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In Depth

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NeuThe fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)27.08.2026 · 1 Std. 2 Min.
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27. Aug. 2026
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Über den Podcast

Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

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  1. The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)

    1 Std. 2 Min.

    In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of …

    Shownotes

    In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation, he breaks down the five ingredients of great engineering leadership, discusses why he'd rather run two competing bets in parallel than forecast a winner, and explains why company culture remains more important than ever for teams to get right.

    In today's episode, we discuss:

    • The five ingredients that separate excellent engineering leadership from the rest
    • How to protect your team from large shifts in public perception
    • The mindset shift organizations need to maintain speed at scale
    • How every layer of the organization needs to stay connected to the customer
    • Why Jay runs "brain trusts" of senior ICs with zero managers in the room

    References

    Where to find Jay

    Where to find Brett

    Where to find First Round Capital

    Timestamps

    00:00 Introduction

    00:36 How leadership changes through exponential growth

    02:21 The five ingredients that define excellent engineering leadership

    07:51 What actually drives culture at a company as it scales

    12:05 The physics behind why everything slows down at scale

    18:57 The fastest team of Jay's career, and why size mattered

    22:44 Why every team should think like an FDE

    26:20 Managing a team through wild swings in public perception

    29:07 What's different about leading through the steepest S-curve moments

    33:58 Why onboarding well means going slow to go fast

    37:41 Is AI actually new, or is history just repeating?

    41:35 What actually counts as a "big bet" worth taking

    45:01 The concrete big bets that reshaped Facebook's entire technology stack

    47:35 Why vertical integration keeps being the right call as companies scale

    51:46 How being a startup CEO reshaped Jay as a leader

    1:01:26 Why Jay overruled Zuckerberg's instinct to skip efficiency

  2. What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

    1 Std. 8 Min.

    In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud …

    Shownotes

    In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams.

    In today's episode, we discuss:

    • Why operators who thrive at massive-scale companies often struggle when they join a startup
    • The hard-won lessons from Checkr's early enterprise push that nearly failed
    • Why Checkr’s C-suite meets every morning with no specific agenda
    • The surprising challenges moving from CRO to COO
    • How Checkr turned AI experiments into operating systems

    References

    Where to find Lindsey

    Where to find Brett

    Where to find First Round Capital

    Timestamps

    00:00 Introduction

    00:06 Why big-company executives often struggle in startups

    02:18 What Checkr's first CRO needed to accomplish

    03:33 How to take on an entrenched category leader

    06:58 Why leaders underestimate how hard the jump to enterprise really is

    10:23 Separating a true deal-blocker from a customer's nice-to-have request

    18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé

    22:08 The biggest challenges of moving from CRO to COO

    28:03 Why Checkr names a single decision-maker for every major decision

    34:42 Why Checkr rebuilt their sales compensation model

    40:39 What actually separates a team's best seller from everyone else

    45:03 Inside Checkr’s daily, no-agenda, c-suite meeting

    50:23 How following data can sometimes lead you in the wrong direction

    57:27 Why hitting 130% of a goal isn’t always a good thing

    58:57 Where AI has changed how Checkr's teams operate day to day

    1:04:33 Advice for all aspiring COOs

  3. How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)

    1 Std. 3 Min.

    In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through …

    Shownotes

    In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also unpacks his hard-won lessons on horizontal versus vertical bets, monetizing AI products, and why nailing onboarding turned out to be the whole game.

    In today's episode, we discuss:

    • Why Gamma's all-in AI launch in March 2023 saved their startup
    • How fixing a simple onboarding problem accidentally uncovered Gamma’s entire product-market fit
    • Why Jon bet Gamma on a horizontal product against the advice of nearly every investor
    • How Gamma's daily signups climbed from hundreds to over 100,000 with zero paid marketing
    • What building three pricing tiers taught Jon about monetizing AI

    References

    Where to find Jon Noronha

    Where to find Brett

    Where to find First Round Capital

    Timestamps:

    00:00 Introduction

    01:47 Gamma’s three-era journey to product-market fit

    03:41 Spotting the blank page problem pre-ChatGPT

    05:11 How Gamma survived with only one year of runway

    07:17 How onboarding fixes revealed the whole product

    09:31 Choosing horizontal over investors' vertical playbook

    13:41 Prototyping by hand before AI coding

    15:36 How Gamma builds with future models in mind

    20:06 The Kool-Aid mistake of a late PowerPoint export

    24:31 Why the presentation industry hadn't evolved since 1987

    33:30 How Gamma solves evals for taste, not just data

    40:21 Jon's hardest lessons monetizing AI since 2023

    44:16 The fast leap from prosumer to enterprise

    47:01 Why product still beats distribution

    52:06 The metric that proved product-market fit

    57:36 Pricing advice for prosumer AI founders

    59:01 The toils and realities of founder life

  4. Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)

    1 Std. 9 Min.

    In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has …

    Shownotes

    In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent times, why he refuses to run at 100% capacity, and how he re-architected the go-to-market function as Plaid scaled.

    In today's episode, we discuss:

    • How Plaid stayed focused after the Visa acquisition fell through and then raised at nearly 3x the price
    • Why great COOs deliberately make themselves obsolete
    • Why Eric treats speed, risk, and cost as a three-way trade-off, and why sometimes going slower wins
    • How refusing to run at 100% capacity helped Plaid win OpenAI, Perplexity, and Replit
    • Why Eric personally cold-calls brand-new employees

    References

    Where to find Eric Sager

    Where to find Brett

    Where to find First Round Capital

    Timestamps

    00:00 Introduction

    00:40 Leading a company through turbulent times

    04:24 How to build a resilient team culture

    08:33 How Plaid avoids bureaucracy, while operating at scale

    10:58 The speed-quality tradeoff: Going faster isn't always better

    15:32 When to move from generalists to specialized customer segments

    20:14 Why Plaid has one owner for entire customer relationships

    22:06 The "quarterback" model: one owner, experts on call

    24:08 Why you should never run your org at 100% capacity

    29:47 "Always available, never needed": the support mantra

    36:49 Eric’s unusual "hit by a bus" test to measure job success

    43:57 Why Eric cold calls brand-new employees

    52:14 Eric's week: 25% ecosystem, 50% business, 25% team

    55:15 How to spot fake mission alignment in interviews

    59:04 The one thing a founder has that no hire can replicate

  5. How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)

    60 Min.

    In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul …

    Shownotes

    In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find product-market fit before blitzscaling. He breaks down how a single tagline change for Supabase unlocked product-market fit, why he runs a fully distributed async team with near-zero attrition, and how he turned PLG signals into a product-led sales motion comped only on incremental uplift.

