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JM Nickels: Why conscious leaders beat optics-first managers

Through self-aware presence, an honest objective function, and first-principles vision; Uber, Waymo, DoorDash veteran treats fear, sadness, anger, joy as data.

JM NickelsguestLenny Rachitskyhost
Oct 6, 20241h 18mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:02

    Introduction to JM

    1. JN

      Get clear on your objective function. And one way that I've gotten clear on it is, like, trying to think about it from future me. 'Cause like five years from now, I'm not gonna give a shit if I made the presentation slightly better, but I'm gonna care a lot about what kind of relationship I have with my daughters. And like, that means that th- the next action, the next thing I do today and tomorrow, those will translate into the relationship with her, right? Not to be, like, morbid, but just again, most of us just aren't really tuned into an awareness that our lives will come to an end. We try to pretend like we're gonna live forever and just not think about it, and the horror of it is that we succeed, right? We mostly manage to just go live our life and eat ice cream and go to work and go on vacation and do what we do. To me, an awareness and mindfulness that our lives will come to an end punctuates reality in a way that requires me to rethink my priorities.

    2. LR

      (instrumental music) Today, my guest is JM Nichols. JM has been a product leader at Waymo, DoorDash, and Uber. He's also an engineering manager at Groupon, and before that, an equity trader at GetGo. At Uber, he built and launched the very first version of Uber Pool, and then went on to lead the team responsible for the infrastructure and algorithms powering the economic and logistics brain behind Uber's matching and pricing systems. At DoorDash, he was head of product for DoorDash platform. At Waymo, he led product for the commercialization of autonomous ride-hailing and last-mile delivery. And he recently returned to Uber to lead product for their mobility team. This conversation is a unique and beautiful mixture of hard skills, soft skills, tactics, and emotions. I won't give away too much about the conversation, but this is a powerful one. Tears are shed, stories are shared, and I am confident you'll become a better leader and human having listened to JM's insights and lessons. 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 JM Nichols.

  2. 2:02 – 3:41

    Conscious leadership explained

    1. LR

      JM, thank you so much for being here and welcome to the podcast.

    2. JN

      Thank you, Lenny. Thanks for having me. I'm thrilled to be here. Um, really appreciate your dedication to helping product managers kind of, like, improve their craft and uplevel. There's not a lot of great resources out there for that. And coaching and development, as I'm sure we'll get into, is a, a passion of mine as well. So, we have a lot of shared interests there.

    3. LR

      Aw, I really appreciate that. I wanna start with a phrase that came up again and again when I asked people what to talk to you about from your colleagues. And this phrase is conscious leadership. What is conscious leadership? What does this phrase mean?

    4. JN

      To me, leadership is, uh, broadly defined as having influence in the world. And so by that definition, to me, everyone is a leader, right? Because we all have influence in some way. You know, it's, it's not about whether you're a manager or not. It's like, I have influence on my kids, or my partner, or my community, right? The world, the way I vote, the way I show up, right? So we all have influence. We're all co-creating, you know, uh, kind of, uh, influences of each other. So, so that's the leadership piece. So just like, the, the conscious piece then is becoming more aware, waking up, right? To me it's like, learning more about my interior world, you know, what, um, you know, my background is, my biases, you know, we all inherit sort of kinda certain belief systems from our parents or our church or our community, and a lot of times they kinda go unquestioned and then they end up in conflict. And so it's really just about, um, becoming more aware and then taking responsibility for the influence that I have. So yeah, taking responsibility for my influence in the world.

  3. 3:41 – 7:34

    The power of soft skills

    1. JN

    2. LR

      As you talk about this, something that came up and something that I thought about as I was preparing for this episode is this idea of soft leadership, the power of soft skills, and just how important that is in success. Is there something there that comes up when I say that, just the power of soft skills and the importance of those in being successful?

    3. JN

      Yeah. Yeah. It's, uh... What was it? Theodore Roosevelt, "Speak softly and carry a big stick."

    4. LR

      Mm.

    5. JN

      Um, yeah, I think I've evolved in that department. I think when I was younger in my career, I thought it was really important that, you know, I gotta show up to the meeting and have the right slides and be the loudest, brightest voice in the room, and you know, that's sort of the way, the way to have influence. And, uh, you know, there's certainly a place for, you know, having leadership in a meeting and presenting a point of view and helping guide the narrative, but to me it's, uh... Yeah, I, I'd say I've evolved more towards sitting back. It's also as I've become a more senior leader, I'm aware that there's, there are power dynamics there, there's imbalances, right? Where junior folks don't feel as comfortable speaking up or I say something's not a good idea and then they're like, "Well, I don't want to disagree with JM." You know? So it's like, back to being more aware of my influence in the world, like, I really try to spend more time being mindful of that and say, you know, "I want to hear from other people first. I want to create space." And like, I don't need to win the argument in the meeting, right? Like, I, there can be a follow-up, right? There's, it's not like (laughs) you know, it's my last chance to say something. But that's also more true when you're more senior, right? 'Cause when you're more junior, it's like, well this is the one presentation I have with Dara for the next six months, right? I really gotta nail it. And so the pressure is a little bit different. Yeah.

    6. LR

      (instrumental music) This episode is brought to you by Pendo, the only all-in-one product experience platform for any type of application. Tired of bouncing around multiple tools to uncover what's really happening inside your product? With all the tools you need in one simple-to-use platform, Pendo makes it easy to answer critical questions about how users are engaging with your product, and then turn those insights into action, all so you can get your users to do what you actually want them to do. First, Pendo is built around product analytics, seeing what your users are actually doing in your apps so that you can optimize their experience. Next, Pendo lets you deploy in-app guides that lead users through the actions that matter most. Then, Pendo integrates user feedback so that you can capture and analyze what people actually want. And the new thing in Pendo, session replays, a very cool way to visualize user sessions. I am not surprised at all that over 10,000 companies use it today.Visit pendo.io/lenny to create your free Pendo account today and start building better experiences across every corner of your product. PS, you want to take your product led know-how a step further? Check out Pendo's lineup of free certification courses led by top product experts and designed to help you grow and advance in your career. Learn more and experience the power of the Pendo platform today at pendo.io/lenny. (singing) Pendo. This episode is brought to you by the Enterprise Ready Conference, a one-day event in San Francisco bringing together product and engineering leaders shaping the future of enterprise SaaS. The event features a curated list of speakers with direct experience building for the enterprise, including leaders from OpenAI, Vanta, Checkr, Dropbox and Canva. Topics include advanced identity management, compliance, encryption and logging, essential yet complex features that most enterprise customers require. If you're a founder, exec, product manager or engineer tasked with an enterprise roadmap, this conference is for you. You'll get detailed insights from industry leaders that have years of experience navigating the same challenges that you face today. And best of all, it's completely free since it's hosted by WorkOS. Spots are filling up quickly. Make sure to request an invite at enterpriseready.com. That's enterpriseready.com.

  4. 7:34 – 12:41

    Navigating Uber’s evolution

    1. LR

      There's a couple of threads I want to follow here. But first, um, I was thinking as you're talking, when people think, uh, Uber and people that work at Uber, I don't think they imagine people like you. (laughs)

    2. JN

      (laughs)

    3. LR

      And I know you were there early and then you joined again. Is that, was that ever like a, what, um, "Is this a place for me?" Did you ever go through that struggle or is it just... Yeah, I don't know.

