(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. I'm your host, Chris Hutchins, and today we're gonna talk about the best strategies and tactics for your work. That means finding a job you love, interviewing, negotiating your comp, managing up, making an impact, getting promoted, and a lot more.

And to do this, I'm joined by Lenny Ruchitsky, who sold his company to Airbnb in 2012 and spent seven years working in product across the company before leaving to start his newsletter and more recently podcast. Now, Lenny is well-known as one of the top minds in the world when it comes to building and growing software products.

And his podcast, Lenny's Podcast, is the number one product podcast in the world. But building products is not why we're here today. It's because he's written so many amazing newsletters about professional work that I've personally found so valuable to my career. So, whether you're looking for a job right now, trying to have more impact in your current role, or thinking about what's next, I am sure you'll love this episode.

And speaking of jobs, I have a big announcement to share on my end. After three amazing years at Wealthfront, I am finally stepping away to focus on all the hacks full-time starting tomorrow, December 1st. It's a bit of a scary jump to leave a stable job, but I love what I'm doing with the podcast and newsletter so much that I felt like I had to see what was possible if I focus on it full-time.

I'll have a lot more to share on this soon, but wanted to make sure you guys heard the news first. All right, let's jump in right after this. Lenny, thanks for being here. - My pleasure, Chris. - So, you have written a ton of content about product management and amongst product managers, which I formerly was, you are well-known in that space for being a thought leader.

However, I found that a lot of your content is very, very applicable outside of product management to anyone who has a job. And now we're probably gonna dig into a little bit more about the transition to creators. I just gotta ask, are you aware of the breadth of applicability of your content?

And do you see a transition in the future to just more than product-related content and just really growing beyond that? - I am aware the content is useful to a lot of people other than product managers because I get emails from people and they're like, "Hey, our marketing team's finding this super useful." The funniest example is my mother-in-law who is 75, I think, something like that.

And she reads every post that I write and find something in there that is applicable to her life. And that just shows me that there's all these little lessons that you can extract from things that are specifically meant for product managers and founders. But I will say, I try very hard to stay focused on a PM, a founder, someone building product, because I think that's the reason it does well is it's solving like a very clear person's problem.

And if I were to try to broaden it too wide, I think it would just lose the power and just become nothing amazing for any one person. So it is a balance, but it is cool that the second order effect becomes useful to a lot of other people. - So for anyone listening, Lenny has a newsletter, Lenny has a podcast.

I have been a guest on his podcast that may or may not have come out before or after this comes out and highly recommend it, even if you're not in product, just like your mother-in-law said. However, we're not gonna talk that much about product today. We're gonna talk about some of those other things.

And in fact, I thought as I went through a lot of your posts that you have a really unique and great perspective on the process of someone going through their career, both getting a job, working at a company, starting on your own. And I've thought a lot about this too.

So I thought we could just have a conversation to walk through that process. And you could share a lot of the lessons you've learned and shared and written about for anyone, whether they're trying to advance their career today or they're looking for something new or they're looking for something right now because we're in an unfortunate situation where some people may have lost their jobs.

And I would love to give them more tools to be successful in their search. So how's that sound? - Sounds great with the caveat that I write these posts and then the content leaves my brain and lives in the post. And part of the reason I write them is like, hey, go read this thing 'cause I forgot all the answers.

So I'll do my best to extract what I can remember. And I did a little prep, but I won't have all of the answers in my head on demand necessarily. - Well, fortunately for you, I try to do a really good job of putting resources in the show notes.

So if there's one that we feel like your answer is lacking in comparison to what I've seen you write, I will make sure that we link that so people can follow up. But let's start with the process of finding the right kind of job. So there are so many types of companies out there.

What advice do you have for people looking for something new, both in just how to narrow down the options and actually stand out to candidates to get that first interview? So just thinking that process. And for side note, Lenny also runs a job board and a talent collective for people in the product space.

So you've seen this both as a person in it and a person creating this thing. So just to recap, how do people narrow down what they wanna do and find a company and then actually stand out to get in the door? - Yeah, let me talk about the job board briefly 'cause I think it's a cool piece of context that shows kind of how much I spend thinking about people's profiles and companies and things like that.

So it's called Lenny's Jobs. It runs on this platform called Palette, which is kind of like the sub stack for job boards. It's kind of this white labeled job platform. And the way it works, there's kind of two parts to it. There's a regular job board where people just post job openings.

And then there's a reverse job board where candidates can sign up because they're interested in new opportunities and they can just be like, hey, I'm open to a new opportunity. I'd love to hear from interesting companies. And it can be anonymous. You could hide yourself from companies that you don't want to see that you're looking for a job.

And it's doing really well. It's become maybe the number one place to find product people. I don't know where else you'd go look for PMs better than this place. And fun fact, I make more income from just a job board than I made at Airbnb in salary. - Wow.

- And so it turns into a really interesting business on the side and shows the power of an audience with the newsletter and like the audience of that being funneled to the job board, creating a marketplace. It's really interesting experience. - If you look at people that actually end up getting jobs from this, is it more from people finding the job from the employer or have things changed in the environment where the employee putting themselves out there is actually leading to more jobs?

- Yeah, so one thing I've learned from this is job boards do not work well. And a job board meaning you post an opening on a job board. If it works for you, it's like the best ROI in the history of hiring 'cause it's like 50 bucks, 100 bucks, 200 bucks to post a job and you find someone for that and then you're done.

But it almost never works is what I found. What actually worked is the reverse, the other piece, where candidates that are awesome apply. I approve them and I only approve about 10% of people to keep the quality by really high. And that has led to so many companies finding.

PMs, that's a product, VPs a product. And so I think that model is a lot more effective now before the economy changed. And so I'm leaning into that. I'm kind of moving away from the job board. - And this site you said, Palette, is there a directory of all the different job boards they power for something like this?

If someone listening is like, I'm not a PM, but I would love to participate in this reverse job search process to put myself out there in front of companies. Are there other job boards or a directory of them to go find places to post yourself? - Yeah, they actually have a cool feature.

I think it's called Spotlight where you work with them and they give you access to a ton of different job boards for specific profiles. And so I get these applications for one company looking for like a designer and they can just only look at my designer. And then they can find candidates.

So yeah, that's pretty cool what they're building. - Awesome. If you're building this profile, right, you're a candidate setting aside that it's in product, but what are the things you think you've seen people do to one, stand out, but also to identify what they're interested in? 'Cause I think there's a world of all kinds of companies you could work at.

- The way I think about it, there's a lot of personal things that are important to people, like where they work, where they live, and how hard they want to work and things like that. But I'd say if you just, if I think of four things that are really important, I think of the people at the company, the stage of the company, the mission of the company, and then just the quality of the business.

