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

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

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

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/ Maven: https://maven.com/ Seth Godin: https://www.sethgodin.com/ Udemy: https://www.udemy.com/ --- Where to find Wes: LinkedIn: https://www.linkedin.com/in/weskao --- 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: (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 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

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. --- In today’s episode, we discuss: How listening to customers revealed an opportunity to pivot The weekend project that became Reducto's breakthrough Landing a Fortune 10 customer A technical founder's guide to sales Key insights from Reducto's fundraising journey Advice for founders: “You’re going to fail” Much more --- Referenced: Anthropic: https://www.anthropic.com/ Chetan Puttagunta: https://www.linkedin.com/in/chetanputtagunta/ Diana Hu: https://www.linkedin.com/in/sdianahu/ Liz Wessel: https://www.linkedin.com/in/elizabethwessel/ Raunak Chowdhuri: https://www.linkedin.com/in/sauhaarda/ Reducto: https://reducto.ai/ Scale AI: https://scale.com/ Stripe: https://stripe.com/ Textract: https://aws.amazon.com/textract/ Y Combinator: https://www.ycombinator.com/ --- Where to find Adit: LinkedIn: https://www.linkedin.com/in/aditabraham/ --- 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) 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. --- In today’s episode, we discuss: Why bootstrapping isn’t always what it’s cracked up to be The switch from a consumer product to B2B Launching before billing — and why that worked When being “too secure” nearly killed the product Becoming CEO… without telling anyone Much more --- Referenced: 1Password: https://1password.com Accel: https://www.accel.com Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/ David Teare: https://www.linkedin.com/in/daveteare/ Floodgate: https://floodgate.com LastPass: https://www.lastpass.com Mike Maples: https://www.linkedin.com/in/maples/ Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca Sara Teare: https://1password.com/company/meet-the-team/sara-teare Shopify: https://www.shopify.com Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/ --- Where to find Jeff: LinkedIn: https://www.linkedin.com/in/jshiner --- 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: 0:03 – 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. -- In today’s episode, we discuss: How working with a small business kickstarted Owner Adam’s unusual outbound strategy Why the pandemic accelerated Owner’s success How Owner’s pivot led to “hyperbolic” product-market fit The two qualities Adam looks for in new hires -- Referenced: Alex Bard: https://www.linkedin.com/in/alexbard/ Dean Bloembergen: https://www.linkedin.com/in/deanbloembergen/ Guisados: https://www.guisados.la/ HubSpot: https://www.hubspot.com/ Jack Altman: https://www.linkedin.com/in/jackealtman/ Kimbal Musk: https://www.linkedin.com/in/kimbalmusk/ Modern Restaurant Management: https://modernrestaurantmanagement.com/ Naval Ravikant: https://www.linkedin.com/in/navalr/ Neil Patel: https://www.linkedin.com/in/neilkpatel/ Peter Thiel: https://www.linkedin.com/in/peterthiel/ P.F. Chang's: https://www.pfchangs.com/ Sean Rad: https://www.linkedin.com/in/seanrad/ Thiel Fellowship: https://thielfellowship.org/ Tim Ferriss: https://www.linkedin.com/in/timferriss/ Y Combinator: https://www.ycombinator.com/ -- Where to find Adam: LinkedIn: https://www.linkedin.com/in/adamharrisonguild/ -- 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) 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. – In today’s episode, we discuss: Eeke’s wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – Referenced: ASML: https://www.asml.com/en Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Constellate: https://constellate.team/ John Collison: https://www.linkedin.com/in/johnbcollison/ Mike Maples Jr.: https://www.linkedin.com/in/maples/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Stripe: https://stripe.com/ Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/ – Where to find Eeke: LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ – 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) 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

Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – 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) Teaser: “I don’t believe in stealth mode” (02:51) Inspiration behind Guideline (07:56) Lessons from a year’s research before Guideline (10:44) Identifying market pull for Guideline (14:28) What Kevin learnt before shipping their first product (19:10) How Guideline set their fees up (27:51) The surprising range of Guideline’s early customers (31:48) Kevin’s insights from the Gusto integration (39:48) Guideline’s first year (44:44) Working with Plaid as Guideline’s first customer (53:28) Guideline’s auto-enrollment feature (57:53) Lucky 8: Kevin’s unexpected pricing strategy (62:04) Franchise opportunities (64:49) Kevin’s reflections on Taskrabbit (71:36) Will Guideline ever go multi-product? (72:37) Kevin’s take on product-market fit (73:30) Guideline’s compounding advantage (78:51) The challenges faced by introverted leaders