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Brian Tolkin

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2024-08-04
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2024-08-04
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  1. “They think about this problem 40, 50, 60 hours a week, and you might think about this problem three hours a week, right? So you bring a breadth, the team brings a depth, and honey marry that.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Yeah, I think definitely part of the culture, but also I'm a firm believer in general that the people closest to the problems also have the best context to solve that problem. And so as a more senior voice in the room, often the job is probing, asking questions, throwing out ideas in a way that says like, hey, this is an idea. This is not a mandate, right? This is a thought, right? And if there's context missing that would inform the product direction, then providing that context in not a question asking sense, but hey, this is context that you might not be aware of. And so I think it's all in how you show up as a leader and what that looks like in terms of probing and pushing the team on dimensions that they've not made that they may not be thinking about and then understanding that the team is bringing a perspective that you don't have, which is”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Also, most importantly, I think this is the primary goal is to help make the product better, right? To help the teams think through a problem and to have that, again, back to our earliest conversation be a very intellectual conversation about the work and how to make the product better and not super scary. Like product reviews hopefully are not feeling like firing squads. That's a scary environment to be in and not necessarily one that's conducive to how do we make the product better obviously sometimes the conversations have to get a little intense, but in general that's what we're shooting for is something that helps the team go back and think through how to make the product better.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “Very kind of whoever mentioned that. But yes, big, big fan of doing them. Actually, in particular, to maybe bridge the conversations in companies that have ops-driven cadences or start out very ops driven because the cadences can sometimes be different. And so the operational cadences that you might have something like a WVR, a weekly business review may not be conducive to always picking your hat up and saying like, hey, where's the product going on a slightly longer time frame? And so I think product reviews in general for all companies are probably really helpful, but actually in particular for some of the product and operations led companies in terms of things I've learned, I think being really intentional about what the goals are, I think it's okay to say that there are two goals, a goal of sort of like accountability and inform to an audience.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “And so there's always another hill to climb. And so I think that was one of the things at Uber and OpenDoor where there's sort of this culture of on the ground experimentation that's really helpful. Yeah, like we were just talking about driver onboarding may now be solved with technologies. So maybe a few extra hours a day. Like how do we get better at optimizing the Uberx system? How do you start tinkering with food delivery? How do you start thinking about higher capacity vehicles? Have you think about better feedback loop for those manual surge pricing sort of toggles that we talked about? So I generally agree it just generally frees up capacity to solve more problems.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Yeah, I actually don't fundamentally, it depends on what the operations is, but I don't fundamentally disagree. But I think the right lens to think about it is. And then those folks can move on to the next challenge.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “At the time, it was probably dozens, if not hundreds, of people running these onboarding sessions all over the country world at the time to do other stuff. And so now you can sort of level that up and say, okay, do we do more analytics? Do we do more, figure out the next process that needs optimization or whatever the case may be in that virtual cycle just continues?”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “That was the next set of scale. But that now suddenly we have a different problem, which is okay, you have to validate all of these credentials. So most driver's license, who they are, all that stuff. At one person, easy. At three to four at a time, easy, 10 at a time, a little more challenging, but fine. At 20 at a time, okay, you're starting to run up onto it. Now at fast forward six months and you're doing a thousand a week or whatever, okay, suddenly your system breaks. And it's like, okay, we have reached the point where like operational system improvements is no longer viable.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Yeah, I mean, maybe a very. Easy good example to pick just one part of the Uber process in the early days is at small scale, actually back when it was the Uber Black drivers, every driver was individually onboarded in like a 90 minute to a two-hour in-person in the office onboarding with deep setting of expectations. The next version of that, so that's obviously very ops-driven. The next version of that is kind of like a small classroom typesetting of three or five or six drivers at a given time, also very obstruct. And then as we got into more mass market products like Uber Taxi or Uber X, I was like, okay, maybe 20 or 30 at a time. Okay, so now it's a little bit bigger classroom setting. And we said, okay, let's make a video. Instead of giving verbally the same presentation, let's just make an onboarding video.