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 because 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.

The question is, how do you stand out? How do you stand out? You do 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 because 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. Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel.

Today, we're going to 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 product building isn't why he's here today. It's because he's written so many amazing newsletters about his professional work that I've found so valuable to my own 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. So let's jump in. Lenny, thanks for being here. My pleasure, Chris. 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 going to dig into a little bit more about the transition to creators. I just got to 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." Or 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 finds 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 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. 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 going to talk that much about product today. We're going to 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, because 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. And 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 a 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 want to do and find a company and then actually stand out to get in the door?

Yeah, let me talk about the job board briefly because I think it's cool. 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 substack 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 go look for PMs better than this place.

And fun fact, they make more income from just the job board than I made at Airbnb in salary. And so it turns into a really interesting business on the side and shows the power of an audience with the newsletter and the audience of that being funneled to the job board, creating a marketplace.

It's really interesting. 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.

They're either, and 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, because 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 as a product, VPs a product.

And so I think it's the model. 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 pallet, does there, you might not know this, but is there a directory of all the different job boards they power for something like this?

You know, 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 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 candidates. So yeah, it's pretty cool what they're building, how, if you're building this profile, right, you're a candidate building a profile, 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, there's a lot of personal things that are important to people like where they work, where they live and are 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, you know, going to go work, trying to go work or already working. And there's kind of 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 to you'll learn a lot more from that group. If you're just working with the smartest people, you can find, you're going to 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. And 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 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 to. I think a lot of people under appreciate the importance of stage of company. There's such a different experience working in a startup versus a big company.

And so I think it's really important to think about what's the stage that you want to 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 going to be like so stressful all the time, but it's not like a meta or Google.

And so that's kind of 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 going to be like, okay, look, I spent three years at this company.

I moved this metric 5%. And so like, you're not going to 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. So and then the fourth is you just want to pay attention to the quality of the business. Like is it going to work out? Is it going to grow? Is it going to, do they have to keep raising money forever? Are they going to be profitable?

Especially important in today's climate. And this is especially important because one of the, and we'll talk about how to stand out, 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 like 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 want to work at a company that ends up being like, oh, wow, they worked that. Now we were going to 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 going to pick a startup.

That's really popular. People will remember. And I was like, oh, what company just raised a bunch of money? What's kind of 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, 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.

I think another way to think about that, those stages is kind of 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 going to be a place where you can really focus on one thing and really hone that, that skill, whether it's a set of managerial skills or, um, you know, anything at an early stage company, you're going to accelerate the speed at which you learn, but it might not be as, as kind of 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, you know, being the janitor sometimes, you know, I think I've had every role at a company except engineer at times. And um, that, 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. You know, if you're trying to jump into a new career, it's going to 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 kind of move, move across very, very easily. Yeah. That reminds me real quick 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. You can solve this problem. Life's going to be so much easier. And so sometimes you want that. Sometimes you don't. Yeah. And my wife was the chief of staff at Lyft for a bunch of years.

She joined when the company was very small and she had, you know, the opposite experience, which is she got to see everything. And it was an amazing opportunity because the company was growing and she had all these different war, 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, because it's really hard. It's not necessarily hard, but 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 for, you know, 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. And so 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.

And 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. Yeah. And if you can find, you know, the Japanese phrase, Ikigai, if you're familiar, if you can find that, obviously it's like the dream, right? It's, which is the intersection of what you love, what you're good at, what the world needs and what you could get paid for.

Like, you know, that's the dream. It's like, you know, 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 you know, I wouldn't necessarily hold out for, for finding something that ticks every box.

I think one way to think about 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, I was a newsletter. And 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.

Yep. And you, I don't know about you, but I went through investment banker, management consultant, founder, uh, or employee PM BD, I did BD then founder, then, uh, went to Google and was a venture capitalist. And then I was, you know, I went through a lot of, and now I'm a creator.

Um, I never knew half of those things more than three months before, you know, like some of them, I was like, I never knew I would be VC. And then that opportunity arose. I never thought I'd be a creator. And then I started a podcast. And so I think you don't need to know the future.

I love this idea of where do you want to be with your life in 10 years? And if you, 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, you know, 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.

And a lot of people don't understand the value of just trying a bunch of different stuff and not feeling like they have to be stuck. Here's the thing I'm going to do for 10 years. You found a handful of jobs. My personal belief is that in today's world, you're much better off trying to narrow it down to three or four companies that you're really excited about and double down on your efforts to get in front of them.

And 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. 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 want to understand who you are, so I know where to slot you in later.

And so 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 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 want to 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, that's it. So 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, kind of 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 because 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.

