Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)

Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:

• How to enable product and ops to work well together

• How to run great product reviews

• How to make good decisions with limited data

• How he uses the jobs-to-be-done framework at Opendoor

• How to stay calm under pressure as a leader

• Wild stories from his time at Uber

• Challenges faced at Opendoor during the pandemic

• Much more

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Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin

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Where to find Brian Tolkin:

• X: https://x.com/briantolkin

• LinkedIn: https://www.linkedin.com/in/briantolkin/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Brian’s background

(02:14) Career beginnings at Uber

(02:49) Transitioning from product operations to product management

(06:47) Product and operations synergy

(10:00) Surge pricing at Uber

(12:18) Scaling challenges, and stories

(15:47) Opendoor and Covid adaptations

(25:38) Product reviews and Jobs to Be Done

(40:30) The challenges of A/B testing

(42:23) Increasing conviction in solutions

(44:33) Leveraging intuition in product decisions

(47:07) Partnering with Zillow

(52:55) Staying calm under pressure

(56:25) Finding the “kernel of truth” in product management

(01:00:21) Failure corner: Early days of Uber Pool

(01:06:11) Lightning round and final thoughts

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Referenced:

• Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

• Opendoor: https://sell.opendoor.com/

• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion

• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennyspodcast.com/the-ultimate-guide-to-jtbd-bob-moesta-co-creator-of-the-framework/

• Zillow: https://www.zillow.com/

• Zillow, Opendoor announce multi-year partnership: https://investor.opendoor.com/news-releases/news-release-details/zillow-opendoor-announce-multi-year-partnership

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Stripe Atlas: https://stripe.com/atlas

• Founders podcast: https://www.founderspodcast.com/

• Uber will deliver ice cream to you today: https://www.dispatch.com/story/lifestyle/food/2016/07/13/uber-will-deliver-ice-cream/24201840007/

• UberKittens: https://www.uber.com/newsroom/uberkittens/

• UberPuppies: https://www.uber.com/blog/uberpuppies-want-to-play/

• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-NIKE/dp/1471146723

• The Black Swan: The Impact of the Highly Improbable: https://www.amazon.com/Black-Swan-Impact-Improbable-Incerto/dp/1400063515

• The Design of Everyday Things: https://www.amazon.com/dp/0465050654

• Shantaram: https://www.amazon.com/Shantaram-SHANTARAM-Paperback-GregoryDavidRoberts/dp/B00QPVJESC

• Full Swing on Netflix: https://www.netflix.com/title/81483353

• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890

• Break Point on Netflix: https://www.netflix.com/title/81569920

• Air on Prime Video: https://www.amazon.com/AIR-Matt-Damon/dp/B0B8Q3JMCG

• Fi smart dog collar: https://tryfi.com/

• Particle: https://particlenews.ai/

• Sara Beykpour on LinkedIn: https://www.linkedin.com/in/sarabeykpour/

• A new-parent gift guide for product managers: https://www.lennysnewsletter.com/p/a-new-parent-gift-guide-for-product

• Jeff Holden on LinkedIn: https://www.linkedin.com/in/jeffholden/

• Travis Kalanick on X: https://x.com/travisk

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.