In Depth

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 [https://www.adp.com/] * Eddie Kim [https://www.linkedin.com/in/edawerd/] * Gusto [https://gusto.com/] * Intuit [https://www.intuit.com/] * Josh Reeves [https://www.linkedin.com/in/joshuareeves/] * Paychex [https://www.paychex.com/] * Steve Jobs’ “Secrets to Life” clip [https://www.youtube.com/watch?v=kYfNvmF0Bqw] * Steve Jobs’ Stanford Commencement Speech [https://www.youtube.com/watch?v=UF8uR6Z6KL] * Wells Fargo [https://www.wellsfargo.com/] * Y Combinator [https://www.ycombinator.com/] Where to find Tomer: * LinkedIn [https://www.linkedin.com/in/tomerlondon/] * Twitter/X [https://x.com/tomerlondon] 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: (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: * 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 [https://www.linkedin.com/in/boxaaron/?ref=review.firstround.com] * Beats by Dre [https://www.beatsbydre.com/?ref=review.firstround.com] * Cursor [https://www.cursor.com/?ref=review.firstround.com] * Dan Levine [https://www.linkedin.com/in/danielmarklevine/?ref=review.firstround.com] * Datadog [https://www.datadoghq.com/?ref=review.firstround.com] * Disqus [https://disqus.com/?ref=review.firstround.com] * Dropbox [https://www.dropbox.com/?ref=review.firstround.com] * Heroku [https://www.heroku.com/?ref=review.firstround.com] * Max Levchin [https://www.linkedin.com/in/maxlevchin/?ref=review.firstround.com] * Okta [https://www.okta.com/?ref=review.firstround.com] * Omar Johnson [https://www.linkedin.com/in/omarjohnson/?ref=review.firstround.com] * Oracle [https://www.oracle.com/?ref=review.firstround.com] * Sentry [https://sentry.io/welcome/?ref=review.firstround.com] * Satya Nadella [https://www.linkedin.com/in/satyanadella/?ref=review.firstround.com] * Stripe [https://stripe.com/?ref=review.firstround.com] * Uber [https://www.uber.com/?ref=review.firstround.com] * VS Code [https://code.visualstudio.com/?ref=review.firstround.com] * WindSurf [https://windsurf.com/editor?ref=review.firstround.com] * Y Combinator [https://www.ycombinator.com/?ref=review.firstround.com] * Yandex [https://yandex.com/?ref=review.firstround.com] Where to find David: * LinkedIn [https://www.linkedin.com/in/dmcramer/?ref=review.firstround.com] * Twitter/X [https://x.com/zeeg?ref=review.firstround.com] Where to find Brett: * LinkedIn [https://www.linkedin.com/in/brett-berson-9986094/?ref=review.firstround.com] * Twitter/X [https://twitter.com/brettberson?ref=review.firstround.com] Where to find First Round Capital: * Website [https://firstround.com/?ref=review.firstround.com] * First Round Review [https://review.firstround.com/] * Twitter/X [https://twitter.com/firstround?ref=review.firstround.com] * YouTube [https://www.youtube.com/@FirstRoundCapital?ref=review.firstround.com] 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 [https://linear.app/blog/building-our-way] 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 [https://www.airbnb.com] * Brian Armstrong [https://www.linkedin.com/in/barmstrong/] * Brian Chesky [https://www.linkedin.com/in/brianchesky/] * Coinbase [https://www.coinbase.com] * Jori Lallo [https://www.linkedin.com/in/jorilallo/] * Linear [https://linear.app/] * Tuomas Artman [https://www.linkedin.com/in/tuomasartman/] * Y Combinator [https://www.ycombinator.com/] Where to find Karri * LinkedIn [https://www.linkedin.com/in/karrisaarinen/] * Twitter/X [https://x.com/karrisaarinen] 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] 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. --- 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… --- Referenced: * AltMBA: https://altmba.com/ [https://altmba.com/] * Maven: https://maven.com/ [https://maven.com/] * Seth Godin: https://www.sethgodin.com/ [https://www.sethgodin.com/] * Udemy: https://www.udemy.com/ [https://www.udemy.com/] --- Where to find Wes: * LinkedIn: https://www.linkedin.com/in/weskao [https://www.linkedin.com/in/weskao] --- Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ [https://www.linkedin.com/in/brett-berson-9986094/] * Twitter/X: https://twitter.com/brettberson [https://twitter.com/brettberson] --- Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [https://review.firstround.com/podcast] --- 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: * 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 [http://accenture.com/] * Anthropic: anthropic.com [https://www.anthropic.com/] * Braze: braze.com [https://www.braze.com/] * Bridgewater Associates: bridgewater.com [https://www.bridgewater.com/] * Charles Yeh: linkedin.com/in/charlesyeh/ [https://www.linkedin.com/in/charlesyeh/] * Christie Kim: linkedin.com/in/christiekimck/ [https://www.linkedin.com/in/christiekimck/] * Clay: clay.com [http://clay.com/] * Kareem Amin: linkedin.com/in/kareemamin/ [https://www.linkedin.com/in/kareemamin/] * MIT: mit.edu [http://mit.edu/] * Newfront: newfront.com [http://newfront.com/] * Palantir: palantir.com/ [https://www.palantir.com/] * Persona: withpersona.com [http://withpersona.com/] * Rippling: rippling.com [http://rippling.com/] * Scale AI: scale.com [http://scale.com/] * Snowflake: snowflake.com [https://www.snowflake.com/] * Square: squareup.com [http://squareup.com/] * Y Combinator: ycombinator.com [http://ycombinator.com/] * Zachary Van Zant: linkedin.com/in/zacharyv/ [https://www.linkedin.com/in/zacharyv/] Where to find Rick: * LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ [https://www.linkedin.com/in/rick-song-25198b24/] Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ [https://www.linkedin.com/in/brett-berson-9986094/] * Twitter/X: https://twitter.com/brettberson [https://twitter.com/brettberson] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [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