    In today's episode, we discuss:

    • How changing one tagline helped Supabase go to #1 in Hacker News - an early sign of product market fit
    • Why Paul ran Supabase like it had only $100K in the bank despite raising real money
    • How Supabase rode three distinct AI waves, from pgvector to Bolt and Lovable, to Claude Code
    • Why Supabase built a sales team comped only on the incremental uplift over a control group
    • What the Toyota production system's "kaizen" taught Paul about unblocking a scaling team

    References:

    Where to find Paul:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    01:32 Why Paul's earlier startups were never destined to be huge

    07:14 Unlearning the "tall poppy" mindset and going all-in on async

    09:54 Reverse-engineering why Supabase was an outstanding idea

    12:04 The accidental Hacker News launch and tagline lesson

    13:58 Where the early roadmap came from: demand vs. technical taste

    17:28 Skill vs. luck, and operating like you have $100K in the bank

    21:42 What actually makes a great developer experience

    23:10 Solving the "graduation problem" Firebase never could

    24:58 The role of open source in Supabase's success

    26:10 The three distinct AI tailwinds: From pgvector to Claude Code

    35:24 Supabase’s egoless, hyper-competitive open-source culture

    42:58 A tactical playbook for raising capital

    48:37 Product-led sales comped on incremental uplift only

    59:27 The production philosophy behind Supabase’s operations

  6. How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)

    1 Std. 1 Min.

    In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads …

    Shownotes

    In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold.

    In today's episode, we discuss:

    • How to run marketing like a portfolio of moonshots
    • The value of disruptive energy for senior marketers
    • Why "Ubiquity is the opposite of cool"
    • How to actually scale taste across an organization
    • What great marketing looks like in the AI era

    Referenced:

    Where to find Sheila:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:07 What excellent marketing actually is in 2026

    01:36 Why giving teams different goals creates dysfunction

    02:36 The most important decision Sheila made as CMO last year

    04:26 The real difference between an SVP and a CMO

    06:05 Marketing is one engine - not separate pieces

    07:15 The tension between brand and growth

    09:25 The decisions a CMO should never be making

    09:55 Running marketing like a portfolio of moonshots

    12:46 "Ubiquity is the opposite of cool"

    15:11 Why a few companies get a flywheel of momentum

    16:44 The Silicon Valley clock and irrational perception cycles

    19:25 How to actually scale taste across an org

    21:09 What changes for a CMO in a post-LLM world

    23:15 Why the artistic side of marketing never really left

    26:05 Whether taste can ever be encoded in software

    27:15 Telling an optimistic, yet realistic story about AI

    30:50 You need to make people care

    32:11 What surprised Sheila about being a public-company CMO

    33:46 Why Figma won enterprise where Dropbox couldn't

    35:25 Sheila’s favorite campaign ever

    37:10 Why announcement videos full of humans, lack humanity

    38:55 Playbooks are obselete, but the fundamentals are not

    40:25 Why marketing in 2026 demands disruptive energy

    41:54 How Sheila architects her week

    48:55 Where corporate politics actually come from

    53:55 "Sheila, are you going to change the world in this job?"

    58:09 What's unique about the CMO and CEO relationship

  7. Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)

    1 Std. 2 Min.

    In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to …

    Shownotes

    In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days.

    In today's episode, we discuss:

    • Why in-person enterprise rollouts still beat product-led motions
    • Building a robust sales process that still leaves room for unscripted moments
    • Why the three highest-leverage early sales hires aren't sellers at all
    • The case for outsized commission accelerators for star sellers — and the kind of person they attract
    • Why most AI companies are skipping the in-person sales work that enterprise customers actually want

    References:

    Where to find Graham:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:32 Has the sales playbook changed in the AI era?

    02:13 Why "showing up" beats letting the marketplace decide

    06:50 Why great salespeople sell to engineers and executives in one motion

    11:37 Selling to AI-native buyers who grew up on ChatGPT

    13:49 Same seller, different tempo: 8 weeks vs. 8 business days

    15:57 How AI-native buyers handle build vs. buy decisions

    17:48 The rep who taught a champion's son guitar over Zoom

    19:03 Raising the floor without capping the ceiling

    22:09 Why too much process narrows the kind of seller you attract

    25:46 The three pillars of GTM excellence

    31:00 Building peers who are 80% aligned, not 100%

    38:03 Whether AI is changing what good enablement looks like

    41:35 Selling against direct and implied competitors at once

    42:45 Instrumenting the funnel from stage zero to close

    45:57 Why post-sales should always roll up to the revenue leader

    48:19 The case for outsized commissions

    52:02 The 96 hours of panic before Cognition acquired Windsurf

    53:04 How far out should a GTM leader be planning?

    57:53 What a normal week looks like in hypergrowth

  8. Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)

    44 Min.

    In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was …

    Shownotes

    In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step functions that took him from IC to CFO, why Figma started acting like a public company three years before IPO, and how AI is rewriting capital allocation and the CFO job itself.

    In today's episode, we discuss:

    • What separates a world-class finance leader from a traffic-cop CFO
    • How Praveer went from Figma's first biz ops hire to CFO of a public company in nine years
    • Why Figma started acting like a public company three years before its IPO
    • What Praveer has learned working alongside Dylan Field for nine years
    • Why Figma intentionally cut its 90% gross margin to invest in AI

    References:

    Where to find Praveer:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    02:13 From banking to Dropbox to Figma

    04:14 The phase shift when Figma's COO left

    05:36 Hiring leaders in functions you don't understand

    07:18 Selling the exec team on AI consumption pricing

    09:48 Using Claude Code to learn new things as CFO

    11:36 Building an internal board of peer CFOs

    13:52 Inside Figma's CFO job description

    16:38 What separates good CFOs from world-class CFOs

    18:42 Capital allocation and risk in a post-ChatGPT world

    21:45 Why Praveer wants to take more bets

    24:32 How AI is materially changing the CFO role

    25:36 The nine-year working relationship with Dylan Field

    29:12 How deeply in the details should a CFO be?

