Becoming a conscious leader: Leading without fear, finding your life’s objective function, and getting better at vision and strategy | John Mark Nickels (Uber, Waymo, DoorDash)

Get clear on your objective function. And one way that I've gotten clear on is like trying to think about it from future me. Because like five years from now, I'm not going to give a shit if I made the presentation slightly better, but I'm going to care a lot about what kind of relationship I have with my daughters. And like that means that 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 going to 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.

Today, my guest is J.M. Nichols. J.M. Has been a product leader at Waymo, DoorDash and Uber. He was 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 UberPool 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 the mobility team. This conversation is a unique and beautiful mixture of heart 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 will become a better leader and human having listened to Jam'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 J.M.

Nichols. J.M., thank you so much for being here.

Welcome to the podcast. Thank you, Lenny.

Thanks for having me. I'm thrilled to be here. I really appreciate your dedication to helping product managers kind of like improve their craft and up level. 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 passion of mine as well. So we have a lot of shared interests there.

Oh, I really appreciate that. I want to start with a phrase that came up again and again when I ask 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?

To me, leadership is 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. 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 kind of influences of each other. So that's the leadership piece. So just like the conscious piece then is becoming more aware, waking up, right? To me, it's like, learning more about my interior world, what my background is, my biases, we all inherit sort of certain belief systems from our parents or our church or our community. And a lot of times they kind of go unquestioned and then they end up in conflict. And so it's really just about becoming more aware and then taking responsibility for the influence that I have. So yeah, taking responsibility for my influence in the world.

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 there's the power of soft skills and the importance of those in being successful?

Yeah, yeah. It's. But what was it? Theodore Roosevelt speaks softly and carry a big stick. 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, we got to show up to the meeting and have the right slides and be the loudest, rightest voice in the room. And, you know, that's sort of the way, the way to have influence. And, 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. Yeah, I 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 we're like, well, I don't want to disagree with JMs, 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 there can be a follow up, right? There's, it's not like, You know, it's my last chance to say something, but that's also more true when you're more senior, right? Because 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. 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. 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, essentially a complex features that most enterprise customers require. If you're a founder, exec, product manager, or engineer tasked with the 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 Work OS. Spots are filling up quickly. Make sure to request an invite at enterprise-ready.com that's enterprise-ready.com There's a couple threads I want to follow here, but first, I was thinking as you're talking, when people think Uber, and people that work at Uber, I don't think they imagine people like you.

And I know you were there early and then you joined again.

Is that ever like a, what am, is this a place for me? Did you ever go through that struggle or is it just, yeah, I don't know. Yeah, yeah.

I mean, 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, When I joined in 2014, there was this mission of making transportation as reliable as running water for anyone, anywhere, which is bold, audacious, and maybe even a little bit pretentious from a little bit of Silicon Valley edge. But you could feel the electricity in the air. There was this energy and this excitement, like we're doing something transformational, like economies coming, car ownership will change, and it just, it's, feel like my vibration, you know? And then, yeah, I think the good parts of that era were like, you know, Travis was a very great visionary product leader. And 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, but he, you know, it was stressful at the time, but, like, looking back, I was like, wow, 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, because it was, like, in 2015, and I was a very junior product manager at that point, you know, kind of in over my head and a fast growing place. And in these weekly reviews, Travis, we were building out Uberpool, and 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 flux, and it was, yeah, very stressful. place. And I was like, I think I'm gonna snap. I don't think I can handle this. And that's kind of what led me to start to explore this 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 pricing thing, which is like, you know, Rider pricing and driver pricing and incentives and how we up bring surge pricing and all that together, and it gets very. I'll go heavy. And we have all these PhDs in the room, right? Some of the best minds in the world. We were able to hire people like Garrett Van Ryzen, who was the foremost or person from Columbia and other people. But everyone's like, back to lizard brain. Everyone's arguing. They're like, well, no, I think we should do it this way. We should do it this way. And I was like, huh. It's like, as much as I enjoy the content of this, believe me, I'm an Algo PM end to end. I love that stuff. But I was like, I don't think this conversation actually needs another, like, you know, PhD or I'm not even PhD, but content expert, right? It's like what we need here is a way to like, you know, like shift again back that, you know, out of that fear, threat, righteousness sort of state into a more co-creative, collaborative, open-minded, curious, trusting sort of space. And that what that got me interested in kind of, you know, pursuing more skills and coaching of individuals and teams. But yeah, to your Uber question, yeah, the Uber 1.0 was crazy. Uber 2.0 was kind of like, Travis is out, the board is feuding, there's leaking to Mike Isaac, whatever. And then Dara comes in and kind of the peacemaker and then tries to stabilize, but the IPO is rocky. And so now I would say we're in Uber 3.0, which is full pirate ship to Navy, in the Hoffman's words, profitable company, we're printing free cash flow or an S&P 500, right? Like, you know, we've kind of established the independent contractor model, right, in a lot of states and jurisdictions. And, you know, it's like there's less kind of, you know, risk of that model changing. And, yeah, I would say we're in an area, an era now of kind of Cambrian explosion of different types of transportation. You know, the company kind of really just built the Uber X model and scaled it out to the world. That's primarily how we got here. And now it's like, you know, we're going out for 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 supply types too, right? Like 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 another era of Uber, right? And transportation that, you know, the next decade or two is gonna be like super exciting.

