ICP
07:30 The Operating Machinery That Keeps a Company Focused
13:00 Taking Over as a Non-Founder CEO
17:15 Flying the Plane While Rebuilding It
22:30 Platform vs. AI Agents
29:00 Building the Executive Team
42:00 The Biggest Challenge
47:30 Where Front Is in Three Years
49:00 Origin Story: From Southampton to Google to Founding TalkIQ
56:00 Two Career-Defining Moments & Advice to His Younger Self- Focus reaccelerates growth:
The Best Deals Aren't the Hottest Deals | Dan Teran - Gutter Capital | Episode #104
Most founders talk about building a company but very few talk about what it actually costs.Dan Teran knows both sides of that story.In this episode, Dan shares how he built Managed by Q from the ground up …
Notas del episodio
Most founders talk about building a company but very few talk about what it actually costs.
Dan Teran knows both sides of that story.
In this episode, Dan shares how he built Managed by Q from the ground up, scaled a team that included nearly 1,000 frontline workers, gave equity to cleaners and handymen, navigated an acquisition by WeWork, and ultimately made the transition from founder to investor.
We talk about the systems behind great culture, why the best founders are usually obsessed with a problem long before they start a company, what most VCs get wrong when evaluating startups, and how AI is changing the economics of company building.
Dan is one of the most thoughtful operators and investors I've met, and this conversation is packed with practical lessons for founders at every stage.
Takeaways:
1. Great cultures are built through systems, not slogans: The strongest company cultures don't come from posters on the wall. They come from who gets hired, who gets promoted, what behaviors get recognized, and what standards leaders reinforce every day.
2. The best founders are deeply connected to the problem they're solving: Dan believes the most resilient founders aren't chasing trends; they're solving problems they've experienced firsthand. That personal connection helps them stay committed when things get difficult.
3. Success is usually the result of hundreds of small decisions: Managed by Q wasn't built through one breakthrough moment. It was years of learning, adapting, fixing mistakes, and making better decisions over time.
4. AI is changing how companies get built: Founders can now test ideas, build products, and reach customers faster than ever before. What once took teams of engineers and millions of dollars can often be done by a handful of people.
5. Building something meaningful still requires hard work: Technology may change, but the reality of company building hasn't. Every successful founder eventually faces uncertainty, setbacks, and difficult decisions. Persistence is still the only way through them.
Quote of the Show: ”If you're lucky enough to find a problem worth working on, that's where the fulfillment comes from.” - Dan Teran, Co-Founder & Managing Partner, Gutter CapitalLinks:
LinkedIn: https://www.linkedin.com/in/danteran/
Website: https://www.gutter.cc/
Chapters:00:00: Trailer
01:18: Meet Dan Teran: Founder, Operator, Investor
04:45: Building a Culture That Actually Scales
11:55: Why Every Employee Received Equity
18:15: The Story Behind the WeWork Acquisition
25:10: Life After Selling the Company
29:00: Starting Gutter Capital
39:00: How Dan Evaluates Founders
52:20: The Operating Blueprint for Startups
Your Pipeline Isn’t Broken, Your Strategy Is - Craig Rosenberg - Scale Venture Partners -Episode#103
Why does your pipeline feel broken… when the real problem is your strategy?In this episode, I sat down with my longtime mentor & friend Craig Rosenberg, Chief Platform Officer at Scale Venture Partners. Craig …
Notas del episodio
Why does your pipeline feel broken… when the real problem is your strategy?
In this episode, I sat down with my longtime mentor & friend Craig Rosenberg, Chief Platform Officer at Scale Venture Partners. Craig taught me how to build inside sales teams 20 years ago, and he’s still one of the sharpest minds in go-to-market strategy.
We break down why most companies are struggling to create pipeline, the power of ruthless micro-segmentation, why the old outbound “spam cannon” is dead, and what actually works right now including smart AI plays and unmistakably human experiences.
If you’re a founder or leader frustrated with pipeline, this is the conversation you need.
Takeaways:
- Your Pipeline Isn’t Broken Your Strategy Is: Most companies are going too broad instead of micro-segmenting their ICP on the other hand the winners are ruthlessly micro-segmenting their ICP around homogeneous use cases.
- Micro-Segmentation Is the New Superpower: Stop fearing you’ll miss pipeline by going narrow. Focus the entire GTM team on a tight subset of accounts with similar needs this unlocks consistent messaging, better win rates, and faster learning cycles.