So 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? You do 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." Like I watch them. Most of the time I talk to them because they put in the effort and they do something unique. So I think it applies to investing too, pick like the people you really want on your cap table and do some extra. I think broadly, like if you don't do anything like this, the things you need, because I'm with the job board, I review, 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.

So like you're not going to be able to do a lot about this, but this is what hiring managers look for. Companies that they respect, that have kind of 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.

So 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, is great. Do something, do something remarkable. I love the idea of like a loom resume.

I wonder if you just like, you're, you know, send in your resume, but it's like, if you'd rather not look at another, 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 by the way, you can put it on two X, if you want to 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. What about interviewing? Have you thought a lot about, you know, both on both sides of it, what people should be focused on versus not like, I don't know if I'm going to give you anything that you haven't heard before, other than just spent 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, 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, I guess, 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, like stuff you hear all the time. So I don't think there's anything dramatically new, but yeah, people want you to ask them questions because they want you to, they want to feel like you care about the company.

I've interviewed people who I'm like, why do you want to work here? And they're like, well, when I had 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.

So 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. 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, uh, 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, you know, from a product standpoint, what are you guys doing to help the marketing team solve this?

And it's like, wow, now you get to learn a lot of stuff, but it actually shows that you're actually trying to solve problems. You're trying to be, you know, get more out of it. So 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.

I think that they can often leave people with a better impression of you and not just be information gathering. It reminds me, one of the most interesting, 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 could probably see a bunch of really fun interview questions.

I will link to that show notes so people can find it. Now let's say you get the job and 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.

You know, 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 in your newsletter. This post ended up being the most popular post of my newsletter of all time, partly because it got on Hacker News and got a ton of views and some recruiters did not like it.

And so I kind of, it's, it's good and bad, but I learned a ton from it. And the reason I asked, 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 she, her full-time job basically is helping candidates negotiate their offers and help them find jobs. So she's done this a ton. And I'm not going to share, go through everything. 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. Her advice is just ask them, like, 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 why is this role open? What's the biggest challenge for someone getting into this role? And the reason that's important is then you can mirror that back when you're pitching yourself. Once you've got an offering, you want to counter, you can highlight, hey, here's what I'm going to help you with.

Here's what I'm going to do in this role. Here's the challenges I'm going to tackle immediately. And people are going to be like, holy moly, that's exactly what we need to know. So the tip there is just mine, like ask these questions so that you 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 want to 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 got to pay him whatever he wants. And the way you do that in her advice is after you get the offer schedule, try to get a meeting with a decision maker, like a director or VP or something. Just like, hey, I just want to chat about this role.

And then 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 going to do there. And then maybe share obstacles that you have in accepting the offer and taking on the role. And generally just get them, try to get them excited about you joining the company.

And with that, then you can come back with like, okay, here, 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 to be like, oh, yes, yes, yes, let's do whatever we need to do.

I love that third tip because, uh, it's almost like, you know, come up with a plan. You could even talk to the person that would be your manager and be like, Hey, you know, I know we're talking about salary negotiation already, but I just want to 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 going to do. And they're like, gosh, we already, we've already decided where first project, like, can we get going? Right. Like get them in the hell. Let's get going.

What are we doing? Negotiate? My, my, my other piece of advice to people is the 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, uh, you know, things like vacation days are flexible.

Some they're just based on tenure or everyone gets the same. Um, some educational reimbursement is one that you can focus on. Um, others, I've found companies that say, you know, we're not really willing to flex on the salary and then, but I've heard from, you know, after I've worked there that they are willing to flex on a signup, a signing bonus, um, you know, they are willing to flex on various other aspects of compensation, like what your estimated bonuses, uh, I helped a friend negotiate.

He said, you know, sometimes it's like, Oh, well now I know the band for the level, but why could I be at the next level? Like 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, 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, 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, uh, 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, you know, 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. So like, if I'm not getting this, then what, why were you telling me that? So you're kind of similar to how you said, getting the buy-in before you negotiate, you're getting the buy-in that you're already going to get approved for this change.

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

He was the CEO of wealth threat. His advice was to always just put the decision in someone else's hand and say, what, what do you think is fair? And he said 90% of the time, uh, 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.

Um, I I'm trying to think, you know, I, I always like sharing negotiation advice, even if it's not relevant to salary. Um, but you could basically say, here's all the data I've collected about what this role should be compensated. I, I, I 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. I feel like, you know, that that's maybe depending on the circumstance, uh, a good last tactic or a starting point, but I like, and have used many times the tactic of letting someone else decide what's fair and not have to throw out the number first.

I like it. Okay. So we've gotten hired. We're now at a company. And I want to focus on something that applies to everyone actually working at the company they're at. Um, there is a lot we could cover here. I don't want to go through every possible thing, but there are a few things that I think you might have, you know, outsized impact on the conversation about.