One quick tangent, UberX, a previous guest shared that the name UberX came from, it was just like the internal code name, UberX, and we'll figure out a real name later. And then that just, it stuck and no one had a better name.

Is that true? Yeah, that's right. I think that's right. That's amazing. When I joined, we were already scaling UberX rapidly. I joined in early 2014. But I did help name UberPool, UberPool, which I, what? Selfishly, I like to bring back, It got renamed to share during my external APM rotation.

Okay, I want to come back to the kind of the thread that I've pushed us off of, which is 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 a couple previous guests. So you say that when you have, so you're in this meeting, you're stressed, there's a lizard brain kicking in, some things like, oh, Dar is gonna think I suck and it's going to 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.

It's going to be okay.

Don't worry about it. Talk about why that is actually more effective.

Yeah, yeah. It's like, my daughter the other day was, you know, had some nightmares and she was like, Dad, how do I stop? thinking thoughts that, you know, kind of, you know, about the nightmare or whatever. And I was like, I said, I said, you can't. Don't try to stop the thought. Just allow it. You know, I was like, let me show you why it doesn't work. I said, don't think of a pink elephant. What did you just think of? And she's like, a pink elephant. And then now I think it's a layer to tell the assistant, don't think of the pink elephant. But yeah, I think you're right. It is a little counterintuitive, but like one of my first coaches actually had a great phrase, What you resist will persist and what you fear will appear. And so in my experience, this is another reason why becoming more aware of my internal world is so, it's 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.

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 pretend like it's not there or don't try to convince you.

Well, that would be the first step. It's just to allow whatever's here, thoughts and emotions are arising. It's, you know, they come, they go, they're transient, it's not permanent, right? It's, there's a lot of wisdom, I think, in the Buddhist lineage around those, those concepts. And then the next piece for me, once I can take a breath and relax a little bit, is coming home to the fact that I this is a little more radical for some people. I don't actually need Dara to approve of me in my presentation in order to be okay.

Right?

Like, what I'm up to over here is trying to Force 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 the job, the bank account, the house, whatever it is. But what I 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 can kind of enjoy it for a little bit and then you get back to like, eh, you know? So it's, it's like a never ending, like sugar addiction. And so that's kind of the next step for me is like, allow it, yes, allow the emotional, allow the thought, come home to, I am okay, even if Darth does think I suck. And then also, it's not, you know, it's not permanent, right? Like, I mean, it was like, sure, there might be some high stakes things in life where you only get one shot, but 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 his practice. The other thing is, like, from the fear threat state, I'm like, -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. from others is no longer a threat. It's actually a gift. It's like, you know, I, it's like, you know, information, right? That I can use or not use to, you know, alter how I show up in the future and the skills I develop and all that good stuff.

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 going to 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?

Yeah, again, and maybe it is a little paradoxical, but what I found was the more I focused on, 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, because like for my first few years of Uber, I was paying out as a senior PM, and then I finally got my groove and started kind of, you know, moving through the product ladder. And it was really like correlated to me at least, maybe causal with, yeah, dropping a lot of the focus on the presentation and how I show up and whether, you know, people like this or not, but, 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've always been particularly passionate about. So it's a good example. And then how can I kind of, you know, 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's just, it's really about I want to 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'm just, 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. And we do great work and it gets recognized.

Wow, that is fascinating. To make that work, you need to really connect with the mission and 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.

Totally. Totally.

It's interesting that you say that optics aren't as important. I think the reason I think about this, 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. 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?

Yeah. 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, you know, leaders are supporting them and presenting and communicating that work so that they get, I mean, the optics 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? Because 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 wanna 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 say the, what the Buddhists say, 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, 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.

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 is strategy and vision. I had 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?

Yeah, thank you. I appreciate the compliment. Thank you, Brent. That was a great quote. Wow. Yeah, I mean, there's no like magic toolkit or manual, you know, I've long ago given up on the notion that I'm one book away from the perfect elusive answer to whatever, you know, plagues you in life. And there's obviously lots of books about strategy and you know, you get into all that. I guess for me, a couple of things have been helpful. One is 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 bet sure it's important. I hope someone does it and figures out how to deal with HIPAA and whatever, all that stuff. But it's like, it's just not for me. It's not my purpose, mission and vision in life. 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?