- Talk to 10 People a Week in Your ICP: Whether you’re at seed or scaling, executives must get in the weeds. Have real conversations, pitch them, and ask for next steps. Gong calls and outsourced interviews aren’t enough. This is how you validate and refine your story fast.
- Use AI as a Multiplier, Not a Crutch: Leverage AI for custom market reports, personalised demos at scale, deep account research, and proprietary signals. But the real advantage comes from pairing AI with unmistakably human interactions in a market flooded with AI noise.
- High-Touch Human Experiences Are Back: Curated dinners, thoughtful direct mail, and once-in-a-lifetime events (like World Cup experiences) outperform digital spam. Buyers can feel when real care and intention went into the interaction.
Quote of the Show: ”Because now AI is about to flood the market, is what are those unmistakably human interactions you can have.” - Craig Rosenberg, Chief Platform Office, Scale Venture Partners
Links:
LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Scale Venture Partners: https://www.scalevp.com/team/craig-rosenberg
Chapters:
00:00: Intro
02:45: Why Pipeline Feels Harder Than Ever
06:10: The Power of Ruthless ICP Micro-Segmentation
10:25: Special Forces Teams for New Market Expansion
14:40: What’s Changed in B2B Buying (2026 Reality)
19:15: Why the Old Outbound Playbook Is Dead
24:50: AI Tactics That Are Actually Working
29:40: The Unmistakably Human Differentiator
35:20: High-Impact Events & Experiences
42:15: Final Advice + How to Stay Ahead
Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102
Most founders think investors decide after the pitch but this investor says the decision is usually made in the first five minutes.In this episode of Not Another CEO, I sat down with Jess Lin, Co-Founder & …
Notas del episodio
Most founders think investors decide after the pitch but this investor says the decision is usually made in the first five minutes.
In this episode of Not Another CEO, I sat down with Jess Lin, Co-Founder & General Partner at Work-Bench, for a deep conversation on what actually separates great founders from everyone else.
Jess breaks down how investors build conviction in founders within minutes, why product-market fit has become harder than ever, and what most startups misunderstand about growth, fundraising, and becoming truly mission critical. The conversation also explores the emotional side of venture capital, imposter syndrome, building a venture firm, and the realities founders face between Seed and Series A.
Takeaways:
From founder obsession and investor psychology to career risk and company building, this episode is a candid look into how elite investors think and what founders need to understand to build enduring companies.- Investors Often Decide Faster Than Founders Realise: Jess explains that initial conviction about a founder is usually formed within minutes. The rest of the process is often about validating or disproving that instinct.
- Growth Alone Is No Longer Enough: Fast revenue growth has become table stakes. The real question investors ask now is: Would customers genuinely care if this product disappeared tomorrow?
- Founder Obsession Matters: The best founders are deeply obsessed with the problem they’re solving. They see something others don’t and cannot stop thinking about it.
- Venture Capital Is Emotionally Uncertain: Jess shares how difficult it is to know whether you’re actually “good” at investing because feedback loops in venture can take 10+ years.
- Building a VC Firm Is Like Building a Startup: From branding and hiring to differentiation and operations, venture firms face many of the same challenges founders do when building companies.
It's better to be fast than to be right. Because if you're fast, if you just have more at bats, you will least be able to course correct. - Jessica Lin, Co-Founder & General Partner at Work-Bench.
Chapters:
Links:
LinkedIn: https://www.linkedin.com/in/jessicalin8
Work-Bench: https://www.work-bench.com/00:00: Trailer
04:12: How investors evaluate founders in the first five minutes
09:35: The founder traits that create investor conviction
15:08: Why Series A has become much harder
20:44: What “mission critical” really means in startups
27:10: Product-market fit vs fast growth
33:26: Imposter syndrome in venture capital
39:41: Career advice, risk & serendipity
46:03: Why building a VC firm feels like building a startup
53:18: Final lessons for founders and investors
The Seven Deadly Sins of Founders - Michael Loeb - Loeb.Nyc - Episode #101
Most founders fail before the market ever gets the chance to beat them the enemy is inside the building.In this episode of Not Another CEO Podcast, David sits down with Michael Loeb, Co-Founder of Synapse Group …
Notas del episodio
Most founders fail before the market ever gets the chance to beat them the enemy is inside the building.
In this episode of Not Another CEO Podcast, David sits down with Michael Loeb, Co-Founder of Synapse Group and founder of Loeb Enterprises, a startup studio and venture collective that has invested in, incubated, and scaled more than 50 companies including five unicorns.