And the first one is actually about having impact in an organization, uh, and hopefully a little bit about how to get promoted on the way. But I know you kind of believe those two things are both similar and very different. So what do you, 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. I think 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.

I think that's like 90% of your success at a company. And 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 like 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 and you're like, how do you find the way you can have that impact? Well, there's one way I think about it. I kind of 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 going to be like so stressful and difficult. They'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 want to optimize like 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 burnt 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. Impacts the most important thing. I've seen you write about how to get promoted effectively and that impact matters. So any comments on that? 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 show you promote Chris, basically you need to give them confidence that you can handle more scope, more responsibility, more, 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.

Now two is part of the idea of a promotion is people are going to 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 want to 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 going to take a year or two. It's going to 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. So, and 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've got to look for things, you've got to find opportunities to take on more scope.

Those are two, there's five more in this post that I wrote, so let me just run through them pretty quick. Three is part of the reason you get promoted is there's this gap that your manager has identified. Like Chris needs to work on a better deadline setting or, or, uh, 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, um, 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, um, create basically a roadmap.

Like I'm going to work on becoming a better public speaker. I am going to get deadlines 90% of the time. I'm going to update our JIRA, uh, to be up to date by the end of Fridays, make a list of the things that are the biggest, uh, things you can actually do that'll bring you to the next level.

And then meet with your manager slash report every month and review the status of each of those things. And 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 the performance review, you, uh, you don't, you're unsurprised 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 the gap for finding someone that can champion you. That's often really powerful at a company, get someone really excited about you and can champion you inside of these calibration sessions. That's really powerful. Um, five is you want to pay attention to what gets promoted at the company.

A lot of companies have these like gray area things that matter a lot that you may not be aware of. So just look at people who are getting promoted and just understand, 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, um, something that's way underappreciated is you just need to ask to get promoted. Sometimes, sometimes managers don't know you want to 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 and 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 going to 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, uh, when I was a venture capitalist, the role of like, I guess, non general partner, we were told it was like, this is a terminal position.

Like they were just very transparent. They're 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. Uh, 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 because the word terminal position just sounds like, you know, going nowhere, but I appreciate the honesty. I appreciate the transparency. The one thing that I learned and you, 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, you know, 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 what do I need to, if I'm a level five manager and I want to 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 going to be promoted to say L seven, there's like, here's what L seven has to be good at, at each of these things. And that's a manager. Look at is Chris ready for all these things in L seven. Makes sense. Like your job is going to now be that you want to 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, 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. Yeah, I've actually, I've actually collected the career ladders at 20 something companies. And I have this doc that we'll link to in the show notes that has all their level names and then the attributes that they live for product managers specifically that they look for to promote people.

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

What do you think is the right balance of, you know, saying no? And what's the value of saying no, as opposed to kind of always being willing to do what other people want? As a PM and just as a leader in general, like you're the person that needs to say no, because you're kind of responsible.

And I'm thinking from a PM perspective, product manager perspective, you're kind of responsible for what a whole team of people does. And so part of your 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 is like, hey, we need to do these things. So I wrote this post with, I think, five ways you can say no that 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 asked you to do something. You could say yes, but here's what's going to 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 want to, I don't want to deprioritize that. Forget that. So that's one trick. Two is you could say yes, but not right now because we got to 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 because it basically communicates, again, here's like a very clear trade off and 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 going to achieve a similar outcome. Basically, this is when you have a better idea, but you want to 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 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 because I was like, no, that's so crazy. Why would we do that? I could have used this. I was never good at, you know, 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 like, 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 like it didn't matter.

And then I joined a company where I wasn't in charge and, and you know, 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 it optimized for the company.

That's the most important thing. That's how I lived in my last companies that I've run. And 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, well that 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. And so just stating your intent before you push back. So people know where you're coming from. It 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 read your mind real quick before we, we talk about what happens when you move on from a job, you know, part of getting things done as being productive. I've talked a lot about time management. I'm a nerd. We don't have to go super deep because 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 full time. 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, 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 had, 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 like funny way to have a block where people know, okay, I see he's like 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, uh, I have no meetings until 3:00 PM. That's my rule.

And only at three, I have meetings and things like this. So that helps them too is just what's like an app or something that keeps you focused when you're working. I use this app called centered dot 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, click play and music starts and it's like Lenny, you're starting 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. It's called make time. Yeah. Sprint guys. And they're, that's one of their key things. Just like pick a highlight. What's going to 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, 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 as 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. Like it 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, uh, I need to get that anyway.

I think about there's deep work and I don't know if you could say flow state and deeper or 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, ah, I got this really big, hard thing.