    31:47 What Dropbox taught Praveer about building strong teams

    33:24 Praveer’s first-principles test for hiring VPs

    38:47 Why Figma acted like a public company in 2022

  9. Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

    50 Min.

    In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at …

    Shownotes

    In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing.

    In today's episode, we discuss:

    • Why a CPO's number one job is raising their team’s ambition, not shipping features
    • How to demand the best from your team without creating a fear-based culture
    • Why organizational politics is actually an incentives problem
    • How Diya is “militant” with her calendar to carve out dedicated thinking time
    • Why you should avoid chasing titles in your career - and what to chase instead

    References:

    Where to find Diya:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:12 How an excellent CPO makes an impact on the business

    02:01 How the CPO role shifts under founders vs hired CEOs

    03:38 Influencing a founder without going deferential

    07:37 How adding value to customers is always a net positive

    08:45 Why roadmaps need more risk in the AI era

    12:30 How to shelter innovation teams from the existing system

    15:12 What's different about being a great CPO in 2026

    17:34 How AI has changed the concept of an app

    18:28 It’s essential for CPOs to fly at a low altitude

    20:34 How misaligned incentives cause organizational politics

    25:13 Being demanding without creating a fear-based culture

    28:10 Why raising ambition is a CPO's number one job

    31:39 The boss who taught Diya to keep raising the bar

    32:43 The hardest part of being a CPO

    35:28 The three buckets Diya uses to delegate

    36:30 How Diya protects deep-work time on her calendar

    42:45 Xero’s game-changing early bet on AI insights

    44:58 How far into the future should CPOs plan for?

    47:14 What it takes to be an excellent C-suite member

    48:53 Why ambitious PMs should chase impact, not titles

    50:28 The four bottlenecks that stall career growth

  10. Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)

    57 Min.

    In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M …

    Shownotes

    In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and why they plan to stay on a texting basis with every customer, even at scale.

    In today's episode, we discuss:

    • How to interview for AI fluency when building an AI-native startup
    • Why founder-market fit is a critical early signal for startup success
    • The surprising lesson Dan learned from founder-led sales
    • How Dan and Shachar are instilling customer-obsession into Artemis’ culture
    • How the two co-founders approach conflict and decision-making

    References:

    Where to find Shachar Hirshberg:

    Where to find Dan Shiebler:

    Where to find Josh:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:06 What Artemis does and why now

    02:51 Shachar’s AWS and Palo Alto playbook

    05:15 Dan’s founder journey: From Twitter to Abnormal

    08:51 Why founder-market fit is critical for startups

    11:38 Finding the right moment to take the leap and build

    13:52 The hiring process that powers a startup in stealth

    16:58 Building a team centered on AI capabilities

    21:48 How AI implementation changes dashboard metrics

    23:22 The ICP they chased and the one they ignored

    26:44 The magic of closing the first customers

    27:49 The surprising signals of early product-market fit

    32:06 Critical lessons from founder-led sales

    33:51 Why the first product should make founders uncomfortable

    36:03 Hiring 30 people while still in stealth

    42:08 “Should we be arguing more?”

    43:37 How the AI security market is evolving

    49:03 Why AI-native beats AI-enabled company structure

    51:09 The most surprising moments as a first-time founder

  11. Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)

    1 Std. 2 Min.

    In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant …

    Shownotes

    In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before DoorDash, Christopher held senior operating roles at Amazon and eBay, where he led a sweeping overhaul of marketplace search. In this conversation, he unpacks what it actually takes to run an atoms-based business versus a software company, shares his "plate spinning" framework for allocating executive attention across a complex org, and makes the case for top-down goal setting over the bottom-up alternative.

    In today's episode, we discuss:

    • How prior industry experience can be a liability when you're trying to reinvent the market
    • How executives can practically focus their attention to stay close to product details
    • What charisma actually looks like in executives—and why it's a staple trait to have
    • The business case for setting ambitious goals top-down, not bottom-up

    References:

    Where to find Christopher Payne:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:14 Why atoms businesses challenge bits executives

    02:35 Hiring executives with a builder mentality

    06:52 Great executives never outgrow the details

    08:05 How ciabatta bread revealed a core DoorDash issue

    10:48 How executives can scale their own impact

    14:22 One-size-fits-all management is a myth

    19:01 Enduring business lessons from Jeff Bezos

    20:56 “I was fired from Tinder after six months”

    25:38 Why specializing too early is a leadership trap

    27:41 Are competitive cultures essential for success?

    31:00 Lessons from Amazon’s hypergrowth

    35:20 Why having industry experience can be a liability

    38:46 Companies spend too much time on job interviews

    40:19 The skills executives need for hypergrowth

    43:34 Why AI will likely flatten organizations

    45:20 Teaching COO 101: What it takes to be world-class

    50:55 Why bottom-up goal setting kills ambition

    55:29 How charismatic leaders help teams in tough times

    58:23 The number-one sign of high-functioning executive teams

    1:02:02 How first-time COOs can increase their chance of success

  12. The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)

    1 Std. 11 Min.

    In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at …

    Shownotes

    In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at HubSpot, where she built one of tech's most distinctive cultures. In this conversation, she unpacks her marketing-minded approach to HR, why she hired deliberately from hospitality rather than corporate backgrounds, and why developing culture should be a strategic priority for any organization.

    In today's episode, we discuss:

    • Why HR leaders should think like marketers
    • The 2.5-year cultural hangover after a layoff
    • The protein vs. sugar rule for employee feedback
    • What it means to be the executive team’s own HR business partner
    • What the Chief People Officer owes the board and what they don't

    References:

    Where to find Katie:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:23 Why HR begins with thinking like a marketer

    01:58 “Don't ask for a seat at the table. Build the table.”

    02:29 Radical transparency after Hubspot’s IPO

    05:14 How HubSpot’s people function drove strategy

    07:01 The trickiest part of the Chief People Officer role

    10:00 Be the Michael Jordan of your exec team

    12:14 Why people leaders need to create “graceful exits”

    16:49 The inevitable two-year layoff hangover

    23:31 The workplace shouldn’t be Disneyland

    26:05 “Our job is not to make you happy every day”

    34:28 Being a Chief People Officer isn’t for the faint of heart

    35:04 How “Berry-Gate” taught HubSpot to manage feedback

    40:51 Chief People Officers should be demanding, by design

    42:01 Why “frequent flyers” are a new-hire red flag

    44:54 Unpacking the role of the VP of People

    49:94 Which company decisions fall to the Chief People Officer?