Because for me, that is the fuel and the motivation that helps me break through to getting the strategy. That's like the first step. So that's where I feel enormously lucky because again, like this, you know, revolutionizing transportation and car ownership and what happens with autonomy and form 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. It's like, whoa, I can feel the chills right now. It's just super motivating. So that's the first place, just getting myself kind of fired up. And then the next thing I guess it'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 crypto and gen AI of this stuff. And a lot of people do. That's great. Nothing wrong with that. But, you know, I've been in this, you know, largely focused on mobility, you know, space for, for 10 years now with some stents 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 sponsors. you know, it's like, it's especially things like this that are super 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, 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, if there's truth in it, I think, you know, that's like, you know, like with Elon's like, well, why does the rocket cost, you know, 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, or even a couple humans, right?

We do an Uber pool or a share.

Right. And you move two humans or three humans. Even then, like, that's pretty inefficient, right? 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. If you want But that's sort of an example of questioning why are things the way they are? And then is the way they are super inefficient or not optimal in some sense? And that is often a doorway to opportunity to see, okay, well maybe things could be different. And so I can extend that at a larger level to the future. My general thing is just like, yeah, that's the mountain thing. It's like I try to just close my eyes, I 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, oh, so we could do this right now. It's okay. You know, 10 years from now, what could San Francisco look like? Or some city, really? What happens to the parking spaces? Are there still parking garages? Are those parks now? You know, 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, how are people living? Do they live in the forest suburbs even more because autonomy and they have a nicer house and they come in or is all the space repurposed and actually it's cheaper to live in the city because we can pack things blah, blah, blah. It's not even about having the right one, it's more just like kind of developing some sort of picture of the future that gets you fired up, right? And then, yeah, you gotta 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 the given. I think most people would probably agree with that. And, you know, we'll probably solve it with just cameras and we'll need LiDAR because humans don't have LiDAR. And, 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, like an 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 then, you know, that would be one and another one would be, yeah, sharing a way. 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, you're 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, yeah, used to when text messages cost 50 cents a piece, how many did you send?

Right?

Versus now with its free, it's in the millions. same thing when they add a lane to a highway, right? The traffic just gets just as bad as before because more people drive and so forth. So if we flood the streets with super cheap autonomous cars with single occupancy, we're just going to have even more gridlock than we do right now. Maybe we'll do the boring company thing and dig tunnels and that seems unlikely, right? So then for me, it's like, well, from first principles, shared rides is going to continue to be an important part of the future transportation. and other modalities where, yeah, back to the three mile thing, it's like, well, there probably will be various form factors of bike scooters and little mini golf cart things and whatever we end up building, right? And so that's kind of 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?

This is great because this is something everyone can do. And there's all this talk of creating a vision, painting a vision, communicating a vision. And what you're describing is how to actually sit there and think about what it might look 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 going to go, most likely. which direction do you usually take?

Yeah, that's a good question. I mean, you could probably do either. I typically like to start with the former, which is just like, what will the world move towards absent 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 XYZ or to have this strategy, how might we influence the outcome? or benefit from it, or is it in congruence with that, or is it 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, both are overcomeable, but having some awareness of the relationship between those things is good, yeah.

And I think 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 photo sharing thing, but on the other hand, not necessarily, right? What in the future? Ten years, how are people going to be paid? How do people work at companies? I think there's an opportunity to do that no matter what you're building. 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? How do you actually practice this? Yeah, it's not like something you can.

Just schedule 30 minutes for in the middle of your day of packed OKR reviews and random one-on-ones meetings. It's like, I like to do it on my own first 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, can I get into a quiet contemplative space? Right? Yeah. So yeah, I like to go for a run and that obviously gives me ideas or I'll go for a hike up in Marin and sometimes I'll just think of stuff or jot something down or make a voice note while I'm doing that. It's kind of get things going. Yeah, the first step for me is just getting out of the craziness of day to day. To me, it's still insane how many product managers, leaders of all kinds, just run the schedule of back-to-back meetings, 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 it's like, it doesn't work, right? And so I'm a big fan of carving out time again, first for myself, a couple hours, whatever, 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 to 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, with a group of folks and, and, and we'll come together also for some extended period of time. Like we recently had an all day, Monday thing where eight of us came into the office to talk about future of marketplace. And, 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. People don't even use the whiteboards anymore. So. But, yeah. And then from there, it's like getting more people, and then. And then you can kind of iterate on. 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 it has a better idea or, you know, you kind of. Then you move into co-creation but I love that. It's like, you know, the. The Pixar calls the brain trust, right? When, if you read at catmole'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 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 riffing with each other. And I love to be in that space with, you know, with other PMs.

And engineers and data scientists. 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 risk. 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.

Mm-.

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, you don't want, you don't trust your brain to go to a place that's fun, but 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 such a simple thing to do.

Just don't turn anything on. Well, it's not really good for your podcast business to tell people not to do it. Okay, everyone, we're cutting this.

What I find really helpful is playing.

Lenny's podcast every time I'm out and about. No, but there's something to what you.

Said, which is there's always a lot of content out there to pursue. And I have been in that mode where I'm like, yeah, more content, more, and then, but yeah, actually similar to you, spend a lot of time now, like 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.