So just to go through them briefly. So with people, what I look for, and what I think you should look for is where the smartest people going to go work, trying to go work, or already working. And there's a few reasons why that's really powerful. One is it's more likely that they'll build an awesome product and awesome business that'll do really well.

So the smartest people working in a company more likely to succeed. Two, you'll learn a lot more from that group. If you're just working with the smartest people, you can find you're gonna learn a lot more. And then three, which is a little bit underappreciated, I think, the alumni network that you build from a company that you work at ends up being a really huge asset if you work at a company that ends up succeeding and doing well and growing.

So there's a lot of benefit to working in a place where you can build this really smart, successful, growing alumni network. As an example, a friend and I started the Airbnb Alumni Investing Syndicate. It's called Air Angels. We invest in companies as a group. There's about 500 of us in the syndicate.

And basically we find companies to invest in. We invest using an SPV and look for ways to be helpful. And it ends up being a really awesome, fun experience we all learn together. That's one, find the place where the smartest people you know are going. Two, I think a lot of people underappreciate the importance of stage of company.

There's such a different experience working at a startup versus a big company. And so I think it's really important to think about what's the stage that you wanna focus on. I find there's like a really nice middle ground where you look for a series B or a series C company where it's not so early that it's likely to go out of business or it's gonna be like so stressful all the time, but it's not like a meta or Google.

And so that's an interesting middle ground where it's still like a lot of upside, still really fast moving. And there's a lot of opportunity but not boring and slow and big company. So stage, I would think about the mission of the company. If you like look back on your life, you're gonna be like, okay, look, I spent three years at this company.

I moved this metric 5%. And so like, you're not gonna be that excited about that unless the mission is something that you really care about. And moving that metric 5% leads to something that matters in the world. As an example, Airbnb, they basically help people travel and go on better trips.

And if you ask people, what would you do? And this applies to your podcast a little bit. Like what would you do if you had all the money in the world? Everyone says I travel. And how cool is it to let people go on better trips, more trips, have better experiences.

So there's a really meaningful mission there. And then the fourth is you just wanna pay attention to the quality of the business. Like, is it gonna work out? Is it gonna grow? Do I have to keep raising money forever? Are they gonna be profitable? Especially important in today's climate.

And this is especially important because one of the most powerful things you can do to give yourself a chance to get a better job is to have a logo or two from a company people recognize and respect because that kind of pre-validates that you're solid. Somebody else has interviewed you that you really trust.

And they've said, Chris is great. We hired him. He worked here two years. That says a lot. They may not necessarily be amazing, but at least it's some level that gives you a quick like, okay, I'll talk to this person. So you wanna work at a company that ends up being like, oh, wow, they worked that.

Now we're gonna talk to them. So those are the four. - I had an idea around that when I first wanted to get a job at a startup. I was like, I'm gonna pick a startup that's really popular, people will remember. And I was like, what company just raised a bunch of money?

What's in the Zeitgeist? It turns out I was wrong. And that company ended up like not actually going on to raise any further funding. But that was a hypothesis I had actually played out because five years later, even though that company was out of business, people were like, oh, I remember that company.

And so just the fact that I worked at this company that was a hot company at the time, even though it went out of business within a small niche of people was valuable. I'll add on a couple thoughts to what you said, which is when you talk about stage and for people listening that aren't in tech, forget whether it's series A, series B or something, it's just a small company, big company.

Another way to think about those stages is the speed at which you will learn and the type of learning you will do. If you want to really hone your craft in a specific vertical, a later stage company is often gonna be a place where you can really focus on one thing and really hone that skill, whether it's a set of managerial skills or anything.

At an early stage company, you're going to accelerate the speed at which you learn, but it might not be as focused on craft or at least so I've found because there's so many opportunities. You might think you're doing one role in product, but you might also be doing a role in marketing and you might also be the janitor sometimes.

I think I've had every role at a company except engineer at times. And that happens at a smaller company. So while you might trade off stability, you might learn a ton and a lot faster and be able to make transitions easier. If you're trying to jump into a new career, it's gonna be a lot easier at a small company to say, "Hey, I've never done this thing, but can I jump in and try it?" And at a small company, someone's like, "Oh, Lenny's really good at this thing.

Let's let Lenny do that." And then you can move across very easily. - Yeah, that reminds me a story of when we sold our company to Airbnb, that's how I joined Airbnb. I went from being the CEO of the startup to a PM at Airbnb and I felt such relief not having to think about all the things at the company and just focus on the one problem that we had to solve at Airbnb.

Like you would think that's painful, but it was so nice. And I have to think about fundraising and I have to think about paying people salaries every month. It was just like, "Cool, we're gonna solve this problem. Life's gonna be so much easier." Sometimes you want that, sometimes you don't.

- My wife was a chief of staff at Lyft for a bunch of years. She joined when the company was very small and she had the opposite experience, which was she got to see everything. And it was an amazing opportunity because the company was growing and she wore every hat there was.

And finally she was like, "Oh, I'm spinning up a team to work on insurance. I don't love that. I'm spinning up a team to work on BD. Oh, I'm like really interested in this. Let's go do that." And then she built a career in BD and loves doing BD and partnership stuff, but she never would have found that if she hadn't joined a company small enough to be able to do lots of stuff.

And then this is a little bit out of the way 'cause it's difficult to find these people, but I think about trying to think about who you want to work for also. So in any industry, there are people that are well-known in their industry. You could look at like any conference for an industry, like who are the people speaking?

Who are the people that are writing? Who are the people you respect? And sometimes there might be a good opportunity to go learn from that person. And it might not be the mission that you love, but it might be the best mentor you can find. And so that's another thing that I think you could focus on when you're trying to figure out where to go, what's important to you.

It's like, do I care about the mission and will that fulfill me? Or do I care about the learning? Will that fulfill me? Or do I care about the resume boost? Will that fulfill me? All of those are options. You just have to process them all. - Yeah, it reminds me of a quote that I don't know if I believe, but a lot of people believe it, that you don't quit a job, you quit a manager.

So to your point, finding a manager that you're really excited about and think you can learn from and want to work from and that will champion you is really important. And I think super underappreciated. In my career, the biggest trajectory inflection was just one manager I had that just taught me a ton and just pushed me to do better.

And to your point, there's so much power and value in finding that person. And if you can find the Japanese phrase Ikigai, if you're familiar, if you can find that, obviously it's like the dream, right? Which is the intersection of what you love, what you're good at, what the world needs and what you could get paid for.

That's the dream. I'm learning as fast as I want at a company with the mission I want. But I will say in my career, it's been very hard to find all of those things all the time and so you've got to prioritize and sometimes they morph into that, but I wouldn't necessarily hold out for finding something that ticks every box.