    49:11 The most common challenges of scaling a company

    51:39 The differences between HubSpot and Harvey

    53:17 How AI is changing the people function

    1:04:28 Why Katie shares her own performance reviews

    1:06:22 How to manage a disagreement with the CEO

  13. What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)

    1 Std. 7 Min.

    Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full …

    Shownotes

    Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition.

    In this episode, we discuss:

    • Why moving from software engineer to CEO requires almost an entirely new skillset
    • The product marketing pyramid Jay built to explain Kafka to the world
    • How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing”
    • The critical difference between what a company can do and what it must do
    • What keeps scaling companies from becoming "Chipotle”

    References:

    Where to find Jay:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    01:18 Making the leap from engineer to CEO

    03:33 The 80% rule: what a CEO actually needs to know

    04:54 Scaling different business disciplines

    09:31 How Confluent’s story began in LinkedIn

    12:13 The growing need for scalable data tech

    13:37 What the early Kafka product looked like

    16:38 Kafka’s underwhelming open-source launch

    18:38 The blog post that accelerated Kafka’s adoption

    20:16 Why so many marketing messages fail

    28:08 The decision to build Confluent

    34:24 Planning to fundraise before building the product

    39:19 Confluent’s early years: Tough product decisions

    47:07 The underrated growth lever question for companies

    55:46 Why founder optimism is an overrated trait

    1:00:29 What should founders give up as they scale?

    1:02:47 Why people become trapped in a failure mindset

    1:08:33 The Chipotle problem: Losing excellence at scale

  14. The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)

    1 Std. 10 Min.

    In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from …

    Shownotes

    In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you.

    In today's episode, we discuss:

    • The mindset shift that made Jeremy's transition to startup CPO work
    • Why it’s essential for the CPO to stay connected to details
    • The rule to ensure teams ship fast while growing quickly
    • Why rigid hierarchies derail quality decision-making
    • How Jeremy uses open office hours for the entire company

    References:

    Where to find Jeremy:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    00:09 Why most big-tech executives fail at startups

    05:38 Great product leaders stay in the details

    09:21 The biggest mindset shift from VP to CPO

    16:24 Revenue and product teams are always at odds

    18:00 The key to a quality CPO and CRO relationship

    23:21 Stop making your team fetch rocks

    25:54 Who ultimately oversees the quality bar?

    32:27 Why rigid hierarchies kill great companies

    36:38 How to leave actionable, detailed feedback

    38:55 Great CPOs should avoid comfort metrics

    47:27 A glimpse into Jeremy’s working week

    49:07 The case for weekly 1:1s

    55:13 Why ICs are the unsung heroes of a company

    58:25 Jeremy’s most formative career moments

    1:07:55 The hardest skills Jeremy had to learn

    1:09:31 Why great managers know when to push

  15. Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)

    1 Std. 11 Min.

    Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives …

    Shownotes

    Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown.

    In today's episode, we discuss:

    • Why Zipline hires teenagers over PhDs
    • Why the best startup employees are "heat-seeking missiles for pain"
    • The 5 leadership attributes Zipline has never shared publicly
    • The brutal firing advice that shaped Keller’s leadership
    • How Rwanda’s health minister changed Zipline’s trajectory

    References:

    Where to find Keller:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Introduction

    02:11 Why Zipline doesn't hire for experience

    06:04 Are founders born or made?

    07:37 Why Zipline hires 17-year-olds over PhDs

    17:03 The employees Zipline doesn't want

    18:53 The ultimate startup hire is a "heat-seeking missile"

    20:36 Why blind references are a non-negotiable

    23:07 Can candidates admit when they screwed up?

    30:10 Zipline's secret leadership playbook

    35:16 Why you should always fire quickly

    36:26 The early vision for Zipline

    39:48 How Zipline almost died - twice

    44:55 From toy robots to drone delivery: Zipline's pivot

    51:35 How Rwanda's health minister changed everything

    57:10 Why Zipline's launch was a "complete disaster"

    1:04:05 Scaling from 1 hospital to 5000

    1:05:17 The 10x hardware cost rule every founder should know

  16. Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)

    60 Min.

    Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In …

    Shownotes

    Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team.

    In today's episode, we discuss:

    • What the CRO job looks like at $10M vs. $1B+
    • Why sales leaders must know how to sell the product themselves
    • The MEDDIC methodology and why it's a founder's best insurance policy
    • How to find the fakers, manage-uppers and passengers in your org
    • What Frank Slootman got right — and wrong — about scaling Snowflake
    • Why most AI companies will face a go-to-market reckoning

    References:

    Where to find Chris:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 What is the job of a CRO?

    01:12 What excellence looks like at different revenue stages

    02:59 Sales leaders need to know how to sell the product

    04:52 The hardest skill leaders have to learn

    08:17 You need to stay open to feedback - at all levels

    14:01 Sales, segmentation, and international expansion

    16:17 Why MEDDIC is the foundation for every sales org

    20:32 The metrics that actually matter

    22:56 A week in the life of a CRO at scale

    28:32 Navigating compensation at a GTM organization

    31:45 What technical CEOs get wrong about GTM

    36:01 The role of hunger in great sales leaders

    40:35 What makes an exceptional IC sales rep

    46:41 Dysfunctional vs. high-performing executive teams

    48:01 Chris' most impactful decisions at Snowflake

    49:53 "When there's doubt, there's no doubt"

    54:49 Learning from world-class leaders

  17. Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

    1 Std. 11 Min.

    Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one …

    Shownotes

    Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028.

    In today's episode, we discuss:

    • Why early revenue hires fail
    • What a top 1% CRO actually does
    • The scaling mistake Stevie made by copying Twilio's playbook at Vanta
    • Why Vanta remains 100% sales-led at every segment
    • AI vs. humans in go-to-market

    References:

    Where to find Stevie:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Why early revenue hires fail

    02:23 Who to hire at $5M in revenue

    04:16 Coin-operated sellers vs. long-term builders

    05:57 What excellence looks like in the CRO role

    07:44 Metrics, confidence, and velocity

    12:04 Should CROs lead sales?

