Brian Tolkin, Head of Product @Opendoor: How to Hire the Best Product Teams | E1257

ℹ️ EPISODE INFO

Released

February 7, 2025

Duration

46m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

Brian Tolkin is the Head of Product @ Opendoor where he has spent the last 6 years and is responsible for product strategy and product and design teams. Before Opendoor, Brian spent an incredible 5 years at Uber through their wildest growth periods. ---------------------------------------------- In Today’s Episode We Discuss: (00:00) Intro (00:44) Lessons from Launching Uber China Pool (04:18) Worst Product Decision at Uber (05:55) How AI is Changing the Role of Product Managers (08:15) How AI is Transforming Product Development (11:55) Balancing Growth vs. Technical Debt at Series A (13:23) Should the CEO Also Be the CPO? (13:51) Lessons in Expanding from Single to Multi-Product (17:16) The Power of Simplification: Finding the Kernel of Truth (21:35) Are People Naturally Suited for Certain Company Stages? (23:34) Speed vs. Taste: What Matters More in Product Development? (28:07) Dictatorial Product Leadership vs. Collaborative Decision-Making (32:32) Lessons from Hiring Mistakes (36:54) The Best Backgrounds for Hiring Great PMs (40:24) Managing Momentum as a Product Leader (41:39) The Case for Staying Longer at One Company (43:13) Quick-Fire Round ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Brian Tolkin on Twitter: https://twitter.com/BrianTolkin Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #briantolkin #uber #venturecapital #product #hiring #headofproduct #startups #teambuilding

🎤 SPEAKERS

• Harry Stebbings

  host

• Brian Tolkin

  guest

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Harry Stebbings and Brian Tolkin, Brian Tolkin, Head of Product @Opendoor: How to Hire the Best Product Teams | E1257 explores brian Tolkin Reveals How To Build, Prioritize, And Hire Product Teams Brian Tolkin, Head of Product at Opendoor and former Uber product leader, discusses his biggest product wins and mistakes, notably UberPool’s upfront pricing and missteps in defaulting users into Pool. He explains how AI is collapsing traditional product-development workflows while leaving core PM skills—customer understanding, problem definition, and business alignment—unchanged.

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