Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users.

In today’s episode, we discuss:

• Ankur’s early lessons on quality from MemSQL

• How frustration with evals at Figma led to Braintrust

• Why they delayed go-to-market (on purpose)

• How to find product-market fit in a new market

• Why building great software comes from a place of “paranoia”

• And much more…

Referenced:

• Airtable: https://www.airtable.com/

• Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/

• Braintrust: https://braintrust.dev

• Brian Helmig: https://www.linkedin.com/in/bryanhelmig/

• Coda: https://coda.io/

• Databricks: https://www.databricks.com/

• David Kossnick: https://www.linkedin.com/in/davidkossnick/

• Figma: https://www.figma.com/

• Goldman Sachs: https://www.goldmansachs.com/

• Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/

• Manu Goyal: https://www.linkedin.com/in/mngyl/

• MemSQL: https://www.singlestore.com/ (now SingleStore)

• Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/

• OpenAI: https://openai.com/

• Snowflake: https://www.snowflake.com/

• Zapier: https://zapier.com/

Where to find Ankur:

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

• Twitter/X: https://x.com/ankrgyl

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

(02:02) Dropping out of college to join MemSQL

(02:24) Key lessons from MemSQL

(05:54) How to build quality software

(08:51) The trick to recruiting well

(12:03) Founding Impira and selling to Figma

(19:45) How Braintrust was born

(25:33) Why good founders are paranoid

(28:08) How to recognize a real market opportunity

(33:37) The biggest mistake at Impira

(35:15) Inside Braintrust’s first six months

(40:57) How AI is reshaping Braintrust’s future

(42:32) The evolution of their prompt playground

(46:53) Fighting to stay mission-driven

(52:45) Make big bets, with extreme clarity

(57:00) The cultural choices that shaped Braintrust

(58:49) Hiring mistakes they won’t repeat

(1:03:07) What PMF really looks like

Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto.

In today’s episode, we discuss:

Referenced:

Where to find Tomer:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(00:00) How a childhood around SMBs shaped Tomer’s founder mindset

(03:24) The three things that led to the creation of Gusto

(07:17) Hiring for humility, not just talent

(09:28) The tug-of-war test for product-market fit

(11:58) Why founders should actively seek rejection

(15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet

(17:45) Betting on SMBs – and ignoring investor advice

(20:44) “It’s not an MVP, it’s something that wows people”

(24:09) Serving SMBs vs. startups

(28:36) How to find the right co-founders

(31:09) The weekly co-founder ritual that built trust

(35:02) Reinventing payroll without any prior experience

(38:49) Gusto’s “start small” GTM playbook

(42:16) The big opportunity Gusto wishes they tackled sooner

(43:58) How switching costs became Gusto’s moat

(47:25) The two lucky breaks that gave Gusto an edge

(51:56) What Tomer learned about customers from his dad’s clothing store

David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO.

In this episode, we discuss:

Referenced:

Where to find David:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(4:01) Learning to code through gaming

(6:31) Dropping out of high school

(9:47) Building infrastructure at Disqus

(10:20) “Software is not that hard”

(12:45) Early interest in open source

(15:45) The birth of Sentry

(23:37) Two common founder mistakes

(27:13) David’s unwavering focus

(28:17) Sentry’s journey to venture backing

(36:43) Finding conviction in decisions

(41:11) How Sentry found PMF

(46:34) More confidence, less ego

(48:08) Is sales valuable?

(51:31) David’s personal philosophy

(1:01:17) Money is not the hardest problem

(1:06:27) Marketing won’t fix a bad product

(1:10:34) What makes Sentry’s market unique

(1:16:24) “You’re gonna mess up”

(1:22:08) Why brand will always matter

(1:30:51) Eliminating all competition

Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase.

In today’s episode, we discuss

Referenced

Where to find Karri

Where to find Brett

Where to find First Round Capital

Timestamps

(1:37) Childhood roots in computers and design

(6:54) Founding Kippt and lessons from a failed bookmarking startup

(13:14) Lessons from a serial entrepreneur

(19:32) Why teams shouldn’t grow too quickly

(25: 03) Linear’s early beginnings

(36:55) The unexpected power of intuition

(42:41) Linear’s unusual approach to user growth

(47:29) What shaped Linear’s early product roadmap

(52:02) Startups shouldn’t try to boil the ocean

(57:30) The power of extreme focus

(59:18) Design “something for someone”

(1:04:29) Flexibility vs. simplicity

(1:17:27) Lead your team with strong principles

(1:24:45) Design founders vs. engineering founders

Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders.