- I think one way to think about it as long as you're getting closer to that, because you, like your wife, you said, she like didn't know she wanted BD and the more experiences you have, the more you kind of narrow in on, okay, here's the thing I really want.

The other way to think about it is I realized this is my fourth career. First I was a engineer, then I was a founder, then I was a PM and I'm whatever I am now, one of the newsletter. So there's always options to go change and go in different directions as you learn more about what you're excited about.

Like you're not stuck in the path that you chose. - I don't know about you, but I went through investment banker, management consultant, employee, PM, BD, then founder, then went to Google and was a venture capitalist. I went through a lot and now I'm a creator. I never knew half of those things more than three months before.

Like some of them I was like, I never knew I was gonna be VC and then that opportunity arose. I never thought I'd be a creator and then I started a podcast. So I think you don't need to know the future. I love this idea of where do you wanna be with your life in 10 years?

And if you're in a career where that exercise is helpful, great. But I can tell you that where would my career be in 10 years, 10 years ago would be so wildly off from where it ended up that maybe it would have been a fun exercise, but it certainly wouldn't have been anywhere close to accurate.

- Yeah, I think to that point, there's so much value in a variety of experiences. Like just doing a lot of different stuff later on ends up being really valuable to whatever you end up doing later. I was just interviewing a newsletter guy who was like the number one tech newsletter on Substack and he's like, yeah, I launched a newsletter.

I got a thousand subscribers really quickly. It just started working. But in reality, I spent six years writing a book on engineering and then working at these jobs, learning a bunch of stuff. So the thing you end up doing later ends up being built on the experiences you have.

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Things I've done in the past are find every person that I can that knows them. I've tried creating a presentation and sending it to them. You could create a video about how excited you are. Lots of things like that. I've had this work for me, and I think it's underappreciated, but as a founder, someone emailed me and said, "I am so excited about your company.

"Here's my ideas." And I was like, "I have to interview this person." Like anyone who would take more than an hour to put something creative together about my company is someone I will want to talk to. And the bigger the company, the more it's like, "Well, they actually have to fit a role we're hiring for." But I've interviewed people who I was like, "I don't even have a role for you, "but I just wanna understand who you are "so I know where to slot you in later." And you can't scale that if you're interviewing, if you have a thousand companies you're excited about.

But if you have three, I'm like, "Go all in on those three "before you try to find three more, "because I think that you can easily stand out "by doing those things." There's an episode I did with Sunil Gupta who wrote a book called "Backable." And one time he just like did customer research for the company and sent it to me.

He was like, "Hey, I interviewed your customers. "Here's what I learned." If you were in sales, you could go close a customer and be like, "Hey, I just convinced a customer "to sign up for you. "I just wanted to let you know." Who doesn't wanna interview a person who's closing deals before they even work there?

So I think if you can go through the hard exercise of figuring out what you want. Those are my tactics of standing out. I'm curious at what you've seen to try to have candidates either who've applied to you or you've done yourself to put yourself out there in different ways.

- I think that's awesome advice. It reminds me, I was teaching a course on Maven about product management. And I was interviewing coaches to help me with the course. And I had about 10 coaches. I was interviewing them with someone else that was helping me out with the course.

And one of the coaches started her own sub stack, subscribed me to it, and then just started writing posts about how she's the perfect fit to coach this course. And I was like, "Holy shit. "We need to make sure that we talk to her for sure." And we did, and it didn't work out there 'cause she wasn't quite the fit, but I found something else to do with her.

And now she's a core part of my newsletter community, helps run a lot of the programs. - That's awesome. - Yeah, I love that advice. I think that's awesome advice. I think generally, the question is how do you stand out? How do you stand out? Is there something really remarkable that gets someone's attention?

There's a lot of ways to do it. I do a lot of angel investing. And whenever I get a founder that makes a loom, "Hey Lenny, I really wanted to talk to you "about the startup I'm building. "Here's why it's awesome." I watch them. Most of the time I talk to them 'cause they put in the effort and they do something unique.

So I think it applies to investing too. Pick the people you really want on your cap table and do some extra. I think broadly, if you don't do anything like this, the things you need, 'cause I'm with the job board, I probably reviewed 3000 profiles of people that applied to join the job board or the collective.

And so the things, like if you think about from the perspective of hiring manager, like what are they looking when they're scanning resumes? They're looking for logos that they recognize from companies that have pre-vetted that person in some form versus like a bunch of random companies they've never heard of.

You're not gonna be able to do a lot about this, but this is what hiring managers look for. Companies that they respect, that have done one pass at this person and they're probably solid. And then I think you mentioned this is just like impact, show some kind of impact that you've driven.

Like they're hiring you to have impact. What impact have you had in your career? And so the more you can highlight those things, the better. But if you don't have those things, your advice is great. Do something remarkable. - I love the idea of like a loom resume. I can imagine getting an email.

If you'd rather not look at another 50th resume of the day, here's a five minute video of me walking through the highlights. And oh, by the way, you can put it on 2X if you wanna get through it in two and a half. - I bet if I got an email that was like a little bit snarky, a little bit funny, but a little bit informative, that would be great.

And if you don't have those logos, it might be exactly what you need to get through that. - Yeah, and then you could track that they watch the video too, which is cool, you get an email. - Oh yeah. The app I use for editing my podcast, Descript, has a loom like feature, but it doesn't have the tracking.

So now I'm like, oh, maybe I should switch over and start using loom. - There you go. - What about interviewing? Let's say I call you, I'm like, oh, I decided I'm done creating a podcast. I want this job. Lenny, what advice do you have for me to nail the interview?

- I like, I don't know if I'm going to give you anything that you haven't heard before, other than just spend a lot of time preparing, like a lot of interview questions or stuff you'll hear from a lot of different people. So I think that's probably 90% of it.

Just spend a bunch of time preparing. If you're interviewing at a big company, my sister was interviewing. There's just like videos of all the interview questions they ask you online. It's pretty crazy. There's like courses you could take, like how to interview at Google. And it's like all the questions they ask you.

And it's like, you can go through all of them. There's like a pool basically. So there's like a lot of answers out there if you put in the time. Another piece is get good at telling your story and why you want to do this job, what you've done in your career, highlight the things that have had impact.

I think it's just like, get good at pitching yourself. And then you want to ask good questions of the interviewee. People want you to ask them questions because they want to feel like you care about the company. - If they want to not just hear it, but feel it.

You said, I've interviewed people who I'm like, why do you want to work here? And they're like, well, I'm at a financial planning startup. And they're like, I just love personal finance. I'm like, that's why you want to work in the industry. That's not why you want to work here.

I would say, especially the smaller the company, but it probably works at any scale. If you don't have a really solid answer for why you want to work at this company, I think that is tough for the other person to hear if they ask you. And even if they don't, I'd try to slot it in because I think that's great.