    14:39 From shy seller to revenue leader

    16:36 Learning to scale at Twilio

    17:44 "There is no CRO playbook"

    19:58 Stevie's scaling mistake at Vanta

    22:16 Why Vanta stays 100% sales-led

    23:16 The value of planning 24-26 months ahead

    29:54 When trusting intuition was the wrong call

    30:49 Do humans still have a place in the future of GTM?

    33:33 Stevie's leadership non-negotiables

    36:36 The myth of hiring for industry expertise

    40:00 What stays centralized in a 600-person company

    47:09 The hidden leverage of a customer's first 30 days

    53:42 Why the CRO role will face enormous changes by 2028

    58:42 What leaders must do now to stay relevant

    01:02:30 Unpacking the CEO-CRO dynamic

  18. Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)

    1 Std. 6 Min.

    In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's …

    Shownotes

    In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used.

    In today's episode, we discuss:

    • Why design leaders who stop designing stop leading
    • The four pillars every design manager must master
    • How to delegate when you're a perfectionist
    • Why leaders need strong opinions
    • How to scale good judgment
    • What Rippling's operating system teaches about speed and commitments

    References:

    Where to find Ryan:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    00:00 Intro

    00:08 What design actually does at a software company

    01:40 The roots of design: from industrial design to software

    03:29 Useful, usable, desirable — and used

    04:49 How design relates to engineering, product, and marketing

    08:15 Measuring success as a design leader

    12:40 The gap between director and VP-level design leadership

    14:23 Why great design leaders jump up and down in altitude

    19:26 The four pillars every design manager must master

    21:34 Over-indexing on quality and the perfectionist trap

    25:11 When lowering the quality bar actually cost the business

    27:53 How to build judgment through pattern matching

    31:25 How Ryan's design team differs from the rest

    34:31 Why Figma is not the source of truth

    36:32 How Ryan spends his week: recruiting, crits, and staff meetings

    38:39 The "Do/Try/Consider" framework

    42:12 The most important decisions of the past year

    44:05 Should one-on-ones exist?

    46:45 How to scale judgment

    50:49 What to look for when hiring your first design leader

    54:54 Advice for young designers who want to lead

    58:24 Demanding yet supportive: A balanced management style

    01:02:43 What Rippling's operating system teaches about execution

  19. Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)

    1 Std. 16 Min.

    In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global …

    Shownotes

    In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget.

    In today's episode, we discuss:

    • What it takes to operate at 30,000 feet and ground level simultaneously
    • The leap from frontline manager to manager of managers
    • Inside Jeanne's executive interview process
    • The inherent value of driver trees for metrics
    • Why context is everything


    References:


    Where to find Jeanne:


    Where to find Brett:


    Where to find First Round Capital:


    Timestamps:

    (01:17) What separates good executives from extraordinary ones

    (02:48) How leadership changes as companies scale

    (04:15) What an executive is actually accountable for

    (06:11) The leap most rising leaders never make

    (07:52) When to dive deep vs. when to step back

    (10:09) Teaching people to think like you do

    (11:56) Creating a shared language across the business

    (13:52) What a COO job description actually looks like

    (17:20) The upside of owning the full customer experience

    (19:10) Why marketing rolls up under a COO

    (21:06) Being demanding and supportive at the same time

    (22:33) Inside the executive interview process

    (27:35) The workshop prompts that reveal everything

    (30:11) The common thread in failed executive hires

    (36:36) Metrics: the driver tree philosophy

    (43:04 What a collaborative exec team looks like

    (57:08) How Stripe got 30 people to operate as one team

    (1:03:50) Working yourself out of a job

    (1:10:32) The review feedback you can't unhear

  20. Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)

    1 Std. 15 Min.

    Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a …

    Shownotes

    Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades.

    In today’s episode, we discuss:

    • Why Anil thinks in 25-year horizons
    • How operating in a monopolistic market shaped Meter’s approach
    • Why Meter scrapped a year of OS work during the R&D phase
    • How Meter is rethinking networking’s business model
    • Surviving COVID, Apple’s M1 transition, and “a thousand bad days”
    • Anil’s contrarian views on planning, OKRs, and management
    • How founders can build companies they’ll want to run for decades


    Where to find Anil:


    Where to find Brett:


    Where to find First Round Capital:


    References:


    Timestamps:

    (01:27) Meter’s unusual timeframes

    (04:06) “We don’t do OKRs”

    (06:32) How to plan without planning

    (08:31) Track your unhappy customers

    (11:43) How Meter’s journey began

    (15:02) Dissecting the 2010s SaaS boom

    (17:06) The networking industry trap

    (21:44) Meter’s first roadblock

    (22:07) Why Shenzhen accelerated Meter’s progress

    (26:29) The process to get a sales-ready product

    (31:02) Why you should own the full stack

    (32:45) The surprising thing you should innovate

    (35:03) Avoiding the one-trick pony trap

    (37:39) The secret to finding an excellent market

    (43:48) How COVID’s constraints propelled growth

    (48:25) Why founders need to know their customers

    (49:34) Why Meter didn’t sell via traditional channels

    (51:44) You need “seller-market fit”

    (54:51) The danger of meta-work

    (56:25) Decoupling management from authority

    (1:02:17) When the person is the problem

    (1:05:05) The inherent value of going slowly

    (1:09:41) Running a company for as long as possible

  21. How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)

    1 Std. 5 Min.

    Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar …

    Shownotes

    Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products.

    In today’s episode, we discuss:

    • Why companies get stuck in the mid-market and struggle to move up into enterprise
    • Why Jyoti deliberately lost Netflix as their customer
    • The difference between product-market-sales fit, and product-market-fit
    • How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals)
    • Diagnosing whether you have a product problem or a distribution problem
    • How to hire and evaluate your first head of sales and top sales leaders
    • Why Jyoti sold AppDynamics three days before IPO
    • The “binary differentiator” rule for launching new products into crowded markets
    • Why Harness runs 16 product lines under one roof


    Where to find Jyoti:


    Where to find Brett:


    Where to find First Round Capital:


    References:


    Timestamps:

    (01:48) Why do companies get stuck in the mid-market?