    4. JN

      Yeah. Yeah. I mean, I, I would say I have been fortunate to experience probably three Ubers at this point. You know, we joke about Uber 1.0, the Travis era. And you hear a lot about, you know, in the media the kind of bad parts of that. But there were some really good parts too. I mean, I think, you know, there was a lot of... Like, when I joined in 2014, you know, there, there was this mission of making transportation as reliable as running water for anyone anywhere, which is, you know, bold, audacious and maybe a little bit, um, pretentious from a little bit of Silicon Valley, uh, (laughs) edge. But, uh, but, but you could feel the electricity in the air. There was this, like, energy and this excitement like we're doing something transformational, like autonomy's coming, you know, car ownership will change. And it just like, it just, uh, it's on the feel, like my vibration, you know? And then yeah, like the good parts of that era were like, you know, Travis was a very great visionary product leader. You know, we started ATG and Elevate and sort of these sort of future-forward things. And you know, the way he would conduct product reviews, I learned a lot. Like he... You know, it was stressful at the time. But like looking back, I was like, "Oh, I learned a lot." But yeah. I would say it was not a very conscious leadership sort of place. You're right. It was a, it was like many organizations that run on fear because you can do that, you know? Carriage and sticks do work. But actually that's kind of how I found this work is it was like in 2015. And I was a very junior product manager at that point, you know, kind of in over my head in a fast-growing place and these weekly reviews with Travis. Uh, because we were building out UberPool. And, uh, I had a six-month-old daughter, my first-born, and we had just moved to San Francisco from Chicago. So my whole life was kind of in a flux and it was, yeah, a very stressful place. And I was like, "I, I think I'm gonna snap. I don't (laughs) think I can handle this." And that's kind of what led me to start to explore the sort of inner work and, yeah, meditation and sort of like finding a way out of that. And that's what got me interested in bringing it to teams too is because like, I remember I was in one meeting where we were working on this future of pricing thing, which is like, you know, rider pricing, driver pricing and incentives and how we up, bring surge pricing and all that together and like gets very, you know, I'll go heavy and, and e- We have all these PhDs in the room, right? Some of the best minds in the world, you know. We, we were able to hire, you know, people like Garrett Van Rysn, who, like was, you know, the foremost

    5. NA

      (laughs) .

    6. JN

      ... OR person, right, from, from Columbia and other people. But everyone's like, uh, back to lizard brain, everyone's like arguing. They're like, "Well, no, I think we should do it this way or this way." And then it's like... (laughs) And I was like, "Huh." It's like as much as I enjoy the content of this, like believe me, I'm an Outgo PM end to end, I love that stuff. But I was like, "I don't think this conversation actually needs another, like, uh, you know, PhD," or I'm not even a PhD, but content expert, right? It's like what we need here is a way to like, whew, you know? (laughs) Like shift again back to that, you know, out of that fear, threat, uh, righteousness sort of state into a more co-creative, collaborative, open-minded, curious, trusting sort of space. And that wha- that got me interested in kind of, per- you know, pursuing more skills and coaching, uh, of individuals and teams. So. But yeah. To your Uber question, yeah, the Uber 1.0 was crazy. Uber 2.0 was kind of like, you know, Travis is out. The board is feuding. There's leaking to Mike Isaac, whatever, and then Dara comes in and, you know, kind of the peacemaker and, and then tries to stabilize but the IPO is rocky and... And so now I would say we're in Uber 3.0 which, you know, is, well it's full pirate ship to Navy, in Reid Hoffman's words. Uh, you know, profitable company. We're printing free cash flow, we're in S&P 500, right? Like, you know, we've, we've, we've kind of established, um, an independent contractor model, right, in a lot of states and jurisdictions. And, uh, you know, it's like there's less kind of the, you know, risk of that model changing. And, and, and yeah. We're, I would say we're in a area, uh, an era now of kind of Cambrian explosion of different types of transportation. You know, the company kind of really just built the UberX model and scaled it out to the world, and that's primarily how we got here. And now it's like, you know, we're going after all these different new sort of modalities whether it's reserving a ride in advance or shared rides or, you know, renting a car or buses. And then different, um, supply types too, right? Like it's, it's not just contractors, right? We have a lot of fleets in the platform. We now have a lot of taxi drivers in the platform. We've seen we've signed deals with Waymo and Cruise and other autonomous players. So, like, I feel like we're now at the beginning of a, another era of Uber, right? And transportation that, you know, the next decade or two is gonna be like super exciting.

    7. LR

      One quick tangent. UberX, a previous guest shared that the name UberX came from, it was just like the internal code name-

    8. JN

      Mm-hmm.

    9. LR

      ... UberX and we'll figure out a real name later. And then it just, it (laughs) it stuck and no one had a better name. Is that-

    10. JN

      Yeah.

    11. LR

      ... is that true?

    12. JN

      Yeah, that's right. I think that's right.

    13. LR

      That's amazing.

    14. JN

      That was before... When I joined, we were already scaling UberX rapidly. I joined-

    15. LR

      Mm-hmm.

    16. JN

      ... in early 2014.

    17. LR

      That's amazing.

    18. JN

      Um, but I did, uh, help name UberPool, UberPool which I- I, uh-

    19. LR

      What?

    20. JN

      ... uh, selfishly li- like to bring back. Uh, uh, it got renamed to Share, uh, during my-

    21. LR

      Oh, wow.

    22. JN

      ... uh, external APM rotation,

  5. 12:41 – 21:46

    Embracing emotions and inner work

    1. JN

      but-

    2. LR

      Okay. I wanna come back to the kinda the thread that we, that I pushed us off of, which is, um, you talked about, you made this really interesting point about emotions. And this is something I've been learning myself recently with having a kid and also pr- couple re- previous guests. So you say that when you have... So w- you're in this meeting, you're stressed, there's lizard brain kicking in. Something's like, "Oh, Dara's gonna think I suck and it's gonna really screw my career if I mess up this presentation." Your advice there is very counterintuitive, I think, for a lot of people, which is accept that emotion. Because when I feel, like, stressed and nervous in a meeting, I'm not, "Embrace the nervousness, let it out." It's more I'm just like, "No, it's fine. Gonna be okay. Don't worry about it." Talk about why that is actually more effective.

    3. JN

      Yeah. Yeah. It's like, uh, my daughter the other day was, uh, you know, had some nightmares and she was like, "Dad, how do I stop, uh, thinking thoughts that, you know, kind of, you know, uh, about the nightmare or whatever?" And I was like-

    4. LR

      Mm-hmm.

    5. JN

      I said, I said, "You can't. Don't try to stop the thought. Just allow it." You know? I was like, uh, "Let me show you why that doesn't work." I said, "Don't think of a pink elephant. (laughs) What'd you just think of?" And she's like, "A pink elephant." And then now she thinks (laughs) it's hilarious to tell her sister, "Don't think of a pink elephant." (laughs) But yeah, I think you're right, it is a little counterintuitive. But, like, one of my first coaches actually had a great phrase, uh, "What you resist will persist, and what you fear will appear." And so in my experience, this is wh- another reason why becoming more aware of my internal world is so, uh, been so important. I have more agency than I realize on the outcome of my experience, right? And so when I think a thought like, "Dara might think I suck," and then I have a thought that I suck, that can become a self-enforcing negative feedback loop where I have a thought that creates stress, anxiety, fear, and then that triggers more thoughts. And we call it cognitive emotive loop where you're kind of in this cycle of, like, thinking stressful thoughts and then having unpleasant, you know, anxious, fearful feelings. And so one way to break that, yeah, is to just allow it and not try to fight it with other thoughts. (laughs)

    6. LR

      Mm-hmm. So the advice is, like, very tactically, it's you're in a meeting with Dara, you're stressed about something, just allow it. Let it be. Don't try to pr- pre- pretend like it's not there or don't try to convince yourself it's not real.

    7. JN

      Well, that would be the first step is just to allow whatever's here, thoughts and emotions are arising. It's, uh, you know, they come, they go. Uh, they're transient. It's not permanent, right? It's, um, there's a lot of wisdom I think in the Buddhist lineage around those, those concepts. And then, uh, the next piece for me once I can take a breath and relax a little bit is coming home to the fact that I, uh... And this is maybe a little more radical for some people. I don't actually need Dara to approve of me and my presentation in order to be okay. Right? Like, what I'm up to over here is trying to s- force, um, self-worth and self-love from within. And so, you know, we talk about, like, approval, control and security. It's very easy to look for that from the world, right? Do you approve of me? And if not, can I control outcomes to get approval or get security and get, you know, the job, the bank account, the house, whatever it is? But what I kind of, uh, woke up to at one point was that as long as I was going out there looking for all that stuff to try to complete something inside of me that was missing, it was like I was like a hungry ghost. It's like it doesn't matter how many Michelin star meals and promotions and money and title and whatever, right? It's like it's never enough. It's like you kind of enjoy it for a little bit, and then you get back to like, "Hmm." You know? So it's, it's like a never-ending, like, sugar addiction. And so that's kinda the next step for me is, like, allow it. Yes, allow the emotion, allow the thought. R- come home to, "I, I am okay, even if Dara does think I suck." (laughs) And then also, uh, it's not, you know, it's not permanent, right? Like I mean, it's like sure, there might be some high stakes things in life where you only get one shot. But for the most part it's like, you know, if I screw, if I didn't do a great job on this presentation, you know, there'll be another one, right? Like, it's okay. You know? It's, and think of it as practice. The other thing is like from the fear threat state, I'm like, "Uh-oh, this is a risk." Alarm bells, right? You know, like, "My career could be over." Whereas if I'm in that trusting, curious, open space, it's like, "This is an opportunity for feedback." You know? "How can I learn? How can I get to become a better presenter?" You know? It's like the feedback, uh, from others is no longer a threat, it's actually a gift. It's like, you know, I, it's like, uh, you know, information, right? Uh, that I can use or not use to, uh, you know, alter how I show up in the future and the skills I develop and all that good stuff.

