ATHLLC6854671700

00:00:00.000 | (upbeat music)

00:00:01.800 | - Hello, and welcome to another episode of All The Hacks,

00:00:04.480 | a show about upgrading your life, money, and travel.

00:00:07.380 | I'm your host, Chris Hutchins,

00:00:08.640 | and today we're gonna talk about the best strategies

00:00:11.060 | and tactics for your work.

00:00:12.880 | That means finding a job you love, interviewing,

00:00:15.240 | negotiating your comp, managing up, making an impact,

00:00:18.580 | getting promoted, and a lot more.

00:00:20.680 | And to do this, I'm joined by Lenny Ruchitsky,

00:00:23.400 | who sold his company to Airbnb in 2012

00:00:25.800 | and spent seven years working in product across the company

00:00:28.760 | before leaving to start his newsletter

00:00:30.480 | and more recently podcast.

00:00:32.320 | Now, Lenny is well-known as one of the top minds

00:00:35.080 | in the world when it comes to building

00:00:36.560 | and growing software products.

00:00:38.080 | And his podcast, Lenny's Podcast,

00:00:40.180 | is the number one product podcast in the world.

00:00:43.340 | But building products is not why we're here today.

00:00:46.360 | It's because he's written so many amazing newsletters

00:00:49.220 | about professional work that I've personally found

00:00:51.760 | so valuable to my career.

00:00:53.940 | So, whether you're looking for a job right now,

00:00:56.480 | trying to have more impact in your current role,

00:00:58.800 | or thinking about what's next,

00:01:00.440 | I am sure you'll love this episode.

00:01:02.280 | And speaking of jobs,

00:01:03.900 | I have a big announcement to share on my end.

00:01:06.200 | After three amazing years at Wealthfront,

00:01:08.440 | I am finally stepping away to focus on all the hacks

00:01:11.840 | full-time starting tomorrow, December 1st.

00:01:14.880 | It's a bit of a scary jump to leave a stable job,

00:01:17.640 | but I love what I'm doing with the podcast

00:01:19.440 | and newsletter so much that I felt like I had to see

00:01:22.480 | what was possible if I focus on it full-time.

00:01:25.000 | I'll have a lot more to share on this soon,

00:01:26.960 | but wanted to make sure you guys heard the news first.

00:01:29.800 | All right, let's jump in right after this.

00:01:32.520 | Lenny, thanks for being here.

00:01:35.800 | - My pleasure, Chris.

00:01:37.520 | - So, you have written a ton of content

00:01:40.400 | about product management and amongst product managers,

00:01:43.200 | which I formerly was, you are well-known in that space

00:01:47.280 | for being a thought leader.

00:01:49.120 | However, I found that a lot of your content

00:01:51.960 | is very, very applicable outside of product management

00:01:55.320 | to anyone who has a job.

00:01:56.680 | And now we're probably gonna dig into a little bit more

00:01:58.520 | about the transition to creators.

00:02:00.080 | I just gotta ask, are you aware of the breadth

00:02:03.320 | of applicability of your content?

00:02:05.040 | And do you see a transition in the future

00:02:08.080 | to just more than product-related content

00:02:10.520 | and just really growing beyond that?

00:02:11.920 | - I am aware the content is useful to a lot of people

00:02:14.360 | other than product managers because I get emails from people

00:02:16.800 | and they're like,

00:02:17.640 | "Hey, our marketing team's finding this super useful."

00:02:19.480 | The funniest example is my mother-in-law who is 75,

00:02:23.760 | I think, something like that.

00:02:24.960 | And she reads every post that I write

00:02:27.360 | and find something in there that is applicable to her life.

00:02:30.000 | And that just shows me that there's all these little lessons

00:02:32.760 | that you can extract from things that are specifically meant

00:02:35.680 | for product managers and founders.

00:02:37.560 | But I will say, I try very hard to stay focused on a PM,

00:02:41.880 | a founder, someone building product,

00:02:43.640 | because I think that's the reason it does well

00:02:45.840 | is it's solving like a very clear person's problem.

00:02:48.560 | And if I were to try to broaden it too wide,

00:02:50.720 | I think it would just lose the power

00:02:51.880 | and just become nothing amazing for any one person.

00:02:55.160 | So it is a balance, but it is cool

00:02:57.640 | that the second order effect becomes useful

00:02:59.640 | to a lot of other people.

00:03:01.080 | - So for anyone listening, Lenny has a newsletter,

00:03:03.560 | Lenny has a podcast.

00:03:04.520 | I have been a guest on his podcast

00:03:06.120 | that may or may not have come out before

00:03:07.600 | or after this comes out and highly recommend it,

00:03:10.520 | even if you're not in product,

00:03:11.920 | just like your mother-in-law said.

00:03:14.000 | However, we're not gonna talk that much

00:03:16.040 | about product today.

00:03:17.000 | We're gonna talk about some of those other things.

00:03:19.160 | And in fact, I thought as I went through

00:03:21.400 | a lot of your posts that you have a really unique

00:03:24.480 | and great perspective on the process

00:03:27.360 | of someone going through their career,

00:03:29.520 | both getting a job, working at a company,

00:03:32.320 | starting on your own.

00:03:33.560 | And I've thought a lot about this too.

00:03:35.320 | So I thought we could just have a conversation

00:03:37.400 | to walk through that process.

00:03:39.120 | And you could share a lot of the lessons

00:03:40.560 | you've learned and shared and written about for anyone,

00:03:43.480 | whether they're trying to advance their career today

00:03:46.400 | or they're looking for something new

00:03:48.400 | or they're looking for something right now

00:03:50.280 | because we're in an unfortunate situation

00:03:52.360 | where some people may have lost their jobs.

00:03:53.960 | And I would love to give them more tools

00:03:56.400 | to be successful in their search.

00:03:58.080 | So how's that sound?

00:03:59.640 | - Sounds great with the caveat that I write these posts

00:04:02.280 | and then the content leaves my brain and lives in the post.

00:04:05.400 | And part of the reason I write them is like,

00:04:06.760 | hey, go read this thing 'cause I forgot all the answers.

00:04:09.080 | So I'll do my best to extract what I can remember.

00:04:11.600 | And I did a little prep,

00:04:13.120 | but I won't have all of the answers in my head

00:04:16.080 | on demand necessarily.

00:04:17.960 | - Well, fortunately for you,

00:04:19.320 | I try to do a really good job

00:04:20.680 | of putting resources in the show notes.

00:04:22.280 | So if there's one that we feel like your answer

00:04:25.200 | is lacking in comparison to what I've seen you write,

00:04:28.240 | I will make sure that we link that so people can follow up.

00:04:30.960 | But let's start with the process

00:04:33.200 | of finding the right kind of job.

00:04:35.080 | So there are so many types of companies out there.

00:04:38.200 | What advice do you have for people looking for something new,

00:04:41.960 | both in just how to narrow down the options

00:04:44.600 | and actually stand out to candidates

00:04:47.680 | to get that first interview?

00:04:48.960 | So just thinking that process.

00:04:50.440 | And for side note, Lenny also runs a job board

00:04:53.640 | and a talent collective for people in the product space.

00:04:57.080 | So you've seen this both as a person in it

00:04:59.520 | and a person creating this thing.

00:05:01.040 | So just to recap, how do people narrow down

00:05:03.920 | what they wanna do and find a company

00:05:06.000 | and then actually stand out to get in the door?

00:05:08.840 | - Yeah, let me talk about the job board briefly

00:05:10.280 | 'cause I think it's a cool piece of context

00:05:12.200 | that shows kind of how much I spend thinking about

00:05:14.680 | people's profiles and companies and things like that.

00:05:17.080 | So it's called Lenny's Jobs.

00:05:18.680 | It runs on this platform called Palette,

00:05:20.360 | which is kind of like the sub stack for job boards.

00:05:22.560 | It's kind of this white labeled job platform.

00:05:25.360 | And the way it works, there's kind of two parts to it.

00:05:27.440 | There's a regular job board

00:05:28.560 | where people just post job openings.

00:05:30.360 | And then there's a reverse job board

00:05:31.920 | where candidates can sign up

00:05:34.080 | because they're interested in new opportunities

00:05:35.720 | and they can just be like,

00:05:36.560 | hey, I'm open to a new opportunity.

00:05:38.280 | I'd love to hear from interesting companies.

00:05:40.000 | And it can be anonymous.

00:05:41.200 | You could hide yourself from companies

00:05:42.480 | that you don't want to see that you're looking for a job.

00:05:44.800 | And it's doing really well.

00:05:47.000 | It's become maybe the number one place

00:05:49.560 | to find product people.

00:05:50.600 | I don't know where else you'd go look for PMs

00:05:52.480 | better than this place.

00:05:53.840 | And fun fact, I make more income from just a job board

00:05:58.200 | than I made at Airbnb in salary.

00:06:00.440 | - Wow.

00:06:01.280 | - And so it turns into a really interesting business

00:06:02.600 | on the side and shows the power of an audience

00:06:05.080 | with the newsletter and like the audience of that

00:06:07.440 | being funneled to the job board, creating a marketplace.

00:06:10.320 | It's really interesting experience.

00:06:12.200 | - If you look at people

00:06:13.080 | that actually end up getting jobs from this,

00:06:15.640 | is it more from people finding the job from the employer

00:06:18.880 | or have things changed in the environment

00:06:20.960 | where the employee putting themselves out there

00:06:24.160 | is actually leading to more jobs?

00:06:25.680 | - Yeah, so one thing I've learned from this

00:06:26.960 | is job boards do not work well.

00:06:29.280 | And a job board meaning you post an opening on a job board.

00:06:32.080 | If it works for you,

00:06:34.000 | it's like the best ROI in the history of hiring

00:06:37.480 | 'cause it's like 50 bucks, 100 bucks, 200 bucks

00:06:39.800 | to post a job and you find someone for that

00:06:41.600 | and then you're done.

00:06:42.720 | But it almost never works is what I found.

00:06:44.880 | What actually worked is the reverse, the other piece,

00:06:47.440 | where candidates that are awesome apply.

00:06:50.720 | I approve them and I only approve about 10% of people

00:06:53.480 | to keep the quality by really high.

00:06:55.320 | And that has led to so many companies finding.

00:06:57.840 | PMs, that's a product, VPs a product.

00:06:59.600 | And so I think that model is a lot more effective

00:07:01.800 | now before the economy changed.

00:07:04.080 | And so I'm leaning into that.

00:07:05.760 | I'm kind of moving away from the job board.

00:07:07.320 | - And this site you said, Palette,

00:07:09.120 | is there a directory of all the different job boards

00:07:11.440 | they power for something like this?

00:07:12.960 | If someone listening is like, I'm not a PM,

00:07:14.600 | but I would love to participate

00:07:16.520 | in this reverse job search process

00:07:18.280 | to put myself out there in front of companies.

00:07:20.120 | Are there other job boards or a directory of them

00:07:22.400 | to go find places to post yourself?

00:07:24.200 | - Yeah, they actually have a cool feature.

00:07:25.520 | I think it's called Spotlight where you work with them

00:07:28.440 | and they give you access to a ton of different job boards

00:07:31.840 | for specific profiles.

00:07:33.280 | And so I get these applications for one company

00:07:35.960 | looking for like a designer

00:07:37.120 | and they can just only look at my designer.

00:07:38.920 | And then they can find candidates.

00:07:39.880 | So yeah, that's pretty cool what they're building.

00:07:42.240 | - Awesome.

00:07:43.080 | If you're building this profile, right,

00:07:43.960 | you're a candidate setting aside that it's in product,

00:07:46.400 | but what are the things you think you've seen people do

00:07:49.320 | to one, stand out,

00:07:50.480 | but also to identify what they're interested in?

00:07:53.160 | 'Cause I think there's a world of all kinds of companies

00:07:56.000 | you could work at.

00:07:57.200 | - The way I think about it,

00:07:58.040 | there's a lot of personal things

00:07:59.120 | that are important to people,

00:08:00.200 | like where they work, where they live,

00:08:02.320 | and how hard they want to work and things like that.

00:08:04.560 | But I'd say if you just,

00:08:05.880 | if I think of four things that are really important,

00:08:08.080 | I think of the people at the company,

00:08:10.360 | the stage of the company, the mission of the company,

00:08:13.080 | and then just the quality of the business.

00:08:15.400 | So just to go through them briefly.

00:08:17.400 | So with people, what I look for,

00:08:19.160 | and what I think you should look for is

00:08:20.840 | where the smartest people going to go work,

00:08:23.120 | trying to go work, or already working.

00:08:26.000 | And there's a few reasons why that's really powerful.

00:08:28.800 | One is it's more likely that they'll build

00:08:31.120 | an awesome product and awesome business

00:08:32.520 | that'll do really well.

00:08:33.560 | So the smartest people working in a company

00:08:35.760 | more likely to succeed.

00:08:37.840 | Two, you'll learn a lot more from that group.

00:08:39.920 | If you're just working with the smartest people,

00:08:41.440 | you can find you're gonna learn a lot more.

00:08:43.720 | And then three,

00:08:44.560 | which is a little bit underappreciated, I think,

00:08:46.960 | the alumni network that you build from a company

00:08:49.400 | that you work at ends up being a really huge asset

00:08:51.640 | if you work at a company that ends up succeeding

00:08:53.800 | and doing well and growing.