    (05:09) Designing a product for enterprise and mid-market

    (07:19) Why Jyoti lost Netflix as a customer - on purpose

    (10:18) Becoming a scalable GTM organization

    (12:32) The real signs of product-market fit

    (14:04) Have you delivered the value?

    (15:46) How to hire your first sales team

    (19:59) The four signs of excellent sales leaders

    (23:16) How to interview a sales leader

    (27:51) Where Jyoti developed his commercial taste

    (29:37) Why early founders need to learn sales

    (32:02) How AppDynamics began

    (36:36) Why Jyoti sold three days pre-IPO

    (41:55) What does a healthy board look like?

    (44:23) How Jyoti perceives competition

    (46:18) Why you need a binary differentiator

    (49:53) How to launch multiple products

    (52:00) “We need to be best of breed”

    (57:38) Why PMs are like mini-entrepreneurs

    (1:00:20) The startup within a startup

    (1:02:45) A culture of continuous improvement

  22. How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)

    1 Std. 24 Min.

    Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever …

    Shownotes

    Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage.


    In today’s episode, we discuss:

    • How 16-year-old Zack turned $2,500 into a wholesale empire
    • Why bootstrapping means being "constrained by capital" and how VC removes that ceiling
    • Why Zack rebuilt their EDI product eight times before launch
    • The snake swallowing a deer: what extreme product-market fit really looks like
    • What software companies can learn from discount retail and Toyota
    • Why Stedi’s new hires are told "everything’s your fault now"
    • And much more


    Where to find Zack:

    • LinkedIn: https://www.linkedin.com/in/zkanter
    • Twitter/X: https://x.com/zackkanter


    Where to find Brett:

    • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
    • Twitter/X: https://twitter.com/brettberson


    Where to find First Round Capital:

    • Website: https://firstround.com/
    • First Round Review: https://review.firstround.com/
    • Twitter/X: https://twitter.com/firstround
    • YouTube: https://www.youtube.com/@FirstRoundCapital
    • This podcast on all platforms: https://review.firstround.com/podcast


    References:

    • Aetna: https://www.aetna.com/
    • Amazon: https://www.amazon.com/
    • AWS: https://aws.amazon.com/
    • Blue Cross Blue Shield: https://www.bcbs.com/
    • Change Healthcare: https://www.changehealthcare.com/
    • Cigna: https://www.cigna.com/
    • Clay: https://www.clay.com/
    • Costco: https://www.costco.com/
    • Ford Motor Company: https://www.ford.com/
    • GM: https://www.gm.com/
    • HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html
    • Jeff Bezos: https://x.com/JeffBezos
    • Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system
    • Microsoft Teams: https://www.microsoft.com/microsoft-teams
    • NetSuite: https://www.netsuite.com/
    • O’Reilly Auto Parts: https://www.oreillyauto.com/
    • Peter Thiel: https://x.com/peterthiel
    • Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx
    • "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail
    • Slack: https://slack.com/
    • Stedi: https://www.stedi.com/
    • Summit Racing: https://www.summitracing.com/
    • Target: https://www.target.com/
    • Walmart: https://www.walmart.com/
    • Zapier: https://zapier.com/


    Timestamps:

    (01:24) Zack’s first business

    (08:54) Why the first customer is tricky

    (10:12) The downside of bootstrapping

    (11:42) Why venture capital is like “going pro”

    (14:20) The confusion between ownership vs. control

    (16:08) Building a company you don’t want to leave

    (20:46) Do things better than other people

    (24:49) Stedi’s early years

    (31:43) Physical vs. digital product-market fit

    (34:41) How Stedi scaled decision-making

    (40:08) Stedi’s journey to product-market fit

    (45:22) Finding founder-approach fit

    (50:42) “All software is a cascade of miracles”

    (52:52) The surprising lessons from discount retail

    (57:50) How the Toyota production system influences software

    (1:01:31) What it means to be a high-agency person

    (1:03:09) The core trait Zack looks for when hiring

    (1:02:57) Maintaining conviction in unconventional practice

    (1:14:19) When should you start to hire managers?

    (1:17:42) “Reality has a surprising amount of detail”

  23. Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)

    1 Std. 23 Min.

    Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at …

    Shownotes

    Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical.

    In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates.


    In today’s episode, we discuss:

    • Why building “in existing categories” can be more powerful than creating new ones
    • The lessons from Verkada that shaped Serval's platform strategy
    • The customer interview question that unlocked the IT buyer’s hidden pain points
    • How Serval's automation builder uses AI to generate code-based workflows
    • Redefining engineering and PM roles with forward-deployed engineers
    • Keeping the hiring bar high in an AI-native startup
    • Why there’s a “land grab” moment right now in enterprise AI
    • And much more...

    Where to find Jake:


    Where to find Brett:


    Where to find First Round Capital:


    References:


    Timestamps:

    (02:25) Lessons from holding different product roles

    (07:29) Turning “hard mode” into a moat

    (10:49) The early days of Serval

    (12:59) Scratching the founder itch

    (14:57) Unconventional interview techniques

    (17:47) Solving core interview challenges

    (21:10) Planning the early product roadmap

    (23:03) The surprising power of patience

    (26:12) Serval’s impressive technical advantage

    (27:35) Disrupting legacy incumbents

    (31:13) Building for mid-market and enterprise

    (33:35) Serval’s enduring roadmap

    (36:08) How to sell to an existing market

    (39:16) The evolving role software plays

    (43:55) Building for AI that didn’t exist yet

    (49:49) Serval’s forward-deployed engineers

    (58:31) The hybrid PM-GM

    (1:00:27) “You can over-prioritize”

    (1:02:48) The unexpected value of panic buttons

    (1:04:50) What Serval looks for in new talent

    (1:07:01) The ultimate hiring litmus test

    (1:13:59) Building out Serval’s go-to-market function

    (1:16:31) The evolving IT market in 2025

  24. The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)

    59 Min.

    Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in …

    Shownotes

    Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media.