    8. LR

      I imagine some people may hear this and feel like if Dara or Travis or whoever is like, "Thinks I suck, my career is at stake and that really matters and everything's gonna fall apart in my life because I get fired," you know, there's like stakes involved with messing up. Is there anything that helped you get past that and not worry so much about just, like, this trickle effect of all the things that could go wrong if you mess something up in an important high stakes meeting or presentation?

    9. JN

      Yeah. Again, and maybe it is a little paradoxical, but what I found was, um, the more I focused on, uh, yeah, the how I show up and optics and having a good deck and all this, the less I got promoted. And then the more I dropped focusing all that... 'Cause like for my first few years at Uber, I was okay, and I was a senior PM, and then I finally got in my groove and started kind of, you know, moving through the, the product ladder. And it was really, like, correlated to me at least, uh, maybe causal with, um, yeah, dropping f- a lot of the focus on the, on the presentation and how I show up and whether, you know, people like this or not, that, and just really focusing on the work. It's like, "You know what?I am here to be a conduit to, from what wants to happen in the world of transportation and mobility and shared rides is like one that I, I was particularly passionate about, so that's a good example. And then how can I kind of, you know, uh, get present and listen to like what wants to happen next in the world of shared rides, right? And there's lots of different ways we can take the product and all that. And it just, it's really about I wanna make a fucking awesome product, right? And it's like whether people like me or think I'm a good PM or presenter, as long as I manifest, you know, a great product into the world that makes riders better off, drivers better off, cities better off, less congestion, all these things, like that to me is the reward. And sure, in order to manifest that, it is often helpful to communicate things, present, align, all those sort of things. But those are a means to a more powerful and transformative end than just my career. I'm tapping into a larger purpose and sense of belonging and identity and sort of meaning. And from that place, it's like I- I'm just, I'd, I've just dropped the kind of egoic self-centered focus on, you know, whether I did good in the presentation or not. And then, yeah, maybe paradoxically, by doing that, it actually goes better. (laughs) And, and we do great work and it gets recognized.

    10. LR

      Wow. That is fascinating. To make that work, you need to really connect with the mission of the company you're working at. Like you really need to believe this is very important and very meaningful. So maybe that could be an issue for people. If they don't really care about what the company's doing, it's gonna be hard to allow for that approach.

    11. JN

      Totally. Totally.

    12. LR

      It's interesting that you say that optics aren't, uh, as important. I think the reason I, I think about this is you talk about a lot of people feel like there's the work and then there's like talking about the work, making the work, like the optics of what you did is really, really important. And I love to hear, like nobody wants to do that, but they always get this advice, so important, the optics, how you share the impact you've done, how you represent yourself. I guess is there anything else you can share there about just helping people relax about that aspect of their job and that being so critical?

    13. JN

      Yeah. And, and to be clear, I do think it's important. Like it can't be all work and no optics or all optics and no work, right? Like there does need to be a balance there. And I think it does change, you know, depending on the size of the company and the level of seniority, right? When you're an IC, you're probably hopefully doing more actual work and, uh, you know, uh, leaders are supporting them and presenting and communicating that work so that they get... I mean, the optics do- does matter, right? Like at some senior level you do spend more time on that and it does have influence, back to the influence piece, right? Which is like, you know, the how will I communicate an idea and the need for engineering resourcing and so forth might mean that team gets more engineers or doesn't get more engineers or we do this project or we don't, right? 'Cause at the end of the day, executive kind of resource allocation is largely based on the, quote unquote, "optics layer." So it does matter. I want to be clear. I'm not saying it doesn't matter, but to me again, it's more about that's a means to an end. It's not about the optic itself. It's like don't... Let's take the, what Buddha said, "Don't mistake the finger pointing at the moon for the moon," and the finger pointing at the moon could be the presentation, the OKR, you know, (laughs) whatever. And it's like that's not the actual outcome we care about, right? Like that's an input to the output that really matters, which is the work, the product.

  6. 21:46 – 41:16

    Crafting strategy and vision

    1. JN

    2. LR

      Okay. I'm gonna shift this to hard skills and another kind of direction. So another thing that came up a bunch when I was asking people what you're amazing at and what you're really good at, uh, is, uh, strategy and vision. I have this quote from one of your colleagues, Brent Goldman. "Jam thinks big, has lots of great ideas, will yes and to other people's ideas, will inspire everyone around him to be more creative, ambitious, and hardworking. He doesn't climb hills, he finds bigger mountains and will bring you there." So along these lines, say someone comes to you and wants to build these skills, wants to get better at strategy, wants to get better at vision, which is something basically every product leader is trying to get better at and every leader wants to get better at. What advice do you generally share? How does one improve in these areas?

