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: Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama Clay: https://www.clay.com/ Index Ventures: https://www.indexventures.com/ Josh Kopelman: https://www.linkedin.com/in/jkopelman/ KLA: https://www.kla.com/ OpenAI: https://openai.com/ Parallel: https://parallel.ai/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Stripe: https://stripe.com/ Where to find Parag: LinkedIn: https://www.linkedin.com/in/paragagr/ X/Twitter: https://x.com/paraga Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ X/Twitter: https://x.com/tjack Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast 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

Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business. In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray. In this episode, we discuss: Mercury’s unusual culture playbook – and why it works How to hire with intention The trap of weak product-market fit Shipping under intense pressure during the SVB crisis And much more… References: Airbnb: https://www.airbnb.com/ Andreessen Horowitz: https://a16z.com/ Apple: https://www.apple.com/ Block: https://block.xyz/ Brex: https://www.brex.com/ Chime: https://www.chime.com/ Gusto: https://gusto.com/ Mercury: https://mercury.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Stripe: https://stripe.com/ SVB (Silicon Valley Bank): https://www.svb.com/ True Link Financial: https://www.truelinkfinancial.com/ Varo: https://www.varomoney.com/ Y Combinator: https://www.ycombinator.com/ Where to find Immad: LinkedIn: https://www.linkedin.com/in/iakhund/ 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: (1:07) Hard-won lessons from serial entrepreneurship (2:02) You shouldn’t copy-paste advice (6:57) Why personality trumps culture playbooks (8:48) How do you hire for cultural fit? (12:38) The values that shaped Mercury’s DNA (14:08) The drivers underpinning Mercury’s success (15:50) The significance of product-market fit (20:41) Don’t fall into the weak product-market fit trap (25:49) How to evaluate startup ideas that scale (30:14) Mercury’s unlikely origin story (33:51) Breaking into the fintech space (37:31) Mindset shift: From “This is hard” to long-term gains (39:43) Building Mercury’s MVP (44:25) Overcoming early obstacles to reach launch (47:36) Navigating Mercury’s rapid growth phase (51:18) Competition isn’t the reason you’re failing (55:58) Crisis management during the SVB collapse

Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch. In today’s episode, we discuss: • The two founder traits Silicon Valley undervalues • How to get 1–3 extra months of work done every year • Lessons from YC on pattern matching and founder feedback • The battle-tested startup formula Qasar used at Applied • Why co-founder fit is make-or-break • Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks • Why Applied went multi-product in the early days • Contrarian takes on startup culture, compensation, and cost control • Why domain expertise is making a comeback • And much more… Referenced: • Applied Intuition: https://www.appliedintuition.com • Ansys: https://www.ansys.com • Bilal Zuberi: https://www.linkedin.com/in/bzuberi • Bosch: https://www.bosch.com • Elad Gil: https://www.linkedin.com/in/eladgil • General Motors: https://www.gm.com • “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/ • “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Kyle Vogt: https://x.com/kvogt • Marc Andreessen: https://x.com/pmarca • “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821 • Paul Graham: https://x.com/paulg • Peter Ludwig: https://www.linkedin.com/in/peterwludwig • Sam Altman: https://x.com/sama • TalkBin: https://www.crunchbase.com/organization/talkbin • “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860 • Waymo: https://waymo.com • Y Combinator: https://www.ycombinator.com • Zoox: https://zoox.com Where to find Qasar: • LinkedIn: https://www.linkedin.com/in/qasar/ 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: (01:26) Two founder traits Silicon Valley undervalues (04:23) Gain 1-3 extra months of productivity yearly (05:52) Why founders should read outside the startup canon (07:27) Lessons from YC (13:44) Why it's harder to start than to quit (15:52) The moment you become a real founder (20:24) How great founders master luck (21:46) Qasar’s battle-tested startup formula (25:37) The founding insight for Applied (31:42) How Applied expanded beyond automotive (38:05) Why Applied went multi-product early (45:45) What no one says about startup secondaries (49:02) Why being cheap is a startup superpower (51:04) The myth of "competition doesn’t matter" (53:50) Early scrappiness: The Sunnyvale house setup (54:50) Why domain knowledge is making a comeback (58:32) The mentors who shaped Qasar

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: 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

Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. – In today’s episode, we discuss: The Braze founders’ early insights into the mobile revolution How a TechCrunch Hackathon sparked Braze's creation The journey from 1,000 beta signups to 2,200+ paying customers Breaking traditional lean startup rules Navigating early fundraising challenges Finding product market fit by “fishing in every pond” Approaching competition strategically like a boxer Much more – Referenced: Accenture: https://www.accenture.com/ Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps Bipul Sinha: https://www.linkedin.com/in/bipulsinha/ Braze: https://www.braze.com/ Bridgewater Associates: https://www.bridgewater.com/ Jon Hyman: https://www.linkedin.com/in/jon-hyman/ Mark Ghermezian: https://x.com/markgher MIT: https://www.mit.edu/ Rubrik: https://www.rubrik.com/ WeWork: https://www.wework.com/ – Where to find Bill: LinkedIn: https://www.linkedin.com/in/billmagnuson/ Twitter/X: https://x.com/billmag – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/ – 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: Finding “terminal value” product market fit (00:24) Introduction (02:34) Bill's insights into the mobile revolution (04:43) Lessons from Bridgewater Associates (09:12) First principles thinking in action at Braze (14:14) Meeting co-founders at an NYC Hackathon (24:35) Braze’s scrappy scaling (33:37) Early product development (39:37) From 1,000 beta signups to 2,200+ paying customers (43:51) Braze’s fundraising struggles (47:01) Breaking the rules of a lean startup (53:02) Riding the mobile wave to success (60:02) Building a global customer base (64:04) The never-ending quest for PMF (70:29) 3 things every founder needs to know (73:56) Navigating competition like a boxer (79:03) When scale helps or hurts (80:32) 1 thing they’ve learned from each other

Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign. – In today’s episode, we discuss: Clay’s unconventional GTM machine 3 changes that unlocked Clay's upmarket motion Layering enterprise customers on top of PLG Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos Thinking long-term about brand and content Building an elite team of people who are “technical enough” Clay’s contrarian take on compensation Much more – Referenced: Anthropic: https://www.anthropic.com/ Clay: https://www.clay.com/ Clay’s Series B expansion: https://www.clay.com/blog/series-b-expansion Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/ Figma: https://www.figma.com/ Jesse Ouellette: https://www.linkedin.com/in/jesseoue/ Kareem Amin: https://www.linkedin.com/in/kareemamin/ Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/ Notion: https://www.notion.com/ Oyster: https://www.oysterhr.com/ Pave: https://www.pave.com/ Rippling: https://www.rippling.com/ Snowflake: https://www.snowflake.com/ Verkada: https://www.verkada.com/ Webflow: https://webflow.com/ Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/ – Where to find Varun: LinkedIn: https://www.linkedin.com/in/vaanand/ Twitter/X: https://x.com/vxanand – 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 + Introduction (03:13) Turning traditional GTM on its head (05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups (08:53) Unpacking Clay's credit-based pricing (14:29) Building Clay's self-serve engine (16:54) Why Clay rejected the usage-based model (19:04) Clay’s big bet on content (23:59) How "reverse demos" win enterprise deals (27:49) 3 changes that unlocked Clay's upmarket motion (36:59) How to build trust with enterprise buyers (38:49) Applying the land and expand model (40:40) Hiring people who are “technical enough” (46:33) Inside Clay’s hands-on interviewing process (48:15) Why Clay invested in brand from day-one (50:21) Clay’s contrarian take on compensation (58:35) The person who shaped Varun’s career

Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace. – In today’s episode, we discuss: Dbt’s explosive growth The strategic pivot from consulting to a software company Unexpected strategies for building a tech category from scratch The critical moment: Why and when dbt Labs sought venture funding How to drive commercial adoption after open-sourcing Two things every founder CEO should do Much more – Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ Bob Moore: https://www.linkedin.com/in/robertjmoore/ Crossbeam: https://www.crossbeam.com/ dbt Labs: https://www.getdbt.com/ Drew Banin: https://www.linkedin.com/in/drewbanin/ Jerry Colonna: https://www.reboot.io/team/jerry-colonna/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics SeatGeek: https://seatgeek.com/ Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/ Squarespace: https://www.squarespace.com/ – Where to find Tristan: LinkedIn: https://www.linkedin.com/in/tristanhandy/ Twitter/X: https://x.com/jthandy – 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) Introduction (02:56) The critical oversight in data analysis (05:41) Becoming an “accidental founder” (07:04) Inside the unique decision to start a consultancy (08:17) The game-changing principle behind dbt Labs’ rapid growth (11:20) Finding dbt Labs’ first customers (15:52) Consulting's hidden scalability (17:25) How dbt Labs created a new category (21:03) The anti-demo strategy (23:59) Community hacking: the Slack group that changed everything (26:00) The open source philosophy (27:39) When growth went exponential (28:49) How consulting engagements shaped the roadmap (30:02) Fundraising only when “things started to break” (32:40) Consultancy superpowers: the hidden advantages (34:04) Pivoting from consulting to software (40:00) Key monetization strategies (48:56) Why “begrudging” CEOs can be successful (51:02) Advice for finding PMF: “It’s not a playbook” (51:59) Lowering your standards is a hack (53:30) Navigating emotional overwhelm (54:25) Every CEO needs a coach

Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. In today’s episode, we discuss: How Figma approaches new products, prioritization, and storytelling Product culture at Uber, Microsoft, Google The difference between “good” and “extraordinary” PMs Tactical advice for storytelling The “un-learning” required in new jobs and industries – Referenced: Figjam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Figma Dev Mode: https://www.figma.com/dev-mode/ Figma Slides: https://www.figma.com/slides/ – Where to find Yuhki: LinkedIn: https://www.linkedin.com/in/yuhki/ Twitter/X: https://x.com/yuhkiyam – 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 – (00:00) Introduction (02:50) Figma's early days (09:11) Product culture across companies (13:42) Knowing when to change things (17:40) How business goals impact product expansion (21:00) Advice for going multi-product (24:30) The skills of a “0 to 1” PM (27:36) Identifying entrepreneurial talent (29:06) Why aren't there more designer founders? (35:22) How Figma launches new products (41:19) “0 to 1” versus “1 to 10” talent (46:01) The role of storytelling at Figma (49:22) How Figma prioritizes product (55:11) Advice for product storytelling (59:02) “Good” vs “extraordinary” product managers (61:21) Why product simplicity matters (63:52) The importance of taste in product and design (67:56) The biggest influence on Yuhki’s product thinking

Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.” This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel. – In today’s episode we discuss: Commercial versus military market strategies Finding mission solution fit The hidden challenges most startups miss Building relationships in National Security The new generation of “defense founders” Much more – Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder/ Department of Defense: https://www.defense.gov/ Eric Ries: https://www.linkedin.com/in/eries/ Hacking for Defense: https://hackingfordefense-prod.stanford.edu/ How Saboteurs Threaten Innovation: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ How to find your customer in the Dept of Defense: https://steveblank.com/2024/09/17/the-directory-of-dod-program-executive-offices-and-officers-peos/ Mission Model Canvas: https://steveblank.com/2019/09/ Pete Newell: https://www.linkedin.com/in/petenewell/ Special Operations Command: https://www.socom.mil/ The Frozen Middle: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ The Hacking for Defense Manual: https://stanfordh4d.substack.com/p/the-hacking-for-defense-manual-a The Hacking for Defense Course: https://www.h4d.us/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The Secret History of Silicon Valley: https://steveblank.com/secret-history/ – Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ – 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 – Timestamps: (00:00) Introduction (02:27) Validating ideas for defense products (03:57) Guide to military sales and procurement (07:15) Rethinking GTM strategies (10:13) Building a network in national security (15:07) The dual-use debate (18:35) Behind the rising number of “defense founders” (22:30) “Mission solution fit” (24:35) Breaking new ground in military tech (26:09) Essential resources for any defense founder (28:59) What’s missing from Silicon Valley

Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today’s episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka’s jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik’s approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom’s acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu’s acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: 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) Introduction (02:11) Inside LiveRamp’s unique growth journey (12:18) Anneka’s first PM role (14:20) Leading LiveRamp’s marketing function (16:17) Why the best product doesn’t win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom’s customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) How 17 diverse roles shaped Anneka’s CPO approach (40:54) The hidden career growth hack (43:15) Where domain experience is overrated (50:33) Mastering the art of altitude shifting (53:54) PMs should undergo the same training as sales reps (59:37) Strategies for selling to new personas (62:40) Lessons from Anneka’s mistake at LiveRamp (67:56) Who had an outsized impact on Anneka