In Depth

First Round
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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

  1. Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)

    قبل يوم واحد

    Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)

    Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions. In this episode, we discuss: Why ClassDojo was built for consumers (teachers, students and parents) instead of schools How ClassDojo grew entirely by word-of-mouth Sam’s unusual approach to building multiple new businesses The founder mindset required to build an industry leader Why relentless resourcefulness is an underrated skill And much more… References: Accel: https://www.accel.com/ Airbnb: https://www.airbnb.com/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Brendan Kereiakes: https://www.linkedin.com/in/product/ ClassDojo: https://www.classdojo.com/ Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/ Geoff Ralston: https://www.linkedin.com/in/geoffralston/ Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/ Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/ Imagine K12: https://www.imaginek12.com// Khan Academy: https://www.khanacademy.org/ Liam Don: https://www.linkedin.com/in/liamdon/ McKinsey: https://www.mckinsey.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Roblox: https://www.roblox.com/ Sal Khan: https://www.linkedin.com/in/khanacademy/ Superhuman: https://superhuman.com/ Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/ Y Combinator: https://www.ycombinator.com/ Where to find Sam: LinkedIn: https://www.linkedin.com/in/samchaudhary/ Twitter/X: https://x.com/samchaudhary Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Timestamps: (01:36) Why education is a “bad market” (02:52) Why enterprise education is broken (03:35) Building for families, not schools (06:53) Early challenges and insights (09:45) Sam’s unusual background (11:42) Meeting co-founder Liam at a hackathon (13:22) Getting into Imagine K12 with a group-making tool (19:47) The conversation with Reid Hoffman that changed everything (21:52) Building a network to reach more families (23:30) Scaling by building a community (33:18) Designing for delight and word-of-mouth growth (40:09) Launching the first monetization feature after 7 years (41:35) How to pick markets and when to go broad (46:04) The explosive expansion into the tutoring industry (55:11) Creating safe online spaces for kids (58:01) Harnessing AI in education (59:52) Lessons from ClassDojo’s playbook

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  2. From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)

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    From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)

    Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks. In this episode, we discuss: Making the leap from India to Silicon Valley The moment Abhinav realized Postman could win His principles behind building for developers and non-developers alike The early monetization experiments that led to their SaaS model The value of progressive complexity in product design How community building became a powerful growth lever And much more… References: Abhijit Kane: https://www.linkedin.com/in/abhijitkane/ Adobe: https://www.adobe.com/ Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/ Figma: https://www.figma.com/ Kong Inc.: https://konghq.com/ National University of Singapore: https://nus.edu.sg/ Postman: https://www.postman.com/ Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/ Slack: https://slack.com/ Stripe: https://stripe.com/ Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Yahoo: http://yahoo.com/ Where to find Abhinav: LinkedIn: https://www.linkedin.com/in/abhinavasthana/ Twitter/X: https://x.com/a85 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: (01:18) Why early computer access changed everything (03:39) The first taste of the entrepreneurial bug (09:58) Building BITS360 in college (11:14) Curating entrepreneurial taste (15:49) The ventures that didn’t make it (20:53) The problems that preceded Postman (29:56) How Postman’s team was formed (34:01) Why clear roles prevent chaos (34:50) Scrappy startup life in the early days (36:26) Postman’s path to monetization (39:59) Building a truly collaborative platform (43:00) Navigating market and customer needs (46:02) Cracking the go-to-market code (49:39) Bridging the developer-enterprise divide (54:43) The open-source dilemma

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  3. How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)

    ٢٠ أغسطس

    How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)

    Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month. Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything. In this episode, we cover: How Canva turned social media managers into early evangelists Balancing a huge vision with scrappy execution Hard lessons from their near-silent launch day The two growth levers that changed everything And much more… References: Adobe: https://www.adobe.com/home Atlassian: https://www.atlassian.com/ Campaign Monitor: https://www.campaignmonitor.com/ Canva: https://www.canva.com/ Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/ Dave Greiner: https://www.linkedin.com/in/davegreiner/ Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/ Melanie Perkins: https://www.linkedin.com/in/melanieperkins/ Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/ New York Stock Exchange: https://www.nyse.com/ Pinterest: https://pinterest.com/ Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/ Where to find Cameron: LinkedIn: https://www.linkedin.com/in/themaninblue/ 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/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:24) The birth of Canva (04:32) Meeting Canva’s co-founders (11:22) Building the first iteration of Canva (15:26) The discovery that changed prototyping (20:48) Why onboarding was the unlock for retention (27:36) The anticlimactic launch day (32:43) How word-of-mouth spurred early retention (36:33) Targeting different user personas (41:02) Building a community on social media (43:38) Two impactful growth levers (47:14) Why Canva should have gone mobile sooner (48:12) What underpins Canva’s dominance today (53:37) Rebuilding for enterprise (58:38) Lessons from Canva’s tough times

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  4. Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)

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    Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)

    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

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  5. Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)

    ٦ أغسطس

    Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)

    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

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  6. Inside the ex-YC partner’s $15B self driving car company | Qasar Younis

    ١ أغسطس

    Inside the ex-YC partner’s $15B self driving car company | Qasar Younis

    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

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  7. What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)

    ٢٤ يوليو

    What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)

    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

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  8. How Gusto built a $9.5 billion company by identifying a burning problem

    ١ يوليو

    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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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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  • صناع العمل
    First Round
  • سنوات النشاط
    ٢٠٢٠ - ٢٠٢٥
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  • التقييم
    ملائم
  • موقع البرنامج على الويب
    In Depth

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