Michael shares the hard-earned lessons from 35 years of building: the character flaws that destroy founders before the market ever gets the chance, what separates real entrepreneurial DNA from people who just like the idea of it, why sociopaths concentrate in startups, and why the entrepreneurial class should be funding itself instead of depending on traditional venture capital.
Takeaways:
1. The character flaws that kill founders are predictable: Michael maps pride, sloth, delusion, and the refusal to listen onto real founder failure stories.
2. Entrepreneurship is innate, not learned: Real founders show up early the lemonade stand, the paper route, the video game rental business in college.
3. Surrender being an option is a dealbreaker: The moment a founder puts quitting on the table, Michael says the relationship is over.
4. Charm is a feature and a warning sign: Sociopaths concentrate in startups because magnetic charm and the ability to make fiction feel real are exactly the qualities that attract early capital.
5. The entrepreneurial class is rich enough to fund itself: Michael's Uncharted model is built on a simple premise: founders who have had exits, understand the journey, and can write a $10,000 check should be backing each other not waiting on institutional capital that is fundamentally optimising for something different.
Quote of the Show:
"When anybody uses those words I'm just going to give up if that is an option, you have no choice. Surrender is not an option. Quitting is not an option. So as soon as that goes on the table, they're done." - Michael Loeb, Founder & CEO, Loeb Enterprises
Links:
LinkedIn: https://www.linkedin.com/in/michaelloeb1/
Website: https://loeb.nyc/
Ways to Tune In:Substack: https://notanotherceo.substack.com/
Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0
Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707
YouTube: https://www.youtube.com/@NotAnotherCEOPodcast
Chapters:00:00 - Trailer
03:45 - The seven deadly sins of founders and the pride that bankrupted a $100M business
06:36 - Sloth, the founder who quit, and why surrender can never be an option
13:35 - How Michael spots real entrepreneurial DNA before writing a check
15:43 - The video game rental kid and what genuine founder instinct looks like in college
20:00 - Envy and why rent-a-CEOs create a different kind of danger
22:00 - The thin line between necessary optimism and dangerous delusion
24:53 - Why charm is both a feature and a warning sign
26:16 - The founder who refuses to listen
31:19 - Why being numeric is a non-negotiable founder requirement
34:58 - Founders Backing Founders
Why CEO's Do It Anyway: Lessons I Learned Talking To 100 Founders - NAC - Episode #100
100 episodes. Over a thousand years of combined CEO experience. Every guest showed up for one reason: to pay it forward.Two years ago I was recording in the corner of my son's bedroom. Everyone said I'd quit …
Notas del episodio
100 episodes. Over a thousand years of combined CEO experience. Every guest showed up for one reason: to pay it forward.
Two years ago I was recording in the corner of my son's bedroom. Everyone said I'd quit after ten episodes.
I didn't. And in this episode I went back and pulled the moments that stopped me cold the lessons I keep referencing, the stories that hold up no matter what stage you're at.
If you're deep in it right now, this one's for you.Links in the comments. If you enjoy the episode, please like and subscribe on your favorite platforms and share with your network.
If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network.
TAKEAWAYS1. The best founders are just built different and they know what they signed up for. Chieh Huang's description of entrepreneurship as a broken glass eating competition is the most accurate thing I've heard in 100 episodes.
2. The minute you lose hope, it's over. Ryan Simonetti watched Convene go from $220M in revenue and a pre-IPO round in process to zero revenue in less than three weeks. His lesson: optimism isn't soft. It's the one thing that kept Convene alive long enough to become what it is today.
3. Layoffs cost more than headcount and founders feel it in ways they don't talk about. Alina Vandenberghe described being hospitalized after Chili Piper had to do layoffs. That vulnerability is exactly what I built this show to surface.4. Every company that wants to survive the AI era will have to refound itself. Shensi Ding walked me through a moment at Merge where a major deal collapsed, morale cratered, and people quit. The refounding wasn't a failure it was the only path to becoming a category leader.
5. Most companies don't die of starvation. They die of indigestion. Amish Jani's line is the one I share most with founders I advise. Tight sequencing and disciplined focus are what separate great companies from the ones that almost made it.6. Fish in a pond, not an ocean. Tom Buiocchi's ICP framework is the most actionable thing I've pulled from the show. When you know the names of all the fish in your pond, your entire go-to-market changes.
TIMESTAMPS
7. The chip on your shoulder is fuel don't waste it. Flint Lane told me he's still trying to prove something to the kids he grew up with. That drive didn't diminish after selling Billtrust for $1.7B it followed him into his next company.