00:08:55.120 | So there's a lot of benefit to working in a place

00:08:57.720 | where you can build this really smart,

00:08:59.760 | successful, growing alumni network.

00:09:01.920 | As an example, a friend and I started

00:09:03.760 | the Airbnb Alumni Investing Syndicate.

00:09:06.240 | It's called Air Angels.

00:09:07.400 | We invest in companies as a group.

00:09:08.680 | There's about 500 of us in the syndicate.

00:09:11.440 | And basically we find companies to invest in.

00:09:13.200 | We invest using an SPV and look for ways to be helpful.

00:09:17.780 | And it ends up being a really awesome, fun experience

00:09:20.040 | we all learn together.

00:09:21.560 | That's one, find the place

00:09:23.360 | where the smartest people you know are going.

00:09:25.540 | Two, I think a lot of people underappreciate

00:09:28.280 | the importance of stage of company.

00:09:30.440 | There's such a different experience

00:09:32.200 | working at a startup versus a big company.

00:09:34.200 | And so I think it's really important to think about

00:09:35.720 | what's the stage that you wanna focus on.

00:09:38.080 | I find there's like a really nice middle ground

00:09:39.920 | where you look for a series B or a series C company

00:09:43.280 | where it's not so early that it's likely

00:09:46.360 | to go out of business or it's gonna be like

00:09:48.160 | so stressful all the time,

00:09:49.680 | but it's not like a meta or Google.

00:09:51.560 | And so that's an interesting middle ground

00:09:52.680 | where it's still like a lot of upside,

00:09:54.080 | still really fast moving.

00:09:55.920 | And there's a lot of opportunity

00:09:57.400 | but not boring and slow and big company.

00:09:59.760 | So stage, I would think about the mission of the company.

00:10:03.120 | If you like look back on your life,

00:10:04.520 | you're gonna be like, okay, look,

00:10:05.800 | I spent three years at this company.

00:10:07.040 | I moved this metric 5%.

00:10:08.560 | And so like, you're not gonna be that excited about that

00:10:11.560 | unless the mission is something that you really care about.

00:10:15.080 | And moving that metric 5% leads to something

00:10:17.520 | that matters in the world.

00:10:18.800 | As an example, Airbnb, they basically help people travel

00:10:21.980 | and go on better trips.

00:10:23.440 | And if you ask people, what would you do?

00:10:24.760 | And this applies to your podcast a little bit.

00:10:26.520 | Like what would you do if you had all the money in the world?

00:10:28.840 | Everyone says I travel.

00:10:30.860 | And how cool is it to let people go on better trips,

00:10:33.400 | more trips, have better experiences.

00:10:35.160 | So there's a really meaningful mission there.

00:10:37.040 | And then the fourth is you just wanna pay attention

00:10:39.720 | to the quality of the business.

00:10:40.760 | Like, is it gonna work out?

00:10:42.240 | Is it gonna grow?

00:10:43.080 | Do I have to keep raising money forever?

00:10:44.360 | Are they gonna be profitable?

00:10:45.600 | Especially important in today's climate.

00:10:48.660 | And this is especially important

00:10:50.600 | because one of the most powerful things you can do

00:10:53.200 | to give yourself a chance to get a better job

00:10:55.840 | is to have a logo or two from a company people recognize

00:10:59.400 | and respect because that kind of pre-validates

00:11:02.000 | that you're solid.

00:11:03.000 | Somebody else has interviewed you that you really trust.

00:11:05.360 | And they've said, Chris is great.

00:11:07.040 | We hired him.

00:11:07.880 | He worked here two years.

00:11:08.700 | That says a lot.

00:11:09.540 | They may not necessarily be amazing,

00:11:10.720 | but at least it's some level that gives you a quick like,

00:11:13.840 | okay, I'll talk to this person.

00:11:15.520 | So you wanna work at a company that ends up being like,

00:11:18.160 | oh, wow, they worked that.

00:11:19.480 | Now we're gonna talk to them.

00:11:21.200 | So those are the four.

00:11:22.400 | - I had an idea around that

00:11:23.440 | when I first wanted to get a job at a startup.

00:11:25.280 | I was like, I'm gonna pick a startup

00:11:26.440 | that's really popular, people will remember.

00:11:28.960 | And I was like, what company just raised a bunch of money?

00:11:31.480 | What's in the Zeitgeist?

00:11:32.640 | It turns out I was wrong.

00:11:33.600 | And that company ended up like not actually going on

00:11:35.800 | to raise any further funding.

00:11:37.000 | But that was a hypothesis I had actually played out

00:11:39.680 | because five years later,

00:11:40.800 | even though that company was out of business,

00:11:42.040 | people were like, oh, I remember that company.

00:11:44.120 | And so just the fact that I worked at this company

00:11:45.960 | that was a hot company at the time,

00:11:47.640 | even though it went out of business

00:11:48.920 | within a small niche of people was valuable.

00:11:52.200 | I'll add on a couple thoughts to what you said,

00:11:54.600 | which is when you talk about stage

00:11:57.080 | and for people listening that aren't in tech,

00:11:59.040 | forget whether it's series A, series B or something,

00:12:01.800 | it's just a small company, big company.

00:12:04.560 | Another way to think about those stages

00:12:06.760 | is the speed at which you will learn

00:12:08.680 | and the type of learning you will do.

00:12:10.720 | If you want to really hone your craft in a specific vertical,

00:12:15.560 | a later stage company is often gonna be a place

00:12:18.240 | where you can really focus on one thing

00:12:20.680 | and really hone that skill,

00:12:22.120 | whether it's a set of managerial skills or anything.

00:12:25.560 | At an early stage company,

00:12:26.960 | you're going to accelerate the speed at which you learn,

00:12:30.160 | but it might not be as focused on craft

00:12:32.520 | or at least so I've found

00:12:33.600 | because there's so many opportunities.

00:12:35.720 | You might think you're doing one role in product,

00:12:37.760 | but you might also be doing a role in marketing

00:12:39.440 | and you might also be the janitor sometimes.

00:12:41.320 | I think I've had every role at a company

00:12:42.880 | except engineer at times.

00:12:44.640 | And that happens at a smaller company.

00:12:46.640 | So while you might trade off stability,

00:12:49.040 | you might learn a ton and a lot faster

00:12:51.760 | and be able to make transitions easier.

00:12:53.840 | If you're trying to jump into a new career,

00:12:56.440 | it's gonna be a lot easier at a small company to say,

00:12:58.920 | "Hey, I've never done this thing,

00:13:00.320 | but can I jump in and try it?"

00:13:01.920 | And at a small company, someone's like,

00:13:03.560 | "Oh, Lenny's really good at this thing.

00:13:05.360 | Let's let Lenny do that."

00:13:06.560 | And then you can move across very easily.

00:13:08.800 | - Yeah, that reminds me a story

00:13:10.320 | of when we sold our company to Airbnb,

00:13:12.640 | that's how I joined Airbnb.

00:13:14.320 | I went from being the CEO of the startup

00:13:15.960 | to a PM at Airbnb and I felt such relief

00:13:20.440 | not having to think about all the things at the company

00:13:23.320 | and just focus on the one problem

00:13:25.080 | that we had to solve at Airbnb.

00:13:27.080 | Like you would think that's painful,

00:13:28.520 | but it was so nice.

00:13:29.640 | And I have to think about fundraising

00:13:31.040 | and I have to think about paying people salaries every month.

00:13:34.400 | It was just like, "Cool, we're gonna solve this problem.

00:13:36.120 | Life's gonna be so much easier."

00:13:37.960 | Sometimes you want that, sometimes you don't.

00:13:39.840 | - My wife was a chief of staff at Lyft for a bunch of years.

00:13:43.280 | She joined when the company was very small

00:13:45.200 | and she had the opposite experience,

00:13:47.480 | which was she got to see everything.

00:13:49.200 | And it was an amazing opportunity

00:13:51.360 | because the company was growing

00:13:52.320 | and she wore every hat there was.

00:13:54.440 | And finally she was like,

00:13:55.640 | "Oh, I'm spinning up a team to work on insurance.

00:13:57.880 | I don't love that.

00:13:58.880 | I'm spinning up a team to work on BD.

00:14:00.760 | Oh, I'm like really interested in this.

00:14:02.680 | Let's go do that."

00:14:03.880 | And then she built a career in BD

00:14:05.920 | and loves doing BD and partnership stuff,

00:14:08.600 | but she never would have found that

00:14:10.080 | if she hadn't joined a company small enough

00:14:12.080 | to be able to do lots of stuff.

00:14:13.280 | And then this is a little bit out of the way

00:14:15.240 | 'cause it's difficult to find these people,

00:14:17.720 | but I think about trying to think about

00:14:20.240 | who you want to work for also.

00:14:22.320 | So in any industry,

00:14:23.800 | there are people that are well-known in their industry.

00:14:26.520 | You could look at like any conference for an industry,

00:14:28.640 | like who are the people speaking?

00:14:29.720 | Who are the people that are writing?

00:14:31.280 | Who are the people you respect?

00:14:32.840 | And sometimes there might be a good opportunity

00:14:35.360 | to go learn from that person.

00:14:37.360 | And it might not be the mission that you love,

00:14:39.400 | but it might be the best mentor you can find.

00:14:42.160 | And so that's another thing

00:14:43.920 | that I think you could focus on

00:14:46.120 | when you're trying to figure out where to go,

00:14:47.720 | what's important to you.

00:14:48.640 | It's like, do I care about the mission

00:14:50.040 | and will that fulfill me?

00:14:51.040 | Or do I care about the learning?

00:14:52.160 | Will that fulfill me?

00:14:53.240 | Or do I care about the resume boost?

00:14:55.080 | Will that fulfill me?

00:14:55.920 | All of those are options.

00:14:57.360 | You just have to process them all.

00:14:58.440 | - Yeah, it reminds me of a quote

00:14:59.640 | that I don't know if I believe,

00:15:00.640 | but a lot of people believe it,

00:15:01.880 | that you don't quit a job, you quit a manager.

00:15:03.720 | So to your point,

00:15:04.640 | finding a manager that you're really excited about

00:15:06.640 | and think you can learn from and want to work from

00:15:08.920 | and that will champion you is really important.

00:15:11.200 | And I think super underappreciated.

00:15:13.040 | In my career, the biggest trajectory inflection

00:15:16.160 | was just one manager I had that just taught me a ton

00:15:19.000 | and just pushed me to do better.

00:15:21.040 | And to your point,

00:15:21.880 | there's so much power and value in finding that person.

00:15:24.960 | And if you can find the Japanese phrase Ikigai,

00:15:27.600 | if you're familiar, if you can find that,

00:15:29.360 | obviously it's like the dream, right?

00:15:31.200 | Which is the intersection of what you love,

00:15:33.400 | what you're good at, what the world needs

00:15:35.400 | and what you could get paid for.

00:15:36.480 | That's the dream.

00:15:37.320 | I'm learning as fast as I want

00:15:38.640 | at a company with the mission I want.

00:15:40.440 | But I will say in my career,

00:15:41.720 | it's been very hard to find all of those things all the time

00:15:45.240 | and so you've got to prioritize

00:15:47.360 | and sometimes they morph into that,

00:15:49.240 | but I wouldn't necessarily hold out

00:15:52.160 | for finding something that ticks every box.

00:15:54.000 | - I think one way to think about it

00:15:54.960 | as long as you're getting closer to that,

00:15:56.280 | because you, like your wife, you said,

00:15:58.240 | she like didn't know she wanted BD

00:16:00.360 | and the more experiences you have,

00:16:02.680 | the more you kind of narrow in on,

00:16:04.800 | okay, here's the thing I really want.

00:16:06.960 | The other way to think about it

00:16:08.040 | is I realized this is my fourth career.

00:16:10.560 | First I was a engineer, then I was a founder,

00:16:13.560 | then I was a PM and I'm whatever I am now,

00:16:15.960 | one of the newsletter.

00:16:17.200 | So there's always options to go change

00:16:19.840 | and go in different directions

00:16:20.840 | as you learn more about what you're excited about.

00:16:22.720 | Like you're not stuck in the path that you chose.

00:16:26.000 | - I don't know about you,

00:16:26.920 | but I went through investment banker,

00:16:28.960 | management consultant, employee, PM, BD,

00:16:32.600 | then founder, then went to Google

00:16:34.640 | and was a venture capitalist.

00:16:35.760 | I went through a lot and now I'm a creator.

00:16:37.200 | I never knew half of those things

00:16:39.320 | more than three months before.

00:16:41.280 | Like some of them I was like,

00:16:42.120 | I never knew I was gonna be VC

00:16:43.280 | and then that opportunity arose.

00:16:44.680 | I never thought I'd be a creator

00:16:46.160 | and then I started a podcast.

00:16:47.760 | So I think you don't need to know the future.

00:16:50.640 | I love this idea of where do you wanna be

00:16:52.240 | with your life in 10 years?

00:16:54.600 | And if you're in a career

00:16:55.680 | where that exercise is helpful, great.

