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

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

5 • 1.5K Ratings

🗓️ 4 August 2024

⏱️ 75 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 [email protected].

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Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Transcript

Click on a timestamp to play from that location

0:00.0	You've worked at two businesses that have done incredibly well combining product in Ops. can fly the plane on one engine for a little bit if you need to, but it's operating most
0:14.4	efficiently and effectively if both are working together.
0:17.3	What has having been in Ops done to make you a better product leader?
0:21.7	Give a really deep understanding of how the business actually works.
0:24.9	It's a pretty good foundation for them going on to say,
0:27.5	okay, what do we actually want to build in a more scalable technology thing?
0:31.0	Something else I've heard that you're very good at is staying very calm under pressure.
0:34.4	I've slept on the floor in China before launching Uber Pool and like when you reflect the stress
0:41.2	onto your teams, everybody tenses up up it counterintuitively doesn't produce better outcomes
0:50.6	Today my guest is Brian Tolkien Brian is currently head of product and design at Open Door.
0:56.0	Before that he spent nearly five years at Uber, where he joined as Employee 100, before Uber had UberX or Uber Pool or any kind of shared rides.
1:05.7	He actually started on the Ops team at Uber, moved into product, ended up leading
1:09.2	product and launch of Uber Pool, and then taking it global.
1:13.2	He also started the product operations function at Uber before that function was really
1:17.1	even a thing, which I didn't know until the chat that we had.
1:20.6	In our conversation, Brian shares a ton of lessons about building products with a heavy operational component
1:26.4	Also how to run great product reviews how he implements the jobs to be done framework at open door successfully
1:31.9	The story behind Zillow trying to compete with
1:34.4	Open Door, failing, and then partnering instead.
1:37.2	Plus a ton of great stories from the early days of Uber and Open Door, and so much more.
1:42.2	If you enjoy this podcast don't forget to
1:43.8	subscribe and followed in your favorite podcasting app or YouTube. It's the best way to
	...

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