8. AI is fast, but it's not without precedent. Donna Dubinsky has lived through desktop computing, handheld computing, the internet, and now AI. Her perspective that the current shift is significant but not categorically unlike what she's seen before is one of the most grounding things I've heard on the show.
9. Being second can be a strategic advantage. Max Junestrand watched the first movers in legal AI burn money on fine tuned models and approaches that didn't pan out. By moving second, Legora could see which paths led nowhere.
10. Real conviction is unmistakable. Jess Lin described meeting April Co, founder of Spring Health, years before the company became what it is. The way she said it made clear: she was doing this with or without any investor.00:00 - Introduction
02:10 - What this show was always meant to be
03:45 - The broken glass eating competition
05:30 - The cost of layoffs no one talks about
08:00 - The chip on the shoulder that never leaves
09:30 - $220M to zero and keeping hope alive
13:00 - What it means to refound from scratch
15:30 - Most companies don't die of starvation
17:00 - Fish in a pond, not an ocean
19:30 - AI through the eyes of someone who's seen everything
22:00 - The second-mover advantage
24:30 - What real founder conviction sounds like
26:30 - ClosingHow it was game over for Guidewire until it wasn’t - Marcus Ryu - Guidewire - Episode #99
Building software is hard but building a category-defining enterprise company for 20 years is a different game entirely.In this episode of Not Another CEO Podcast, David sits down with Marcus Ryu, Co-Founder …
Notas del episodio
Building software is hard but building a category-defining enterprise company for 20 years is a different game entirely.
In this episode of Not Another CEO Podcast, David sits down with Marcus Ryu, Co-Founder and former CEO of Guidewire, the software platform that transformed the insurance industry and grew into a public company generating over $1.5 billion in revenue.
Marcus shares the hard-earned lessons from building Guidewire from zero: developing strategic clarity, surviving years-long sales cycles, learning how to sell as a founder, navigating investor pressure, handling lawsuits from incumbents, and sustaining the emotional intensity of being a founder CEO for nearly 20 years.
Takeaways:1. Strategic coherence matters more than speed:
This conversation is a masterclass on company building, resilience, leadership, and the psychological realities behind building enduring businesses.Marcus explains how Guidewire constantly revisited its assumptions whenever new information appeared maintaining ruthless intellectual honesty around strategy instead of blindly executing.
2. Every founder must learn how to sell:Despite not coming from sales, Marcus says learning sales became one of the most valuable skills of his entire career. Great CEOs are constantly persuading customers, employees, investors, and markets.
3. Enduring companies require patience:Guidewire’s early sales cycles lasted 1–2 years, and implementations could take another 1–2 years. Marcus shares why building meaningful companies often demands long-term thinking and delayed gratification.
4. Capital efficiency creates resilience:Guidewire raised only $29 million throughout its journey to IPO. Marcus discusses how treating every dollar like it could be the last shaped the company’s discipline and culture.
5. Intensity without serenity can become dangerous:Looking back, Marcus says he spent years carrying catastrophic pressure and anxiety as a founder. His biggest reflection is learning that great CEOs can be both intensely driven and internally calm at the same time.
Quote of the Show:“If you can be intense and serene at the same time, then you really have a superpower.” - Marcus Ryu, Founder & Former CEO, Guidewire
Chapters:00:00 - Trailer
02:10 - The importance of strategic coherence in company building
08:45 - Why startups need an enemy and a clear sense of differentiation
15:20 - Discovering the broken insurance software market
27:20 - Learning sales as a founder CEO
31:00 - Getting the first customers & surviving long enterprise sales cycles
36:20 - Building Guidewire with extreme capital efficiency
43:10 - The pressure modern founders feel to grow at impossible speeds
49:40 - Surviving lawsuits and competitive attacks from incumbents
58:00 - Transitioning from founder CEO to investor at Battery Ventures
01:06:30 - Marcus’s biggest personal reflection after two decades as CEO
From Sticky Notes on My Door to $1.5B Logistics Disruptor - Itamar Zur - Veho - Episode #98
He walked back to his apartment and found 50 sticky notes on the door. "Sorry we missed your package." That problem became a $1.5 billion company competing directly with UPS and FedEx.Itamar Zur, Co-Founder and …
Notas del episodio
He walked back to his apartment and found 50 sticky notes on the door. "Sorry we missed your package."
That problem became a $1.5 billion company competing directly with UPS and FedEx.
