In Depth

• 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

  --------  

  1:01:52

  --------

  1:01:52
• 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

  --------  

  1:00:25

  --------

  1:00:25
• 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

  --------  

  1:10:04

  --------

  1:10:04
• 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

  --------  

  55:01

  --------

  55:01
• How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)

  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

  --------  

  1:41:24

  --------

  1:41:24

More Business podcasts

Trending Business podcasts

About In Depth

In Depth: Podcasts in Family