00:16:58.080 | But I can tell you that

00:16:59.760 | where would my career be in 10 years, 10 years ago

00:17:02.880 | would be so wildly off from where it ended up

00:17:06.080 | that maybe it would have been a fun exercise,

00:17:08.440 | but it certainly wouldn't have been

00:17:09.640 | anywhere close to accurate.

00:17:11.160 | - Yeah, I think to that point,

00:17:12.280 | there's so much value in a variety of experiences.

00:17:15.320 | Like just doing a lot of different stuff

00:17:17.280 | later on ends up being really valuable

00:17:19.880 | to whatever you end up doing later.

00:17:22.320 | I was just interviewing a newsletter guy

00:17:24.840 | who was like the number one tech newsletter on Substack

00:17:26.800 | and he's like, yeah, I launched a newsletter.

00:17:28.560 | I got a thousand subscribers really quickly.

00:17:30.280 | It just started working.

00:17:31.520 | But in reality, I spent six years

00:17:33.480 | writing a book on engineering

00:17:35.440 | and then working at these jobs, learning a bunch of stuff.

00:17:37.800 | So the thing you end up doing later

00:17:39.640 | ends up being built on the experiences you have.

00:17:42.520 | And a lot of people don't understand the value

00:17:44.600 | of just trying a bunch of different stuff

00:17:46.280 | and not feeling like they have to be stuck.

00:17:48.080 | Like here's the thing I'm gonna do for 10 years.

00:17:49.840 | (air whooshing)

00:17:50.920 | Do you know about donor advised funds?

00:17:53.000 | They're tax advantaged financial accounts

00:17:55.080 | for the sole purpose of charity.

00:17:56.760 | Think 401ks and IRAs, but just for charity.

00:17:59.880 | And DAFI is bringing them to the masses,

00:18:02.320 | which is why I'm excited to partner with them

00:18:04.280 | for this episode.

00:18:05.320 | DAFI is a new modern way to give

00:18:07.640 | and it stands for the donor advised fund for you.

00:18:10.800 | With DAFI, it's so much easier

00:18:12.680 | to put money aside for charity.

00:18:14.360 | You can make your tax deductible contributions all at once,

00:18:17.360 | or you can set aside a little each week or month.

00:18:20.080 | And you don't just have to donate cash.

00:18:22.320 | You can easily contribute stocks, ETFs, or crypto.

00:18:25.720 | Then you can give to more than 1 1/2 million charities,

00:18:28.840 | schools, and faith-based organizations

00:18:30.760 | in a matter of seconds.

00:18:32.120 | My favorite part is that it lets you be more strategic

00:18:34.700 | with your giving and your tax planning

00:18:37.000 | by having a single source of charitable deductions.

00:18:39.760 | Plus, you don't have to deal with the hassle

00:18:42.040 | of tracking receipts from your donations.

00:18:44.320 | To start giving today and get your free $25

00:18:47.360 | to give to the charity of your choice,

00:18:49.320 | go to allthehacks.com/DAFI.

00:18:52.480 | Again, that's allthehacks.com/D-A-F-F-Y.

00:18:57.480 | I wish I could say that I'm eating

00:19:00.160 | a fully balanced diet every day,

00:19:02.280 | but the reality is that I am definitely not.

00:19:04.880 | So I love having an easy way

00:19:06.760 | to get my daily nutritional insurance,

00:19:08.960 | which is why I kickstart my day with Athletic Greens,

00:19:11.840 | and I am excited to be partnering with them

00:19:13.720 | for this episode.

00:19:14.960 | I started taking it because I wanted to see

00:19:16.960 | what all the hype was about,

00:19:18.280 | and I've kept it in my daily routine for months.

00:19:21.360 | Every morning, I mix it up with some cold water,

00:19:23.760 | add a few ice cubes, it tastes so good when it's cold,

00:19:26.880 | and I head to my office feeling focused

00:19:29.120 | and energized for the day,

00:19:30.480 | which is a feeling I absolutely love.

00:19:33.240 | I also love that it's made from 75 high-quality vitamins,

00:19:36.600 | minerals, and superfoods,

00:19:38.080 | and contains less than one gram of sugar.

00:19:40.900 | It also has no GMOs, nasty chemicals,

00:19:43.360 | or artificial anything.

00:19:45.060 | To make giving it a try easy,

00:19:46.840 | Athletic Greens is gonna give you a free one-year supply

00:19:50.360 | of immune-supporting vitamin D

00:19:52.280 | and five free travel packs with your first purchase.

00:19:55.680 | All you have to do is visit

00:19:57.200 | allthehacks.com/athleticgreens.

00:20:00.880 | Again, that's allthehacks.com/athleticgreens

00:20:04.720 | to take ownership over your health

00:20:06.760 | and pick up the ultimate daily nutritional insurance.

00:20:09.720 | It's like you found a job, you found a handful of jobs.

00:20:12.280 | My personal belief is that in today's world,

00:20:15.680 | you're much better off trying to narrow it down

00:20:17.880 | to three or four companies

00:20:19.080 | that you're really excited about

00:20:20.800 | and double down on your efforts to get in front of them.

00:20:23.380 | Things I've done in the past are

00:20:25.040 | find every person that I can that knows them.

00:20:27.320 | I've tried creating a presentation and sending it to them.

00:20:30.920 | You could create a video about how excited you are.

00:20:33.420 | Lots of things like that.

00:20:35.240 | I've had this work for me,

00:20:36.920 | and I think it's underappreciated,

00:20:39.260 | but as a founder, someone emailed me and said,

00:20:42.520 | "I am so excited about your company.

00:20:44.120 | "Here's my ideas."

00:20:45.560 | And I was like, "I have to interview this person."

00:20:47.400 | Like anyone who would take more than an hour

00:20:50.080 | to put something creative together about my company

00:20:53.480 | is someone I will want to talk to.

00:20:56.000 | And the bigger the company, the more it's like,

00:20:58.040 | "Well, they actually have to fit a role we're hiring for."

00:21:00.880 | But I've interviewed people who I was like,

00:21:02.160 | "I don't even have a role for you,

00:21:03.520 | "but I just wanna understand who you are

00:21:05.040 | "so I know where to slot you in later."

00:21:06.960 | And you can't scale that if you're interviewing,

00:21:08.840 | if you have a thousand companies you're excited about.

00:21:10.840 | But if you have three, I'm like,

00:21:12.200 | "Go all in on those three

00:21:13.720 | "before you try to find three more,

00:21:15.600 | "because I think that you can easily stand out

00:21:19.340 | "by doing those things."

00:21:20.360 | There's an episode I did with Sunil Gupta

00:21:22.480 | who wrote a book called "Backable."

00:21:24.000 | And one time he just like did customer research

00:21:26.760 | for the company and sent it to me.

00:21:28.440 | He was like, "Hey, I interviewed your customers.

00:21:29.720 | "Here's what I learned."

00:21:30.560 | If you were in sales, you could go close a customer

00:21:33.320 | and be like, "Hey, I just convinced a customer

00:21:35.140 | "to sign up for you.

00:21:35.980 | "I just wanted to let you know."

00:21:37.560 | Who doesn't wanna interview a person

00:21:38.800 | who's closing deals before they even work there?

00:21:40.680 | So I think if you can go through the hard exercise

00:21:43.440 | of figuring out what you want.

00:21:44.800 | Those are my tactics of standing out.

00:21:46.420 | I'm curious at what you've seen

00:21:47.720 | to try to have candidates either who've applied to you

00:21:50.200 | or you've done yourself

00:21:51.120 | to put yourself out there in different ways.

00:21:52.680 | - I think that's awesome advice.

00:21:54.040 | It reminds me, I was teaching a course on Maven

00:21:57.120 | about product management.

00:21:58.000 | And I was interviewing coaches to help me with the course.

00:22:01.760 | And I had about 10 coaches.

00:22:03.220 | I was interviewing them with someone else

00:22:04.760 | that was helping me out with the course.

00:22:06.600 | And one of the coaches started her own sub stack,

00:22:09.540 | subscribed me to it,

00:22:10.840 | and then just started writing posts

00:22:12.200 | about how she's the perfect fit to coach this course.

00:22:15.440 | And I was like, "Holy shit.

00:22:17.140 | "We need to make sure that we talk to her for sure."

00:22:20.620 | And we did, and it didn't work out there

00:22:22.040 | 'cause she wasn't quite the fit,

00:22:23.200 | but I found something else to do with her.

00:22:25.060 | And now she's a core part of my newsletter community,

00:22:27.400 | helps run a lot of the programs.

00:22:29.080 | - That's awesome.

00:22:29.920 | - Yeah, I love that advice.

00:22:31.340 | I think that's awesome advice.

00:22:32.800 | I think generally, the question is how do you stand out?

00:22:35.000 | How do you stand out?

00:22:35.840 | Is there something really remarkable

00:22:37.360 | that gets someone's attention?

00:22:38.600 | There's a lot of ways to do it.

00:22:39.980 | I do a lot of angel investing.

00:22:41.600 | And whenever I get a founder that makes a loom,

00:22:44.480 | "Hey Lenny, I really wanted to talk to you

00:22:46.840 | "about the startup I'm building.

00:22:47.900 | "Here's why it's awesome."

00:22:49.480 | I watch them.

00:22:50.900 | Most of the time I talk to them

00:22:51.960 | 'cause they put in the effort and they do something unique.

00:22:55.040 | So I think it applies to investing too.

00:22:56.640 | Pick the people you really want on your cap table

00:22:59.080 | and do some extra.

00:23:01.080 | I think broadly, if you don't do anything like this,

00:23:04.240 | the things you need, 'cause I'm with the job board,

00:23:06.480 | I probably reviewed 3000 profiles of people

00:23:08.440 | that applied to join the job board or the collective.

00:23:10.960 | And so the things, like if you think about

00:23:12.680 | from the perspective of hiring manager,

00:23:14.840 | like what are they looking when they're scanning resumes?

00:23:17.240 | They're looking for logos that they recognize

00:23:19.760 | from companies that have pre-vetted that person

00:23:22.400 | in some form versus like a bunch of random companies

00:23:25.200 | they've never heard of.

00:23:26.040 | You're not gonna be able to do a lot about this,

00:23:27.280 | but this is what hiring managers look for.

00:23:28.980 | Companies that they respect,

00:23:30.360 | that have done one pass at this person

00:23:32.200 | and they're probably solid.

00:23:33.200 | And then I think you mentioned this is just like impact,

00:23:35.720 | show some kind of impact that you've driven.

00:23:38.160 | Like they're hiring you to have impact.

00:23:40.440 | What impact have you had in your career?

00:23:42.840 | And so the more you can highlight those things, the better.

00:23:45.160 | But if you don't have those things, your advice is great.

00:23:48.360 | Do something remarkable.

00:23:50.080 | - I love the idea of like a loom resume.

00:23:51.680 | I can imagine getting an email.

00:23:52.840 | If you'd rather not look at another 50th resume of the day,

00:23:56.160 | here's a five minute video

00:23:57.200 | of me walking through the highlights.

00:23:58.400 | And oh, by the way, you can put it on 2X

00:24:00.320 | if you wanna get through it in two and a half.

00:24:01.920 | - I bet if I got an email that was like a little bit snarky,

00:24:04.320 | a little bit funny, but a little bit informative,

00:24:06.100 | that would be great.

00:24:06.940 | And if you don't have those logos,

00:24:09.360 | it might be exactly what you need to get through that.

00:24:11.120 | - Yeah, and then you could track

00:24:12.080 | that they watch the video too,

00:24:13.080 | which is cool, you get an email.

00:24:14.760 | - Oh yeah.

00:24:15.580 | The app I use for editing my podcast, Descript,

00:24:17.160 | has a loom like feature, but it doesn't have the tracking.

00:24:19.920 | So now I'm like, oh, maybe I should switch over

00:24:21.600 | and start using loom.

00:24:22.520 | - There you go.

00:24:23.340 | - What about interviewing?

00:24:24.180 | Let's say I call you, I'm like,

00:24:25.280 | oh, I decided I'm done creating a podcast.

00:24:27.480 | I want this job.

00:24:28.400 | Lenny, what advice do you have for me to nail the interview?

00:24:31.000 | - I like, I don't know if I'm going to give you anything

00:24:32.640 | that you haven't heard before,

00:24:33.480 | other than just spend a lot of time preparing,

00:24:35.680 | like a lot of interview questions

00:24:36.880 | or stuff you'll hear from a lot of different people.

00:24:39.560 | So I think that's probably 90% of it.

00:24:42.060 | Just spend a bunch of time preparing.

00:24:44.000 | If you're interviewing at a big company,

00:24:45.560 | my sister was interviewing.

00:24:47.160 | There's just like videos of all the interview questions

00:24:49.000 | they ask you online.

00:24:49.840 | It's pretty crazy.

00:24:50.680 | There's like courses you could take,

00:24:51.840 | like how to interview at Google.

00:24:53.600 | And it's like all the questions they ask you.

00:24:55.920 | And it's like, you can go through all of them.

00:24:57.640 | There's like a pool basically.

00:24:59.160 | So there's like a lot of answers out there

00:25:02.560 | if you put in the time.