Itamar Zur, Co-Founder and CEO of Veho, shares the full story of building one of the most disruptive logistics companies in America from a business school dorm room to 65 markets, nearly 1,000 employees, tens of thousands of drivers, and over $300 million raised from General Catalyst, SoftBank, and Tiger Global.
In this conversation, Itamar opens up about what it really took: obsessing over the Day One customer experience in a way most founders never do, rebuilding the company's values from scratch after 2022 nearly broke everything, and creating a deliberate program to identify and invest in top performers before someone else does.
If you're building a company and want to understand what championship-level execution actually looks like from the inside, this episode is worth your time.
Takeaways:- Obsess Over the Day One Experience: Itamar would send detailed end-of-day reports not just to his buyer but to the CEO, CMO, and CFO of every new customer anyone whose email he could find. By the next call, those buyers weren't asking how things were going. They were asking what other markets Veho could go to. First impressions compound.
- Values Must Evolve as the Company Evolves: Veho launched with human-first, idealistic values. When the market turned in 2022 and performance management became non-negotiable, those values created internal friction. Itamar rebuilt them from scratch around a championship team mentality. The wrong people left. The right people finally had language for what they had been doing all along.
- Your 10X People Know They Are 10X Invest in Them Before Someone Else Does: High performers don't complain, don't ask silly questions at all-hands, and quietly deliver results every single day.
- The Co-Founder Decision Is the Most Important One You Will Make: Two original co-founders left over a fundamental strategic disagreement. Itamar refused to compromise on the vision, finding Fred one person he had met once at a conference changed the entire trajectory of the company.
- This Is a Marathon Protect the Runner: When the market shifted, the mental and physical toll hit all at once. He now meditates, exercises, sleeps 7–8 hours, and treats it the same way a professional athlete treats training. Everything else depends on it.
Quote of the Show: "The way you do anything is the way you do everything." - Itamar Zur, Co-Founder & CEO, Veho
Links:
LinkedIn: https://www.linkedin.com/in/itamarzur/
Veho Website: https://www.shipveho.com/
Chapters:
00:00 – Intro: From a sticky note to a $1.5B logistics company
01:19 – The one thing: obsessing over the Day One customer experience
05:30 – Sending reports to the CEO, CMO, and CFO why it worked
09:45 – The moment of truth: lessons from Procter & Gamble
14:20 – Veho's original values and why they had to change 18:05 – Championship team mentality: rebuilding culture mid-flight
22:40 – How top performers act and why they never speak up
27:15 – The Force Multipliers program: investing in your all-stars
31:50 – Finding Fred: the co-founder story
38:30 – 2022: the year that almost broke everything
46:00 – The coach conversation that changed how he leads 52:00 – Taking care of your body and mind as a founder 58:10 – Advice to his younger self: give yourself time to learnThe 10 Step Hiring Framework - April Pulse - Episode #97
Description:Most companies don’t fail because of bad strategy they fail because of bad hires.In this solo episode, David Politis breaks down a battle-tested 10-step interview framework built from 20+ years of …
Notas del episodio
Description:
Most companies don’t fail because of bad strategy they fail because of bad hires.
In this solo episode, David Politis breaks down a battle-tested 10-step interview framework built from 20+ years of experience, hundreds of CEO conversations, and real-world hiring mistakes. From uncovering the real motivations behind a candidate’s story to spotting red flags most interviewers miss, this episode is a masterclass in hiring with intention.
David challenges the common belief that “people are your greatest asset” and reframes it: the right people are everything. Because the cost of getting it wrong isn’t just time it can be millions in lost value, broken teams, and missed opportunities.
Takeaways :- 1. “The right people” > just “people”: Hiring isn’t a volume game. One wrong hire especially at leadership level can cost millions in enterprise value and derail entire teams.
- 2. Most companies are “winging” interviews: Very few leaders are formally trained in hiring. Lack of structure leads to poor candidate experience, wasted leadership time, and bad hires.
- 3. Depth beats polish in interviews: Great candidates can go into the details. If someone can’t get into the weeds metrics, decisions, outcomes that’s a major red flag.
- 4. The power of “why” questions: Asking layered “why” questions helps you move past rehearsed answers and uncover true motivations, decision-making, and character.
- 5. Hiring is about alignment, not just capability: Understanding what energizes a candidate and where they want to go is critical. Even great talent fails when there’s misalignment with the role.