And I would also try to come up with a personal question that I know this sounds like a lot of work, but try to come up with the best question you can ask someone. Because whenever anyone asks me a really hard question, I remember that person. I'm like, that person really thought hard about this.

Or they transferred from interview to interview. They're like, oh, this person told me this is your biggest problem that your company's facing. And in the next one, they'd come in and say, hey, I talked to the head of marketing and they said this is the biggest challenge you're facing.

From a product standpoint, what are you guys doing to help the marketing team solve this? And it's like, well, now you get to learn a lot of stuff, but it actually shows that you're trying to solve problems. You're trying to get more out of it. I just try to say as the candidate, don't forget you can ask questions and don't assume that the questions you ask are purely selfish.

They can often leave people with a better impression of you and not just be information gathering. - So I have a TikTok account for my podcast. It's called Lenny's Podcast on TikTok. And I think it's like, my name is the actual handle. And the most popular content is guests talking about their favorite interview question.

I ask that often at the end of my podcast episodes. And so if you're looking for more questions to practice on, if you go to Lenny's Podcast on TikTok, you'll sort, I think by views, you can probably see a bunch of really fun interview questions. - I will link to that in the show notes so people can find it.

Now, let's say you get the job. This is something I know you've written about. And I know it was actually a guest post, but I'm hoping you have some of the takeaways because they were fantastic about salary negotiation. I think it's something that people spend far less time on than they should.

And you highlighted a lot of that in the post you put out on your newsletter. - Yeah, this post ended up being the most popular post of my newsletter of all time, partly 'cause it got on Hacker News and got a ton of views and some recruiters did not like it.

And it's good and bad, but I learned a ton from it. So the author's Nia Drugova. And the reason I asked her to write this is because I'm really bad at negotiation. I don't even know if I've ever negotiated a salary. And so I wanted to learn how to do this well.

And her full-time job basically is helping candidates negotiate their offers. And help them find jobs. So she's done this a ton. There's 10 kind of steps that she shares. I'll share a few highlights, things that I thought were most interesting. One is she super recommends you never give a number of what you think your salary should be or the range you're thinking about.

Here's the question she suggests you ask. Can you tell me the salary band for this level? I'm happy to let you know if it's within my range and we can discuss the specific number later once I've met the team. That's her advice. And that range ends up being really useful later when you start to negotiate.

That's tip one. Tip two is to mine for intel from your hiring manager and the recruiter into what they're looking for from this role. Like what's the number one priority of the team right now? Why is this role open? What's the biggest challenge for someone getting into this role?

And the reason this is important is then you can mirror that back when you're pitching yourself. Once you've got an offer you wanna counter, you can highlight, hey, here's what I'm gonna help you with. Here's what I'm gonna do in this role. Here's the challenges I'm gonna tackle immediately.

And people are gonna be like, holy moly, that's exactly what we need. How did you know? So the tip there is just mine. Like ask these questions so that you can have notes when you're actually pitching yourself later. And then the third tip that I love is once you get an offer, her advice is don't counter it immediately and don't come back with, no, I think this is a better, more fair number.

Instead you wanna win the hearts and minds of the decision makers. You want them to feel like, oh my God, we need Chris in this company. We gotta pay him whatever he wants. And her advice is after you get the offer, try to get a meeting with a decision maker, like a director or VP or something.

Just like, hey, I just wanna chat about this role. In the discussion, ask questions about how they would want you to create meaningful impact. Share some ideas maybe you've had about what you're gonna do there. And then maybe share obstacles that you have in accepting the offer and taking on the role.

And try to get them excited about you joining the company. And with that, then you can come back with like, okay, I've talked to everyone. I understand the role better. Here's where I think the offer should be. And in theory, if you got them really excited, they'd be like, oh yeah, yes, yes, yes.

Let's do whatever we need to do. So those are some nuggets. - I love that third tip. It's almost like come up with a plan. You could even talk to the person that would be your manager and be like, hey, I know we're talking about salary negotiation already, but I just wanna figure out like, what's the 90-day plan?

What can I hit the ground running on? And you get them to like buy into, this is what this person's gonna do. And they're like, gosh, we've already decided their first project. Can we get going? - Right, like get them in the hell, let's get going. What are we doing?

- Yeah. - Negotiating over here. - My other piece of advice to people is, salary is a component of your compensation, but there's often a lot of flexibility in other places. So it's not the only place to focus on. Some companies, things like vacation days are flexible. Some they're just based on tenure or everyone gets the same.

Some educational reimbursement is one that you can focus on. Others, I've found companies that say, we're not really willing to flex on the salary, but I've heard from after I've worked there that they are willing to flex on a signing bonus. They are willing to flex on various other aspects of compensation, like what your estimated bonus is.

I helped a friend negotiate. He said, sometimes it's like, oh, well now I know the band for the level, but could I be at the next level? And I'm not trying to tell you how much to pay me. I'm trying to tell you that I'm at the next level.

And they said, well, we're not confident you're at that level. And he said, great, how about we have a check-in in six months and you tell me what I need to demonstrate. I will demonstrate that. And if I will, would you retroactively update my compensation as if I came in at that level?

If you're not willing to believe I'm there now, let me prove it to you. And he set out a series of things that they needed to demonstrate. Three months in, he checked in with them and said, am I on track to demonstrate these things? Which by the way, genius move for this person because it's so much easier for your manager to say you're on track for something than actually getting your promotion put through or getting your compensation adjusted.

But then when you check in six months later and you say, three months ago, you said I was on track. Like we haven't had any conversation to the contrary. If I'm not getting this, then why were you telling me that? Similar to how you said getting the buy-in before you negotiate, you're getting the buy-in that you're already gonna get approved for this change.

So I just think there's a lot of wiggle room about things other than your salary. And if a company's not willing to flex there, go down all the other paths. - Still so hard to do this negotiation thing. - I kind of love negotiating. I worked with Andy Ratcliffe for a while.

He was the CEO of Wealthfront. His advice was to always just put the decision in someone else's hand and say, what do you think is fair? He said 90% of the time they do what's fair and 10% of the time they don't. And you know that they're trying to kind of screw you over and maybe that's just not the right fit.

I always like sharing negotiation advice, even if it's not relevant to salary, but you could basically say, here's all the data I've collected about what this role should be compensated. I'd like to be compensated fairly with this data. Here's the data, let me know what you think. And like force it on them to make a fair decision, depending on the circumstance, a good last tactic or a starting point.

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So, please consider supporting those who support us. Okay, so we've gotten hired. We're now at a company, and I wanna focus on something that applies to everyone, actually working at the company they're at. There is a lot we could cover here. I don't wanna go through every possible thing, but there are a few things that I think you might have outsized impact on the conversation about, and the first one is actually about having impact in an organization, and hopefully a little bit about how to get promoted on the way, but I know you believe those two things are both similar and very different.