    3. JN

      Yeah. Thank you. I appreciate the compliment, and thank you, Brent. That is a great quote. Wow. Um, yeah. I mean, uh, there's no like magic toolkit or manual, you know. I- I've, I've long ago given up on the notion that, uh, I'm one book away from the, the perfect elusive answer to whatever, you know, plagues you in life. And, uh, there's obviously lots of books about strategy and, you know, we can get into all that. I guess for me, uh, a couple things have been helpful. Um, one is, uh, you mentioned earlier finding a mission that you're really passionate about. Like I think it would be hard for me to come up with a strategy for improving the healthcare system. Like it's like I... Uh, sure it's important. I hope someone does it and figures out how to deal with HIPAA and whatever, all this stuff, but it's like, it's just not for me. It's not my purpose, mission, and vision in life. And so step one is like am I working at a place and in a product area in which I have a tremendous amount of passion, right? 'cause for me that is the fuel and the motivation that helps me break through to getting the strategy. That's like the, the first step. So that's where I feel enormously lucky 'cause again, like this, you know, revolutionizing transportation and car ownership and what happens with autonomy and foreign factors and future of cities is something that I'm super excited about. I think about my daughters growing up and having a, you know, a different world to live in that's safer and more environmentally friendly, all this stuff, right? And like I get really jazzed when I think about wow, the work I do could actually impact their future lives and other people. And it's like, whoa, I can feel the chills right now. It's just like super motivating. So that's the first place, just getting myself kind of fired up. And then the, the next thing I guess that's been helpful is, you know, I've deeply immersed myself. You know, I have. It's also, you know, I haven't really jumped around between, you know, crypto and gen AI, all this stuff, and a- a lot of people do that. It's great. Nothing wrong with that. But, you know, I've been in this, you know, largely focused on, uh, mobility, you know, space for, for 10 years now.... with some stints, uh, over in the restaurant tech and delivery side, but, but very related in terms of last-mile logistics. And so, you know, I think it's hard to come up with a great strategy if you've only been working in an area for, like, six months or such. You know, it's like, it's like... especially with things like this, which are nuanced. Like shared rides is another good example where it's a super hard problem to crack and, like, you know, it's, like, going deep on that for a long time is, uh, is a precursor to being successful. The other thing I would say though is like, you know, people always talk about first principles thinking, but, uh, if there's truth in it, I think, you know, that's like, you know w- uh, like when Elon's like, "Well, why, why does the rocket cost, you know, a gazillion dollars to launch?" And, you know, like there's no reason they have to throw away the materials and, you know, it's all blah, blah, blah. You know, one example might be why do we need a 4,000-pound vehicle to move a human three miles? Okay. Well, um, or even a couple humans, right? If we do an UberPool or a share, right, and you move two humans or three humans. Even then, like, that's pretty inefficient, right? Like if you think about, like the, just the physics there of, like the energy expenditure, right? It's like... and that's where I think, you know, you might come up with bikes and scooters and little other things, right? And, and sure, it's not always... it's raining, maybe you want the car. But that's sort of an example of, like, questioning, like, why are things the way they are? And then are... is the way they are, like super inefficient or like not optimal from... in some sense, right? And that is often a doorway to opportunity, right? To see, okay, well maybe things could be different. And so I can extend that, you know, at a... at a larger level to the future, you know. My, my general thing is just like, yeah, that's the mountain thing is like I- I try to just like close my eyes and imagine the future as far out as I can. You know, it's like five years from now, 10 years from now, whatever, and it's like develop a really salient picture of what that looks like, you know? It's like, it's like always we could do this right now. It's okay. You know, 10 years from now, what could San Francisco look like or some city? (laughs) What, what happens to the parking spaces? Are there still parking garages? Are those parks now? Um, what are the modes of transport? Are there, are there, like, bus-like things that are autonomous that are connecting people to bikes and scooters and, you know, how are people living? Do they live in the far suburbs even more because autonomy and they have a nicer house and they come in? Or, or is all the space repurposed and actually it's cheaper to live in the city because we compact things, blah, blah, blah. You know, it's not even about having the right one, it's more just, like, kind of developing some sort of, you know, picture of the future that gets you fired up, right? And then, yeah, you got to go, like, you know, articulate that and communicate it and get people to come on the journey with you. But like from that picture, it's like, well, what... first principles, what's going to be true, you know, 10, 20 years from now? Well, autonomy is like a given. I think most people would probably agree with that and, uh, you know, we'll probably solve it with just cameras and we'll need LiDAR 'cause humans don't have LiDAR and, uh, you know, the cost of vehicles and sensors will come down, remote support will come down, and at some point it'll be super cheap. And it's like, okay, I can extrapolate that will be a thing separate from which player wins, I'm not saying I can predict, you know, the ecosystem of companies that will win here, it's more about just the underlying dynamics, right? And, and then, you know, so that would be one and then the other one would be, yeah, sharing away. It's like well, a lot of people are like, "Oh, well, once we have cheap autonomous cars, like everyone could just have their own super cheap Uber, Tesla or whatever it is here on the city," and you're like, well, that doesn't work because then we're going to hit this induced demand concept, right? Which is like what economists call it when like, you know, you used to... when text messages cost 50 cents apiece, how many did you send (laughs) , right? Versus now when it's free you send a million. Same thing when they add a lane to a highway, right? The traffic just gets just as bad as before 'cause more people drive and so forth. So, if we flood the streets with super cheap autonomous cars for... with single occupancy, uh, we're just gonna have even more gridlock than we do right now. May- maybe we'll do the Boring Company thing and dig tunnels and... (laughs) but I think that's unlikely, right? So, so then that... from... for me it's like, well, from first principles, shared rides is, is going to continue to be an important part of the future transportation and, and other modalities where, yeah, back to the three-mile thing, it's like, well, there probably will be various form factors of bikes, scooters and little mini golf cart things and whatever we (laughs) end up building, right? And so that's kind of, uh, hopefully an example of how I try to think about, right, like what are the likely things to be true in the future and then how does that lead to a potential kind of ecosystem and strategy around what we might build, you know, towards that future?

    4. LR

      This is great because this is something everyone can do and there's all this talk of, like, creating a vision, painting a vision, communicating a vision, and what you're describing is how to actually sit there and de- think about what it might look like. Like sit there, close your eyes and in your head visualize in the next five or 10 years what does the future actually look like? And do you do this in a state of if we were to do this product and change or is it just even if we're not around, here's where the future is gonna go most likely? Is... How... Which, which direction do you usually take?

    5. JN

      Yeah, it's a good question. I think you could probably do either. I typically like to start with the former which is just like what will the world move towards absent of me just trying to take a, you know, kind of bird's-eye view of what I think is... the trajectories are and trends and what's gonna happen. And then, yeah, you could apply a lens of, okay, if we were to build product X, Y, Z or have this strategy, how might we influence the outcome or benefit from it or, you know, is it in congruence with that or is it, you know, rubbing against that and trying to change that? Either could be good, right? You might say we're gonna... it's a tailwind or a headwind, you know? Both are overcome-able but, like, having some awareness of, of the relationship between those things is, is good. Yeah.

    6. LR

      And I think, like, you know, transportation, Uber, Waymo, it's like in theory it might be easier to visualize that future and how exciting that might be versus a B2B SaaS payroll app or some, like, photo sharing thing. But on the other hand, not, not necessarily, right? The... in... what... in the future 10 years, how are people gonna be paid? How do people work at companies? Like I think there's an opportunity to do that no matter what you're building. H- how do you actually... is this something you actually do? You just sit there in the office, close your eyes and just imagine? Is this more of an iterative process where you get with your team? Like how do you actually practice this?

    7. JN

      Yeah, it's not like something you can just schedule 30 minutes for in the middle of your day of packed OKR reviews and ran- one-on-ones and meetings. You know, it's like, uh, I like to do it on my own first, uh, if I... you know, unless it's something that I already have a kind of outline for and I'm ready to move into a team space. So for me, it's like, yeah, like, can I get into a quiet, contemplative space, right? I- uh, so yeah, I like to go for a run, and that obviously gives me ideas, or I'll go for a hike up in, you know, Marin, and sometimes I'll just like think of stuff or jot something down or make a voice note while I'm doing that, you know, to kind of get things going, um, but yeah, like the first step for me is just getting out of the craziness of day-to-day. Like to me, it's still insane, like how many product manager, leaders of all kinds, right, just run this schedule of like back to back meetings, you know, 30-minute reviews, big meaty topics, you run out of time, run to the next thing, answer a bunch of emails, and then cram some PRDs in there, and like, it's like, you know, y- you, it doesn't work, right? And so I'm a big fan of carving out time, again, first for myself, a couple of hours, you know, whatever that's... where I can just like get out of the day-to-day craziness and, you know, get into that headspace of five, 10 years from now, right? It's just a different place, so you need to transition into that. And then, yeah, bring that to teams. Like if I have like an outline of that kind of future of transportation in my head, I might share that with, uh, with a group of folks and, and, and we'll come together, uh, also for some extended period of time. Like we recently had an all day, uh, Monday thing where, like eight of us came into the office to talk about future of marketplace and, uh, it was super productive. It was like, you know, laptops down, we're gonna spend all day together on a whiteboard. It's like a lost art. (laughs) People don't even use the whiteboards anymore. So, uh, but yeah, and then from there it's like getting more people and then, and then you can kind of iterate on it, right? It's like I had some vision of the future and someone points out something that, you know, is a little bit, you know, off with it or has a better idea or, you know, you kind of, you're... then you move into co-creation. But I love that. It's like, you know, the, what Pixar calls the brain trust, right? When... if you read, uh, Kat Mull's book, right? Where like how they come up with Toy Story and Inside Out and all these things, right, is like they have this group of people that just sits around riffing on ideas and again, there's, there's no judgment, there's no attachment to being right, there's no... you know, they're in a co-creative sort of space where they're just like co-exploring and, and riffing with each other, and I, I love to be in that space with, you know, with other PMs and engineers and, and data scientists.

    8. LR

      (instrumental music) This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. Something I've started to do, which is hard, but I find really valuable is when I'm driving to not play anything on the radio and not listen to any podcasts.

    9. JN

      Mm-hmm.

    10. LR

      And it's so unnatural and it's like, "Oh, this is hard." Like I just... I don't want my brain to just go... like it... you don't want... you don't trust your brain to go to a place that's fun, but it always does, it always ends up being like, "Oh, that was so interesting just to like, think of this idea that just came up." So I've been trying to do that and that's, uh, such a simple thing to do. Just don't turn anything on.

    11. JN

      Well, it's not really good for your podcast business to tell people not to listen to podcasts.

    12. LR

      (laughs) Okay, everyone, we're cutting this. What I find really helpful is playing Lenny's podcast every time I'm out and about.

    13. JN

      No, but there's something to what you said, which is, um, there's always a lot of content out there to pursue and I've been in that mode where I'm like, yeah, more content, more-

    14. LR

      Yeah.

    15. JN

      ... and then... but yeah, actually similar to you, I spend a lot of time now like, uh, not listening to anything. You know, go on a hike where you don't listen to a podcast or music or yeah, your commute, and see what happens. (laughs) You might be surprised.