Quote of the Show : "The reality is that we're winging it. And the cost of winging it is very, very high. The cost of hiring the wrong person there could be literally millions, if not tens of millions of dollars of enterprise value lost." - David Politis, Host of Not Another CEO
Chapters00:00 – Why hiring is the highest-leverage decision you make
06:14 – “The right people” vs. just people
08:30 – The hidden cost of bad hiring decisions
11:00 – Why most companies are winging interviews
13:30 – The importance of preparation and alignment
16:00 – The power of taking decision-grade notes
18:30 – Step 1–3: Setting the tone, story, and “why” questions
21:00 – Going deep: testing real experience and competence
25:00 – Finding what energizes candidates
29:00 – Anti-selling the role + spotting red flags in questions
He Lost Everything Twice…But Didn’t Stop Building - Rob LoCacsio - LivePerson - Episode #96
What happens when the company you built… is no longer yours?Rob LoCascio, Founder of LivePerson, shares the full, unfiltered reality of building, scaling, losing, and rebuilding as a founder. From starting with …
Notas del episodio
What happens when the company you built… is no longer yours?
Rob LoCascio, Founder of LivePerson, shares the full, unfiltered reality of building, scaling, losing, and rebuilding as a founder. From starting with almost nothing to taking his company public, scaling it from $900M to $4B in just 12 months during COVID and then facing the brutal reality of losing control of what he built.
In this conversation, Rob opens up about the hardest chapter of his career: fighting to hold onto his company, the emotional toll of watching it decline after his departure, and the moment he realized that everything he created was at risk.
He also dives into what separates founders who come back from those who don’t, why creativity is the one asset no one can ever take from you, and how to rebuild your identity when the company you built is no longer yours.
This isn’t just a story about success or failure it’s about ownership, resilience, and what it really means to be a builder.
If you’re building something or afraid of losing it this episode will hit hard.
Takeaways:
They Can Take the Company, Not the Builder: Rob’s biggest realization came after losing control everything external can be stripped away, but your ability to create, build, and execute is untouchable. That’s the real edge founders have.
Scaling Fast Comes With Hidden Risk: Going from $900M to $4B in 12 months sounds like a dream but hypergrowth brings pressure, expectations, and fragility that most people don’t see until it’s too late.
Founder Identity Is the Real Battle: Losing a company isn’t just financial it’s deeply personal. Rob breaks down what it feels like to lose something you poured your life into, and how to rebuild from that.
Fighting for What You Built Isn’t Optional: When things started slipping, Rob didn’t walk away he fought. And he explains why that fight was the hardest thing he’s ever faced as a leader.
Your Gift Is the Only Constant: Markets change, companies rise and fall but your creativity, vision, and ability to build are the only things that stay with you for life.
Quote of the Show:
"They can take your company. They can take your money. But they can’t take your creativity, the ability to build again." - Rob LoCascio
Links:
- LinkedIn: https://www.linkedin.com/in/rlocascio/
- LivePerson: https://www.liveperson.com
- KID Company: https://www.kidco.ai/
- Uare.ai: https://www.uare.ai/
Chapters:
00:00 – Intro
01:19 – From nothing: $5K, a couch, and starting over
02:10 – Building LivePerson and going public
05:30 – The COVID surge: $900M to $4B in 12 months
09:45 – When things started to break
14:20 – Losing control of the company he built
18:05 – The hardest fight of his career
22:40 – Watching the company decline after leaving
27:15 – The emotional toll of losing everything
31:50 – Identity beyond the company
36:10 – Why founders can always build again
41:25 – Creativity as the ultimate unfair advantage
46:00 – What Rob is building next
50:30 – The real meaning of success and failureNot Taking Money Off the Table Can Cost You Everything - Ra’anan Cohen - Bringg & MobileMax (#95)
What really happens when you bet it all on your company & end up with nothing?Ra'anan Cohen, Author & Founder of MobileMax and Bringg, pulls back the curtain on what most founders never talk about going from …
Notas del episodio
What really happens when you bet it all on your company & end up with nothing?
Ra'anan Cohen, Author & Founder of MobileMax and Bringg, pulls back the curtain on what most founders never talk about going from IPO to broke, rebuilding from zero, and finally selling at a $1 billion unicorn valuation with the scars to prove it.
In this conversation, he shares why he turned down $10M in stock at a public company and lived to regret it, how he secretly rebuilt himself while the whole industry thought he was already rich, and what changed at Bringg that made him finally know when to pull the plug.
If you're building something and trying to figure out when to hold and when to fold, this episode is for you.
Takeaways:- Build the Team First, Everything Else Second: The single biggest factor in both MobileMax and Bringg was team. Ra'anan implemented a strict no-asshole policy at Bringg not just hiring for talent, but for personality, attitude, and the ability to endure a long, grinding journey.