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “It becomes a little bit more of a paramount. One other thing. Last thing I would say is I think the companies evolve as well. So what I talked about at the beginning of Uber being very focused from an engineering and product side on the dispatching system and the pricing system, obviously over time that's evolved. Now there's centralized all of these functions as the company got bigger and more mature and scale and optimization started to be more important and expansion and sort of that petitish of trying new stuff and the tools got better and the tech got easier and there was more internal infrastructure. And so over time things can start one way and shift over time as the business needs.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Scarcity of resources. And so I think the second one is being really intentional about where those tech resources are and then being really forthcoming and saying, hey, that means all these other places where yes, it can make things easier, more efficient, etc., etc. We are okay not investing in right now. And that needs to be an explicit decision and very transparent. And then the last bit, I would say, is a deep understanding that The real world has entropy and it's hard and it's messy. For us at Open Door, we go into homes. Someone may not be home scheduling may be off at Uber or driver may cancel. There may be a low GPS. All these things happen, right? Computers are deterministic, but humans aren't, right? And so building products that have a little bit more flex or a little bit more fail safes in case those things happen.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Yeah, the first one we touched on, which is hey, there's just got to be mutual respect, right? Both functions have their time and their place and their skill sets. And you just don't build big businesses of this type without respecting the fact that they both need to exist. The second, particularly on the product and engineering side, is really understanding where and how the technology leverage comes from the business and then being really focused on making sure generally especially in the earlier days you are more limited on the technical resourcing side than you might be on the operational resourcing side. And so how do you be really focused on where to invest your time effort and energy technically, which is why most of the engineering effort for Uber was on the dispatching system and the pricing system. That's just where the leverage was at the time given the”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “We're a digital platform to buy and sell real estate. The core product today is a seller focused product where people can go online, enter some information about their home, and I'll cash offer to be able to sell sort of simplicity and certainty. And yeah, so the product really works for people who have a want something that is certain and simple and easy. I don't know if you've ever sold a home, but it can be a very, very valuable. Stressful, difficult process with showings in open houses and how to price it, and will it sell and all of that stuff. And so we offer basically a way to skip the whole process.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “More when you do. So again, a fond memory to look back on a very stressful time in the moment where it feels very, ready to go.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Yeah, I mean, another one more recent for Open Door was when COVID hit, right? We physically, we buy and sell homes. And so we were physically going into people's homes and, you know, in March 2020, like going into people's homes was not something people were comfortable with. And you look at the real estate data coming out of China at the time and it looked like sort of coming to a standstill. And so we actually turned off the core business and we stopped buying homes for a few months. Hey, we can't go in and we don't know if anyone's going to be buying any homes. And so, you know, what do we do? And we took those few months that are in came out the other side and had virtualized the whole process and it was pretty stressful, right? Because you're looking at a business that relies on going into people's homes and suddenly you can't do that.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “Is it working? And we're like, oh my God, now whatever 5 p.m. the day before, we're supposed to go live, 6 p.m., 7 p.m. Okay, let's get on the phone with the US, try and figure out what's going on. I remember I slept about 30 minutes that night between 2 and 3 a.m. Being like, okay, like we have to go live at 6 a.m. I think there was some press around it. Like we were planning on going live. And I think we got everything finally working at probably about 530 or 6 in the morning and launched just in the nick of time. And I'll never forget it was we launched. It was great. We monitored. Everything was good. And then we walked out for breakfast at like 7.30 in the morning. Everyone sleep depraved. No one slept all night. And we got this like pancake street food things. And I have to imagine they were not that good. But in my mind, it was like the best meal I've ever had in my life.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “One that Good about scaling Uberpool in China is yes. So we were launching Uber pool in China, and this was going to be China at the time was pretty big for Uber, but Uber Pool was not there yet. And so we're going to launch and myself and a few other folks were in Chengdu, China, which is the first Chinese market that we were launching with Mapula in. We were going to be on the ground to launch. We wanted to go live at, I believe it was 6 a.m. for rush hour on. Whatever Monday morning. And sort of there over the weekend getting ready to set up. And at the same time, we were doing some data center testing. And so we flipped on all the testing infrastructure and thought I was going to work and nothing works. And the matching algorithm”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Yeah, so in the early days of Uber, one kind of fun story is obviously Uber acts as a mainstream product, but has a kind of funny, silly name, Uber, Uber X. This product in the early days was going to be all hybrid and added bunch of different potential names. I was not personally driving this. This was someone else on the operations team, but they built the model for what this product could be. And there was no name for it yet. So it was going to be a placeholder. So what do you put as a placeholder? X. So Uber X, and then the company was moving quickly enough. The product got greenlight and launched. And here we are, I don't know, 12 years later, 11 years later, whatever it is. And UberX is the name that stuck.