So, what do you think people should be optimizing for when they're working at any company? - If I had to pick one thing, I would say have impact on the company in their bottom line. If you think about it like, why the hell are they paying you a salary?

It's to have impact on their business, to help them grow faster. And so, if there's any one thing that you can just always come back to, if you deliver more impact, you will do better. That's like 90% of your success at a company. Then there's like, people need to know about your impact.

You need to be working on things that matter. Like, you could have an impact on a leaf at the end of the tree of the business, or you could have impact on the core number one goal, and that's a big difference, but I'd say if you had to pick anything, it's just how can I deliver more impact?

And it's especially important for PMs who are basically marshaling the resources of their team. And the more you focus on how can our team have more impact, the better everyone on the team does. - Let's pretend you just started a new company. How do you find the way you can have that impact?

- I think about Lord of the Rings and the Eye of Sauron. If you think about like, what's the most important project to the CEO right now? I think about that as the Eye of Sauron. He's looking at that, or she's looking at that, and that's gonna be like so stressful and difficult.

You're like right on you, on your butt. And then the alternative is you could be working in a shire where nobody cares what's going on. Like you could have the most amazing product and everyone's like, that's nice, good job. I would say generally you wanna optimize on average to be like not in the Eye of Sauron, but right off to the side.

Work on something that's really important, but not like the most important thing to the company, at least for a long time, because you just get burned out being in that thing that's like the number one most important product. So that's just like a general piece of advice. Work on something really important, but maybe not the most important thing.

Just a tip there. And then in terms of just like, how do you find what the most important thing? Like it's pretty clear usually. It's like what's getting resourced? What are the execs really excited about? Where are the best people going? Those sorts of things, like what's being prioritized?

- Impact's the most important thing. I've seen you write about how to get promoted effectively, and that impact matters. Any comments on that? - Yeah, if you're like, why am I not getting promoted? It usually means that you're not delivering enough impact or people don't have confidence that you will deliver the impact that you need to at a higher level.

So if you think about working backwards from a hiring manager or the company, thinking about, should we promote Chris? Basically, you need to give them confidence that you can handle more scope, more responsibility, more impact. So how do you show that? One, deliver more impact. Find ways to hit more ambitious goals, maybe lead a really important project, work on something closer to the eye of Sauron, something higher visibility and more important, maybe help the company save money or run more efficiently, just like find ways where you can show that you've done things that are really important to the company.

So that's one. Two is, part of the idea of our promotion is people are gonna give you more scope, more responsibility, and again, they have to have confidence that you can handle it. How do you do that? You take on more scope, more responsibility before you are promoted to show people, look at me, I can handle this.

So you wanna find ways to take on work maybe your manager's doing. And knock it out, take on a project that someone else is doing while they're out and do it for them. Pick a really ambitious project that's just gonna take a year or two that's gonna be really important to the company.

Take the reins on like a visioning exercise and just like, look at me, I did this thing, this is awesome. I think what's important here is a lot of people only get promoted after they've shown they can handle this additional scope. And so you gotta find opportunities to take on more scope.

There's five more, and it's posted around, so let me just run through them pretty quick. Three is part of the reason you're getting promoted is there's this gap that your manager has identified. Like Chris needs to work on better deadline setting or hiring. There's usually like a gap that keeps you from the next level.

And it's really important that you and your manager are aligned. Here's the gaps that keep you from the next level. Like you shared this story about your friend. Am I on track for this next level? There's usually like a set of things that your manager gives you feedback on, usually in your performance review.

A tip that I would suggest that I found really powerful, either as a manager or as a report, is when you have a performance review, align with your manager on like a spreadsheet of things that you plan to do in the next, say, six months until the next performance review.

Create basically a roadmap. Like I'm gonna work on becoming a better public speaker. I am gonna hit deadlines 90% of the time. I'm gonna update our JIRA to be up to date by the end of Fridays. Just make a list of the things you can actually do that'll bring you to the next level.

And then meet with your manager/report every month and review the status of each of those things. It becomes this little roadmap where you're aligned on, here's the things, say, Chris is working on and how they're going. So that by the time you get to performance review, you're not surprised.

Like here, we did five of these things. We didn't get to these things. So that's where you're at. So demonstrate you've addressed a gap. Four, find someone that can champion you. That's often really powerful at a company. Get someone really excited about you and can champion you inside these calibration sessions.

That's really powerful. Five is you wanna pay attention to what gets promoted at the company. A lot of companies have these gray area things that matter a lot that you may not be aware of. So just look at people who are getting promoted. Look for things that they're doing maybe that you're not doing.

Maybe you have to be friends with the CEO. I don't know. Maybe you have to be really good at communication. That really matters at the company. And then two more. Something that's way underappreciated is you just need to ask to get promoted sometimes. Sometimes managers don't know you wanna be promoted.

So simplest thing you could do is just like, hey, I would love to be promoted to the next level. What do I need to do to get there? What are my gaps? And that often leads to the biggest impact on getting promoted. And then the last idea and tip is just sometimes you need to leave and work somewhere else.

Sometimes you're just like stuck in a rut and you just have, I don't know, certain reputation. Your manager is just not good at championing you. So sometimes you're not gonna get promoted and it's time to try some other place where you kind of start with a clean slate. - I remember it was so depressing, but when I was a venture capitalist, the role of non-general partner, we were told it was like, this is a terminal position.

They were just very transparent. They were like, the expectation for this job is not that you will get promoted to be a general partner of the fund. That is just how it works. And we just want you to know that so you don't have those expectations. And it was like very clearly set.

I think it was a little depressing at times 'cause the word terminal position just sounds like going nowhere. But I appreciate the honesty. I appreciate the transparency. The one thing that I learned and you reminded me in what you said was a lot of times in order to get promoted, you don't need to meet the expectations of your role.

You need to demonstrate that you can handle the next role. And I think I'd always thought as someone who hasn't studied this or been a prolific manager at any point in time, I always thought, oh, when someone could do their job really well, you move to the next level.

But it's actually in a lot of companies, it's when someone could demonstrate that they can do the job that they want to get promoted to is when that happens. And so it's really important to understand if I'm a level five manager and I wanna be a level six director, it's like, what do I need to demonstrate to be a director?

Not what do I need to do as a manager? Because sometimes you need to do the next level's job to get the promotion. - Yeah, and that's how it works in calibration. When you're looking at someone's level, there's like a lot of big companies have these ladders and they tell you what each level needs to achieve.

And so if someone's gonna be promoted to say L7, there's like, here's what L7 has to be good at in each of these things. And that's what managers look at, is Chris ready for all these things in L7? It makes sense, like your job is gonna now be that.