    In today's episode, we discuss:

    • How fal pivoted from data infrastructure to generative inference
    • fal’s explosive year and how they scaled
    • Why "generative media" is a greenfield new market
    • fal's unique hiring philosophy and lean <50-person team
    • Building a brand that resonates with developers
    • What the world looks like in 2027 when AI-generated video becomes mainstream
    • And much more…


    Where to find Gorkem:


    Where to find Todd:


    Where to find First Round Capital:


    References:

    • Adobe: https://www.adobe.com/
    • Amazon: https://www.amazon.com/
    • Anthropic: https://www.anthropic.com/
    • Base10: https://base10.vc/
    • Black Forest Labs: https://blackforestlabs.ai/
    • Burkay Gur: https://www.linkedin.com/in/burkaygur/
    • Canva: https://www.canva.com/
    • Clay: https://www.clay.com/
    • Coinbase: https://www.coinbase.com/
    • Cursor: https://www.cursor.com/
    • DALL-E: https://openai.com/dall-e-2
    • Databricks: https://www.databricks.com/
    • Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/
    • fal: https://fal.ai/
    • Google DeepMind: https://deepmind.google/
    • LLaMA: https://ai.meta.com/llama/
    • OpenAI: https://openai.com/
    • Oracle: https://www.oracle.com/
    • Perplexity: https://www.perplexity.ai/
    • Shopify: https://www.shopify.com/
    • Snowflake: https://www.snowflake.com/
    • Sora: https://openai.com/sora
    • Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion
    • Stability AI: https://stability.ai/
    • Together AI: https://www.together.ai/

    All images and videos generated using models run on fal.ai


    Timestamps:

    (01:43) The generative media industry

    (02:29) From $2M to $100M ARR: fal's explosive year

    (04:06) How Gorkem met co-founder Burkay Gur

    (05:38) The hardest decision that saved the company

    (09:52) Spotting the opportunity in generative media

    (13:28) Turning Todd into George Clooney

    (15:29) The early adopters of the first fal product

    (17:54) The transition from toy to tool

    (19:27) Why 2025 is the year of AI-generated video

    (21:44) Staying nimble as a 45-person company

    (24:42) Predicting AI-generated film in 2027

    (27:24) Why generative media is a greenfield market

    (30:33) fal’s greatest optimization wins

    (34:42) Why fal has 500 Slack channels

    (36:02) Competing in a fast-moving, fragmented market

    (42:06) How to build a world-class team

    (47:24) Learning sales as a technical founder

    (50:55) How fal built a brand without a marketer

    (53:21) The story behind "GPU Rich / GPU Poor"

    (54:22) Inside fal’s rule-breaking playbook

    (56:09) The hardest part of scaling fal

  25. From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)

    1 Std. 9 Min.

    Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first …

    Shownotes

    Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company. In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat. In today’s episode, we discuss:

    • Why school shootings were the catalyst for building safety software
    • Navigating the most challenging customer base: government and public safety agencies
    • Why Prepared gave away its first product for free — for years
    • Lessons from evolving a wedge product into an AI-driven suite
    • How Michael balanced conviction with customer feedback
    • Building long-term investor relationships
    • Staying true to the mission through headwinds and tailwinds
    • And much more…


    Where to find Michael:

    • LinkedIn: https://www.linkedin.com/in/michaelchime/


    Where to find Meka:

    • LinkedIn: https://www.linkedin.com/in/mekaasonye/
    • Twitter/X: https://x.com/bigmekastyle


    Where to find First Round Capital:

    • Website: https://firstround.com/
    • First Round Review: https://review.firstround.com/
    • Twitter/X: https://twitter.com/firstround
    • YouTube: https://www.youtube.com/@FirstRoundCapital
    • This podcast on all platforms: https://review.firstround.com/podcast


    References:

    • Axon: https://www.axon.com/
    • Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/
    • March for Our Lives: https://marchforourlives.org/
    • Neal Soni: https://www.linkedin.com/in/neal-soni/
    • OpenAI: https://openai.com/
    • Peter Thiel Fellowship: https://thielfellowship.org/
    • Prepared: https://www.prepared911.com/
    • Sam Altman: https://x.com/sama
    • Slack: https://slack.com/
    • Uber Eats: https://www.ubereats.com/
    • Yale University: https://www.yale.edu/

    Timestamps:

    (3:03) Staying mission-oriented under pressure (3:54) Negotiating an acquisition from a hospital bed (06:25) How Sandy Hook shaped the Prepared story (09:15) From school safety app to 911 platform (10:02) Why are 911 systems so outdated? (13:02) Prepared’s first product iteration (16:04) Why attempt to tackle the govtech market? (18:36) Mission as fuel: staying resilient through endless rejections (20:03) Should young people drop out of college? (23:10) How Michael nurtured a learner’s mindset (25:23) Forging unwavering founder conviction (31:41) Landing Prepared’s first user (32:39) “I want to be terrible at sales” (34:35) Expanding to a premium product line (36:55) Leveraging AI to expand the product surface area (41:49) How much should you listen to customers? (45:35) Building in headwinds vs. tailwinds (47:18) Navigating partnerships and competition (54:52) Michael’s unconventional approach to fundraising (1:02:54) Has Prepared found product-market fit? (1:04:00) Reflecting on the founder journey

  26. Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)

    1 Std. 9 Min.

    Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for …

    Shownotes

    Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B.

    In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled.

    In this episode, we discuss:

    • Lessons from Meraki’s acquisition by Cisco
    • How Kiren hires for intrinsic motivation
    • Why Samsara was built for operations industries
    • The early hardware prototype and the Cowgirl Creamery insight
    • Building broad vs. niche from day one
    • The shift from founder-selling to a scalable sales motion
    • Organizing product teams around revenue vs. experience
    • How Samsara uses LLMs and AI today
    • What Kiren learned from longtime co-founder Sanjit Biswas


    Where to find Kiren:


    Where to find Brett:


    References:


    Timestamps:

    (01:27) Meraki’s growth and acquisition by Cisco

    (03:25) The "evaporating" exit strategy from Meraki

    (04:42) Identifying the IoT market gaps

    (07:38) The early keys to success at Samsara

    (09:39) What does quality mean to Kiren?

    (10:54) Building a customer-centric roadmap

    (17:34) Early customer research and the failed fridge monitoring idea

    (20:57) How a cheese producer helped create Samsara’s first prototype

    (28:06) Balancing depth and breadth in customer profiles

    (33:45) Developing customer trust to build feedback loops

    (40:27) How “ease of use” became a growth secret

    (44:23) Pricing strategies and market positioning

    (51:51) How Meraki influenced Samsara’s GTM strategy

    (57:19) Helping customers navigate change management

    (1:00:48) How Samsara’s team evolved during rapid growth

    (1:04:03) What AI means for an IoT giant

  27. Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)

    1 Std. 12 Min.

    Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode …

    Shownotes

    Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions.

