Lenny Rachitsky: recommendation

Transcript context

…I have a couple. I think it's very much not that way. I feel like it was a lot of squiggly lines to get here. The biggest I'd say is just founding a company, raising a bunch of money, having employees, and then having to shut it down and tell your investors that you've lost the money and that you had a vision of what you're going to do and that it's not going to happen. And so that I think is probably the biggest one. We spent three years on it. It was not like a, "Oh, we tried something part-time." It was like, "No, we went for it." We had spent three years, raised a couple of mil. We had maybe seven, 10 employees at our biggest. And it was something that we really believed in. It was around mental health and how you can quantify mental health to help understand or get early predictors of things like generalized anxiety, major depression. So it's stuff that we really, really believed in. But ultimately, in our early 20s, we had no idea what we're doing at the time and many things I do differently, but that was just a very, very, very painful process. I think the good thing was we kept our investors in the loop the whole time, so 20 founders who are struggling out there. Send those monthly investor updates. It's really easy to send those when things are great. It's really hard to send those when things are bad. You just bat it down. You sit down and send an update to your investors about why everything you talked about last month did not go to plan, but it's just the right thing to do, and it keeps people in the loop, and it avoids surprises. But it's still so tough when you're then calling up the investors to be like, "Hey, we're shutting down or making that decision," everyone who believed in you and it becomes such a big part of the identity. It's very, very tough. So man, that was just brutal. It's brutal. And it took me, I think, a number of years to truly get over. I think that it's a tough thing, but you get so much from that experience that it's hard to see in the moment. And I think without doing that, I would not have gone into this. I was not a PM before. I didn't have any of these skills. I'd never worked on products. I didn't know how to cold email really. And so it was through that job that I learned a ton of the skills that made this career path viable for me. And it's just really hard to see that in the moment when you're looking at a point in time. It's much easier to draw the line looking back. But I think that'd be my takeaway is just keep in mind that it's a long game and some of those things... I'm so grateful for that experience now. I'm so grateful that it failed and went that way, actually. It's very painful because it wouldn't have led to what I'm doing now. And so it's a tough thing, but the positives can come from it. What I love about this is a lot of people have these times in their career where they're like, "It's all over. I failed in such a big way and my reputation's screwed and people were counting on me and now they see I'm an imposter. I never knew what I was doing. And after all, now they finally see." And just seeing that, and this was three years, I'm looking at your LinkedIn, you had seven employees, something like that, and then it's like masterclass, Mercury, Anthropic. I think it's inspiring to hear a story like that to know that you can have a big failure like that and things can work out. That is not the end. Okay. So at 2023, I was going to go on pat leave because my wife's pregnant and I was just like, "Wait, what do I do with the newsletter? I need to take some time off. That would be really nice to take a month or two off." And so my plan was, "Okay, I'm going to do a bunch of guest posts where people line up." I put out a call for guest posts, people apply, I pick a few and then I kind of slot them in ahead of time so I could take time off. So I put out this call, "Hey, who wants to write a guest post for my newsletter?" I got 500 plus applications. One of those applications was from you and the pitch was essentially how a traumatic brain injury made me a better product manager. And I still remember reading the first draft you sent me and I was just like, "Holy shit, this story is incredible." It's just like you feel such feelings and it was just so tactically interesting and useful like, "Oh wow, this is actually going to make me a better product manager. " Share the story of the brain injury that you went through and just the journey that you went on there because this is going to blow people's minds. It was the toughest time in my life. It made shutting down a company being like, "Oh, that was nothing actually." Just funny how perspective works that way. Back in early 2022, I had a traumatic brain injury. So I'd done MMA for many years. I'd done Muay Thai, which is a type of martial arts for many years, never had a problem. And it's just one of the things that happens, the wrong session. It's just a normal day of sparring, nothing crazy. You get the wrong hit to the head in the wrong way, and my whole life changed. And basically I spent nine months. I was off work for nine months. The first couple of months were brutal. It took me roughly half a year till I was comfortable walking again. It was very, very difficult. The first two, three months beyond just showering and going to the bathroom, my wife did everything for me, including texting my friends. I would listen to music for maybe 20 seconds and feel like I needed to vomit. I couldn't look at screens at all. And it was a very, very long recovery. It was not clear to me that I would ever work again for a while actually. And it was like we'd even discussed my wife, what would we do in that case, et cetera. And we had to think even on those levels. And through a lot of pushing and really working through myself, and you have to just slowly increase your tolerance to things. It's a brutal process, but you need to slowly expose yourself to different things and just get better and better at each little thing, actively work on that, don't push it too far, otherwise you have a big setback. It basically got to the point then where over nine months and then that it returned to work and then it slowly got better. And the part, Lenny, you don't know is in mid-2023, we posted that newsletter and a month later I got re-injured actually.…

Stored transcript either side of the excerpt. The highlighted words are the published quote; the surrounding text is unedited source, never generated.