00:25:03.480 | Another piece is get good at telling your story

00:25:06.080 | and why you want to do this job,

00:25:08.640 | what you've done in your career,

00:25:10.800 | highlight the things that have had impact.

00:25:13.000 | I think it's just like, get good at pitching yourself.

00:25:15.320 | And then you want to ask good questions of the interviewee.

00:25:18.620 | People want you to ask them questions

00:25:20.160 | because they want to feel like you care about the company.

00:25:22.760 | - If they want to not just hear it, but feel it.

00:25:24.720 | You said, I've interviewed people who I'm like,

00:25:26.440 | why do you want to work here?

00:25:27.280 | And they're like, well,

00:25:28.120 | I'm at a financial planning startup.

00:25:29.400 | And they're like, I just love personal finance.

00:25:30.840 | I'm like, that's why you want to work in the industry.

00:25:32.360 | That's not why you want to work here.

00:25:33.880 | I would say, especially the smaller the company,

00:25:36.520 | but it probably works at any scale.

00:25:38.440 | If you don't have a really solid answer

00:25:40.720 | for why you want to work at this company,

00:25:43.120 | I think that is tough for the other person to hear

00:25:45.920 | if they ask you.

00:25:46.800 | And even if they don't, I'd try to slot it in

00:25:48.720 | because I think that's great.

00:25:49.760 | And I would also try to come up with a personal question

00:25:53.800 | that I know this sounds like a lot of work,

00:25:55.480 | but try to come up with the best question

00:25:56.720 | you can ask someone.

00:25:57.840 | Because whenever anyone asks me a really hard question,

00:26:01.600 | I remember that person.

00:26:02.960 | I'm like, that person really thought hard about this.

00:26:05.680 | Or they transferred from interview to interview.

00:26:07.640 | They're like, oh, this person told me

00:26:08.680 | this is your biggest problem that your company's facing.

00:26:10.720 | And in the next one, they'd come in and say,

00:26:12.400 | hey, I talked to the head of marketing

00:26:14.320 | and they said this is the biggest challenge you're facing.

00:26:16.680 | From a product standpoint,

00:26:18.280 | what are you guys doing

00:26:19.200 | to help the marketing team solve this?

00:26:20.920 | And it's like, well, now you get to learn a lot of stuff,

00:26:23.480 | but it actually shows that you're trying to solve problems.

00:26:25.720 | You're trying to get more out of it.

00:26:27.000 | I just try to say as the candidate,

00:26:29.040 | don't forget you can ask questions

00:26:30.800 | and don't assume that the questions you ask

00:26:32.960 | are purely selfish.

00:26:34.400 | They can often leave people with a better impression of you

00:26:37.600 | and not just be information gathering.

00:26:39.840 | - So I have a TikTok account for my podcast.

00:26:41.680 | It's called Lenny's Podcast on TikTok.

00:26:43.760 | And I think it's like, my name is the actual handle.

00:26:46.400 | And the most popular content is guests talking

00:26:50.080 | about their favorite interview question.

00:26:51.840 | I ask that often at the end of my podcast episodes.

00:26:54.800 | And so if you're looking for more questions to practice on,

00:26:58.640 | if you go to Lenny's Podcast on TikTok,

00:27:00.560 | you'll sort, I think by views,

00:27:01.960 | you can probably see a bunch

00:27:02.840 | of really fun interview questions.

00:27:05.560 | - I will link to that in the show notes

00:27:06.960 | so people can find it.

00:27:08.240 | Now, let's say you get the job.

00:27:09.760 | This is something I know you've written about.

00:27:11.400 | And I know it was actually a guest post,

00:27:12.840 | but I'm hoping you have some of the takeaways

00:27:14.640 | because they were fantastic about salary negotiation.

00:27:18.400 | I think it's something that people spend far less time on

00:27:21.560 | than they should.

00:27:22.400 | And you highlighted a lot of that

00:27:23.680 | in the post you put out on your newsletter.

00:27:25.600 | - Yeah, this post ended up being the most popular post

00:27:28.080 | of my newsletter of all time,

00:27:29.560 | partly 'cause it got on Hacker News and got a ton of views

00:27:33.000 | and some recruiters did not like it.

00:27:35.040 | And it's good and bad, but I learned a ton from it.

00:27:37.800 | So the author's Nia Drugova.

00:27:40.200 | And the reason I asked her to write this

00:27:42.000 | is because I'm really bad at negotiation.

00:27:44.080 | I don't even know if I've ever negotiated a salary.

00:27:46.600 | And so I wanted to learn how to do this well.

00:27:48.920 | And her full-time job basically

00:27:50.640 | is helping candidates negotiate their offers.

00:27:53.660 | And help them find jobs.

00:27:54.760 | So she's done this a ton.

00:27:56.720 | There's 10 kind of steps that she shares.

00:27:59.160 | I'll share a few highlights,

00:28:00.120 | things that I thought were most interesting.

00:28:02.440 | One is she super recommends you never give a number

00:28:06.200 | of what you think your salary should be

00:28:08.560 | or the range you're thinking about.

00:28:10.200 | Here's the question she suggests you ask.

00:28:11.880 | Can you tell me the salary band for this level?

00:28:14.940 | I'm happy to let you know if it's within my range

00:28:17.040 | and we can discuss the specific number later

00:28:18.960 | once I've met the team.

00:28:21.040 | That's her advice.

00:28:22.240 | And that range ends up being really useful later

00:28:24.960 | when you start to negotiate.

00:28:26.840 | That's tip one.

00:28:28.340 | Tip two is to mine for intel

00:28:31.920 | from your hiring manager and the recruiter

00:28:33.800 | into what they're looking for from this role.

00:28:36.400 | Like what's the number one priority of the team right now?

00:28:39.160 | Why is this role open?

00:28:40.900 | What's the biggest challenge

00:28:42.120 | for someone getting into this role?

00:28:43.880 | And the reason this is important

00:28:44.760 | is then you can mirror that back

00:28:46.560 | when you're pitching yourself.

00:28:47.920 | Once you've got an offer you wanna counter,

00:28:50.260 | you can highlight,

00:28:51.260 | hey, here's what I'm gonna help you with.

00:28:53.320 | Here's what I'm gonna do in this role.

00:28:55.720 | Here's the challenges I'm gonna tackle immediately.

00:28:58.460 | And people are gonna be like,

00:28:59.300 | holy moly, that's exactly what we need.

00:29:00.760 | How did you know?

00:29:01.680 | So the tip there is just mine.

00:29:03.200 | Like ask these questions so that you can have notes

00:29:05.120 | when you're actually pitching yourself later.

00:29:06.980 | And then the third tip that I love is

00:29:09.800 | once you get an offer,

00:29:11.360 | her advice is don't counter it immediately

00:29:14.080 | and don't come back with,

00:29:14.920 | no, I think this is a better, more fair number.

00:29:17.940 | Instead you wanna win the hearts and minds

00:29:20.340 | of the decision makers.

00:29:21.800 | You want them to feel like,

00:29:23.240 | oh my God, we need Chris in this company.

00:29:25.440 | We gotta pay him whatever he wants.

00:29:27.360 | And her advice is after you get the offer,

00:29:29.600 | try to get a meeting with a decision maker,

00:29:31.720 | like a director or VP or something.

00:29:33.520 | Just like, hey, I just wanna chat about this role.

00:29:35.520 | In the discussion,

00:29:37.320 | ask questions about how they would want you

00:29:39.880 | to create meaningful impact.

00:29:41.200 | Share some ideas maybe you've had

00:29:42.920 | about what you're gonna do there.

00:29:44.840 | And then maybe share obstacles that you have

00:29:47.920 | in accepting the offer and taking on the role.

00:29:50.460 | And try to get them excited about you joining the company.

00:29:53.220 | And with that, then you can come back with like,

00:29:55.740 | okay, I've talked to everyone.

00:29:56.660 | I understand the role better.

00:29:58.020 | Here's where I think the offer should be.

00:30:00.260 | And in theory, if you got them really excited,

00:30:01.900 | they'd be like, oh yeah, yes, yes, yes.

00:30:03.140 | Let's do whatever we need to do.

00:30:04.460 | So those are some nuggets.

00:30:07.000 | - I love that third tip.

00:30:08.380 | It's almost like come up with a plan.

00:30:10.260 | You could even talk to the person that would be your manager

00:30:12.220 | and be like, hey,

00:30:13.580 | I know we're talking about salary negotiation already,

00:30:15.780 | but I just wanna figure out like, what's the 90-day plan?

00:30:17.960 | What can I hit the ground running on?

00:30:19.340 | And you get them to like buy into,

00:30:21.880 | this is what this person's gonna do.

00:30:23.240 | And they're like, gosh,

00:30:24.080 | we've already decided their first project.

00:30:25.920 | Can we get going?

00:30:26.760 | - Right, like get them in the hell, let's get going.

00:30:28.800 | What are we doing?

00:30:29.640 | - Yeah. - Negotiating over here.

00:30:31.080 | - My other piece of advice to people is,

00:30:33.000 | salary is a component of your compensation,

00:30:35.560 | but there's often a lot of flexibility in other places.

00:30:38.440 | So it's not the only place to focus on.

00:30:41.600 | Some companies, things like vacation days are flexible.

00:30:44.280 | Some they're just based on tenure or everyone gets the same.

00:30:47.260 | Some educational reimbursement is one

00:30:49.380 | that you can focus on.

00:30:50.420 | Others, I've found companies that say,

00:30:52.740 | we're not really willing to flex on the salary,

00:30:55.020 | but I've heard from after I've worked there

00:30:57.360 | that they are willing to flex on a signing bonus.

00:30:59.940 | They are willing to flex on various other aspects

00:31:02.400 | of compensation, like what your estimated bonus is.

00:31:05.060 | I helped a friend negotiate.

00:31:06.700 | He said, sometimes it's like,

00:31:08.460 | oh, well now I know the band for the level,

00:31:10.040 | but could I be at the next level?

00:31:11.500 | And I'm not trying to tell you how much to pay me.

00:31:13.460 | I'm trying to tell you that I'm at the next level.

00:31:15.140 | And they said, well, we're not confident

00:31:16.540 | you're at that level.

00:31:17.420 | And he said, great, how about we have a check-in

00:31:19.420 | in six months and you tell me what I need to demonstrate.

00:31:23.420 | I will demonstrate that.

00:31:24.700 | And if I will, would you retroactively update my compensation

00:31:28.580 | as if I came in at that level?

00:31:30.340 | If you're not willing to believe I'm there now,

00:31:31.880 | let me prove it to you.

00:31:33.180 | And he set out a series of things

00:31:35.460 | that they needed to demonstrate.

00:31:37.180 | Three months in, he checked in with them and said,

00:31:39.360 | am I on track to demonstrate these things?

00:31:41.420 | Which by the way, genius move for this person

00:31:44.220 | because it's so much easier for your manager

00:31:46.180 | to say you're on track for something

00:31:48.100 | than actually getting your promotion put through

00:31:50.620 | or getting your compensation adjusted.

00:31:52.940 | But then when you check in six months later and you say,

00:31:55.380 | three months ago, you said I was on track.

00:31:57.300 | Like we haven't had any conversation to the contrary.

00:31:59.860 | If I'm not getting this, then why were you telling me that?

00:32:02.300 | Similar to how you said getting the buy-in

00:32:03.860 | before you negotiate, you're getting the buy-in

00:32:05.540 | that you're already gonna get approved for this change.

00:32:08.180 | So I just think there's a lot of wiggle room

00:32:10.860 | about things other than your salary.

00:32:12.740 | And if a company's not willing to flex there,

00:32:15.100 | go down all the other paths.

00:32:16.380 | - Still so hard to do this negotiation thing.

00:32:19.360 | - I kind of love negotiating.

00:32:21.240 | I worked with Andy Ratcliffe for a while.

00:32:22.580 | He was the CEO of Wealthfront.

00:32:23.420 | His advice was to always just put the decision

00:32:26.100 | in someone else's hand and say, what do you think is fair?

00:32:29.540 | He said 90% of the time they do what's fair

00:32:32.140 | and 10% of the time they don't.

00:32:33.500 | And you know that they're trying to kind of screw you over

00:32:35.780 | and maybe that's just not the right fit.

00:32:37.180 | I always like sharing negotiation advice,

00:32:38.760 | even if it's not relevant to salary,

00:32:40.380 | but you could basically say,

00:32:41.520 | here's all the data I've collected

00:32:43.420 | about what this role should be compensated.

00:32:46.060 | I'd like to be compensated fairly with this data.

00:32:48.980 | Here's the data, let me know what you think.

00:32:50.900 | And like force it on them to make a fair decision,

00:32:53.580 | depending on the circumstance,

00:32:54.980 | a good last tactic or a starting point.

00:32:56.900 | But I like and have used many times the tactic

00:32:59.900 | of letting someone else decide what's fair

00:33:01.740 | and not have to throw out the number first.

00:33:03.340 | - I like it.

00:33:04.980 | - I wanna tell you all about the most amazing way

00:33:07.340 | to buy a second home.

00:33:08.720 | And I know because we actually bought one

00:33:10.740 | for 1/8 the cost.