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Yeah, I think it was probably a function of a bunch of stuff, one of which is like, hey, this is a fairly new concept and it's powerful and dangerous. And so let's make sure we understand what's happening. The second is kind of this belief that, yeah, local city teams know their cities best. And so you might know that an event is happening, a baseball game gets out, right? And it's like, oh. I know that this baseball game is going to get out at 10 p.m. So I'm going to set surge at 9 45. And the algorithm may not be able to pick that up. And then the third is, yeah, the technical constraint of like nowadays, clearly it's all automated, but it's really hard to build a fully dynamic, always on geospatially aware pricing system and not just a little bit of time.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “That would have been probably a little bit before my time. But that being said, one thing that is true is that. Surge pricing for actually quite some time, all of 2012 certainly, 2013, probably, I don't know, when we necessarily switched was very much a human in the loop system or a very manual system where GMs in every city would control basically the parameters in which Surge would operate. And so much of the time that would mean, for example, like Monday through Friday, there would be no search. Like it was just it couldn't flip on. And then Friday nights and Saturday nights it would flip on from whatever you set 7 p.m. to 3 a.m. And the cap was, you know, X whatever the cap was. And then within those parameters, the algorithm would optimize for what the price was. But yeah, GM controlled whether it was on or off and what geographies were surging.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “I don't think so because at the time, I believe Google had a function. I don't remember what Google called it. It was something slightly different, but I met with a few folks who had been in similar type roles at Google and a couple other places. So I don't take credit for certainly for inventing it. And other people have sort of actually dabbled in this model at Uber before me. There was just a formalization of it and their actual building up of the organization.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Yeah, sure. So I should probably define what operation flaws at Uber. It was basically this notion that we had a centralized, this was later in my career at Uber, but we had a centralized product team building stuff mostly in San Francisco, not strictly their offices, but at this point around the world, but mostly in San Francisco. And then we had a very globally distributed operations team. And there was sort of a bi-directional feedback loop that wasn't super strong in that feedback loop was basically when the EPD teams in San Francisco built new features. How do we effectively put it in global markets? And then how do we effectively get input from global markets to better build features? And so one solution to that problem, our solution at the time, was to start up a new function called product operations who had accountability and reported into operations, but physically sat with”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “San Francisco can't be in an open doors case 50 markets walking houses every single day. In Uber's case, you know, whatever, a thousand cities. Safety in South America, right? It's just like not possible. But what you can do is foster a really good relationship and a really good feedback loop of how people who do deeply understand those things can help give insights. Now it's actually the birth of product operations was sort of that insight as well.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “Yeah, it's a great question. And I think Uber always had this mentality in Open Door does too of kind of like a twin turbine jet plane where you can like 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. And I think that's really true, right? The reality is operations teams, local teams can iterate faster. scale talking to customers really much more efficiently have great qualitative insights. And so if it's seen more as like a harmony instead of a competition, I think that's really, really helpful, where it's like, okay, how do we get the insights that are happening day in and day out in the field on the ground, whatever that may be, and help us build better products because of that, right? Like a pm sitting in”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “Starting on the operation side gave a really deep understanding of how the business actually works. You are truly operating it day in, 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. 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. 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 way?”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “I've slept on my floor in China before launching Uber Pool. And like when you reflect the stress onto your teams, everybody tenses them. It counterintuitively doesn't produce better outcomes.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “Give him 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?”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “Uber always have this mentality, and Open Door does two 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.”

    2024-08-04 · Lenny's Podcast · Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · IDENTIFIED FROM THE TRANSCRIPT · source