In Depth

Welcome to In Depth, a podcast from The 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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Every guest on In Depth

180 guests, ranked by how many people never want them back.

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Eric Sager
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid) · Jul 2026

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Graham Moreno
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel) · May 2026

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Jeff Shiner
1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO) · Apr 2025

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Kate Taylor
A deep-dive into product-led growth & self-serve strategies — Notion’s & Dropbox’s Kate Taylor · Apr 2021

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Kiren Sekar
Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO) · Sep 2025

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Lindsey Scrase
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr) · Jul 2026

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May Habib
Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer) · Feb 2024

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Nick Caldwell
Nick Caldwell on the engineering cultures that power Microsoft, Reddit, Looker & Twitter · Jul 2021

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Sara Varni
What startups can learn from enterprise corporate messaging — Sara Varni’s lessons from Salesforce & Twilio · Oct 2022

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Zach Kitschke
The story of why Canva worked: Zach Kitschke shares his lessons from early hire to current CMO · Nov 2021

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Colin Bryar

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Cristina Cordova
Partnerships lessons from Stripe & Notion — Cristina Cordova on creating win-win deals · Dec 2020

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Don Faul
How to lead with transparency amidst adversity — Don Faul, CEO of CrossFit and former Google, Facebook & Pinterest exec · Feb 2023

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Adam Guild
Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner) · Mar 2025

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Ashley Kramer
The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO) · Oct 2023

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Jay Parikh
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft) · Aug 2026

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Max Mullen
Instacart co-founder Max Mullen gets tactical on crafting company values and intentionally building culture · Nov 2021

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Meka Asonye
Never done sales before? Meka Asonye shares GTM playbooks from Stripe, Mixpanel, and backing founders at First Round · Mar 2022

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Aaron Zamost
Why comms deserves its own spot on the exec team — Aaron Zamost’s lessons from Square · Feb 2023

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Adrian McDermott
Buy or build? Focus on the core product or innovate? Zendesk CTO Adrian McDermott's advice for scaling · Dec 2021

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Alex Buder Shapiro
Getting startup employees to stick around & learning from couples therapy — Flatiron’s Alex Buder Shapiro · Jul 2021

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Alex Kracov
The zero to one B2B marketing playbook | Alex Kracov (Lattice, Dock) · Aug 2023

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Alyssa Henry
Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft) · Apr 2024

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Amber Feng
IC? Manager? Technical Founder? How to chart your engineering career path — Stripe & Cocoon’s Amber Feng · Mar 2022

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Andrew Ofstad
Airtable’s path to product-market fit — co-founder Andrew Ofstad on building horizontal products · Aug 2022

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Anil Varanasi
Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO) · Dec 2025

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Anique Drumright
Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom) · Aug 2023

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Anna Binder
How to build your culture like a product — Lessons from Anna Binder, Asana’s Head of People · Jan 2023

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Artem Kroupenev
How to measure product-market fit with the REV model — Artem Kroupenev · Apr 2023

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Ben Lang
Lessons from Notion on building a thriving decentralized community — Ben Lang · Mar 2023

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Brian Rieger

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Brie Wolfson
From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson · Feb 2023

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Bryant Chou
From a narrow ICP to a wide-open market – Lessons from Webflow’s Bryant Chou on using customer empathy to get product-market fit · Mar 2023

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Colleen McCreary
People leaders aren’t the CEO of culture, they’re product managers — Credit Karma’s Colleen McCreary · Jun 2021

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Dan Shiebler

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Daniel Debow
What founders need to know about acquisitions: Shopify’s Daniel Debow on M&A lessons from selling three startups · Jan 2023

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David Cramer
How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO) · Jun 2025

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Deepak Rao
Deepak Rao on how X1 pivoted, launched, built a +600K-long waitlist and fundraised in tough times · Dec 2022

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Dennis Pilarinos
Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft) · Mar 2024

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Diya Jolly
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero) · Apr 2026

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Recent episodes

185 episodes from the feed, newest first.

The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
with Jay Parikh

Aug 2026
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
with Lindsey Scrase

Jul 2026
How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
with Jon Noronha

Jul 2026
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)
with Eric Sager

Jul 2026
How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)
with Paul Copplestone

Jun 2026
How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)
with Sheila Joglekar Vashee

Jun 2026
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
with Graham Moreno

May 2026
Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)
with Praveer Melwani

May 2026
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
with Diya Jolly

Apr 2026
Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
with Shachar Hirshberg

Apr 2026
Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
with Christopher Payne

Apr 2026
The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)
with Katie Burke

Apr 2026
What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)
with Jay Kreps

Mar 2026
The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
with Jeremy Epling

Mar 2026
Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)
with Keller Rinaudo Cliffton

Mar 2026
Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
with Chris Degnan

Feb 2026
Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)
with Stevie Case

Feb 2026
Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)
with Ryan Lucas

Feb 2026
Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
with Jeanne DeWitt Grosser

Feb 2026
Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
with Anil Varanasi

Dec 2025
How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
with Jyoti Bansal

Nov 2025
How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
with Zack Kanter

Nov 2025
Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)
with Jake Stauch

Oct 2025
The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)
with Gorkem Yurtseven

Oct 2025
From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)
with Michael Chime

Oct 2025