In Depth

145 Episodes

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

   Published: 3/27/2025
2. What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)

   Published: 3/6/2025
3. Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)

   Published: 2/20/2025
4. Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO)

   Published: 2/6/2025
5. Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations)

   Published: 1/23/2025
6. Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace)

   Published: 12/19/2024
7. How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft)

   Published: 12/5/2024
8. How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense)

   Published: 11/14/2024
9. Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp)

   Published: 10/10/2024
10. How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers)

    Published: 9/26/2024
11. How to find — and keep — product-market fit | Bob Moore (Co-founder and CEO at Crossbeam, ex-RJMetrics and Stitch Data)

    Published: 9/19/2024
12. Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO

    Published: 9/5/2024
13. Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google)

    Published: 8/1/2024
14. Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs)

    Published: 6/6/2024
15. How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)

    Published: 5/30/2024
16. Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)

    Published: 5/16/2024
17. How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

    Published: 4/25/2024
18. Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)

    Published: 4/18/2024
19. Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple)

    Published: 4/4/2024
20. A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong)

    Published: 3/28/2024