- Know When to Take the Money: Turning down $10M in stock from institutional investors during MobileMax's IPO when the company was worth $100M cost Ra'anan everything. He walked away from Bringg at $1B because the 8-year scar from MobileMax kicked in.
- Fake It Till You Make It Has a Dark Side: After MobileMax collapsed, Ra'anan went to startup meetups while secretly broke and struggling watching everyone else perform success. He later learned everyone was doing the same thing. His book, Confessions of a Unicorn Founder, exists specifically to break this culture open.
- Secondary Is a Founder's Right, Not a Weakness: Old-school investors want founders "hungry." Ra'anan disagrees. Taking secondary closes the open loops in your brain the daily stress about going to zero and actually frees founders to dream bigger and swing harder, not less.
Quote of the Show:"People like to say startup is like a roller coaster. I think this is very misleading. In the startup life as a founder, 90, 95% of the time I'm in crisis mode. It's not a roller coaster it's a marathon." - Ra'anan Cohen, Author & Founder of MobileMax & Bringg
Links:- Book: Confessions of a Unicorn Founder - available on Amazon
- LinkedIn: https://www.linkedin.com/in/raananc/
- Website: www.raanancohen.com
Chapters:00:00 – Intro: From IPO to zero to unicorn Ra'anan's full arc
01:22 – The one thing that had the biggest impact: team building
06:00 – The no-asshole policy and how to hire for attitude
08:50 – Framing hard weeks as progress the "great week" mantra
13:48 – MobileMax: the IPO, the $10M phone call, and saying no
16:32 – Why Ra'anan didn't sell a single stock and what it cost him
18:54 – When the iPhone reshaped mobile and MobileMax spiraled
25:05 – Broke and "the guy who made it" faking it at startup meetups
32:14 – The personal cost: family, presence, and the founder's obsession
34:13 – How a late pizza sparked the idea for Bringg
36:39 – Bringg's rise: customers, unicorn valuation, and pulling the plug
38:35 – Secondary, investor philosophies, and closing the open loop
45:26 – Fairness for founders: why secondary isn't just smart, it's right
50:15 – Writing Confessions of a Unicorn Founder and what comes next
52:02 – The one piece of advice Ra'anan would give his younger self
Knew each other for 2 hours before We Co-Founded - Erica Jain - Healthie - Episode #94
What if the reason your company isn’t growing… is because you’re spending too much time inside the company instead of with your customers?Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless …
Notas del episodio
What if the reason your company isn’t growing… is because you’re spending too much time inside the company instead of with your customers?
Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless customer-first mindset shaped every part of the business from product decisions to hiring to long-term strategy.
In this conversation, she shares how they got their first customers with no sales experience, why internal inefficiency is a bigger risk than doing too much, and what it really takes to maintain speed as a company scales. She also dives into rebuilding the product after early success, hiring for values, and staying in control while growing a profitable company.
If you want to build faster, stay close to your customers, and avoid the trap of internal complexity slowing you down this episode is for you.
Takeaways:- Obsess Over Customers as Your True North Star: The single most important thing is to instill a true customer-first mindset across the entire company. Customers literally “keep our lights on” every decision, roadmap, and internal process should revolve around delivering an incredible experience for them.
- Simplify Your Values Ruthlessly: Erica and her team reduced their values from eight which nobody could remember to just the Three R’s: Respect, Resilience, and Reliability. Hire for values far more than skills, especially as technology changes rapidly.
- Profitability Equals Control: They chose to remain profitable for most of the company’s life to always stay in control of their destiny. Build a generational business and raise capital only when it serves clear long-term goals, never out of desperation.
- Mediocrity Is the Real Killer: Companies don’t usually die from doing too many things they die from descending into mediocrity caused by slow internal processes, too many meetings, and inefficient decision-making. Speed and execution velocity matter enormously.
- Hiring, Team Building, and Scaling Challenges: Hiring for values, the difficulty of identifying customer-first people in interviews, retaining talent (many team members 5–7+ years), going through a major codebase rewrite, and the constant battle against internal inefficiency as the company grows.
Quote of the Show:
- The one thing I would do is instill… a true customer first mindset. There is something incredibly, incredibly powerful about waking up every single minute of every single day and wholeheartedly focusing on making sure our customers are taken care of.”- Erica Jane, CEO & Co-Founder of Healthie.