You might be surprised. 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 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?

Well, it wasn't maybe a specific wrinkle, but one of the things that were I was thinking a lot about, I'm fortunate to be involved in trying to help 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 ahas for us is, you know, as we move away from the kind of, in some ways, simpler world of UberX, right, being the predominant product, which is, you know, it used to be pretty simple, right? You, 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 writer side, it's like, sure, there's some surge pricing based on supply and demand, but it's one product that's pretty straightforward. And so this future of multimodality and on the both demand side and the supply side is what makes marketplace even more complex and challenging to build. And so it's kind of all of us around like, okay, well, now that we have taxis in the platform and we have fleet providers, and we're starting to add Waymos and Cruise 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 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 and 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 so forth? And then that all has, you know, feedback loops into the pricing and matching itself as well. So the dynamics of the thing, when I think about the future of marketplace Uber is like, whoa, it's like, and I don't think it's ever built that. That's the super cool thing about it. 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, you know, relative to like digital marketplaces, for example, Just different 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 convection to that. So, yeah, but the aha was like, I guess, yeah, we gotta think about all that stuff and think about how the supply and demand relate to each other.

Oh my God.

Yeah, it's gonna be cool.

It's just a infinitely sighted marketplace now. That's wild. One last nugget I wanted to just reinforce that you shared about how to become better at strategy and vision developing great and interesting and innovative strategy and vision is going really deep on a topic. So you've been in the space for a long time. There's this idea that Paul Graham talks about, I think they call it 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. I'm just going to say, and just have one core focus, the more likely it is you're going to come up with new interesting ideas because your brain's going to keep working on it when you're driving around, listening to Lenny's podcast. Uh, just kidding. Or going on 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 is there anything else just comes up as I say that? I've just had to do that.

Yeah. Well, there's also, that's at the macro level, maybe spending 10 years in a space, but at the micro level, back to kind of like, don't defrag your day. Don't just do the 30 minute meetings, you know, 20, 30 minute meetings on, on 20 different topics. Like, sure, sometimes it's brought first and, like, you got to do that. 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 you're right, I think it was Peter Thiel from the early PayPal guys talked about that too, right? Like 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 to me again translates to, yeah, I don't have a two list of 20 things, right? I try to have a two 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.

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 at 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. I've accomplished really great, important things. Totally. I tried to do the David Allen GTD thing once, you know, the super complicated, You know, organization system. And it's like, it was too much structure for me. Like I couldn't do it. It's like, at the end of the day, when you says, 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. 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 do the whole thing, like that book I recommend people read. Because there's just like, if you pick a couple things from there, 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.

Totally.

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

The concept of like the not whatever structure you use, I think the most powerful takeaway from that book for me was if it's in your head, you're screwed. Because it's like you're trying to keep track of stuff and be creative and come up with the future transmutation and remember to pick up something from the pharmacy. It's like it doesn't, it's just not, it's a recipe for disaster. Like this whole idea of like empty mind, you know, beginner's mind. Well, you have to empty the mind.

Of all the to dos first. Just get that out of the head.

Absolutely.

I think it was mind like water. That's the one that stuck with me. Where nothing you need to remember can be in your head. It needs to be written down somewhere. Anyway, let's not go into a whole productivity podcast here. 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. You have a really good take on how to find this balance. and you've seen it work well and not well, 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 can you share about just what you learned about how to find that balance and what you've seen work and not work?

Yeah, I think you can go too far either direction, right? You could, it's like everything in life is about balancing the polarity between two opposing forces. And so in this one, it's like, yeah, you go too hard in division and theory land, you know, I've seen that go off the axle at early Uber, where 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. There's a beautiful whiteboard diagram, what did it look like? And then it's like, well, how do we actually build this thing? And engineers are like, this is like boiling the ocean, you know? And like, 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 the vision theory land.

And this was, you're describing the original plan to make a really good search pricing algorithm.

Yeah, this was a plan to try to bring together, say how we do driver pricing, time and distance rates, but also we do incentives for drivers where it's like if you drive this many hours a week, you get a bonus. And there's also search pricing and how to tie all the systems together in a very sophisticated sort of way. This was back in 2017 or something, and it was just it is winged a little too hard in the theory land. And we still have that bias sometimes. We joke about marketplace, especially when we talk about with other teams, they're trying to integrate in the marketplace. Like say they add fleets or teams as a big new product, right? And then marketplace people would be like, well, have you thought about this one random problem that could happen two years from now if teams become this much of demand and blah, blah, blah, whatever. and it's just like we do get wrapped around the axle on that sometimes. But yeah, so the future price is a really good example where we wing it too far into 3-1, but 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 leaders would be like, it's like, ready, fire, aim. 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.

So yeah, I think it's about balance.