You wanna be confident that they can handle that. - And if that ladder is not public, ask for it. There are some companies that might not publish it on any internal doc, but you could say, hey, to my boss, could you please show me the career ladder for my role or could the requirements of the next level of my role?

And hopefully you can get that and understand it so you can work towards it. - I've actually collected the career ladders at 20 something companies and I have this doc that has all their level names and then the attributes for product managers specifically that they look for to promote people.

- That's awesome. We'll link to that in the show notes. One of the things I tell people is they think that to be promoted, that strategy is to always do whatever your boss wants and never push back. I am someone who probably has never adhered to that, maybe to my own demise and pushed back too much.

What do you think is the right balance of saying no and what's the value of saying no as opposed to always being willing to do what other people want? - I'm thinking from a PM perspective, product manager perspective, you're kind of responsible for what a whole team of people does.

Like you could almost say your job is to say no so that you can say yes to the stuff that is really important. So it's really important to say no, to push back. It's still very hard, especially if your manager's like, hey, we need to do these things. So I wrote this post with five ways you can say no and many of them are you say yes to say no.

So I'll share some of these quotes that you can steal and they're also in this post. So the first two is someone asks you to do something. You could say yes, but here's what's gonna have to change. If we do that, should we move forward? And oftentimes they're like, yes, let's go ahead.

Or otherwise they're like, no, shoot. I don't wanna deprioritize that, forget that. So that's one trick. Two is you could say yes, but not right now because we gotta stay focused on X because of X, Y, Z. Do you agree with that? Or do you think we should deprioritize that?

So that often works really well 'cause it basically communicates. Again, here's like a very clear trade off on why it's important. Another way you could say no is no, but how about we do X, Y, Z instead of that? And it's gonna achieve a similar outcome. Basically, this is when you have a better idea, but you wanna communicate here's something.

We could basically do exactly what you want, but here's a better approach to doing that. Another way you could say no is no, but there's something there. There's like something to this idea. How about we explore this a little bit further and here's the next step that I suggest.

And then the fifth way you could approach it is just like, no, I don't think this is a good idea. Here's why. Would you agree or is there something I'm missing? - So first off, I wish I had read this post earlier in my career 'cause I was like, no, that's so crazy.

Why would we do that? Politics is the wrong word, but I was never good at a lot of this stuff. And one of the tactics I shared when we spoke on your show was that I was so confrontational about things because I was so used to working at a company that I started where everyone always knew that obviously I was always optimizing for the company because it didn't matter.

And then I joined a company where I wasn't in charge. And it turns out that in big companies, there are a lot of people who are optimizing for themselves way more than the company. I didn't really realize that. I was like, everyone's got to optimize for the company. That's the most important thing.

That's how I lived in my last companies that I've run. So a tactic that helped me when I was pushing back on people, colleagues, bosses, is just always making sure that I told people, hey, I'm thinking about this from the perspective of trying to maximize the impact from the company.

And because sometimes I'd say, oh, we shouldn't do that. That's not a good idea. And people would be like, oh, well, you just don't want to do more work or you want to focus on this thing you're more excited about. And that wasn't true. But the more I just transparently said, here's how I'm thinking about this.

Here's what I'm focused on. It just helped so much. So just stating your intent before you push back so people know where you're coming from was very helpful for me and hopefully helpful for some others. - Yeah, I think we all fall into this. Like people are going to read our mind and know exactly why we think no or why we're saying this.

And it turns out people cannot. - So real quick, before we talk about what happens when you move on from a job, part of getting things done is being productive. I've talked a lot about time management. I'm a nerd. We don't have to go super deep 'cause I've done a few episodes, but any few tactics you want to pull out on how you manage your time and get a lot done and be effective with your output so that you do have impact?

- Yeah, and it's especially important in this world of writing and podcasting. I'll share a few things that worked really well when I was working full-time. And I don't think anything will be revolutionary, but these things really work for me at least. One is I blocked three hours on Monday, Wednesdays, and Fridays on my calendar.

And I called the meeting, "Do not book or I will slap you." And it made people laugh, but it really worked really well. People did not book over these slots. They were like, "Okay, I get it." And so find some funny way to have a block where people know, "Okay, I see.

"He's really serious about this time. "Let me leave him alone." Because I'm sure you've talked about deep work and the importance of focus and all that, but I find that that's so important for creative work. In my new life of newsletter or podcast person, I have no meetings until 3 p.m., that's my rule.

And only at 3, I have meetings and things like this. So that helps a ton. Two is just, what's an app or something that keeps you focused when you're working? I use this app called Centered.app. That's kind of like Brain.fm, which is this like binaural beat music, meets a to-do list, meets like a playlist.

So once you're ready to work, you click play and music starts and it's like, "Lenny, start with your newsletter posts." And then you can knock them off as you're working through them. And it works really well for me. Something I'm trying right now that works well is picking one highlight of the day, one top goal for the day.

There's this book I'm reading right now called "Make Time." - Oh yeah, John Zeratsky and Jake Knapp. - Yeah, sprint guys. And that's one of their key things. Just like pick a highlight. What's gonna be like a highlight of your day that you look back on? That I did this thing, you'll feel good no matter what else happened.

So I'm trying to do that and that's been working really well. Another tip is to have a waiting for list. It's very like getting things done, David Allen style, where I have all these open threads of people doing stuff. And I keep a list of who am I waiting for on these things so that the to-do, even though it's on someone else's plate, I don't lose track of.

And the way I do it is in my to-do list, I just have W for Chris and then it's like record podcast or whatever. So that ends up being really helpful. The other interesting thing I find is procrastination has a bad rap. I find that sometimes I procrastinate on a hard thing, but I get a lot of other smaller things done.

So I like work through this list of stuff that isn't important, but I get them done. And there's value to just procrastinating off the thing that's like really hard because you still get other stuff done. So I try to channel my procrastination and get stuff done that I need to get done anyway.

That ends up being kind of interesting. - I love using the word flow state. There's deep work. And I don't know if you could say flow state and deep work are the same thing, but I think that sometimes it just takes a little bit of momentum to get into that flow state.

So it's like, I got this really big, hard thing. Do I want to sit down and do all this research? Or do I want to knock off a few quick things? And then I'm like, oh yeah, I'm making progress. I just cleaned up this set of my emails. I just got this one thing done and now I'm feeling really productive.

And at least for me, once I start feeling productive, it's just so much easier to be more productive and get more done. And then I find myself like, oh, I just wish I could work longer. I've got so much. So I love making momentum in that. So gosh, those are some really great tips.

I won't share too many of mine because I've done an episode with Ali Abdaal on productivity, with Cal Newport on deep work and Laura Vanderkam on time management. So if you're new here, there's a lot in the archives to go check out. So go check those out. But let's talk about moving on because you said you've left here.