    16. LR

      Yeah, and it always ends up being like, oh, that was cool, and you know, that's where shower ideas come from and all these things. Maybe just to see if there's something here, is there... in this meeting that you have, this li- ideation brainstorming meeting, is there anything that came out of that that was like really surprising or new from a recent experience? Is there anything there just like, oh wow, we really uncovered this potential wrinkle of the future that we really need to think about differently?

    17. JN

      Well, uh, it wasn't maybe a specific wrinkle, but one of the things that we're thinking a lot about, like I'm fortunate to be involved in trying to, um, help, uh, develop and articulate kind of a multi-year, three-year sort of product or even overall sort of tech strategy for the mobility business at Uber, and one of the, I guess, big a-has for us is, uh, you know, as we move away from the kind of, um, in some ways simpler world of Uber X, right, being the predominant product, which is... you know, it used to be pretty simple, right? You... um, it's kind of like a taxi meter on the driver's side, right? There's a time and distance rate that everybody gets and then on the rider side it's like sure, there's some surge pricing based on supply and demand, but you know, it's one product and it's pretty straightforward. And so, you know, this future of multimodality and, and, and, uh, on the both demand side and the supply side is what makes marketplace like even, uh, more complex and uh, and challenging to build. And so it was kind of all just around like, okay, well, you know, now that we have taxis in the platform and we have fleet providers and we're starting to add Waymos and Crews and other things, you know, we have to have a marketplace that's aware of those different types of supply and you know, which ones might be available for what trips and how to think about cost and quality and kind of allocation of, of, of trips and all that. And then on the demand side, it's like, yeah, we've got all these different products like shared rides and reserved rides and, you know, comfort in X and, you know, priority and it's like, how do we think about how to price those relative to each other, right? How do we think about which ones to show which user? You know, how do you think about the ranking and the... and so forth?And, uh, and then that all has, you know, feedback loops into the, to the pricing and matching itself as well. So, the d- the dynamics of the thing, when I think about the future of marketplace Uber is like, "Whoa." (laughs) You know? It's like... And I don't think anyone's ever built that. That's a, a super cool thing about it, is I think we have the best logistics marketplace tech on the planet and we've built something that no one else has ever built. And, uh, y- you know, relative to like digital marketplaces for example, uh, just different, uh, physical world requirements. And then this next arc of what I described of thinking about, you know, different types of supply and different kind of demand channels just adds even more complexity to that. So, um, so yeah. The ah... But the aha was like, uh, I guess... Yeah. We gotta, uh, p- think about all that stuff and think about how the supply and demand relate to each other, and um-

    18. LR

      Oh my God.

    19. JN

      Yeah. It's gonna be cool.

    20. LR

      It's just a infinitely sited marketplace now.

    21. JN

      (laughs)

    22. LR

      That's wild. One last nugget I wanted to just reinforce that you shared about how to become better at strategy and vision developing, create an interesting and innovative strategy and vision, is going really deep on a topic. So you, you've been in this space for a long time. There's this idea that Paul Graham talks about, I think called Your Top Idea or something like that, that when you have one... Like, whatever your top idea is, the more you can just think about that and keep that top of mind as you go about your day and just have one core focus, the more likely it is you're gonna come up with new interesting ideas because your brain's gonna keep working on it when you're driving around listening to Lenny's podcast. Uh, just kidding. Or going on a hike. So I think that's a really important point is like if you're finding you can't... You're not coming up with a great strategy or vision and just like having struggles, part of it might just be you're not spending enough time in that space, you're not going deep enough in the problem area. One approach is just spend like a decade in that space. Is there, there anything else just comes up as I say that of just how to do that?

    23. JN

      Yeah. Well there's also the, that's at the macro level maybe spending 10 years in a space.

    24. LR

      Mm-hmm.

    25. JN

      But at the micro level is back to kind of like don't... You know, defrag your day. Don't just do the 30 minute meetings, you know, 20, 30 minute meetings on, on 20 different topics. Like it... Sure, sometimes it's breadth first and like you gotta do that if you have a large team. Like I do obviously reviews across teams. I'm not saying I don't do that on some days. But it's like, yeah, like what are my top few things, right? Like I think, I think you're right, I think it was Peter Thiel or some of the early PayPal guys talked about that too, right? Like have, going really deep and having a person or a leader like really responsible for one core deep thing for the company and that's like something they immerse themselves in. And so in the micro that, that to me even translates to, yeah, I don't have a to-do list of 20 things, right? I try to have a to-do list of three of the most important highest leverage things that could, you know, kind of have impact broadly across the company and then try to just like you said like let that one top thing marinate and, and, and chew on it.

    26. LR

      I love that. And I, I recently had a post about how to be... All these productivity tricks and one of the things that I find really helpful is at the beginning of each day and also the beginning of each week just write down here's the one to three things that I need to do and get done. And everything else like I might have this really long list but here's the three things. If I get done, life will be good. I've done a lot and I've accomplished really great and important things.

    27. JN

      Totally. I tried to do the David Allen GTD thing once, you know? The super complicated, uh, you know, organization system and it's just like it was too much structure for me. It was like I couldn't do it. It's like at the end of the day when you... Just right. There's basically three things that I need to do next and then there's like just some random backlog that I can just scan through periodically and that's it. That gets you most of the way. (laughs)

    28. LR

      It's crazy. I read that book like 20 years ago at this point and there's just like elements that still make things like I leverage and benefit from. Like even if you don't proce- do the whole thing. Like that book I recommend people read because there's just like if you pick a couple things from there, uh, your life gets better. The things that have stuck with me, the main one is this waiting for concept of if you're waiting... If you like email your designer and like, "Hey, I need you to review this product," just like note waiting for Dan to review design and just having that thread written down and not in your head really helped me, um-

    29. JN

      Totally.

    30. LR

      Yeah. Anyway, I'm not gonna go into-

  7. 41:16 – 46:13

    Balancing vision and execution

    1. LR

      Um-

    2. JN

      Perfect.

    3. LR

      So we talked about vision strategy. So there's kind of like classically two problems people have with vision strategy. One is how do I get better at it? The other is just like I need to actually get shit done. I can't spend all my time thinking about vision. Uh, you have a really good take on how to find this balance and you've seen it work well and not well with just vision versus execution. When do I go big vision? How much do I spend vision versus just get shit done, execute, execute, execute? What could you share about just what you learned about how to find that balance and what you've seen work and not work?

    4. JN

      Yeah. I think, uh, you can really go too far either direction, right? You could, uh... It's like everything in life is about balancing the polarity between two opposing forces. Um, and so in this one it's like yeah, you go too hard into vision and theory land. You know, I've seen that go off the axle e- early Uber where we're again back to the future of pricing. It's like you know we have all the data scientists and PhDs walked in a room for two weeks and there's a beautiful whiteboard diagram of what it could look like and then it's like well how do we actually build this thing and engineers are like, like this is like boiling the ocean, you know? Uh, and like, uh, you just get wrapped around the axle of like well that sounds really good in theory but I have no idea how to even start executing on this. So that's probably an example of like we tilted a little too far towards, you know, the vision theory land. Um-

    5. LR

      And this was... You're describing like the original plan to make a really good surge pricing algorithm?

    6. JN

      Yeah, this was, uh, what client had tried to bring together, you know, say how we do driver pricing, you know, time and distance rates. But also, you know, we do incentives for drivers where it's like, if you drive this many hours a week, you get a bonus.

    7. LR

      Hmm.

    8. JN

      And there's also surge pricing, and like how to tie all those systems together in a very-

    9. LR

      Cool.

    10. JN

      ... sophisticated sort of way. Um, this was, you know, yeah, back in 2017 or something, and it was just, uh, it was, uh, winged a little too hard into theory land. Um, and, and we, we still have that buy sometimes, you know? We joke about marketplace, you know, uh, especially when we talk about with other teams, you know, that are trying to integrate in the marketplace. Let's say they add, you know, fleets or, uh, you know, teams as a big new product, right? And then marketplace people will be like, "Well, have you thought about this one random problem that could happen two years from now if, uh, teams become this much in demand and..." Blah, blah, blah, you know, whatever. And it's just like, we, we do get wrapped around the axle on that, on that sometimes. But yeah, so the future pricing is a really good example where we went too far into theory land. Um, but you get, you could probably go too far into execution land, too. And I'd say, you know, DoorDash, in my experience, would do that sometimes where we used to actually even half-joke there. Some of us, uh, leaders would be like, it's like ready, fire, aim. (laughs)

    11. LR

      (laughs)

    12. JN

      And it was like people would be like, "I'm just gonna run through a wall. I have no idea if that's the right wall to run through, but at least I know I'm running through a wall." (laughs)

    13. LR

      (laughs) Yeah.