And it's, you know, 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 got to pivot. Maybe you're a startup and you're not working and you want to think about, and it's like, okay, well, pull off the gas a little bit. ease up on the execution and let's lean into, you know, the strategy 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. I just went to this acquired podcast event at the Jay Center with and Zuck was there, and the CEO of Spotify was there, too. And there's two, two quick 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 going to be a mark shaped hole in the wall very soon because they're just going to run through and get things done that they need to get done. And I really love that mentality of, like, once we're sure we're going, we're going to bust through these walls.

That's awesome.

The other is a really interesting value at Spotify. So Daniel Lax shared this. He said, is that 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 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 spent a lot of time in Spotify refining their ideas and discussing until they're really sure something is right. and I guess any reaction to that? Because I thought that was really interesting. Yeah, I love that.

It's almost 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.

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, at least, you know, describing the problem statement or future 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 you talk a lot, you know, that's what.

Made me think of that. So, yeah. Awesome. Okay. Couple more things I wanna spend some time on. One is you've worked at a lot of really interesting, successful hyper growth companies. DoorDash, Uber, Waymo, you're 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. Sure.

So you talk about DoorDash a bit. 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 want to do in the future, or here's something they weren't amazing.

At that I learned not to try to avoid? Yeah, yeah. It's really amazing to get to see different places and kind of pick the best of what you like. And also, the other thing is back to like, for me, there's no right or wrong. It's just like differences have pros and cons, right? There's always like two sides of the coin, right? so, like, what's interesting, I think, about Uber and door Dash is first back to the mission and the strategy. They started with different DNA, right? So, like, you know, Uber started with, you know, it was still, like, utilize block cars. So, 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, you know, can 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, for a long time, I think Uber kind of took that too far. We got to the polarities, like drivers are a commodity, you know, blah, blah, blah. And they had to flip that back and start, you know, really investing more on 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 centricism of Uber that started with rides then transitioned 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, 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? Amazon always been more consumer focused. Shopify is obviously very merchant focused. And by the way, either of those, again, there's no right or wrong. is a fine strategy. They're both great companies. And I actually don't know if you could do both, right? Like, 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 with enough resources and time, but that would lose focus. So it's like there's a trade off there. Yeah. Yeah.

That's like at Airbnb, there's always this, should we optimize for hosts? Should we optimize for guests? And there's always this like, this time guests are most important. All right, right now host more, when you make, you know, make these trade off decisions in the marketplace. So it's interesting that at Uber, your insight there is Uber is always very writer focused and DoorDash was from its DNA was very merchant focused. You also talk about at DoorDash, there's 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? Yeah, I think it's, it's a balance. It's back to, I don't want to, to deliberate and pontificate for weeks on end about which door I should run through. And I don't want to go the other extreme and just like, you know, spend 30 seconds thinking about what to do and just go, go, go. So it's like finding that, that kind of 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 erring on the other side of deliberating too long without action.

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

You know, Waymo is, you know, you've probably seen people in San Francisco, right? They're quite prolific now in terms of, you know, they're all over San Francisco and you see them all the time. And I'm not sure, I can't remember the last time I saw one Toad. So, you know, they, I don't want to say that, you know, they've solved self-driving, but they are, you know, obviously driving 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 to the car or whatever. But, but yeah, I would say what's really interesting about Waymo is they've, they've largely solved the self-driving piece, right? However they've done that. Right. 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, like, wow, that's pretty cool. But I think what, what, what Waymo was learning, and I was trying to help them learn, is that, you know, building a self-driving car on a test track is a very different problem statement than 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 R share Network? It's like, okay, we got to build an app and, and we got to acquire users and do classic growth stuff and. 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, warning that those are different things and trying to hire for that and build culture around that was probably hard, honestly. You know, it's just like you're kind of a different, 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 commercialization people were there, it's like, well, I'm gonna make money with this thing. So I think, you know, it's that, that's an example where, like, your overall vision would say Waymo is, is to build Waymo one, you know, it's like, you gotta just be mindful that it's more than just one, 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. Right.

Yeah. It's so interesting that you were your title is lead product for commercialization of autonomous autonomous ride hailing at Waymo. And now it's come full circle. We're at Uber. It's that's going to be in a sense the way that people call Waymo. And so it's so interesting that you've seen both sides of this.

Yeah, well, we'll see what happens. I think you know, yeah, Uber got out of the autonomy business, right, when it divested autonomous technologies group or advanced technologies group. And right now, you know, our kind of stated, you know, strategy is to be an aggregator, right? So it's like we are partnering with Waymo, with Cruise, emotional, others in China, et cetera. And then, you know, the idea is to have every vehicle on the platform, really, right? It's autonomous or not. And then, yeah, use the power of the platform. We have this big demand base. We have a lot of riders. and so I think, 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, 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, but, you know, it might, 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 Lambo, like, why does Uber have so many thousands of engineers? How hard can it be to build a Rideshare app? 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 on and on and on, right? And it's like, you know, those are all the depth of the iceberg that you don't really realize or think of when you're like, oh, I could just pull the red shirt out, right? You know, Tesla publishes their Sigma design and some, you know, earnings report, and everyone goes crazy. Like, wow, okay. Well, I don't want to bet against Elon because that sounds scary, but there is more to it than just, so yeah, I think these companies will have an interesting question, right? Like, do they go it alone, build their own rideshare network to capture all the value, or do they say, well, I could just work with Uber and, you know, 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 Cruz will come back to some city next year, I think. And then wait, but Waymo is also still bullying their own thing, right? So they're kind of hedging their butts at the moment.