Do I want to sit down and do all this research and you know, 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, this set of my emails. I just, you know, 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, get more done.

Then I find myself like, oh, I just wish I could work longer. I've got so much. So, um, I love making momentum in that. So 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 on with Cal Newport on deep work and, uh, with 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 know, you said, uh, you've left here. You're no longer a full time employee with a company you're doing on your own. How did you make that decision to move on?

How did you create space for it? Um, and, and did you ever think about ways to test out, uh, going out on your own before before that? That's a lot. So, uh, maybe, maybe start with, uh, how did you even kind of 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 year and a half, and then worked at Airbnb for seven years. And uh, I, like, I never thought I'd stay there that long.

They bought our startup and I'm like, oh, 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. Um, and the way that it happened that I left is I took a sabbatical, uh, they gave me a sabbatical. So I took three months off, uh, 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? And I just, 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, 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, like, am I, am I, is there like a new team?

Maybe I could work on a new project that would get me excited. But basically the way it felt as 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 it took a month basically to think about 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 rare. It's like very fortunate to be able to have that feeling of like, I can leave and things aren't going to, I'm not going to go bankrupt and live on the street. So it's a really, 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. When you're thinking 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, 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 I'm 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 grading this business on my own. Just like you did it.

It's like actually putting it somewhere. It takes it one step further. I think it has even more it because 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. 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 in our, 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. That's like, there's deadlines, 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 going to 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 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 because it became a cool way to update my friends on what I was up to. And just like, Hey, you want to join this list I'm doing. And so that's a tip in your, if you don't have enough structure around your, your free time.

I think one thing interesting that I've thought a lot about recently is, you know, as a creator, which you, you know, you left and you started, I think the first thing out of, 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 kind of experiment before you leave. I would encourage everyone to, you know, get it cleared to make sure that, you know, your company isn't going to own whatever you're working on, you know, clear that don't do it on your work computer, do it on your personal computer and all those good things.

But how did you start to think about, because I think, I think one thing for me that was strange was I had all this knowledge about optimization, like, but I, 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, you know, 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, I, it's so hard. I found that like, 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 a podcast or anything like that.

It's like very, very hard. And I think the advantage folks like you and I have that are doing this full-time is there's, I find there's a strong correlation between quality and, and how well it does. And so we just, and time, sorry, 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 going to 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.

When 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. And then just kind of 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 going to start a company, like why am I spending time writing? This is such a not going to go anywhere. Time invested, my wife's like, what are you doing writing?

You're not a writer, I thought you wanted to start a company, why don'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 a 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 is the newsletter now? It's about to hit 300,000 subscribers. Yeah, it's a number one newsletter and massive number one business newsletter on Substack. And growing fast. I love it. It's kind of the core of my, 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. So you know, now I'm like, I've got to channel that energy. And for everyone listening, now I'm focused on what kinds of products and experiences and communities and all of the things that I build around what I've done with all the hacks.

It's hard to come there, but it's been it was very helpful. So thank you for that. Anything we missed in this process, we went through, you know, finding a job standing out, running through, you know, working and having impact and moving on. 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. Really 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 1, 2, 3.

Here are my current priorities, 1, 2, 3. And then here's what's on my mind in general, 1, 2, 3, 4, 5. 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, they can unblock stuff that I'm blocked by, which a lot of times I 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 competitors doing this thing.

So just that one email can make a huge dent and really simple, just like blockers, priorities, what's on your mind, send your manager that once a week and honestly great things are going to happen. Yeah. I mean, I said earlier, you don't want to 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 making it, 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. And this has been so helpful. I, you know, I wish that some of these things I had taken before, but like I said, you know, 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 want to 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, I'm not like the guy people go to for advice on what to do in a place, but yeah, 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, there's a little agenda.

If you can want to come to Marin, I'd say stay at this hotel called Cavallo Point Lodge. It's going to blow your mind. Then go 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 Yule game bridge. There's this art piece called the wood line in the Presidio that is this like curvy piece of wood that you could 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 Ham, there's like a thousand trails you could go on.

So maybe spend a few hours hiking around Mount Ham, sorry, biking around Mount Ham. Then have dinner in Fairfax or there's another cute little town, San Anselmo, and then head home to your little, your cute little hotel in Sausalito. 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. It meets the requirement of being Bay Area expensive, but also delicious. I love that. 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?" 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." If you need a place to just relax for an hour and a half or two, I 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. The bakery is called Flower Craft and it's gluten-free, all gluten-free. My wife's got celiac and so it's her favorite place. 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.

The hub of all things I do is lennysnewsletter.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. Lennysnewsletter.com. Just check out lennyspodcast.com, the newer thing, but doing super well and I'm really proud of it.

So check that out. And I'm @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 going to 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.