Links:
- LinkedIn: https://www.linkedin.com/in/ericajain/
- Website: https://www.gethealthie.com/
Chapters00:00 – Intro: Healthie’s growth, impact & profitability
00:56 – The power of a true customer-first mindset
03:11 – How to build with customers from day one
06:00 – Hiring for values: the “3 R’s” framework
08:53 – Evolving culture as the company scales
12:54 – Operating systems & using OKRs effectively
16:50 – Why inefficiency kills companies (not ambition)
19:35 – Profitability, fundraising & staying in control
24:08 – Starting Healthie & getting first customers
30:30 – Biggest challenges: tech debt & rebuilding the product
March Pulse - The 5 Cs to Align Your Team - Episode #93
How can one simple strategy drive your company’s success? In this solo episode of Not Another CEO Podcast, host David Politis dives deep into the significance of alignment and prioritization within a company …
Notas del episodio
How can one simple strategy drive your company’s success? In this solo episode of Not Another CEO Podcast, host David Politis dives deep into the significance of alignment and prioritization within a company. Reflecting on a personal article shared via Substack, David emphasizes the importance of refocusing and reprioritizing company goals as new challenges and opportunities arise.
Takeaways:- Concentration of Efforts: Narrowing down the focus to one primary goal can unify and effectively drive a company's momentum. By concentrating efforts, every team member can contribute to company growth.
- Effective Communication: Regular and focused communication is key to keeping everyone aligned with the company's goals. David suggests updating the team weekly to maintain a cadence that ensures urgency and focus.
- Culture of Outcome-Based Work: Create a work culture that rewards achievements based on outcomes rather than just effort. It’s crucial for employees to understand their work's impact on the company's success.
- Celebration of Successes: Recognizing and celebrating achievements fosters a positive work environment and encourages further productivity. Celebrations can be as simple as an email recognition or a shoutout during all-hands meetings.
- Strategic Compensation: Implementing flexible compensation structures isn't limited to sales teams. Properly aligning compensation with company goals can motivate teams across the board to go above and beyond.
- Removing Distractions: Encourage leadership to stay concentrated on key goals by avoiding changes in priorities throughout the quarter. Written notes can capture evolving ideas, which can then be revisited during the next planning phase.
- Leadership Involvement: Leaders should actively remove barriers for their teams rather than changing priorities. This approach helps maintain focus and supports execution on high-priority initiatives.
Quote of the Show:
- “The less you communicate about the other things, and the more you just make all the communication about that thing, people are gonna understand this is what we're focusing on." - David Politis
Ways to Tune In:
- Substack: https://notanotherceo.substack.com/
- Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0
- Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707
- YouTube: https://www.youtube.com/@NotAnotherCEOPodcast
- Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #MarchPulse
Chapters:
00:00 Intro
00:48 Q2 Reprioritization Problem
02:36 Five Cs Framework
02:47 Concentrate Efforts
04:32 Communicate With Cadence
05:55 Outcome Driven Culture
06:44 Celebrate The Wins
08:13 Compensation Drives Behavior
11:26 Stay Focused For A Quarter
12:49 Outro
Pivoting to Financial Clarity - Didi Gurfinkel - Datarails - Episode #92
What does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails …
Notas del episodio
What does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails. Together, they delve into Didi's decade-long journey of building a successful financial platform from scratch, discussing both the struggles and triumphs of his entrepreneurial path.
From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.
Takeaways:- The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.
- Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.
- Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.
- Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.
- Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.
- Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.
Quote of the Show:
- “If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi Gurfinkel
Links:
- LinkedIn:https://www.linkedin.com/in/didigurfinkel/
- Website: https://www.datarails.com/
Ways to Tune In:
- Substack: https://notanotherceo.substack.com/
- Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0
- Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707
- YouTube: https://www.youtube.com/@NotAnotherCEOPodcast
Chapters:
00:00 Intro
01:21 Co-Founders Matter Most
02:28 Finding the Right Partners
05:47 Evolving Founder Roles
07:28 Five Tough Early Years
09:28 Building Tech Without Sales
13:08 Staying Motivated to Pivot
18:05 The Breakthrough Pivot
20:52 Why FP&A and Mid-Market
24:40 Scrappy Early Go-To-Market
26:38 LinkedIn Phone Number Hack
28:17 Knowing Product Market Fit
30:43 Removing Buying Friction
32:47 Zero to One Million ARR
35:26 AI and Finance OS Vision
41:38 Three Year Company Outlook
43:06 Founder Origin Story
46:25 Israel Startup Mindset
47:50 No Work Life Balance
51:02 Outro
Aquí están los 40 episodios más recientes de 122. Los anteriores están en el feed del podcast.
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