00:33:12.580 | And don't worry, I'm not talking timeshares,

00:33:14.700 | I'm talking about Picasso,

00:33:16.340 | and I'm excited to partner with them for this episode.

00:33:18.860 | So how does it work?

00:33:19.820 | Picasso buys amazing luxury homes

00:33:22.200 | in over 40 world-class destinations,

00:33:24.700 | creates an LLC for each home,

00:33:26.700 | and you can buy as little as 1/8 of the property.

00:33:29.740 | But it doesn't stop there.

00:33:31.060 | Picasso also professionally manages the home,

00:33:33.940 | handling design, cleaning, bills, repairs, taxes, and more.

00:33:38.940 | And the scheduling system makes it fair and equitable

00:33:41.880 | for everyone to enjoy their home.

00:33:44.160 | When we found Picasso, it felt like it was made just for us.

00:33:47.840 | That same week, we found the perfect place in Napa,

00:33:50.960 | we toured it, and the next week we were closing.

00:33:53.880 | Since then, it's truly become our second home,

00:33:56.340 | and it's been so amazing.

00:33:57.960 | And it's true real estate ownership.

00:34:00.240 | Owners can sell at any time, set their own price,

00:34:03.640 | and tap into Picasso's active marketplace of buyers.

00:34:06.940 | In fact, on average, Picasso listings resell in 12 days

00:34:11.120 | with a 12% annualized gain.

00:34:13.480 | For a modern way to buy and own a second home,

00:34:16.720 | go to allthehacks.com/picasso,

00:34:19.800 | where our listeners will get a free Picasso access account,

00:34:23.320 | which means you can see new listings

00:34:25.000 | before they go on the website

00:34:26.800 | and get up to $10,000 in credit towards closing costs.

00:34:30.880 | Again, that's allthehacks.com/picasso,

00:34:34.760 | P-A-C-A-S-S-O.

00:34:37.420 | Getting the crew together isn't as easy as it used to be.

00:34:42.260 | I get it, life comes at you fast, but trust me,

00:34:45.800 | your friends are probably desperate for a good hang.

00:34:48.680 | So, kick 2024 off right by finally hosting that event.

00:34:52.740 | Just make sure you do it the easy way

00:34:54.680 | and let our sponsor Drizly,

00:34:56.640 | the go-to app for drink delivery, take care of the supplies.

00:35:00.360 | All you need to come up with is the excuse to get together.

00:35:03.160 | It doesn't even have to be a good one.

00:35:05.020 | It could be your dog's birthday,

00:35:06.440 | that the sun finally came out,

00:35:08.400 | or maybe you just wanna celebrate

00:35:09.880 | that you got through another week.

00:35:11.960 | With Drizly, you can make hosting easy

00:35:14.060 | by taking the drink run off your to-do list,

00:35:16.600 | which means you can entice your friends

00:35:18.360 | to leave their houses without ever leaving yours.

00:35:21.460 | And since I know you like a good deal,

00:35:23.120 | Drizly compares prices on their massive selection

00:35:25.680 | of beer, wine, and spirits across multiple stores.

00:35:28.680 | So, when I really wanted to make a few cocktails

00:35:30.700 | while we were hosting family last week,

00:35:32.540 | not only could I get an Italian Amaro

00:35:34.600 | delivered in less than an hour,

00:35:36.240 | but I found it for $15 less than my local liquor store.

00:35:39.720 | So, whatever the occasion,

00:35:41.360 | download the Drizly app or go to drizly.com.

00:35:44.640 | That's D-R-I-Z-L-Y.com today.

00:35:48.680 | Must be 21 plus, not available in all locations.

00:35:51.900 | I just wanna thank you quick for listening to

00:35:55.800 | and supporting the show.

00:35:57.280 | Your support is what keeps this show going.

00:36:00.120 | To get all of the URLs, codes, deals,

00:36:02.840 | and discounts from our partners,

00:36:04.600 | you can go to allthehacks.com/deals.

00:36:08.160 | So, please consider supporting those who support us.

00:36:11.400 | Okay, so we've gotten hired.

00:36:13.020 | We're now at a company,

00:36:14.460 | and I wanna focus on something that applies to everyone,

00:36:17.360 | actually working at the company they're at.

00:36:19.920 | There is a lot we could cover here.

00:36:21.320 | I don't wanna go through every possible thing,

00:36:23.780 | but there are a few things that I think you might have

00:36:26.660 | outsized impact on the conversation about,

00:36:29.280 | and the first one is actually about having impact

00:36:32.260 | in an organization, and hopefully a little bit

00:36:34.200 | about how to get promoted on the way,

00:36:35.920 | but I know you believe those two things

00:36:37.620 | are both similar and very different.

00:36:39.600 | So, what do you think people should be optimizing for

00:36:42.400 | when they're working at any company?

00:36:43.860 | - If I had to pick one thing,

00:36:45.040 | I would say have impact on the company

00:36:47.240 | in their bottom line.

00:36:48.360 | If you think about it like,

00:36:49.200 | why the hell are they paying you a salary?

00:36:50.580 | It's to have impact on their business,

00:36:53.320 | to help them grow faster.

00:36:55.400 | And so, if there's any one thing

00:36:57.240 | that you can just always come back to,

00:36:59.160 | if you deliver more impact, you will do better.

00:37:02.360 | That's like 90% of your success at a company.

00:37:05.300 | Then there's like, people need to know about your impact.

00:37:07.960 | You need to be working on things that matter.

00:37:09.640 | Like, you could have an impact on a leaf

00:37:12.080 | at the end of the tree of the business,

00:37:14.040 | or you could have impact on the core number one goal,

00:37:16.760 | and that's a big difference,

00:37:17.740 | but I'd say if you had to pick anything,

00:37:19.120 | it's just how can I deliver more impact?

00:37:21.360 | And it's especially important for PMs

00:37:22.960 | who are basically marshaling the resources of their team.

00:37:27.040 | And the more you focus on how can our team have more impact,

00:37:30.400 | the better everyone on the team does.

00:37:32.080 | - Let's pretend you just started a new company.

00:37:33.600 | How do you find the way you can have that impact?

00:37:36.660 | - I think about Lord of the Rings and the Eye of Sauron.

00:37:39.720 | If you think about like,

00:37:40.560 | what's the most important project to the CEO right now?

00:37:43.920 | I think about that as the Eye of Sauron.

00:37:45.640 | He's looking at that, or she's looking at that,

00:37:47.720 | and that's gonna be like so stressful and difficult.

00:37:50.600 | You're like right on you, on your butt.

00:37:53.000 | And then the alternative is you could be working in a shire

00:37:55.400 | where nobody cares what's going on.

00:37:56.760 | Like you could have the most amazing product

00:37:58.840 | and everyone's like, that's nice, good job.

00:38:00.840 | I would say generally you wanna optimize on average

00:38:04.040 | to be like not in the Eye of Sauron,

00:38:05.920 | but right off to the side.

00:38:07.320 | Work on something that's really important,

00:38:09.120 | but not like the most important thing to the company,

00:38:11.680 | at least for a long time,

00:38:12.560 | because you just get burned out being in that thing

00:38:14.320 | that's like the number one most important product.

00:38:16.880 | So that's just like a general piece of advice.

00:38:18.680 | Work on something really important,

00:38:19.960 | but maybe not the most important thing.

00:38:22.200 | Just a tip there.

00:38:23.720 | And then in terms of just like,

00:38:24.800 | how do you find what the most important thing?

00:38:26.040 | Like it's pretty clear usually.

00:38:27.680 | It's like what's getting resourced?

00:38:29.800 | What are the execs really excited about?

00:38:32.320 | Where are the best people going?

00:38:34.280 | Those sorts of things, like what's being prioritized?

00:38:36.320 | - Impact's the most important thing.

00:38:37.760 | I've seen you write about how to get promoted effectively,

00:38:40.480 | and that impact matters.

00:38:41.680 | Any comments on that?

00:38:43.120 | - Yeah, if you're like, why am I not getting promoted?

00:38:45.800 | It usually means that you're not delivering enough impact

00:38:49.000 | or people don't have confidence that you will deliver

00:38:51.400 | the impact that you need to at a higher level.

00:38:53.840 | So if you think about working backwards

00:38:55.760 | from a hiring manager or the company,

00:38:58.120 | thinking about, should we promote Chris?

00:39:00.560 | Basically, you need to give them confidence

00:39:02.040 | that you can handle more scope,

00:39:03.840 | more responsibility, more impact.

00:39:06.480 | So how do you show that?

00:39:08.480 | One, deliver more impact.

00:39:10.400 | Find ways to hit more ambitious goals,

00:39:13.440 | maybe lead a really important project,

00:39:15.480 | work on something closer to the eye of Sauron,

00:39:17.840 | something higher visibility and more important,

00:39:20.480 | maybe help the company save money or run more efficiently,

00:39:23.800 | just like find ways where you can show

00:39:26.200 | that you've done things that are really important

00:39:27.720 | to the company.

00:39:28.560 | So that's one.

00:39:29.400 | Two is, part of the idea of our promotion

00:39:31.480 | is people are gonna give you more scope,

00:39:33.720 | more responsibility, and again,

00:39:35.600 | they have to have confidence that you can handle it.

00:39:37.520 | How do you do that?

00:39:38.360 | You take on more scope, more responsibility

00:39:40.240 | before you are promoted to show people,

00:39:42.160 | look at me, I can handle this.

00:39:44.200 | So you wanna find ways to take on

00:39:46.280 | work maybe your manager's doing.

00:39:47.640 | And knock it out, take on a project

00:39:50.040 | that someone else is doing while they're out

00:39:51.440 | and do it for them.

00:39:52.880 | Pick a really ambitious project

00:39:54.880 | that's just gonna take a year or two

00:39:56.440 | that's gonna be really important to the company.

00:39:58.120 | Take the reins on like a visioning exercise

00:40:00.600 | and just like, look at me, I did this thing,

00:40:02.320 | this is awesome.

00:40:03.320 | I think what's important here is a lot of people

00:40:05.240 | only get promoted after they've shown

00:40:06.960 | they can handle this additional scope.

00:40:09.120 | And so you gotta find opportunities to take on more scope.

00:40:12.320 | There's five more, and it's posted around,

00:40:13.960 | so let me just run through them pretty quick.

00:40:15.560 | Three is part of the reason you're getting promoted

00:40:18.200 | is there's this gap that your manager has identified.

00:40:21.040 | Like Chris needs to work on better deadline setting

00:40:24.560 | or hiring.

00:40:26.440 | There's usually like a gap

00:40:27.280 | that keeps you from the next level.

00:40:28.680 | And it's really important

00:40:30.120 | that you and your manager are aligned.

00:40:31.720 | Here's the gaps that keep you from the next level.

00:40:34.120 | Like you shared this story about your friend.

00:40:35.880 | Am I on track for this next level?

00:40:37.520 | There's usually like a set of things

00:40:38.720 | that your manager gives you feedback on,

00:40:40.360 | usually in your performance review.

00:40:42.480 | A tip that I would suggest that I found really powerful,

00:40:45.120 | either as a manager or as a report,

00:40:48.200 | is when you have a performance review,

00:40:51.120 | align with your manager on like a spreadsheet of things

00:40:53.760 | that you plan to do in the next, say, six months

00:40:56.840 | until the next performance review.

00:40:58.080 | Create basically a roadmap.

00:40:59.080 | Like I'm gonna work on becoming a better public speaker.

00:41:01.960 | I am gonna hit deadlines 90% of the time.

00:41:05.000 | I'm gonna update our JIRA to be up to date

00:41:07.960 | by the end of Fridays.

00:41:09.280 | Just make a list of the things you can actually do

00:41:11.040 | that'll bring you to the next level.

00:41:12.840 | And then meet with your manager/report every month

00:41:16.200 | and review the status of each of those things.

00:41:18.200 | It becomes this little roadmap where you're aligned on,

00:41:20.720 | here's the things, say, Chris is working on

00:41:23.280 | and how they're going.

00:41:24.400 | So that by the time you get to performance review,

00:41:26.560 | you're not surprised.

00:41:27.400 | Like here, we did five of these things.

00:41:28.840 | We didn't get to these things.

00:41:30.560 | So that's where you're at.

00:41:31.920 | So demonstrate you've addressed a gap.

00:41:35.040 | Four, find someone that can champion you.

00:41:37.400 | That's often really powerful at a company.

00:41:39.000 | Get someone really excited about you

00:41:40.920 | and can champion you inside these calibration sessions.

00:41:44.240 | That's really powerful.

00:41:45.080 | Five is you wanna pay attention

00:41:46.280 | to what gets promoted at the company.

00:41:48.320 | A lot of companies have these gray area things

00:41:51.400 | that matter a lot that you may not be aware of.

00:41:53.320 | So just look at people who are getting promoted.

00:41:55.720 | Look for things that they're doing maybe

00:41:56.880 | that you're not doing.

00:41:58.000 | Maybe you have to be friends with the CEO.

00:41:59.480 | I don't know.

00:42:00.320 | Maybe you have to be really good at communication.

00:42:02.120 | That really matters at the company.

00:42:03.480 | And then two more.

00:42:04.320 | Something that's way underappreciated

00:42:05.440 | is you just need to ask to get promoted sometimes.