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

One is back to kind of being aware of your internal state and allowing emotions and thoughts is emotions in the workplace. A lot of people have the thing of like, well, there's no need for emotion in the workplace, right? We're going to be logical. We're going to be data driven. Keep your feelings at home. Just show up and presentation in JM mode. And I guess in my experience, there's this thing around whole body intelligence and whole body yes, which is yes, there is signal from the head and logic and data. you know, left brain reasoning are amazing and it could be great. But there's also like, like heart and like gut, right? And like there's, you know, to me, what is an emotion? It's just energy moving on the body, right? And often it's correlated with a thought too, as well. You know, I might have a thought that creates fear and so forth. But like to me, there's wisdom and emotion, right? And I can, 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 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 is joy, where is creative energy, where is fear or sadness, anger, and then noticing those in a meeting or in a conversation or review. And actually, if you're willing, even just voice to other people, that's like the next step. But start with just, you know, acknowledging it to yourself. For me, the wisdom of emotions is fear is something wants to be paid attention to. There can be the Sabretooth tiger 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, let's say back at Waymo, you want to be really intentional about safety and you want to be super, 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, did 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, it's fear. It's like, great. The wisdom of that is something wants to be paid attention to and listened to. Okay, great. Right? Sadness for me is 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 wanna do it, this or that, 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 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. I just let go of that. Poof, welcome to sadness, right? Anger to me is 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, pay attention to that. I want to change something. And then joy is like something 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, 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 going to birth an idea or a vision or, yeah, some new product thing. And then, you know, that, you know, just tuning into that. So, yeah, I would say welcome emotions, maybe even talk about them, God forbid, in the workplace. 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, you could tell everyone's kind of fearful. And if someone was just like, wow, I, I noticed that, I just feel fear around this. Everyone was like, wow, I feel fear too, right? Like, that would just totally change the tone of the conversation.

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

Totally.

I love that. Okay, so I want to 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 going to be helpful to a lot of people. What have you found to be keys to a successful, impactful, rich, fun life?

It's a great question, and I think lots of people have different prescriptions for that. And I don't, claim to have, you know, the one truth around that. But the first thing I would say as a meta observation is, you know, 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 so I really am ingrained in this idea of, like, we have an objective function for our life. And then, like, the problem is that a lot of us aren't conscious of it. It's just kind of like an implied OF that you inherited values from your church or community or what your parents valued or what you kind of learned to be good at. And, you know, I do this for work and blah, blah, blah. 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, and, you know, or like, Clayton Christensen wrote a great book that he's less known for. He's obviously known for innovation, but But he wrote a book called How Will youl Measure youe Life. And he was trying to answer this question of like, he teaches whatever, you know, MBA students at Harvard. And he's like, wow, all these executives are super successful. They're like, Fortune 500 execs. They're like, you know, super successful, but they're all like divorced and their kids hate them and their personal lives are mess. Like, it's very, what's happening?

Right?

And so, like, you know, one of the key insights he comes to is like, It's Sunday night and you have the choice of, you know, 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, that's a burrito, 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, 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 executive, you know, successful people are very short term OF driven. They're like, well, presentations 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. And the problem is that he's 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 we're just not conscious of that. So to me, the first piece of advice would be, get clear on your objective function. And one way that I've gotten clear on is like trying to think about it from future me, right? Because like five years from now, I'm not going to give a shit if I made the presentation slightly better, but I'm going to care a lot about what kind of relationship I have with my daughters. And like that means that the next action, the next thing I do today and tomorrow, those will translate into the relationship with her, right? Like that. And I think a lot of us aren't you know, just tune into that. You know, there's, you know, I love the stoic stuff, you know, 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, 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 that can lead us to doing things that ultimately don't matter in the long run, right? And focusing on the wrong things. And so to me, it's like an awareness and mindfulness that our lives will come to an end punctuates reality in a way that requires me to rethink my priorities. you know, stop wasting time on things that don't matter with people who matter, you know, like this relationship, this.

This.

This journey, it will come to an end. You know, I'm actually just tearing up and feeling similarly just saying that it's like, even right now, come back to it. How am I going to spend my afternoon? Am I going to hug my daughters? Am I going to spend time with them after work, or am I going to do email all night? What would I wish I had done when I'm in my last breath?

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 the only people that'll remember you working late every night is your kids.

Wow. Yeah, no.