You're no longer a full-time employee with a company. You're doing it on your own. How did you even decide maybe I should move on? I'm ready for a big change. - If you look at my resume, I'm like a serial monogamist of career. I worked at my first company for nine years, then at a startup.

That was the short stint, a year and a half. And then worked at Airbnb for seven years. I never thought I'd stay there that long. They bought our startup and I'm like, ah, I'm going to be out of here in three years when I'm going to start another company.

And then seven years later, here I am. And along the way, I thought about leaving, but it never felt like it was time. It was always interesting. There's always reasons to keep working there and try new stuff. And the way that it happened that I left is they gave me a sabbatical.

So I took three months off right around when I was reaching seven years. And about halfway through, I remember just opening my email for the first time. So a month and a half in the work email, just to see what was going on. And I just had this like heart sinking feeling where I'm like, I don't care about this at all anymore.

What the heck is, what is going on here? I don't want to think about any of this ever again. And so that was kind of an important moment where I was like, wow, maybe I'm not excited about this work anymore. I still came back to Airbnb after that and kind of wanted to feel out.

Am I ready for some new, is there like a new team maybe I could work on, new project that would get me excited? But basically the way it felt is I got there and I immediately felt like my heart was done with that work, but my brain wasn't ready to move on.

It was like, maybe there's something more interesting. Maybe there's a new manager. Maybe there's something else I could work on. So I took a month basically to think and talk to people about other roles, other teams, other opportunities. But I'd say at the end of the month, it was like, nope, nothing that gets me very excited.

It's time to do some new. And we'll say, it's like very fortunate to be able to have that feeling of like, I can leave and I'm not going to go bankrupt and have to live on the street. So I'm grateful that I have the opportunity to even have thought that, but I did.

And so what I decided to do is I'm going to leave Airbnb and I'm going to give myself six months to think about what I want to do next. And something that really helped there, and here's a tip if you ever think about something like this, is to figure out a personal runway of like how much it's going to cost you to take six months off and just budget that.

Like it's going to be $30,000 to take six months off, to pay all the things I'm paying. And just knowing that number ahead of time gives you so much less stress, knowing like burning through money as I'm not working, but I've already accounted for that. And it's like maybe sitting in a bank account somewhere and that gives you more freedom to just explore and not have to worry about, oh my God, I need to find something as soon as possible.

- And I'll just highlight the importance of actually putting it in an account. It's one thing to be like, well, I know I have enough savings to take time off. And this is something that I'm actively thinking about now that I'm creating this business on my own, just like you did.

It's like actually putting it somewhere. It takes it one step further. 'Cause a lot of it's emotional. It's not always rational. It's like, gosh, I don't have a salary coming in. I almost went as far as to take the salary, put it in a bank account and automate the transfers.

So it like simulated as if I was getting my paycheck so that I felt like it was not as scary to not have that stability. - No, that was great. The other thing that I found really powerful during this time, in addition to the personal runway, is there's so little structure when you aren't working.

Like I worked for, I think, 19 years, since like, you know, 18 years old. And I never take a break. And it's so weird to not have structure in your life. There's no deadlines. There's no like, I need to achieve this thing by then. Like you could work all day, you could not work at all.

Nobody's gonna say anything. And it's hard to work without that. Like it feels like it shouldn't be, but it really is. So what I did is I created structure for myself. And the way I did that is I created these little sprints where every two weeks I wrote down, here's the three goals I have for the next two weeks that are work goals and three personal goals.

And I emailed that to three friends that became kind of this like personal board of directors kind of group. And I had no expectation they'd reply. I didn't need them to reply. I just found that just emailing them, here's what I'm trying to accomplish. And then circling back in two weeks and sharing, here's how I did, created so much accountability and gave me some focus for these two weeks.

And I ended up doing that for a year straight every two weeks. I did a little check-in in one weekend just to like, here's how it's going so far per sprint. And that was so powerful and important to where I ended up just creating a little bit of structure.

And that email list ended up being like 30 people eventually just 'cause it became a cool way to update my friends on what I was up to. And just like, hey, you wanna join this list I'm doing? So that's a tip if you don't have enough structure around your free time.

- I do not yet. And I'm going to adopt that tip. - I will send you the template. It's so simple and easy and so powerful. - Maybe I'll make a Google doc, just a template one if you don't mind and we could just share it with everyone. - Let's do it.

- Put it in the show notes. - Yeah, absolutely. - I think one thing interesting that I've thought a lot about recently is as a creator, which you left and you started, I think the first thing out of Airbnb was a newsletter. I think a lot of people are kind of scared.

I don't know what my thing is, but I love the idea of experimenting with creation. And I think depending on the company you work at, you might be able to experiment before you leave. I would encourage everyone to get it cleared to make sure that your company isn't gonna own whatever you're working on.

Clear that, don't do it on your work computer, do it on your personal computer and all those good things. I think one thing for me that was strange was I had all this knowledge about optimization, but it didn't really click that it could actually be a thing that I do that could be a business that could be how I spend my days.

Do you have any advice for someone who hasn't quite figured that out? And they're like, I would love to do that, but I don't know what my thing is or I don't know how I could test if it really is a thing. - I think there's two things I'll cover there.

One is, can you start something while you're at a company? My experience is it's so hard. I found that I'm done at the end of the day working at a full-time job, like Airbnb. I'm just like, I have no brain energy left to experiment with writing awesome posts or podcast or anything like that.

It's very, very hard. And I think the advantage folks like you and I have that are doing this full-time is, I find there's a strong correlation between quality and time. There's a strong correlation between how much time you put into something and the quality of that work. And people that have a full-time job are not gonna have as much time as someone like you and I that are doing this full-time.

And so I think it's just really hard to try something like this for real when you have a full-time job. So don't feel weird if like, oh my God, everyone's writing all these side projects and writing things and starting podcasts. Like very, very hard. And I started writing, like I hadn't really written anything public in my life before I started this newsletter, just experiment with it.

And to segue to the second question is like, how did I discover this path? I just had like stuff I wanted to get out of my head when I left Airbnb, just to make sure I don't forget it in case I start another company. And so I just started, I wrote a Medium post, it did shockingly well.

I wrote a few more posts, they did well. In the sprint goal thing that I talked about, I just had like every sprint, just like, write one more post, see how that goes. So I just kept along that path. And the whole time I was like, why am I doing this?

I thought I was gonna start a company. Like, why am I spending time writing? This is such a not, I'm gonna go anywhere. Time investing, my wife's like, what are you doing writing? You're not a writer. I thought you wanted to start a company. Why aren't you spending time on that?