00:42:08.120 | Sometimes managers don't know you wanna be promoted.

00:42:10.640 | So simplest thing you could do is just like,

00:42:12.720 | hey, I would love to be promoted to the next level.

00:42:15.400 | What do I need to do to get there?

00:42:16.920 | What are my gaps?

00:42:18.240 | And that often leads to the biggest impact

00:42:20.360 | on getting promoted.

00:42:21.880 | And then the last idea and tip is just

00:42:23.880 | sometimes you need to leave and work somewhere else.

00:42:25.800 | Sometimes you're just like stuck in a rut

00:42:27.760 | and you just have, I don't know, certain reputation.

00:42:30.680 | Your manager is just not good at championing you.

00:42:33.080 | So sometimes you're not gonna get promoted

00:42:34.840 | and it's time to try some other place

00:42:36.880 | where you kind of start with a clean slate.

00:42:39.360 | - I remember it was so depressing,

00:42:40.600 | but when I was a venture capitalist,

00:42:42.760 | the role of non-general partner,

00:42:45.680 | we were told it was like, this is a terminal position.

00:42:48.920 | They were just very transparent.

00:42:50.280 | They were like, the expectation for this job

00:42:52.360 | is not that you will get promoted

00:42:53.840 | to be a general partner of the fund.

00:42:55.640 | That is just how it works.

00:42:56.760 | And we just want you to know that

00:42:58.480 | so you don't have those expectations.

00:42:59.920 | And it was like very clearly set.

00:43:01.680 | I think it was a little depressing at times

00:43:03.080 | 'cause the word terminal position

00:43:04.320 | just sounds like going nowhere.

00:43:06.360 | But I appreciate the honesty.

00:43:08.080 | I appreciate the transparency.

00:43:09.760 | The one thing that I learned

00:43:11.040 | and you reminded me in what you said

00:43:12.920 | was a lot of times in order to get promoted,

00:43:16.240 | you don't need to meet the expectations of your role.

00:43:18.600 | You need to demonstrate that you can handle the next role.

00:43:21.360 | And I think I'd always thought

00:43:22.840 | as someone who hasn't studied this

00:43:24.280 | or been a prolific manager at any point in time,

00:43:27.160 | I always thought, oh,

00:43:28.000 | when someone could do their job really well,

00:43:29.360 | you move to the next level.

00:43:30.720 | But it's actually in a lot of companies,

00:43:32.400 | it's when someone could demonstrate

00:43:33.800 | that they can do the job that they want to get promoted to

00:43:37.720 | is when that happens.

00:43:38.720 | And so it's really important to understand

00:43:40.480 | if I'm a level five manager

00:43:42.520 | and I wanna be a level six director,

00:43:44.120 | it's like, what do I need to demonstrate to be a director?

00:43:47.560 | Not what do I need to do as a manager?

00:43:50.000 | Because sometimes you need to do the next level's job

00:43:52.600 | to get the promotion.

00:43:53.560 | - Yeah, and that's how it works in calibration.

00:43:55.160 | When you're looking at someone's level,

00:43:56.800 | there's like a lot of big companies have these ladders

00:43:59.520 | and they tell you what each level needs to achieve.

00:44:02.400 | And so if someone's gonna be promoted to say L7,

00:44:05.040 | there's like, here's what L7 has to be good at

00:44:07.480 | in each of these things.

00:44:08.640 | And that's what managers look at,

00:44:09.760 | is Chris ready for all these things in L7?

00:44:12.600 | It makes sense, like your job is gonna now be that.

00:44:15.160 | You wanna be confident that they can handle that.

00:44:17.360 | - And if that ladder is not public, ask for it.

00:44:19.480 | There are some companies that might not publish it

00:44:21.080 | on any internal doc, but you could say,

00:44:22.600 | hey, to my boss, could you please show me

00:44:24.800 | the career ladder for my role

00:44:26.600 | or could the requirements of the next level of my role?

00:44:29.040 | And hopefully you can get that and understand it

00:44:31.360 | so you can work towards it.

00:44:32.480 | - I've actually collected the career ladders

00:44:34.520 | at 20 something companies

00:44:36.680 | and I have this doc that has all their level names

00:44:38.880 | and then the attributes for product managers specifically

00:44:41.560 | that they look for to promote people.

00:44:43.640 | - That's awesome.

00:44:44.480 | We'll link to that in the show notes.

00:44:45.960 | One of the things I tell people

00:44:47.080 | is they think that to be promoted,

00:44:49.480 | that strategy is to always do whatever your boss wants

00:44:52.640 | and never push back.

00:44:53.720 | I am someone who probably has never adhered to that,

00:44:56.120 | maybe to my own demise and pushed back too much.

00:44:59.280 | What do you think is the right balance of saying no

00:45:02.960 | and what's the value of saying no

00:45:05.200 | as opposed to always being willing

00:45:06.760 | to do what other people want?

00:45:08.520 | - I'm thinking from a PM perspective,

00:45:09.800 | product manager perspective,

00:45:11.440 | you're kind of responsible

00:45:12.280 | for what a whole team of people does.

00:45:14.600 | Like you could almost say your job is to say no

00:45:16.800 | so that you can say yes to the stuff

00:45:18.400 | that is really important.

00:45:19.720 | So it's really important to say no, to push back.

00:45:22.800 | It's still very hard, especially if your manager's like,

00:45:24.760 | hey, we need to do these things.

00:45:25.920 | So I wrote this post with five ways you can say no

00:45:30.160 | and many of them are you say yes to say no.

00:45:32.760 | So I'll share some of these quotes that you can steal

00:45:35.600 | and they're also in this post.

00:45:37.400 | So the first two is someone asks you to do something.

00:45:40.400 | You could say yes, but here's what's gonna have to change.

00:45:44.560 | If we do that, should we move forward?

00:45:46.280 | And oftentimes they're like, yes, let's go ahead.

00:45:47.960 | Or otherwise they're like, no, shoot.

00:45:50.360 | I don't wanna deprioritize that, forget that.

00:45:53.040 | So that's one trick.

00:45:54.720 | Two is you could say yes, but not right now

00:45:57.480 | because we gotta stay focused on X because of X, Y, Z.

00:46:01.080 | Do you agree with that?

00:46:02.080 | Or do you think we should deprioritize that?

00:46:04.920 | So that often works really well

00:46:06.240 | 'cause it basically communicates.

00:46:07.720 | Again, here's like a very clear trade off

00:46:10.000 | on why it's important.

00:46:10.840 | Another way you could say no is no,

00:46:13.400 | but how about we do X, Y, Z instead of that?

00:46:17.320 | And it's gonna achieve a similar outcome.

00:46:19.240 | Basically, this is when you have a better idea,

00:46:21.680 | but you wanna communicate here's something.

00:46:23.040 | We could basically do exactly what you want,

00:46:24.280 | but here's a better approach to doing that.

00:46:26.800 | Another way you could say no is no,

00:46:28.840 | but there's something there.

00:46:30.680 | There's like something to this idea.

00:46:32.960 | How about we explore this a little bit further

00:46:34.760 | and here's the next step that I suggest.

00:46:37.440 | And then the fifth way you could approach it is just like,

00:46:40.120 | no, I don't think this is a good idea.

00:46:42.080 | Here's why.

00:46:42.920 | Would you agree or is there something I'm missing?

00:46:45.000 | - So first off, I wish I had read this post

00:46:46.920 | earlier in my career 'cause I was like,

00:46:48.320 | no, that's so crazy.

00:46:49.280 | Why would we do that?

00:46:50.160 | Politics is the wrong word,

00:46:51.480 | but I was never good at a lot of this stuff.

00:46:54.280 | And one of the tactics I shared when we spoke on your show

00:46:57.360 | was that I was so confrontational about things

00:47:00.840 | because I was so used to working at a company

00:47:03.640 | that I started where everyone always knew

00:47:06.800 | that obviously I was always optimizing for the company

00:47:09.640 | because it didn't matter.

00:47:11.240 | And then I joined a company where I wasn't in charge.

00:47:13.800 | And it turns out that in big companies,

00:47:15.520 | there are a lot of people who are optimizing for themselves

00:47:17.640 | way more than the company.

00:47:19.040 | I didn't really realize that.

00:47:20.080 | I was like, everyone's got to optimize for the company.

00:47:22.200 | That's the most important thing.

00:47:23.440 | That's how I lived in my last companies that I've run.

00:47:26.280 | So a tactic that helped me when I was pushing back

00:47:29.480 | on people, colleagues, bosses,

00:47:31.520 | is just always making sure that I told people,

00:47:33.920 | hey, I'm thinking about this from the perspective

00:47:36.160 | of trying to maximize the impact from the company.

00:47:39.560 | And because sometimes I'd say, oh, we shouldn't do that.

00:47:42.640 | That's not a good idea.

00:47:43.520 | And people would be like,

00:47:44.360 | oh, well, you just don't want to do more work

00:47:45.520 | or you want to focus on this thing

00:47:46.600 | you're more excited about.

00:47:47.680 | And that wasn't true.

00:47:49.400 | But the more I just transparently said,

00:47:51.880 | here's how I'm thinking about this.

00:47:53.120 | Here's what I'm focused on.

00:47:54.360 | It just helped so much.

00:47:55.720 | So just stating your intent before you push back

00:47:58.320 | so people know where you're coming from

00:47:59.720 | was very helpful for me

00:48:01.040 | and hopefully helpful for some others.

00:48:02.680 | - Yeah, I think we all fall into this.

00:48:04.120 | Like people are going to read our mind

00:48:05.320 | and know exactly why we think no or why we're saying this.

00:48:08.840 | And it turns out people cannot.

00:48:10.600 | - So real quick, before we talk about what happens

00:48:13.640 | when you move on from a job,

00:48:15.400 | part of getting things done is being productive.

00:48:17.360 | I've talked a lot about time management.

00:48:19.240 | I'm a nerd.

00:48:20.080 | We don't have to go super deep

00:48:21.080 | 'cause I've done a few episodes,

00:48:22.720 | but any few tactics you want to pull out

00:48:24.840 | on how you manage your time and get a lot done

00:48:27.200 | and be effective with your output

00:48:28.680 | so that you do have impact?

00:48:30.080 | - Yeah, and it's especially important

00:48:31.240 | in this world of writing and podcasting.

00:48:33.520 | I'll share a few things that worked really well

00:48:35.200 | when I was working full-time.

00:48:36.920 | And I don't think anything will be revolutionary,

00:48:38.720 | but these things really work for me at least.

00:48:40.840 | One is I blocked three hours on Monday, Wednesdays,

00:48:44.080 | and Fridays on my calendar.

00:48:45.560 | And I called the meeting,

00:48:47.560 | "Do not book or I will slap you."

00:48:50.280 | And it made people laugh, but it really worked really well.

00:48:52.680 | People did not book over these slots.

00:48:54.400 | They were like, "Okay, I get it."

00:48:56.880 | And so find some funny way to have a block

00:48:59.440 | where people know, "Okay, I see.

00:49:01.240 | "He's really serious about this time.

00:49:02.920 | "Let me leave him alone."

00:49:04.440 | Because I'm sure you've talked about deep work

00:49:06.360 | and the importance of focus and all that,

00:49:08.280 | but I find that that's so important for creative work.

00:49:11.200 | In my new life of newsletter or podcast person,

00:49:14.480 | I have no meetings until 3 p.m., that's my rule.

00:49:16.880 | And only at 3, I have meetings and things like this.

00:49:19.160 | So that helps a ton.

00:49:20.680 | Two is just, what's an app or something

00:49:23.120 | that keeps you focused when you're working?

00:49:26.000 | I use this app called Centered.app.

00:49:27.960 | That's kind of like Brain.fm,

00:49:29.840 | which is this like binaural beat music,

00:49:32.360 | meets a to-do list, meets like a playlist.

00:49:34.760 | So once you're ready to work, you click play

00:49:36.920 | and music starts and it's like,

00:49:38.240 | "Lenny, start with your newsletter posts."

00:49:41.240 | And then you can knock them off

00:49:42.360 | as you're working through them.

00:49:43.400 | And it works really well for me.

00:49:44.720 | Something I'm trying right now that works well

00:49:47.000 | is picking one highlight of the day,

00:49:49.000 | one top goal for the day.

00:49:50.760 | There's this book I'm reading right now

00:49:51.920 | called "Make Time."

00:49:53.240 | - Oh yeah, John Zeratsky and Jake Knapp.

00:49:55.560 | - Yeah, sprint guys.

00:49:56.760 | And that's one of their key things.

00:49:58.880 | Just like pick a highlight.

00:49:59.840 | What's gonna be like a highlight of your day

00:50:01.400 | that you look back on?

00:50:02.480 | That I did this thing, you'll feel good

00:50:03.720 | no matter what else happened.

00:50:05.200 | So I'm trying to do that

00:50:06.040 | and that's been working really well.

00:50:08.000 | Another tip is to have a waiting for list.

00:50:11.520 | It's very like getting things done, David Allen style,

00:50:14.340 | where I have all these open threads of people doing stuff.