In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards.

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In today’s episode, we discuss:

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Referenced:

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Where to find Wes:

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(1:54) Charisma is misunderstood

(4:44) What underpins authenticity?

(13:53) Clarity in communication

(16:02) Start with your ideal outcome

(22:05) The role of power dynamics

(26:39) Should you work on weaknesses?

(29:02) Effective self-reflection

(32:13) Role-strength fit

(37:39) What do you resent?

(39:17) “Be more strategic”

(45:20) Stack ranking

(51:45) How AltMBA started

(60:04) Defining your craft

Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation.

In today’s episode, we discuss:

Referenced:

Where to find Rick:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(0:05) Life before Persona

(2:11) The push from Charles

(3:09) Early reluctance and low expectations

(9:50) Winning the first $50 customer

(13:08)“Invalidating” Persona

(16:43) How Persona found their edge

(19:35) Transitioning from MVP to platform

(24:18) Turning down a $5K deal on principle

(26:47) Generalizing bespoke solutions

(28:28) Finding product-market fit

(33:51) Founder-led sales and consultative approach

(39:30) Building a culture of reactivity

(45:47) Landing the first enterprise customers

(51:34) Silicon Valley’s obsession with frameworks

(58:17) Developing first principles thinking

(1:00:24) Stay competitor-informed

Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab.

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In today’s episode, we discuss:

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Referenced:

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Where to find Adit:

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Hackathons, YC, and an unexpected pivot

(05:23) The weekend project that became Reducto's breakthrough

(09:11) How customer signal led to PDF processing

(14:46) Landing a Fortune 10 customer

(22:42) Building “transferable features”

(25:58) How caring beats sales skills in startup growth

(30:28) The strategy behind Reducto's horizontal expansion

(36:18) Hire slow, go-to-market fast

(41:45) A technical founder's guide to sales

(43:45) “You’re going to fail”

(46:27) Why startups win

(48:30) Key insights from Reducto's fundraising journey

(51:43) Less structure, more impact

(55:00) How frustrations shaped Reducto’s culture

(57:35) The question you should always ask in meetings

Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations.

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In today’s episode, we discuss:

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Referenced:

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Where to find Jeff:

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

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

0:03 – How Jeff got involved with 1Password

2:01 – How 1Password was initially set up

10:41 – The secret CEO

13:44 – What Jeff’s first six months encompassed

16:13 – The lightbulb moment that caused a pivot

17:50 – 1Password’s unusual company journey

22:08 – Creating an aligned product roadmap

29:19 – Retaining a customer-centric focus at scale

30:40 – Why 1Password’s first B2B product failed

39:43 – How Jeff thinks about competitors

46:44 – Building different go-to-market functions

52:45 – Staying bootstrapped for 15 years

57:17 – Jeff’s one regret

1:02:00 – 1Password’s most pivotal moments

Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B.

Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner.

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In today’s episode, we discuss:

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Referenced:

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Where to find Adam:

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

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Where to find Brett:

Where to find First Round Capital:

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Timestamps:

(00:00) Intro

(01:29) Adam’s first business

(04:15) The transition from Minecraft to Owner

(05:58) The dark side of the gaming industry

(14:20 Adam’s scrappy strategy to landing his first customers

(16:52) The COVID pivot

(21:31) The quest to find product-market fit

(30:53) What actually worked to get new customers

(36:03) Inside Owner’s explosive growth

(46:41) How Owner secured its crucial first round of funding

(53:34) The bet on going multi-product

(64:28) What Adam wishes he knew at 17

(76:22) Sales-led vs. product-led growth

Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.

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In today’s episode, we discuss:

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Referenced:

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Where to find Eeke:

• LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Should you ‘buy or build’ a leader

(03:45) Why do executive hires fail so often?

(09:35) Why the stakes are so high for leadership hires

(12:26) The hardest document Eeke ever wrote

(14:06) Two red flags in a new hire

(17:27) An example of an outstanding leader

(21:40) What creates dysfunctional exec relationships

(22:38) The three steps towards hiring successful leaders

(30:30) What you should know about outside hires

(33:12) Eeke’s advice for easing leadership transitions

(42:06) How to notice success patterns

(47:21) Why high-functioning executive teams are like parents

(52:02) The most surprising lesson from Eeke’s first stint at Stripe

(55:11) The leadership data Eeke wishes we had