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

**Lenny Rachitsky** (0:00)
You've worked at two businesses that have done incredibly well combining product and ops.

**Brian Tolkin** (0:03)
Uber always have this mentality, and Opendoor does too, of the product operations, twin turbine jet plane, where you can fly the plane on one engine for a little bit if you need to, but it's operating most efficiently and effectively if both are working together.

**Lenny Rachitsky** (0:17)
What has having been in ops done to make you a better product leader?

**Brian Tolkin** (0:21)
Given really deep understanding of how the business actually works, it's a pretty good foundation for them going on to say, okay, what do we actually want to build in a more scalable technology?

**Lenny Rachitsky** (0:31)
Something else I've heard that you're very good at is staying very calm under pressure.

**Brian Tolkin** (0:34)
I've slept on the floor in China before launching UberPool, and when you reflect the stress on to your teams, everybody tenses up. It counter-intuitively doesn't produce better outcomes.

**Lenny Rachitsky** (0:50)
Today, my guest is Brian Tolkin. Brian is currently head of product and design at Opendoor. Before that, he spent nearly five years at Uber, where he joined as employee 100, before Uber had UberX or UberPool or any kind of shared rides. He actually started on the ops team at Uber, moved into product, ended up leading product and launch of UberPool, and then taking it global. He also started the product operations function at Uber, before that function was really even a thing, which I didn't know until the chat that we had. In our conversation, Brian shares a ton of lessons about building products with a heavy operational component. Also how to run great product reviews, how he implements the jobs to be done framework at Opendoor successfully, the story behind Zillow trying to compete with Opendoor failing and then partnering instead, plus a ton of great stories from the early days of Uber and Opendoor, and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Brian Tolkin.
Brian, thank you so much for being here. Welcome to the podcast.

**Brian Tolkin** (2:00)
Thank you. Appreciate it. Thanks for having me.

**Lenny Rachitsky** (2:02)
First of all, just a huge thank you to Kayvon Beykpour for connecting us, introducing us. He said all kinds of amazingly nice things about you. He also gave me some very hard questions to ask you. I hope you come prepared.

**Brian Tolkin** (2:12)
Terrific. Put me in the Ops seat.

**Lenny Rachitsky** (2:14)
Okay. I want to spend a bunch of time talking about product and ops. You started your career in operations at Uber. You actually started on the ops team, and you moved into product. You've also worked at both Uber and at Opendoor, which have both huge operational components. I think it's really rare that people want to see a company scale to the heights of Uber and Opendoor with such a heavy operational component that are still tech companies. And also it's really where someone starts an ops and then moves into product and ends up where you are, where you're a chief product officer, really successful company. So I have a bunch of questions here. Maybe the first is just, what has having been in ops done to make you a better product leader? How does that change the way the operator is a product leader?

**Brian Tolkin** (2:58)
Starting on the operation side, give a really deep understanding of how the business actually works.
You are truly operating it day in and day out. And the success of the city is in large part driven by the inputs that you are putting into it every single day on the ground and whether or not those rain that weekend, which was a nice driver of metrics. But talking to customers every single day, like one-on-one onboarding drivers, responding to support tickets, there's no centralized support team. There was no closer to the customer. So I think that foundation actually for really understanding what moves the business and being super close to the customer, actually is a pretty good foundation for them going on to say, okay, what do we actually want to build in a more scalable technology?

**Lenny Rachitsky** (3:51)
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