00:50:17.280 | And I keep a list of who am I waiting for on these things

00:50:20.160 | so that the to-do, even though it's on someone else's plate,

00:50:22.880 | I don't lose track of.

00:50:24.160 | And the way I do it is in my to-do list,

00:50:25.640 | I just have W for Chris

00:50:27.720 | and then it's like record podcast or whatever.

00:50:30.760 | So that ends up being really helpful.

00:50:32.640 | The other interesting thing I find is procrastination

00:50:35.440 | has a bad rap.

00:50:36.760 | I find that sometimes I procrastinate on a hard thing,

00:50:39.240 | but I get a lot of other smaller things done.

00:50:41.640 | So I like work through this list of stuff

00:50:43.680 | that isn't important, but I get them done.

00:50:46.280 | And there's value to just procrastinating off the thing

00:50:49.120 | that's like really hard

00:50:50.400 | because you still get other stuff done.

00:50:51.520 | So I try to channel my procrastination

00:50:54.000 | and get stuff done that I need to get done anyway.

00:50:57.000 | That ends up being kind of interesting.

00:50:59.280 | - I love using the word flow state.

00:51:00.760 | There's deep work.

00:51:01.920 | And I don't know if you could say flow state

00:51:03.600 | and deep work are the same thing,

00:51:05.200 | but I think that sometimes it just takes

00:51:07.280 | a little bit of momentum to get into that flow state.

00:51:10.000 | So it's like, I got this really big, hard thing.

00:51:12.040 | Do I want to sit down and do all this research?

00:51:14.160 | Or do I want to knock off a few quick things?

00:51:17.400 | And then I'm like, oh yeah, I'm making progress.

00:51:19.080 | I just cleaned up this set of my emails.

00:51:21.480 | I just got this one thing done

00:51:22.960 | and now I'm feeling really productive.

00:51:24.360 | And at least for me, once I start feeling productive,

00:51:27.400 | it's just so much easier to be more productive

00:51:29.560 | and get more done.

00:51:30.400 | And then I find myself like,

00:51:31.640 | oh, I just wish I could work longer.

00:51:32.920 | I've got so much.

00:51:33.760 | So I love making momentum in that.

00:51:35.560 | So gosh, those are some really great tips.

00:51:37.480 | I won't share too many of mine

00:51:38.480 | because I've done an episode with Ali Abdaal

00:51:40.680 | on productivity, with Cal Newport on deep work

00:51:43.280 | and Laura Vanderkam on time management.

00:51:45.160 | So if you're new here,

00:51:46.360 | there's a lot in the archives to go check out.

00:51:48.360 | So go check those out.

00:51:49.840 | But let's talk about moving on

00:51:51.080 | because you said you've left here.

00:51:53.040 | You're no longer a full-time employee with a company.

00:51:55.480 | You're doing it on your own.

00:51:56.760 | How did you even decide maybe I should move on?

00:51:59.320 | I'm ready for a big change.

00:52:01.080 | - If you look at my resume,

00:52:02.080 | I'm like a serial monogamist of career.

00:52:04.880 | I worked at my first company for nine years,

00:52:07.400 | then at a startup.

00:52:08.720 | That was the short stint, a year and a half.

00:52:10.280 | And then worked at Airbnb for seven years.

00:52:12.120 | I never thought I'd stay there that long.

00:52:13.440 | They bought our startup and I'm like,

00:52:14.600 | ah, I'm going to be out of here in three years

00:52:16.640 | when I'm going to start another company.

00:52:18.880 | And then seven years later, here I am.

00:52:21.240 | And along the way, I thought about leaving,

00:52:23.000 | but it never felt like it was time.

00:52:24.920 | It was always interesting.

00:52:26.640 | There's always reasons to keep working there

00:52:28.600 | and try new stuff.

00:52:29.760 | And the way that it happened that I left

00:52:32.440 | is they gave me a sabbatical.

00:52:33.560 | So I took three months off

00:52:35.360 | right around when I was reaching seven years.

00:52:37.880 | And about halfway through,

00:52:39.760 | I remember just opening my email for the first time.

00:52:42.800 | So a month and a half in the work email,

00:52:44.720 | just to see what was going on.

00:52:46.240 | And I just had this like heart sinking feeling

00:52:49.320 | where I'm like, I don't care about this at all anymore.

00:52:52.040 | What the heck is, what is going on here?

00:52:55.280 | I don't want to think about any of this ever again.

00:52:57.240 | And so that was kind of an important moment

00:52:58.880 | where I was like, wow,

00:52:59.760 | maybe I'm not excited about this work anymore.

00:53:01.720 | I still came back to Airbnb after that

00:53:04.000 | and kind of wanted to feel out.

00:53:06.840 | Am I ready for some new,

00:53:08.800 | is there like a new team maybe I could work on,

00:53:11.080 | new project that would get me excited?

00:53:13.120 | But basically the way it felt is I got there

00:53:15.160 | and I immediately felt like my heart was done with that work,

00:53:19.120 | but my brain wasn't ready to move on.

00:53:20.600 | It was like, maybe there's something more interesting.

00:53:22.040 | Maybe there's a new manager.

00:53:22.920 | Maybe there's something else I could work on.

00:53:24.280 | So I took a month basically to think and talk to people

00:53:26.920 | about other roles, other teams, other opportunities.

00:53:29.720 | But I'd say at the end of the month,

00:53:31.000 | it was like, nope, nothing that gets me very excited.

00:53:34.720 | It's time to do some new.

00:53:36.040 | And we'll say, it's like very fortunate

00:53:37.560 | to be able to have that feeling of like,

00:53:39.600 | I can leave and I'm not going to go bankrupt

00:53:41.280 | and have to live on the street.

00:53:42.480 | So I'm grateful that I have the opportunity

00:53:44.440 | to even have thought that, but I did.

00:53:47.080 | And so what I decided to do is I'm going to leave Airbnb

00:53:49.920 | and I'm going to give myself six months

00:53:51.160 | to think about what I want to do next.

00:53:53.560 | And something that really helped there,

00:53:54.640 | and here's a tip if you ever think about something like this,

00:53:57.000 | is to figure out a personal runway

00:53:59.600 | of like how much it's going to cost you

00:54:00.840 | to take six months off and just budget that.

00:54:03.280 | Like it's going to be $30,000 to take six months off,

00:54:07.320 | to pay all the things I'm paying.

00:54:08.920 | And just knowing that number ahead of time

00:54:10.760 | gives you so much less stress,

00:54:12.760 | knowing like burning through money as I'm not working,

00:54:15.280 | but I've already accounted for that.

00:54:16.400 | And it's like maybe sitting in a bank account somewhere

00:54:19.000 | and that gives you more freedom to just explore

00:54:20.920 | and not have to worry about,

00:54:21.760 | oh my God, I need to find something as soon as possible.

00:54:25.160 | - And I'll just highlight the importance

00:54:26.960 | of actually putting it in an account.

00:54:29.160 | It's one thing to be like,

00:54:30.000 | well, I know I have enough savings to take time off.

00:54:32.920 | And this is something that I'm actively thinking about

00:54:35.120 | now that I'm creating this business on my own,

00:54:37.440 | just like you did.

00:54:38.360 | It's like actually putting it somewhere.

00:54:41.200 | It takes it one step further.

00:54:42.400 | 'Cause a lot of it's emotional.

00:54:43.400 | It's not always rational.

00:54:44.760 | It's like, gosh, I don't have a salary coming in.

00:54:47.360 | I almost went as far as to take the salary,

00:54:50.000 | put it in a bank account and automate the transfers.

00:54:52.480 | So it like simulated as if I was getting my paycheck

00:54:55.640 | so that I felt like it was not as scary

00:54:58.840 | to not have that stability.

00:55:00.520 | - No, that was great.

00:55:01.360 | The other thing that I found really powerful

00:55:03.280 | during this time, in addition to the personal runway,

00:55:06.440 | is there's so little structure when you aren't working.

00:55:09.520 | Like I worked for, I think, 19 years,

00:55:12.680 | since like, you know, 18 years old.

00:55:15.040 | And I never take a break.

00:55:16.360 | And it's so weird to not have structure in your life.

00:55:18.600 | There's no deadlines.

00:55:19.720 | There's no like, I need to achieve this thing by then.

00:55:22.200 | Like you could work all day, you could not work at all.

00:55:24.640 | Nobody's gonna say anything.

00:55:25.920 | And it's hard to work without that.

00:55:27.700 | Like it feels like it shouldn't be, but it really is.

00:55:29.960 | So what I did is I created structure for myself.

00:55:32.760 | And the way I did that is I created these little sprints

00:55:35.440 | where every two weeks I wrote down,

00:55:38.520 | here's the three goals I have for the next two weeks

00:55:41.440 | that are work goals and three personal goals.

00:55:43.840 | And I emailed that to three friends

00:55:46.440 | that became kind of this like personal board of directors

00:55:48.880 | kind of group.

00:55:49.960 | And I had no expectation they'd reply.

00:55:51.720 | I didn't need them to reply.

00:55:52.920 | I just found that just emailing them,

00:55:55.760 | here's what I'm trying to accomplish.

00:55:57.160 | And then circling back in two weeks and sharing,

00:55:59.120 | here's how I did, created so much accountability

00:56:01.800 | and gave me some focus for these two weeks.

00:56:03.760 | And I ended up doing that for a year straight

00:56:05.320 | every two weeks.

00:56:06.360 | I did a little check-in in one weekend

00:56:08.680 | just to like, here's how it's going so far per sprint.

00:56:10.680 | And that was so powerful and important

00:56:13.280 | to where I ended up just creating a little bit of structure.

00:56:16.200 | And that email list ended up being like 30 people

00:56:18.480 | eventually just 'cause it became a cool way

00:56:19.880 | to update my friends on what I was up to.

00:56:21.920 | And just like, hey, you wanna join this list I'm doing?

00:56:24.160 | So that's a tip if you don't have enough structure

00:56:26.960 | around your free time.

00:56:28.360 | - I do not yet.

00:56:29.240 | And I'm going to adopt that tip.

00:56:30.720 | - I will send you the template.

00:56:32.040 | It's so simple and easy and so powerful.

00:56:34.200 | - Maybe I'll make a Google doc, just a template one

00:56:36.120 | if you don't mind and we could just share it with everyone.

00:56:37.760 | - Let's do it.

00:56:38.600 | - Put it in the show notes. - Yeah, absolutely.

00:56:39.600 | - I think one thing interesting

00:56:40.600 | that I've thought a lot about recently

00:56:42.040 | is as a creator, which you left and you started,

00:56:44.400 | I think the first thing out of Airbnb was a newsletter.

00:56:47.520 | I think a lot of people are kind of scared.

00:56:48.680 | I don't know what my thing is,

00:56:49.960 | but I love the idea of experimenting with creation.

00:56:53.280 | And I think depending on the company you work at,

00:56:55.160 | you might be able to experiment before you leave.

00:56:58.560 | I would encourage everyone to get it cleared

00:57:00.840 | to make sure that your company

00:57:02.240 | isn't gonna own whatever you're working on.

00:57:04.000 | Clear that, don't do it on your work computer,

00:57:05.840 | do it on your personal computer and all those good things.

00:57:08.240 | I think one thing for me that was strange

00:57:09.720 | was I had all this knowledge about optimization,

00:57:12.120 | but it didn't really click

00:57:13.680 | that it could actually be a thing that I do

00:57:16.080 | that could be a business that could be how I spend my days.

00:57:19.960 | Do you have any advice for someone

00:57:21.200 | who hasn't quite figured that out?

00:57:22.840 | And they're like, I would love to do that,

00:57:24.120 | but I don't know what my thing is

00:57:25.360 | or I don't know how I could test if it really is a thing.

00:57:28.000 | - I think there's two things I'll cover there.

00:57:29.360 | One is, can you start something while you're at a company?

00:57:32.800 | My experience is it's so hard.

00:57:35.720 | I found that I'm done at the end of the day

00:57:38.200 | working at a full-time job, like Airbnb.

00:57:40.400 | I'm just like, I have no brain energy left

00:57:42.800 | to experiment with writing awesome posts

00:57:45.280 | or podcast or anything like that.

00:57:47.120 | It's very, very hard.

00:57:49.320 | And I think the advantage folks like you and I have

00:57:51.560 | that are doing this full-time is,

00:57:53.320 | I find there's a strong correlation

00:57:54.720 | between quality and time.

00:57:56.280 | There's a strong correlation between

00:57:57.840 | how much time you put into something

00:57:58.960 | and the quality of that work.

00:58:00.680 | And people that have a full-time job

00:58:02.160 | are not gonna have as much time as someone like you and I

00:58:04.800 | that are doing this full-time.

00:58:06.760 | And so I think it's just really hard

00:58:09.040 | to try something like this for real

00:58:11.320 | when you have a full-time job.

00:58:12.760 | So don't feel weird if like, oh my God,

00:58:14.400 | everyone's writing all these side projects

00:58:15.880 | and writing things and starting podcasts.

00:58:18.000 | Like very, very hard.

00:58:19.040 | And I started writing,

00:58:20.560 | like I hadn't really written anything public in my life

00:58:24.160 | before I started this newsletter, just experiment with it.