    14. JN

      Uh, so yeah. I think it's, it's about balance, um, and it's, you know, can you, can you adjust? Again, it's dynamic. I think there's times where you're in a soul-searching sort of, "What is our product strategy?" You know, we gotta pivot. Maybe you're a startup and you're not working, and you wanna think about... And then it's like, okay, well off the, pull off the gas a little bit. Ease up on the execution and let's lean into, you know, uh, uh, the strategy and vision piece. And then there's times where the strategy and vision is pretty baked, at least for the next, whatever, six months, year. And it's like, okay, pedal to the metal. Let's just go execute. Let's get it done.

    15. LR

      I just went to this, uh, Acquired podcast event at the Chase Center with, and Zuck was there, and the CEO of Spotify was there, too. And there's two, two quick, uh, anecdotes that you remind me of. One is Zuck talked about how once Facebook and Zuck and the team align on, "Here's where we're going," no matter how many walls appear in front of them, there's gonna be a Mark-shaped, uh, hole in the wall-

    16. JN

      (laughs)

    17. LR

      ... very soon because they're just gonna run through and get things done that they need to get done. And I really love that mentality of like, "Once we're sure where we're going, we're gonna bust through these walls."

    18. JN

      That's awesome.

    19. LR

      The other is a really interesting value at Spotify, so Daniel Ek shared this. He said, he said, "At Spotify, we have this core value. Talk is cheap." And when you hear that, you think it's saying talk is not valuable, and it's actually they look at it as a virtue. Talk is cheap. We can talk, and it costs us no money, very little money compared to building something. So, they actually spend a lot of time at Spotify refining their ideas and discussing until they're really sure something is right. And I guess any reaction to that? 'Cause I thought that was really interesting.

    20. JN

      Yeah, I love that. It's, uh, almost a, a different flavor of I think the Bezos saying of, you know, he's like, "I like a crisp, a crisp doc and a messy meeting," right?

    21. LR

      Hmm.

    22. JN

      Like the whole Amazon thing, if you have the, you know, the three-page or seven-page narrative, it's, you know, written with the clarity of angels singing from on high. (laughs) At least, you know, describing of the problem statement or feature or whatever, um, and so it's like super crisp and organized and, you know, well-articulated. And then you might have a meeting where you pick it apart and, uh, you talk a lot. You know, that's what made me think of that. So yeah.

  8. 46:13 – 52:32

    Lessons from DoorDash, Uber, and Waymo

    1. JN

    2. LR

      Awesome. Okay. Couple more things I wanna spend some time on. One is you've worked at a lot of really interesting, successful hypergrowth companies, DoorDash, Uber, Waymo. You were also in finance for a while. I wanna pick on a few of these and just see what's a lesson you took away or what's an experience from that time that might be interesting or helpful to people?

    3. JN

      Sure.

    4. LR

      So, you talked about DoorDash a bit. What e- what did you take away from your time at DoorDash? What's something you saw there that either is like, "Wow, that's a really cool thing I wanna do in the future," or, "Here's something they weren't amazing at that I learned not to try to avoid"?

    5. JN

      Yeah, yeah. It's really amazing to get to see different places and kind of pick the best of what you like. And, and also there's a lot... The other thing is back to like, for me, there's no right or wrong. It's just like differences, like, have pros and cons, right? There's always like two sides to the coin, right? Um, so like what's interesting I think about Uber and DoorDash is first back to the mission and the strategy. They started with different DNA, right? So like, you know, uh, Uber started with, uh, you know, it was to like utilize blocked cars at, you know, at the airport that were like not doing trips. But it was more about the riders, right? It was like whatever origin story you believe. You know, Travis and whoever, uh, you know, could get a ride in Paris, right? And so then it was about like, you know, better than taxi and all this stuff, right? But it was very rider-centric. It was consumer-centric in that sense, right? And so, you know, uh, for a long time, I think Uber kind of took that too far, got to the point where it was like drivers are a commodity, you know, blah, blah, blah. And they had to flip that back and start, you know, really investing more in the driver's side of the marketplace. But you look at DoorDash and it's like, you know, Tony grew up in his parents' restaurant kitchen and, you know, the DoorDash thesis was how can we help small businesses be more successful? And delivery was just the first instantiation of that sort of meta purpose of DoorDash, right? And so they're much more merchant-centric as opposed to consumer-centric, right? By the way, the consumer-centrism of Uber that started with rides then translated to eats, right? I think when Uber started with eats, it was like, well, we just want Lenny to have some great Thai food and, you know, sushi and have some options. But selection is, uh, is a means to Lenny having a great, you know, eater experience. Whereas DoorDash with their merchant focus is like we want every Thai restaurant in this city to be successful and be on DoorDash. So their motivation for selection is we want all of the merchants to thrive and survive. And so that happens to give you better selection as a result. But the motivation was very different, right? So the analogy I use is like Uber is to Amazon as DoorDash is to Shopify.... if that makes sense, right?

    6. LR

      Mm-hmm. Yeah.

    7. JN

      Amazon has always been more consumer-focused. Shopify is obviously very merchant-focused.

    8. LR

      Interesting.

    9. JN

      And by the way, either of those ... Again, there's no right or wrong. It's a fine strategy. They're both great companies, and I actually don't know if you could do both, right? Like, i- is it possible to be Amazon and Shopify, to really focus on, you know, consumers and build all the merchant restaurant tech and, you know, maybe w- with enough resources and time, but, uh, i- i- that, that would lose focus, so, so it's like there's a trade-off there, yeah.

    10. LR

      Yeah. That's ... Like, at Airbnb there was always this, "Should we optimize for hosts or should we optimize for guests?" And it was always this like, at this time, guests are most important or right now hosts more when you're making ... And make these trade-off decisions in the marketplace.

    11. JN

      Yeah.

    12. LR

      So, it's interesting that at Uber, your insight there is Uber was always very rider-focused and DoorDash was, from its DNA, was very merchant-focused. You also talk about, at DoorDash, there was this mentality of just, like, going before figuring out where to go. Is there anything more there that might be helpful, either as a cautionary tale or as a lesson?

    13. JN

      Yeah. I think it's a, it's a balance. It's back to, like, I don't wanna deliberate, uh, and pontificate for weeks on end about which door I should run through, and I don't wanna go to the other extreme and just, like-

    14. LR

      (laughs) Yeah.

    15. JN

      ... you know, spend 30 seconds thinking about what to do and just go, go, go. Um, so it's like finding that, that kinda happy medium. If I had to pick one, I'd rather bias towards running through a wall than not doing anything, because you still get learnings from that and you either make progress or you don't, and that gives you feedback and you can run through another wall as a result. So, I think the biggest failure case is probably, uh, erring on the other side of, uh, deliberating too long without action.

    16. LR

      What about Waymo? What's something that you took away from that experience as a thing that you wanna do more of or something you wanna try to avoid?

    17. JN

      You know, Waymo is, uh, you know ... Uh, you've probably seen people in San Francisco, right? They're, they're quite, uh, prolific now in terms of, you know, they're all over San Francisco and you see 'em all the time and, uh, I- I'm not sure. I- I can't remember the last time I saw one towed, so, you know, they ... I don't wanna say that, uh, you know, they've solved self-driving, but they are, you know, obviously driving, uh, at scale with very minimal, at least real-world intervention. Like, you know, you can't tell by looking at the cars how many humans behind the scenes might be, you know, helping provide guidance of the car or whatever. But, but yeah. I would say what's really interesting about Waymo is they've, they've largely solved, uh, the self-driving piece, right? Uh, however they've done that, right? A- and we ... And in a complex environment like San Francisco and they ... You see them driving in fog and rain and puddles and, like, you know, it's like, "Wow. That's pretty cool." But I think what, what, what Waymo, uh, was learning and I was trying to help them learn is that, you know, uh, building a self-driving car on a test track is a very different problem statement than, uh, scaling a fleet of thousands of cars and how do you operate them, clean them, charge them, maintain them? And then how do you build a rideshare network? It's like, okay, we gotta build an app and, and we gotta acquire users and do classic growth stuff and, you know, think about that marketplace and matching and pricing and ... You know, those are, like, very different skills, right? And so, it's like, you know, uh, learning that, that those are, those are different things and, um, trying to, um, hire for that and build culture around that i- was probably was, was hard honestly. You know? It's just like you're kind of a, a different, uh, you know, thing than the host organism. You know, most of the host organism is just obsessed with, like, perception and planning and, you know, kind of all the core autonomy pieces, and you're like ... The, the commercialization people are there. It's like, "Well, I'm gonna make money with this thing." (laughs) That's why I think, you know, it, it, it's ... That, that's an example of where, like, your overall vision, let's say Waymo is, is to build Waymo One. You know, it's like you gotta r- just be mindful that it's more than just one ... There, there's multiple pillars of that, right? There's the self-driving piece. There's, you know, getting a lot of cars at scale, financing them, operating the fleet, getting the demand, filling the cars with people, right? And then, you know, it has to all come together, right?