An important reminder. Um, jam, we've covered a lot of stuff. Is there anything else that you think might be helpful for people that you want to leave listeners with? We just, or we're going to have a lightning round coming up, but before we get that, we ended on a really powerful impactful note. Is there anything else along these lines that you think might be helpful for people? that you want to leave them with?

The one thing I'd encourage folks to do out of all of these 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 justices and things happening. But most of us, 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 the conditions and circumstances of life. And I feel like life is happening to me. And so to me, the most empowering and radical 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 of learning. How am I co-creating it? Even things that I play a small part in and justice in the world, how am I perpetuating that and being willing to see the world as I am the painter of my existence, right? Like I think, you know, 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 has given, he gave a talk after he was freed. 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 conversation with my partner, a meeting or whatever it is.

Yeah. 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 you back and all the things that are hard for me versus other people. Shifting to here's, I need to take responsibility for my own success and no one else will. And just taking agency is a really powerful thing. It's easier said than done. There's a lot of hardships people have, a lot of things that they don't have that other people have that are hurting there. Career and hurting their ability to be successful. But still, the more you can take responsibility and have agency, and the less you have this victim mentality, I 1000% agree. There's so much power there. So that's an awesome lesson to end on. With that, we've reached our very exciting lightning round jam. Are you ready? I'm ready.

Let's do it.

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

In the realm of the soft skills and conscious leadership, the best one is the 15 Commitments of Conscious Leadership by Diana Chapman and Jim Dethmer. And those were my kind of early coaches and teachers, you know, almost 10 years ago. And Diana is still my coach. So I think that's a fantastic book that will 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. that'd be one that I'd definitely recommend first. Another one more in the content world is I think you had Nancy Dwore on your podcast at one point. Yeah, I love her book Resonate. I know she has some other ones too on slide design stuff, but like what was so cool about that? I give it to PMs all the time when I'm trying to help them develop their communication, storytelling and presentation skills. You know, she goes through like those TED Talks and Martin Luther King, I have a Dream and go to the moon and basically make the spark line against it to understand this concept of resonance with the audience. And it's actually a great skill for back to vision and north stargazing. She said what all these things do is they alternate tension between the world as it is and the world as it might be. And it's like, here's that beautiful future of transportation, San Francisco, blah, blah, blah. But here's why it sucks today. All these problems and this and that. But here's how I could look in a few years. And then, you know, you're creating that tension. The audience at the end is like sweaty palms and like, I want to help build that future. You know, what do you need? You need money, time, resources, you need to join your company. Like, great, you know? So anyway, resonate, Nancy Duarte, great book. Those would be some of the top two that I recommend. There's not one specific book, but I really love Alan Watts' books. If you're into, like, you know, he was one of the first people to articulate and kind of import Buddhism and that sort of Eastern thinking into the West. And he just has a very satirical, comical sort of not taking myself too seriously style and just like the way he explains a lot of those concepts. So that'd be another one. He also has an amazing voice. If you listen to recordings of him.

With music, it's just so fun to listen to. Totally.

Actually, Sam Harris is waking up, you know, that now has the entire... He worked with, I think, Alan Watts' son. So the waking up out has all like 80 or 100 hours of recorded Alan Watts lectures. Oh my God.

I've been these YouTube videos. There's some awesome YouTube videos of him that are worth watching. We'll link to some of those. And then Nancy Duarte, she shared exactly that lesson on the podcast that she had, that we had together. So if you don't want to read the book and listen to her give this tactic of this way to communicate a vision, you can listen to that episode. We'll link to it. Next question. Do you have a favorite recent movie or TV show you have really enjoyed?

Yeah, the last movie I really enjoyed was Inside Out 2, my kids, which is very good.

I see why you'd love that.

Yes, consistent with the emotional awareness and allowing the different emotional parts. And don't want to spoil the movie, I may have everyone hasn't seen it, but it's very simpatica with that lesson of like, you can't just let one emotion run the show. They all have wisdom, you know, on the first one, right? Sadness, joy, learning that sadness is necessary, right? It's all about integration and kind of, you know, but it was beautiful the way kids can understand it. And it's a way to teach emotional literacy to your kids. So I think what they've done there.

With those Inside Out movies is just like brilliant. Do you have a favorite product you've.

Recently discovered that you really love? It could be an app, it could be some physical. Yeah. So Eight Sleep, you know, as a smart mattress company, they're on their third or fourth rev now. But it has like, it's like a Tempurpedic mattress or you can put their cover on any mattress, but it has a cover that has little like tubes of water and then it has like a little computer thing and you fill it with water and then an app. And basically what you do is you program it and it learns it has sensors. It can measure your heart rate, your HRV, body temperature, all that. And it, but you're basically trying to program a temperature curve to help you maximize your kind of REM sleep and deep sleep and get more value out of the sleep that you do have. And so for me, it's like, you know, super cool early for deep sleep. And then it warms you up as you want to wake up, which is like, you know, or the mental alarm and all that. But it's, you know, back to my thing about like wanting to, you know, show up with, you know, the right mindset and energy and aliveness. Having really high quality sleep is a really key part of that is like, if I don't sleep well, you know, didn't get enough sleep or didn't sleep well, like you're already starting off a bad foot. So yeah, if you haven't checked out Eight Sleep, great product.