00:58:27.760 | And to segue to the second question is like,

00:58:29.440 | how did I discover this path?

00:58:31.680 | I just had like stuff I wanted to get out of my head

00:58:33.640 | when I left Airbnb, just to make sure I don't forget it

00:58:36.120 | in case I start another company.

00:58:38.080 | And so I just started, I wrote a Medium post,

00:58:39.640 | it did shockingly well.

00:58:41.320 | I wrote a few more posts, they did well.

00:58:43.040 | In the sprint goal thing that I talked about,

00:58:45.240 | I just had like every sprint, just like,

00:58:47.240 | write one more post, see how that goes.

00:58:49.160 | So I just kept along that path.

00:58:50.520 | And the whole time I was like, why am I doing this?

00:58:53.040 | I thought I was gonna start a company.

00:58:54.920 | Like, why am I spending time writing?

00:58:56.560 | This is such a not, I'm gonna go anywhere.

00:58:58.960 | Time investing, my wife's like, what are you doing writing?

00:59:01.400 | You're not a writer.

00:59:02.680 | I thought you wanted to start a company.

00:59:04.400 | Why aren't you spending time on that?

00:59:06.440 | And I had this really important conversation

00:59:08.080 | with a friend who pointed out,

00:59:10.920 | okay, you really enjoy this thing.

00:59:12.680 | People seem to value it.

00:59:13.920 | That's like very rare.

00:59:15.240 | You found like some kind of product market fit.

00:59:17.360 | Maybe this goes somewhere if you keep at it.

00:59:20.080 | And even if there's no way you could ever make money with it,

00:59:22.760 | maybe just double down on that

00:59:25.000 | and forget the startup stuff for now

00:59:26.200 | and just see where it goes.

00:59:27.720 | And that's exactly what I did.

00:59:28.920 | I just started writing every week,

00:59:30.120 | launched a newsletter just to create

00:59:31.840 | a little time pressure to post something once a week

00:59:34.400 | and did that for nine months every week.

00:59:36.640 | And then at that point, I'm like, huh,

00:59:37.960 | this is still going great, growing fast.

00:59:40.520 | Maybe I could charge for this.

00:59:41.560 | I launched the paid plan that went well

00:59:44.000 | and I just kept following that path.

00:59:45.320 | And so it was very one step at a time

00:59:47.040 | without any master plan.

00:59:49.320 | - And you say it just kind of grew.

00:59:50.720 | How big's the newsletter now?

00:59:51.560 | - It's about to hit 300,000 subscribers.

00:59:54.080 | - Yeah, so it's a massive newsletter.

00:59:55.720 | - Massive, number one business newsletter on Substack

00:59:58.920 | and growing fast.

01:00:00.600 | I love it.

01:00:01.520 | It's kind of the core of my work

01:00:02.920 | and then the podcast kind of spun out of that.

01:00:05.080 | - Well, I've enjoyed it thoroughly.

01:00:06.760 | In fact, in preparation for this interview,

01:00:09.000 | I was a little stressed out

01:00:10.120 | because I was thinking, gosh, I'm leaving my job,

01:00:13.240 | but I really do love building products.

01:00:14.960 | And I was like scrolling through,

01:00:16.120 | trying to like look at all the posts you've written.

01:00:18.080 | And I was like, gosh, wow,

01:00:19.640 | I really want to build this impactful project.

01:00:21.520 | Like I really want to make another roadmap.

01:00:23.200 | I've got to channel that energy.

01:00:25.080 | And for everyone listening,

01:00:26.080 | now I'm focused on what kinds of products

01:00:28.400 | and experiences and communities,

01:00:29.880 | all of the things could I build around

01:00:31.560 | what I've done with all the hacks.

01:00:32.440 | So more to come there, but it's been very helpful.

01:00:35.680 | So thank you for that.

01:00:37.320 | Before we wrap, anything we missed in this process?

01:00:39.720 | I know you've written so many great newsletters.

01:00:41.200 | So I want to make sure we hit on something

01:00:42.640 | that you've thought about.

01:00:43.920 | - There's something that I thought would be good to share,

01:00:46.120 | which is around managing up.

01:00:47.640 | I find that whenever I tweet about managing up,

01:00:49.600 | it's like the most popular tweets ever.

01:00:52.120 | Clearly people really want to learn

01:00:53.560 | how to manage up better.

01:00:55.280 | And there's one thing that I'll share

01:00:56.520 | that I found really effective,

01:00:58.160 | which is around how to keep your manager

01:01:00.680 | aware of what you're up to.

01:01:02.240 | There's a lot of value in your manager knowing

01:01:04.960 | what's on your mind, what's important to you right now,

01:01:06.680 | what can they help with?

01:01:08.000 | So something that I found to be really powerful

01:01:09.920 | is an email that I call the state of me email.

01:01:13.840 | So it'd be like the state of Lenny email.

01:01:16.160 | I call it the subject line state of Lenny.

01:01:18.360 | And in the email, and I email this to my manager

01:01:20.720 | every Monday or every Friday, once a week,

01:01:23.520 | I write out, here's blockers that I need your help with.

01:01:27.080 | One, two, three.

01:01:28.320 | Here are my current priorities.

01:01:29.840 | One, two, three.

01:01:31.000 | And then here's what's on my mind in general.

01:01:33.320 | One, two, three, four, five.

01:01:35.080 | And then at the end, just like,

01:01:36.160 | let me know if there's anything that I can clarify,

01:01:38.160 | if you have any questions about anything.

01:01:40.080 | And I found that one email created so much value

01:01:43.080 | because my manager knew what I was up to.

01:01:45.320 | They could tell me, hey, why are you working on that?

01:01:47.800 | They can unblock stuff that I'm blocked by,

01:01:50.280 | which a lot of times they don't know

01:01:51.200 | that you're blocked by some.

01:01:52.680 | And then generally there's stuff on your mind.

01:01:53.880 | Like, hey, I'm thinking about this project.

01:01:55.720 | This person's thinking about leaving.

01:01:57.600 | This competitor's doing this thing.

01:01:59.920 | So just that one email can make a huge dent,

01:02:02.440 | and it's really simple.

01:02:03.480 | Just like blockers, priorities, what's on your mind.

01:02:06.200 | Send your manager that once a week,

01:02:07.800 | and honestly, great things are gonna happen.

01:02:10.200 | - I said earlier, you don't wanna be

01:02:11.480 | always saying yes to your manager,

01:02:13.200 | but making your manager's life easier

01:02:15.280 | is certainly something that is a very valued

01:02:18.040 | attribute of an employee.

01:02:19.280 | So in making it easier for them

01:02:21.040 | to understand everything you're working on,

01:02:22.120 | making it easier for them to say,

01:02:23.840 | I love this email idea.

01:02:25.080 | It's like, oh, no, actually work on this.

01:02:26.800 | That will let you have more impact.

01:02:27.960 | So love it.

01:02:29.000 | This has been so helpful.

01:02:30.200 | I wish that some of these things I had taken before,

01:02:32.720 | but like I said, I didn't know where I'd be now.

01:02:35.120 | Who knows where I'll be in 10 years?

01:02:36.680 | And certainly many people listening

01:02:39.040 | will hopefully get a lot of value out of this

01:02:40.760 | and out of the newsletter.

01:02:42.240 | Before we go, I do wanna ask you,

01:02:44.440 | is there a place that you feel like

01:02:46.600 | you could give some recommendations to people

01:02:48.400 | who might find themselves there on,

01:02:50.520 | whether it's eating, activities, drinks, something to do?

01:02:53.400 | - Sure, I'm not like the guy people go to

01:02:55.240 | for advice on what to do in a place,

01:02:57.240 | but you gave me a heads up on this question.

01:02:59.160 | And so here's what I got for you.

01:03:00.640 | I live in Marin, California, which is north of San Francisco.

01:03:04.200 | And so here's a little agenda.

01:03:05.720 | If you wanna come to Marin,

01:03:07.000 | I'd say stay at this hotel called Cavallo Point Lodge.

01:03:10.680 | It's gonna blow your mind.

01:03:12.400 | Then take a little walk around Sausalito along the water.

01:03:15.080 | There's this boardwalk that goes along the water.

01:03:17.560 | Then just grab lunch at a restaurant there.

01:03:19.960 | There's like these piers

01:03:20.960 | with these beautiful seafood restaurants.

01:03:23.240 | Then take a drive to San Francisco

01:03:25.360 | across the Yuletide Bridge.

01:03:26.600 | There's this art piece called the Woodline in the Presidio

01:03:29.280 | that is this like curvy piece of wood

01:03:31.520 | that you can walk along amongst these huge eucalyptus trees.

01:03:34.440 | And that's right across the bridge.

01:03:36.440 | Then you can go to say Fillmore Street or Chestnut

01:03:40.520 | in the Marina and get a coffee,

01:03:44.620 | buy some nice fancy things in some of the nice stores.

01:03:48.040 | Then I'd say drive back to Marin and maybe to Fairfax,

01:03:51.460 | which is further North, rent a mountain bike,

01:03:54.780 | find some trails, mountain biking was invented in Fairfax.

01:03:58.080 | And there's this huge mountain, Mount Tam,

01:04:00.200 | there's like a thousand trails you could go along.

01:04:02.560 | So maybe spend a few hours hiking around Mount Tam,

01:04:05.000 | sorry, biking around Mount Tam.

01:04:06.880 | Then have dinner in Fairfax

01:04:09.520 | or there's another cute little town, San Anselmo.

01:04:12.240 | And then head home to your cute little hotel in Sausalito.

01:04:15.920 | - I love it.

01:04:17.040 | If you're in Sausalito,

01:04:18.040 | I'll throw out a recommendation for a place called Fish,

01:04:20.400 | which is just like a seafood restaurant on the water.

01:04:22.500 | - Sweet, there's your lunch spot, great.

01:04:24.460 | - It meets the requirement of being Bay Area expensive,

01:04:27.380 | but also delicious.

01:04:28.540 | So I love that.

01:04:29.860 | And I don't know if you've been

01:04:31.220 | to the Mill Valley Lumber Yard.

01:04:33.460 | - Oh yeah, the cutest little complex.

01:04:36.700 | - Someone was like, can we meet at this bakery in Mill Valley?

01:04:39.100 | And I showed up and I was like,

01:04:40.740 | this is literally like this quintessential cute little shops

01:04:44.700 | and a little flower store and a bakery and a little creperie.

01:04:47.340 | And so if you need a place to just relax

01:04:50.000 | for an hour and a half or two,

01:04:51.480 | highly recommend that as a stop in Mill Valley.

01:04:53.680 | I have not spent much time in Marin,

01:04:55.440 | but that place was just an awesome spot.

01:04:57.600 | - Yeah, it's like very unknown, but so cute.

01:04:59.560 | And the bakery is called Flower Craft

01:05:01.120 | and it's all gluten free.

01:05:02.120 | My wife's got Celiac and so it's her favorite place.

01:05:05.920 | - Great bakery, awesome.

01:05:07.560 | Well, before we wrap,

01:05:09.420 | where can people go find all of these great newsletters,

01:05:12.000 | all the conversations you're having with people,

01:05:14.720 | myself included,

01:05:15.800 | which depending on whether this comes out at the same time,

01:05:18.360 | we had a great conversation over there.

01:05:20.720 | Let everybody know.

01:05:21.560 | - The hub of all things I do is Lenny'snewsletter.com.

01:05:24.300 | That's where my newsletter is, my podcast.

01:05:26.760 | It's designed for anyone that's building product,

01:05:28.920 | growing product, mostly product managers, founders,

01:05:31.960 | designers, engineers, anyone basically working on software.

01:05:34.840 | Lenny'snewsletter.com.

01:05:36.040 | You could also check out Lenny'spodcast.com.

01:05:38.160 | It's a newer thing, but doing super well.

01:05:40.600 | And I'm really proud of it.

01:05:41.880 | So check that out and @LennySan on Twitter.

01:05:46.320 | - What's the story behind the San?

01:05:47.640 | - One of my friends, when I was in high school,

01:05:49.320 | just called me Lenny San for some unknown reason

01:05:51.680 | and I stuck with it.

01:05:52.820 | I didn't know I was gonna be stuck with that username

01:05:54.340 | for the rest of my life, but here we are.

01:05:56.540 | - Awesome.

01:05:57.380 | All right, thank you so much for being here.

01:05:59.320 | - My pleasure, Chris.

01:06:00.160 | Thanks for having me.

01:06:01.000 | (upbeat music)

01:06:02.480 | - I really hope you enjoyed this episode.

01:06:04.280 | Thank you so much for listening.

01:06:06.040 | If you haven't already left a rating and a review

01:06:08.160 | for the show in Apple Podcasts or Spotify,

01:06:10.920 | I would really appreciate it.

01:06:12.640 | And if you have any feedback on the show,

01:06:14.080 | questions for me, or just wanna say hi,

01:06:16.440 | I'm Chris@allthehacks.com or @Hutchins on Twitter.

01:06:20.720 | That's it for this week.

01:06:21.760 | I'll see you next week.

01:06:23.000 | (upbeat music)

01:06:25.780 | (electronic music)

01:06:28.700 | (electronic music fades)

01:06:32.120 | [BLANK_AUDIO]