    In this episode, we discuss:

    • Why ClassDojo was built for consumers (teachers, students and parents) instead of schools
    • How ClassDojo grew entirely by word-of-mouth
    • Sam’s unusual approach to building multiple new businesses
    • The founder mindset required to build an industry leader
    • Why relentless resourcefulness is an underrated skill
    • And much more…


    References:


    Where to find Sam:


    Where to find Brett:


    Timestamps:

    (01:36) Why education is a “bad market”

    (02:52) Why enterprise education is broken

    (03:35) Building for families, not schools

    (06:53) Early challenges and insights

    (09:45) Sam’s unusual background

    (11:42) Meeting co-founder Liam at a hackathon

    (13:22) Getting into Imagine K12 with a group-making tool

    (19:47) The conversation with Reid Hoffman that changed everything

    (21:52) Building a network to reach more families

    (23:30) Scaling by building a community

    (33:18) Designing for delight and word-of-mouth growth

    (40:09) Launching the first monetization feature after 7 years

    (41:35) How to pick markets and when to go broad

    (46:04) The explosive expansion into the tutoring industry

    (55:11) Creating safe online spaces for kids

    (58:01) Harnessing AI in education

    (59:52) Lessons from ClassDojo’s playbook

  28. From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)

    1 Std. 6 Min.

    Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome …

    Shownotes

    Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks.


    In this episode, we discuss:

    • Making the leap from India to Silicon Valley
    • The moment Abhinav realized Postman could win
    • His principles behind building for developers and non-developers alike
    • The early monetization experiments that led to their SaaS model
    • The value of progressive complexity in product design
    • How community building became a powerful growth lever
    • And much more…


    References:

    • Abhijit Kane: https://www.linkedin.com/in/abhijitkane/
    • Adobe: https://www.adobe.com/
    • Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/
    • Figma: https://www.figma.com/
    • Kong Inc.: https://konghq.com/
    • National University of Singapore: https://nus.edu.sg/
    • Postman: https://www.postman.com/
    • Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/
    • Slack: https://slack.com/
    • Stripe: https://stripe.com/
    • Stewart Butterfield: https://www.linkedin.com/in/butterfield/
    • Yahoo: http://yahoo.com/


    Where to find Abhinav:

    • LinkedIn: https://www.linkedin.com/in/abhinavasthana/
    • Twitter/X: https://x.com/a85


    Where to find Brett:

    • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
    • Twitter/X: https://twitter.com/brettberson


    Where to find First Round Capital:

    • Website: https://firstround.com/
    • First Round Review: https://review.firstround.com/
    • Twitter/X: https://twitter.com/firstround
    • YouTube: https://www.youtube.com/@FirstRoundCapital
    • This podcast on all platforms: https://review.firstround.com/podcast


    Timestamps:

    (01:18) Why early computer access changed everything

    (03:39) The first taste of the entrepreneurial bug

    (09:58) Building BITS360 in college

    (11:14) Curating entrepreneurial taste

    (15:49) The ventures that didn’t make it

    (20:53) The problems that preceded Postman

    (29:56) How Postman’s team was formed

    (34:01) Why clear roles prevent chaos

    (34:50) Scrappy startup life in the early days

    (36:26) Postman’s path to monetization

    (39:59) Building a truly collaborative platform

    (43:00) Navigating market and customer needs

    (46:02) Cracking the go-to-market code

    (49:39) Bridging the developer-enterprise divide

    (54:43) The open-source dilemma

  29. How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)

    1 Std. 4 Min.

    Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month. Before starting Canva, Cameron was a designer …

    Shownotes

    Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month.

    Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything.


    In this episode, we cover:

    • How Canva turned social media managers into early evangelists
    • Balancing a huge vision with scrappy execution
    • Hard lessons from their near-silent launch day
    • The two growth levers that changed everything
    • And much more…

    References:

    Where to find Cameron:

    Where to find Brett:

    Where to find First Round Capital:

    Timestamps:

    (01:24) The birth of Canva

    (04:32) Meeting Canva’s co-founders

    (11:22) Building the first iteration of Canva

    (15:26) The discovery that changed prototyping

    (20:48) Why onboarding was the unlock for retention

    (27:36) The anticlimactic launch day

    (32:43) How word-of-mouth spurred early retention

    (36:33) Targeting different user personas

    (41:02) Building a community on social media

    (43:38) Two impactful growth levers

    (47:14) Why Canva should have gone mobile sooner

    (48:12) What underpins Canva’s dominance today

    (53:37) Rebuilding for enterprise

    (58:38) Lessons from Canva’s tough times

  30. Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)

    1 Std. 6 Min.

    Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as …

    Shownotes

    Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny.


    In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly.


    We also discuss:

    • Why Parallel designs for AI as the primary customer
    • Lessons from 11 years at Twitter and applying them to a startup
    • Potential business models to keep the web open for AI
    • Hiring philosophy: balancing high potential and experienced talent
    • The evolving role of engineers in an AI-assisted world
    • Why “agents” are finally becoming useful in production
    • And much more…

    References:

    Where to find Parag:

    Where to find Todd:

    Where to find First Round Capital:

    Timestamps:

    (1:26) Founding Parallel with an AI-first mission

    (3:23) From Twitter CTO/CEO to startup founder

    (6:20) What the AI era spells for companies

    (7:58) The CEO to founder pipeline

    (11:18) Reflections on Twitter’s transformation

    (17:48) How Parallel was born

    (22:31) Early use cases for Parallel

    (31:42) How has Parallel’s ICP changed?

    (34:37) AI’s impact on competitor dynamics

    (36:06) When should founders launch?

    (37:43) Parag’s fundraising framework

    (40:14) Building a high-impact engineering team

    (44:49) Counterproductive uses of AI

    (47:35) How will the software engineer role evolve?

    (49:10) How are Parallel’s customers using AI?

    (53:27) Defining agents in 2025

    (55:02) Parallel’s long-term vision

    (1:03:43) Parag’s growth as a founder

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