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In Depth

In Depth

By: 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 Economics Leadership Management Management & Leadership
Episodes
  • How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)

    How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)
    Jun 19 2025
    David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss: How David went from managing a Burger King to landing his first job as a software engineer How an code snippet grew into a ubiquitous monitoring platform Why open source is an underrated distribution hack How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise And so much more… Referenced: Aaron Levie Beats by Dre Cursor Dan Levine Datadog Disqus Dropbox Heroku Max Levchin Okta Omar Johnson Oracle Sentry Satya Nadella Stripe Uber VS Code WindSurf Y Combinator Yandex Where to find David: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube Timestamps: (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David’s unwavering focus (28:17) Sentry’s journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David’s personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won’t fix a bad product (1:10:34) What makes Sentry’s market unique (1:16:24) “You’re gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competition
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    1 hr and 41 mins
  • Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)

    Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)
    Jun 10 2025
    Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase. In today’s episode, we discuss Karri’s childhood love for computers that shaped his career The lessons he learned from a failed first startup Linear’s founding principles The early validation strategies used to shape the product Why Karri believes in small teams And much more… Referenced Airbnb Brian Armstrong Brian Chesky Coinbase Jori Lallo Linear Tuomas Artman Y Combinator Where to find Karri LinkedIn Twitter/X Where to find Brett LinkedIn Twitter/X Where to find First Round Capital Website First Round Review Twitter/X YouTube Timestamps (1:37) Childhood roots in computers and design (6:54) Founding Kippt and lessons from a failed bookmarking startup (13:14) Lessons from a serial entrepreneur (19:32) Why teams shouldn’t grow too quickly (25: 03) Linear’s early beginnings (36:55) The unexpected power of intuition (42:41) Linear’s unusual approach to user growth (47:29) What shaped Linear’s early product roadmap (52:02) Startups shouldn’t try to boil the ocean (57:30) The power of extreme focus (59:18) Design “something for someone” (1:04:29) Flexibility vs. simplicity (1:17:27) Lead your team with strong principles (1:24:45) Design founders vs. engineering founders
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    1 hr and 33 mins
  • How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)

    How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)
    May 22 2025
    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
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    1 hr and 20 mins
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