    18. LR

      Right.

    19. JN

      So

  9. 52:32 – 55:18

    The future of autonomous ride-hailing

    1. JN

      ...

    2. LR

      Yeah. It's so interesting that you were a ... Your, your title is Lead Product for Commercialization of Autonomous, Autonomous Ride-Hailing at Waymo, and now it's come full circle where at Uber, it's ... That's gonna be, in a sense, the way that people call Waymo. And so, it's so interesting that you've seen both sides of this.

    3. JN

      Yeah. Well, we'll, we'll see what happens. I think, um, you know, the ... Yeah. Uber got out of the autonomy business, right, when it divested Autonomous Technologies Group, or Advanced Technologies Group, um, and right now, you know, our kind of stated, uh, you know, strategy, uh, is to be an aggregator, right? So, it's like we are partnering with Waymo, with Cruise, Motional, others in China, uh, et cetera. And then, you know, the idea is to have every vehicle on the platform really, right? So it's, uh, autonomous or not. Um, and then, yeah, use the power of the kind of platform. We have this big demand base. We have a lot of riders. And so, I think, uh, you- you- you know, what you're seeing is, you know, Waymo and Cruise and others are like, "Okay, now that we've developed autonomy, you know, w- what's the path, like, to, to, you know, profitability for us, right?" And so they can go it alone and try to build a rideshare network and, you know, Waymo is doing that with Waymo One, and, uh ... But, you know, it might, uh ... It turns out it takes a while. You know, it's funny. People ... I feel like engineers too are always, like, skeptical of why other people's engineering problems take so much work, right? Like, you know, there'd be engineers at Waymo who'd be like, "Why does Uber have so many thousands of engineers?"

    4. LR

      Yeah.

    5. JN

      "How hard can it be to build a rideshare app?" (laughs) But, you know, when you look at what made Uber successful, you know, what we've been perfecting for the last decade, A, the marketplace tech that I alluded to earlier, but also, yeah, like, how we manage a large rider base and doing rider support and driver support and logistics and, you know, all of the, you know, helping finance electric vehicles and working with regulators and cities and making sure we have safe and accessible pickup points. Like, so on and on and on, right? And it's like, you know, those are all the, the depth of the iceberg that you don't really realize or think of when you're like, "Oh, I could just build a rideshare app," right? You know, Tesla publishes their Figma design and some, you know, earnings report and everyone goes crazy. They're like, "Wow. Okay." (laughs) Well, uh, I don't wanna bet against Elon 'cause that sounds scary, but, but there is more to it than just, uh, the app and the autonomy.So yeah, I think these companies will have an interesting question, right? Of like, do they go it alone, build their own ride share network to capture all the value? Or do they say, "Well, I could just work with Uber and, uh, you know, uh, you know, have a faster path to, you know, high utilization of the vehicles which unlocks financing and more vehicles." And right, like that gets them to scale faster. And so, you know, if you look at the landscape right now, it's a bit of both, right? Like Waymo is obviously working with Uber in Phoenix, and we just announced Cruise will come back to some city next year I think, um, and then W- but Waymo's also still building their own thing, right? So they're kind of hedging their bets at the moment.

  10. 55:18 – 59:47

    Contrarian corner: Embracing emotions in the workplace

    1. JN

    2. LR

      I wanna take us to a recurring segment on the podcast that, uh, I call Contrarian Corner. I feel like you're gonna have a good answer here. What's something that you believe that most other people don't believe?

    3. JN

      One is, uh, uh, back to kind of being aware of your internal state and allowing emotions and thoughts, is, um, you know, emotions in the workplace. You know, a lot of people have the, the thing of like, "Well there, there's no need for emotion in the workplace," right? "We're gonna be logical. We're gonna be data driven." You know? (laughs) Like, uh, you know, "Keep your feelings at home." (laughs) Just, you know, show up and, whoop, presentation JM mode. And I guess in my experience, um, there's this thing around like whole body intelligence, and like w- whole body yes which is yes, there is signal from the head, and logic and data and, you know, left brain reasoning are amazing and they can be great, but there's also like, like heart and like gut, right? And like, there's, you know, to me, um, what is an emotion? It's just energy moving on the body, right? And often it's correlated with a thought too as well. Like a, you know, I might have a thought that creates fear and, and so forth. But like, to me there's wisdom in emotion, right? And I can, and, and I can start to access like noticing them more. Like where do I feel sadness in the body? Like I notice I feel fear, you know, in, in the kind of center of my chest, and then sadness is like a sinking feeling in my stomach, and I notice when I'm angry, my jaw gets tight, my eyes furrow a little bit, right? And so, you know, those are common ones but you may have your own little signatures of like you pick up, you know, where, where is joy? Where is creative energy? Where is fear or sadness, anger? And then noticing those in a meeting or in a conversation, a review, and actually if you're, if you're willing even just voice it with other people as like the next step, but start with just acknowledging it to yourself. And so for me, the wisdom of emotions is, you know, fear is something wants to be paid attention to, right? Like if there, where there, there can be the saber-toothed tiger, you know, is not really Dara disapproving of me, whatever. I shouldn't be afraid of that. But there are times where fear is applicable. There might be fear around like, you know, what say back at Waymo, you know, you're, you want to be really intentional about safety and you want to be super, you know, they're, that's one of the things I love about Waymo is they're very committed to having a super strong safety record. And so there might be fear around do we really consider all the edge cases of what might happen if a dog runs in the street or a ball or a child or whatever, and you might see, wow, there's fear here. It's like, well, great. That's the wisdom of that is something wants to be paid attention to and, and, and listened to. Okay great, right? Sadness for me is, uh, something wants to be let go of, right? There's a mourning, there's a letting go of like I had an idea or vision for the future that will no longer be because, you know, whatever. Something happened. Other people don't want to do it, this or that. Or, but it could be a vision of a relationship, it could be a vision of, you know, what you thought your life would look like, you know, whatever. We all go through those sorts of things and, and, and there might be micro moments of sadness of like, wow, that feature didn't work, you know? It's like, I really wanted it to be successful and I just let go of that. Welcome the sadness, right? Anger to me is, um, something is not of service to me or my people or my mission or whatever I'm up to. And so again, that can be a great signal that to like, okay, I'll pay attention to that. I want to change something. And then joy is like something that wants to be celebrated, right? Like, you know, we had a great win. We nailed the OKR, we had a great product launch. Like, you know, it's a lot of times we spend too much time moving back into the next, okay, let's set another goal. You know, it's like, what? It's okay to stop and celebrate. And then like creative energy is like something wants to be born into the world, right? It's like what, it's almost like I'm gonna birth an idea or a vision or, you know, some new product thing and then, you know, that, you know, uh, just tuning into that. So yeah. I would say welcome emotions. Maybe even talk about them, God forbid, in the workplace, you know?

    4. LR

      (laughs)

    5. JN

      You know, like imagine if instead of having a OKR review where like you're behind target and everyone's like blaming other people and like, you know, everyone's kind of fearful and, and if, if someone was just like, "Wow. I, I notice that, um, I just feel fear around this." Everyone was like, "Wow. I, I feel fear too," right? Like that would just totally change the tone of the conversation.