And I had this really important conversation with a friend who pointed out, okay, you really enjoy this thing. People seem to value it. That's like very rare. You found like some kind of product market fit. Maybe this goes somewhere if you keep at it. And even if there's no way you could ever make money with it, maybe just double down on that and forget the startup stuff for now and just see where it goes.

And that's exactly what I did. I just started writing every week, launched a newsletter just to create a little time pressure to post something once a week and did that for nine months every week. And then at that point, I'm like, huh, this is still going great, growing fast.

Maybe I could charge for this. I launched the paid plan that went well and I just kept following that path. And so it was very one step at a time without any master plan. - And you say it just kind of grew. How big's the newsletter now? - It's about to hit 300,000 subscribers.

- Yeah, so it's a massive newsletter. - Massive, number one business newsletter on Substack and growing fast. I love it. It's kind of the core of my work and then the podcast kind of spun out of that. - Well, I've enjoyed it thoroughly. In fact, in preparation for this interview, I was a little stressed out because I was thinking, gosh, I'm leaving my job, but I really do love building products.

And I was like scrolling through, trying to like look at all the posts you've written. And I was like, gosh, wow, I really want to build this impactful project. Like I really want to make another roadmap. I've got to channel that energy. And for everyone listening, now I'm focused on what kinds of products and experiences and communities, all of the things could I build around what I've done with all the hacks.

So more to come there, but it's been very helpful. So thank you for that. Before we wrap, anything we missed in this process? I know you've written so many great newsletters. So I want to make sure we hit on something that you've thought about. - There's something that I thought would be good to share, which is around managing up.

I find that whenever I tweet about managing up, it's like the most popular tweets ever. Clearly people really want to learn how to manage up better. And there's one thing that I'll share that I found really effective, which is around how to keep your manager aware of what you're up to.

There's a lot of value in your manager knowing what's on your mind, what's important to you right now, what can they help with? So something that I found to be really powerful is an email that I call the state of me email. So it'd be like the state of Lenny email.

I call it the subject line state of Lenny. And in the email, and I email this to my manager every Monday or every Friday, once a week, I write out, here's blockers that I need your help with. One, two, three. Here are my current priorities. One, two, three. And then here's what's on my mind in general.

One, two, three, four, five. And then at the end, just like, let me know if there's anything that I can clarify, if you have any questions about anything. And I found that one email created so much value because my manager knew what I was up to. They could tell me, hey, why are you working on that?

They can unblock stuff that I'm blocked by, which a lot of times they don't know that you're blocked by some. And then generally there's stuff on your mind. Like, hey, I'm thinking about this project. This person's thinking about leaving. This competitor's doing this thing. So just that one email can make a huge dent, and it's really simple.

Just like blockers, priorities, what's on your mind. Send your manager that once a week, and honestly, great things are gonna happen. - I said earlier, you don't wanna be always saying yes to your manager, but making your manager's life easier is certainly something that is a very valued attribute of an employee.

So in making it easier for them to understand everything you're working on, making it easier for them to say, I love this email idea. It's like, oh, no, actually work on this. That will let you have more impact. So love it. This has been so helpful. I wish that some of these things I had taken before, but like I said, I didn't know where I'd be now.

Who knows where I'll be in 10 years? And certainly many people listening will hopefully get a lot of value out of this and out of the newsletter. Before we go, I do wanna ask you, is there a place that you feel like you could give some recommendations to people who might find themselves there on, whether it's eating, activities, drinks, something to do?

- Sure, I'm not like the guy people go to for advice on what to do in a place, but you gave me a heads up on this question. And so here's what I got for you. I live in Marin, California, which is north of San Francisco. And so here's a little agenda.

If you wanna come to Marin, I'd say stay at this hotel called Cavallo Point Lodge. It's gonna blow your mind. Then take a little walk around Sausalito along the water. There's this boardwalk that goes along the water. Then just grab lunch at a restaurant there. There's like these piers with these beautiful seafood restaurants.

Then take a drive to San Francisco across the Yuletide Bridge. There's this art piece called the Woodline in the Presidio that is this like curvy piece of wood that you can walk along amongst these huge eucalyptus trees. And that's right across the bridge. Then you can go to say Fillmore Street or Chestnut in the Marina and get a coffee, buy some nice fancy things in some of the nice stores.

Then I'd say drive back to Marin and maybe to Fairfax, which is further North, rent a mountain bike, find some trails, mountain biking was invented in Fairfax. And there's this huge mountain, Mount Tam, there's like a thousand trails you could go along. So maybe spend a few hours hiking around Mount Tam, sorry, biking around Mount Tam.

Then have dinner in Fairfax or there's another cute little town, San Anselmo. And then head home to your cute little hotel in Sausalito. - I love it. If you're in Sausalito, I'll throw out a recommendation for a place called Fish, which is just like a seafood restaurant on the water.

- Sweet, there's your lunch spot, great. - It meets the requirement of being Bay Area expensive, but also delicious. So I love that. And I don't know if you've been to the Mill Valley Lumber Yard. - Oh yeah, the cutest little complex. - Someone was like, can we meet at this bakery in Mill Valley?

And I showed up and I was like, this is literally like this quintessential cute little shops and a little flower store and a bakery and a little creperie. And so if you need a place to just relax for an hour and a half or two, highly recommend that as a stop in Mill Valley.

I have not spent much time in Marin, but that place was just an awesome spot. - Yeah, it's like very unknown, but so cute. And the bakery is called Flower Craft and it's all gluten free. My wife's got Celiac and so it's her favorite place. - Great bakery, awesome.

Well, before we wrap, where can people go find all of these great newsletters, all the conversations you're having with people, myself included, which depending on whether this comes out at the same time, we had a great conversation over there. Let everybody know. - The hub of all things I do is Lenny'snewsletter.com.

That's where my newsletter is, my podcast. It's designed for anyone that's building product, growing product, mostly product managers, founders, designers, engineers, anyone basically working on software. Lenny'snewsletter.com. You could also check out Lenny'spodcast.com. It's a newer thing, but doing super well. And I'm really proud of it. So check that out and @LennySan on Twitter.

- What's the story behind the San? - One of my friends, when I was in high school, just called me Lenny San for some unknown reason and I stuck with it. I didn't know I was gonna be stuck with that username for the rest of my life, but here we are.

- Awesome. All right, thank you so much for being here. - My pleasure, Chris. Thanks for having me. (upbeat music) - I really hope you enjoyed this episode. Thank you so much for listening. If you haven't already left a rating and a review for the show in Apple Podcasts or Spotify, I would really appreciate it.

And if you have any feedback on the show, questions for me, or just wanna say hi, I'm Chris@allthehacks.com or @Hutchins on Twitter. That's it for this week. I'll see you next week. (upbeat music) (electronic music) (electronic music fades)