The Exchanges

Q So guys, You're going to enjoy the next 10 minutes. You sort of got a sense of where Lenny is today, but it all started really back in 2010, 20 11 with one of his first companies called Local Mind. Lenny, what was the idea behind Local Mind?

A LocalMind was built back in the day when check-ins were really cool. Foursquare and Guala and Facebook. So what we did is we sat on top of their data and allowed you to talk to people that are checked in anywhere in the world to find out what's happening, where they're at. So if you're thinking about going out to a bar, hey, is this bar fun right now? If you're thinking about going to a concert, what's happening there right now? Or what's the special of the day? So it was called LocalMind and the idea is to give you this LocalMind anywhere you're thinking about going to. And ran it for about a year and a half, uh, raised the money, moved to San Francisco, and then sold the company to Airbnb, which is how I joined Airbnb.

AI assessment note: “allowed you to talk to people that are checked in anywhere in the world”

Q From what I can see. Yes. This is extremely, extremely well. And so you, you made some capital off of this and then sort of pick up from there. What happened after this?

A So I just kept writing. I wrote five more pieces around how to get into product management. Uh, actually how, what, uh, what Buddhism taught me about product management, because in that three months I took off, I actually went on a meditation retreat and that actually informed a little bit of how I was thinking about life at that point. Uh, and so I kept writing, kept doing well, uh, not as well as that first one. And, uh, and then eventually someone convinced me to switch to sub stack because the take was the pitch was just like, Why are you giving medium all of your content? They're gaining all of the upside, all of the SEO, all the subscribers. You don't get any email addresses of your audience. So you have no access if you leave. And so that was the benefit of sub stack. And it was totally true.

AI assessment note: “So I just kept writing. I wrote five more pieces”

Q As you experimented your, your first shot at like the call to action to convert people from free to paid. What was your first stab at that?

A So, so one thing I did is I gave them a discount if they subscribed in the first 48 hours. So I priced it at 15 bucks a month or 150 a year. And, uh, if you subscribed in the first 48 hours after I launched, it was 10 bucks a month or a hundred year. And the call to action is just subscribe now. Uh, I gave them a week. I think it was two weeks actually before when I announced to when I was going paid. So I gave people two weeks of more free and the call to action is really simple to subscribe now, you know, support this kind of work. If you found value in this thing, the way I pitched it essentially was if you can make one better decision a year through this, that's worth a 150 bucks a year, especially if you can expense it to your company, which some folks do.

AI assessment note: “the call to action is really simple to subscribe now, you know, support this”

Q Yeah. And so what were you expecting when you launched the paywall? You launch it, you then go to bed or your developers, maybe you launch it like two AM and then you like wake up at 11. What happened?

A Uh, no, I launched at a reasonable hour. Uh, I, so I launched it. I got a bunch of help on the way of to frame the launch and how to price it and things like that from just like various smart friends. And I kind of crafted a whole pitch of why this makes sense and why this is valuable. And yeah, it was like nine months of free every week up to that point. Partly what gave me confidence to do it as I had kept it up for nine to 10 months every week. Which was not obvious to me that I could keep this up for that long. And at that point, I was like, oh, wow, I could keep going for years, probably doing the same thing. So let's just give it a shot. Uh, and so, yeah, I launched it and I got about 200 paid subscribers in the first couple of days. And then I got up to about 400 something in the first month and just kept growing.

AI assessment note: “I launched it and I got about 200 paid subscribers in the first couple”

Q So what happened because you're sitting on a, I assume you see internal metrics, you know, you're sitting on a rocket ship. Uh, you, you're giving up a big salary. What was the catalyst that you say, you know what? The opportunity cost is too high to stay. I need to leave and create space to invent something new.

A Honestly, it was a very visceral kind of a non-rational feeling. Uh, I went on a sabbatical. I was there seven years, took some time off, came back, and I just felt like, like the Kool-Aid had worn off, and I was just ready for something new. I just came back, and it just didn't have the same energy and drive that I had before that, and then I spent another month rationally kind of getting there by talking to other teams and leaders to see if there was a different role or another opportunity, but it just kind of felt like Naturally, this is the time to go. And I didn't actually have a plan when I left. I was just, I'm just going to see what happens. I'm going to give myself six months to explore and ended up taking me a year to figure out this is the path I want to go down.

AI assessment note: “Honestly, it was a very visceral kind of a non-rational feeling.”

Q I've done with Noah and how I grew AppSumo and Drew recently launched in trends, the same sort of deals concept. There's a lot of people sort of trying this. And so I'm curious, what angle are you taking? Is it going to be exclusive to B to B SaaS or different? And what advantage do you think you have over an app sumo or drew it trends, if any?

A So this, honestly, this again comes back to just how do I provide more value to readers? I want it to become such an obvious, 15 bucks a month, of course. So if I could do like, if you save like hundreds of dollars a year from some deal that I can give you, that's amazing. So it's as simple as that. Someone on Twitter put it really well that I'm trying to create an Eleni Prime. You pay 15 bucks a month and you get all these incredible resources, a Slack community, the deals thing. I'm working on a curated guide and resources of just like the best Reads on any topic. So you're not just filtering through millions of articles. It's like, what's the best read on SEO? What's the best read on getting into product? So I'm just trying to bundle more and more value. That's it.

AI assessment note: “I'm trying to create an Eleni Prime. You pay 15 bucks a month”

Q Yeah. Um, let me get one, let me get one question to you on Substack before I go back and get more of your history. Um, if you were, because you're, I mean, your business is on top of Substack. If you were leading, if you were the lead PM at Substack, what does the Substack product look like a year from now?

A I I've been talking with the sub stack guys a little bit about this, honestly, and it's, it's a big challenge. Uh, at some point the fees end up being a lot and I don't know what the answer is to be honest. I think they basically have two options. One is drive hand and make it such that it's well worth paying this fee because they're making me more money directly. The other is make it a lot easier for me to do this job. So provide tons of tooling and support and other things where I just can't get that anywhere else. And it makes up for the costs. And I honestly don't know what I would do. It's a, it's a tough place to be, but, uh, but I'm bullish. I'm a big, I'm a big fan.

AI assessment note: “I think they basically have two options. One is drive hand... The other is make it a lot easier”

Q Lenny, how do we encourage more people to do that? There's a lot of people that don't know how to get their mind in a place to just say, I don't know what I'm going to do, but I have six months of runway in my life. You cover my expenses. I'm just going to go be in an empty space for a while. How do we encourage that?

A The key is having that runway. A lot of people aren't fortunate to have that. So I had savings where I could, the way I did it is I just budgeted. Okay. Six months. Here's so much it's going to cost me to live with no income. I'm just going to set that aside and I'm going to That's going to be my cost for this, uh, time that I'm going to give myself. And that, that alone made me feel a lot more comfortable, uh, giving up the salary and investing. That's a whole different story, but, but at some point that has to end, like it never ends. There's always going to be more salary investing if you're at a tech company. So, so a lot of it was just, I was just like ready to take a leap. I had savings to give myself a chance and I never thought I'd be there seven years. So it's kind of this like, okay, what the hell am I still doing here? Seven years later, uh, I probably want to start another company or do something else. Let's just do it.

AI assessment note: “the way I did it is I just budgeted. Okay. Six months.”