    6. LR

      So the advice here is bring your emotions into work. Like don't let emotions that can, the, what most people believe is leave your emotions at home, don't bring your emotions into the workplace, and what you've found is they actually can make you, um, more effective and makes, make your teams more effective, and you even talked about it helps you make decisions in a more intelligent way 'cause your gut and lizard brain almost tells you things that you should pay attention to.

    7. JN

      Totally.

  11. 59:47 – 1:04:45

    Keys to a fulfilling life

    1. JN

    2. LR

      I love that. Okay, so I wanna close with a question that is rooted in something that you shared with me when we were chatting about this podcast that I think is gonna be helpful to a lot of people. What have you found to be keys to a successful, impactful, rich, fun life?

    3. JN

      It's a great question and I think lots of people have, you know, different prescriptions for that, and I don't claim to have, you know, the, the one truth around that. But I, the first thing I would say as a meta-observation is, um, you know, I, I spent a lot of time thinking about objective functions, right? We design algorithms to do matching and pricing and think about short term effects and long term effects and, and so I, I really am ingrained in this idea of like we have an objective function for our life and then, uh, like, the problem is that a lot of us aren't, um, conscious of it. It's just kind of like an implied OF that you, you know, inherited values from your church or community or what your parents valued or what you've kind of learned to be good at and, you know, I do this for work and blah, blah, blah, and I'm just kind of bobbing along.That's why I love like Ray Dalio's principle thing, where it's like, "Hey, write down your values and your principles and get, you know, clear on what they are." And, uh, and, uh, you know, or like Clayton Christensen w- wrote a great book that he's less known for, he's obviously known for Innovative Dilemma, but he wrote a book called How Will You Measure Your Life? And, uh, he was trying to answer this question of like, you know, he teaches whatever, you know, MBA students at, at Harvard, and, um, he's like, "Wow, all these executives are super successful, they're like Fortune 500 execs, they're like, you know, most super successful, but they're all like divorced and their kids hate them and like (laughs) their personal lives are a mess." Like it's very off- what's happening, right? And so, like uh, you know, one of the key insights he comes to is like, it's Sunday night and you have the choice of, you know, uh, playing with your daughter, you know, or you're reading a book or playing a game and, and you have a presentation to Dara, you know, back to the real... You know, on Monday. And you say, "Oh, I could make those slides a little bit better and, you know, I could go practice or, you know, could knock out some emails," or whatever it is you want to do, right? And so, the, what he basically found was like the type A execut- uh, you know, successful people are very short term OF driven. They're like, "Well, the presentation's tomorrow and that can either go great or okay based on Sunday night." Whereas like, "My daughter will be here, I'll play with her next week," you know? (laughs) It's like a... And the problem is that they get in this cycle where it's like, okay, you start working every Sunday night and then years and years go by and suddenly you don't have a relationship with your daughter who's now a teenager, and it's like... But like, I think w- we're just not conscious of that. So, to me the, the first piece of advice would be get clear on your objective function. And one way f- that I've gotten clear on is like trying to think about it from future me, right? 'Cause like five years from now, I'm not gonna give a shit if I made the presentation slightly better, but I'm gonna care a lot about what kind of relationship I have with my daughters. And like, that means that the, the next action, the next thing I do today and tomorrow, the, th- those will translate into the relationship with her, right? Like that... And I think a lot of us aren't, you know, just tuned into that. You know, it's this, you know, I love the stoic stuff, you know, uh, you know, being mindful of death, you know, Seneca, Marcus Aurelius all those great ones. Not to be like morbid, but just like, again, most of us just aren't really tuned into an awareness that our lives will come to an end. And we try to avoid that, right? We, and we, we try to pretend like we're gonna live forever and just not think about it. And the horror of it is that we succeed, right? We mostly manage to just go live our life and eat ice cream and go to work and go on vacation and do what we do. And, and that can lead us to doing things that, uh, that ultimately don't matter in the long run, right? And like, you know, focusing on the wrong things. And so, to me it's like, you know, an awareness and mindfulness that our lives will come to an end, um, punctuates reality in a way that, you know, requires me to rethink my priorities. You know?

    4. LR

      Mm-hmm.

    5. JN

      Stop wasting time on things that don't matter with people who matter, you know? Like, this relationship, this, this, this journey, it, it will come to an end. You know, I'm actually just tearing up and feeling tingly just saying that. It's like even right now, I'll come back to it.

    6. LR

      Hm.

    7. JN

      How am I gonna spend my afternoon? Am I gonna hug my daughters? Am I gonna spend time with them after work or am I gonna s- do email all night? What would I wish I had done when I'm in my last breath? (exhales)

    8. LR

      There's a, there's a quote that I heard once that really stuck with me that I think is gonna hit a lot of people really hard, which is that the only people that'll remember you working late every night is your kids.

    9. JN

      Hmm. Wow. Yeah.

    10. LR

      Yeah. An important reminder. Um, Jam, we've covered a lot of stuff. (laughs)

  12. 1:04:45 – 1:07:29

    Taking responsibility and agency

    1. LR

      Is there anything else that you think might be helpful for people that you wanna leave listeners with? We just, uh... Or we're gonna have a lightning round coming up, but before we get that, we ended on a really powerful and impactful note. Is there anything else along these lines that you think might be helpful for people that you wanna leave them with?

    2. JN

      The one thing I'd encourage folks to do, out of all the things we talked about, is to see if you'd be willing to commit to breaking out of victim consciousness and mentality, right? And it's not to say there aren't victims in the world, there are real injustices and things happening, but most of us, uh, you know, I've experienced, you know... I, I often can fall into a trap of living my life at the effect of, right? I'm at the effect of other people and what they do. I'm at the effect of circumstances like COVID or Trump or whatever. I'm at the effect of, you know, the conditions and, uh, and circumstances of, of life. And I feel like life is happening to me, right? And so, to me, the most empowering and radical kind of transformation that I've been able to cultivate and develop is shifting from that to a state of I am willing to take responsibility for how I see the world. And I may not be able to change the weather or the election or all that, but I can change how I'm being in relationship to it and choose to see it as a growth opportunity, as learning how am I co-creating it? Even things that I play a small part in, injustice in the world, how am I, you know, perpetuating that and being willing to, to see the world as, uh, you know, I am the painter of my existence, right? Like, I think, you know, uh, Viktor Frankl's Man's Search For Meaning is probably the best example of that. Like, he's in a super oppressive, you know, situation that is very horrific and tragic, and the way he described his relationship with the people in the camp and the guards and, and he, uh, he has given... He, he had talked after he was freed and the amount of compassion and empathy he had for his oppressors was like, just like amazing. So, I'm like, well, if he can do that in the face of those conditions, I can show up differently in a, in a product review or in a, you know, in a, in a conversation with my partner or meeting or whatever it is. Yeah.

    3. LR

      Yeah. I think just that skill alone is such a powerful unlock for a lot of people. Instead of here's all the things that I don't have and here's all the things that are setting me back and all the things that are hard for me versus other people-... shifting to here's... Like, I need to take responsibility for my own success, and no one else will. And just taking agency is, is a really powerful thing. It's ea- har- easier said than done, you know? There's a lot of hardships people have, a lot of things that they don't have that other people have that are hurting their career and hurting their ability to be successful. But still, the more you can take responsibility and have agency, and the less you ha- have this victim mentality, I 1,000% agree. There's so much power there. So, that's an awesome lesson to end

  13. 1:07:29 – 1:08:15

    Lightning round and final thoughts

    1. LR

      on. With that, we've reached our very exciting lightning round. Jam, are you ready?

    2. JN

      I'm ready. Let's do it.

    3. LR

      Okay. First question, what are two or three books that you've recommended most to other people?

    4. JN

      Uh, in the realm of the soft skills and conscious leadership, um, uh, the, the best one is, uh, The 15 Commitments of Conscious Leadership by, uh, Diana Chapman and Jim Duthie, and those were my kind of early coaches and teachers, um, you know, almost 10 years ago. Uh, and I still... Diana is still my coach. Um, so I think that's a f- a fantastic book that we'll go into more detail about some of the things we talked about around, you know, fear and threat versus trust and drama triangle and all that great stuff. Um, that'd be one that I definitely recommend first. Another one, uh, more in the content world is, um... I think you had Nancy Duarte on your podcast at one point.

    5. LR

      Yeah. Nancy Duarte, yeah.

Episode duration: 1:18:05

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