No endorsement fee for me, but so far. And what's also cool about it is it tracks your sleep. It gives you all these stats, like instead of wearing a ring, it gives you all the stats about your sleep quality. And there's a guy, Brian Johnson, and if you follow him, he's like this hell, this guy that's trying to stay alive as long as possible. And he had a perfect sleep score for six months in a row. He set the record. Yeah, he knows what he's doing over there. Okay, two more questions. Do you have a favorite life motto that you often come back to think of when you're in useful in work or in life?

Yeah, I probably have had different ones over the years. The one right now that really serves me is there's this track called Sit Around the Fire, if you, John Hopkins, but it's on Spotify or Apple Music, but it's basically music with one of Rah Das' talks, Western New York talks. And so the mantra that's been really serving me recently is the very first part of that, which is he says, Beyond all polarities, I am. Let the judgments and opinions of the mind be the judgments and opinions of the mind. And you exist behind that. Awesome. So sometimes I have a abbreviated version of that where I'm noticing I'm activated, I'm clinging to an opinion, I'm arguing with somebody, and they're like, I'm just like, Beyond all polarities. I do that in front of my kids and they laugh at me. Daddy is so weird sometimes.

Beyond all polarities kids. That's so funny. Oh man. There's another Ram Dass line that I often use with my wife, Be Here Now, which is the title of his book that everyone sees with the blue cover. And I do that when she's like on her phone and we're doing something, I'm like, Be Here Now. which is like, okay, okay, I'll put my phone away. Yeah.

Yeah.

Final question. I was gonna ask you about the line tracking and what you learned from that. And you already shared an awesome lesson from that time. So let me ask you something else. I'll ask you about Travis. Any crazy, fun, memorable stories of working with Travis? Callanick. However you say his last name, Callanick.

Travis Callanick. Yeah. Yeah. I'll share a quick one that's short but. But sweet or hilarious to me. maybe less known. So what we were, we used to have the Uber office at 1455 Market.

Right.

And so there was a one conference room we'd often do reviews with Travis and it wasn't the war room, whatever, I don't know why it's taken, that was interior, no windows. But so this room had windows overlooking, what was that? 11th Street, right? So kind of 11th in market. And so we'd have like a presentation up on the projector, you know, some big screen, we'd have to go through some of Travis and reliably, and Every time he'd come in, he would close the blinds of the windows and we're like, crap, what are we doing? It's not because there was glare, like they were orthogonally to the screen. And then one day I was like, why are you doing that? He's like, I'm pretty sure Lyft has drones outside the windows of our office and they're spying on our presentation.

Oh my God.

I was like, whoa. Your competitor, paranoia runs deep, man. Okay. Yeah, yeah. Anyway, it's hard to mention a Lyft doing that.

I could see Uber doing that to Lyft. Old Uber, Uber 1.0.

Old Uber.

Yeah. Wow, that's amazing. It's like coaches in, you know, the NFL that are covering their lips always when they're telling and giving plays. Just like, I wonder if people actually do that. That's amazing. Like, yeah, I get that. You know, it's like high stakes. You never know, might be a drone out there. Amazing. Jam, what a roller coaster of a conversation. We covered so much ground. I can't even name all the things we covered. So let me just ask you two final questions. Where can folks find you online and reach out if they want to work with you? I know you work with folks, talk about that. And then finally, how can listeners be useful to you?

Yeah, yeah. So I am occasionally on Twitter at NicholsJM, but I don't tweet a lot, but maybe I should start. But the best place to find more about my kind of thoughts and, you know, thinking on, on the soft skill stuff is a website called rhythmofbeing.com and, you know, I've got some blog posts up there that go into detail on some of these things. And yeah, I do a little bit of coaching on the side with folks. I do very little now. My day job at Uber and my night job with my kids takes up most of my waking hours, but, you know, for the right person and a few select spots, I can I can make time, but yeah, that's the best place to find me is RhythmOfBeing.com and.

Then how can listeners be useful to you?

Well, in the spirit of welcoming and embracing feedback, you could most be useful by, you know, yeah, reaching out, telling me what resonated, what didn't, what was useful. Where did your energy go up when I talked? And where did your energy go down? because that to me is a signal of where I'm, you know, back to tracking the life, right? Where's the juice? And then that way in the future, when I do other versions of this or other conversations, I'll pay more attention to the Energy Up stuff and kind of go more there and the Energy Down was like, okay, maybe that wasn't as interesting.

It didn't resonate. Right. No problem.

Jam, thank you so much for being here.

Thank you, Jam.

Thank you for having me.

Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenniespodcast.com. see you in the next episode.