How Gusto built a $9.5 billion company by identifying a burning problem
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:
Reinventing payroll without any prior experience
Why you should hire for humility, not just talent
Gusto’s scrappy customer research: cold calling from a walk-in closet
Why founders should embrace customer rejection
Why “emotional urgency” matters more than polite feedback
The weekly co-founder ritual that built trust
How Gusto expanded from payroll to a multi-product platform
Building products customers actually love
And so much more
Referenced:
ADP
Eddie Kim
Gusto
Intuit
Josh Reeves
Paychex
Steve Jobs’ “Secrets to Life” clip
Steve Jobs’ Stanford Commencement Speech
Wells Fargo
Y Combinator
Where to find Tomer:
LinkedIn
Twitter/X
Where to find Brett:
LinkedIn
Twitter/X
Where to find First Round Capital:
Website
First Round Review
Twitter/X
YouTube
This podcast on all platforms
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
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55:01
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55:01
How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)
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:
How David went from managing a Burger King to landing his first job as a software engineer
How an code snippet grew into a ubiquitous monitoring platform
Why open source is an underrated distribution hack
How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise
And so much more…
Referenced:
Aaron Levie
Beats by Dre
Cursor
Dan Levine
Datadog
Disqus
Dropbox
Heroku
Max Levchin
Okta
Omar Johnson
Oracle
Sentry
Satya Nadella
Stripe
Uber
VS Code
WindSurf
Y Combinator
Yandex
Where to find David:
LinkedIn
Twitter/X
Where to find Brett:
LinkedIn
Twitter/X
Where to find First Round Capital:
Website
First Round Review
Twitter/X
YouTube
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
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1:41:24
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1:41:24
Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)
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
Karri’s childhood love for computers that shaped his career
The lessons he learned from a failed first startup
Linear’s founding principles
The early validation strategies used to shape the product
Why Karri believes in small teams
And much more…
Referenced
Airbnb
Brian Armstrong
Brian Chesky
Coinbase
Jori Lallo
Linear
Tuomas Artman
Y Combinator
Where to find Karri
LinkedIn
Twitter/X
Where to find Brett
LinkedIn
Twitter/X
Where to find First Round Capital
Website
First Round Review
Twitter/X
YouTube
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
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1:33:04
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1:33:04
How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)
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:
Wes’ “personality-message fit” framework
Why charisma is misunderstood
How anyone can improve their communication
What being told you need to “be more strategic” actually means
and much more…
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Referenced:
AltMBA: https://altmba.com/
Maven: https://maven.com/
Seth Godin: https://www.sethgodin.com/
Udemy: https://www.udemy.com/
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Where to find Wes:
LinkedIn: https://www.linkedin.com/in/weskao
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Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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
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1:19:34
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1:19:34
From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
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:
How Rick’s skepticism shaped Persona’s early strategy
What it takes to scale a true platform company
Successful execution in hypercompetitive markets
What Rick’s learned from his co-founder, Charles Yeh
and much more…
Referenced:
Accenture: accenture.com
Anthropic: anthropic.com
Braze: braze.com
Bridgewater Associates: bridgewater.com
Charles Yeh: linkedin.com/in/charlesyeh/
Christie Kim: linkedin.com/in/christiekimck/
Clay: clay.com
Kareem Amin: linkedin.com/in/kareemamin/
MIT: mit.edu
Newfront: newfront.com
Palantir: palantir.com/
Persona: withpersona.com
Rippling: rippling.com
Scale AI: scale.com
Snowflake: snowflake.com
Square: squareup.com
Y Combinator: ycombinator.com
Zachary Van Zant: linkedin.com/in/zacharyv/
Where to find Rick:
LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/
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:
(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
Welcome to In Depth, a new podcast from 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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