“Did I intend to stay there for seven years? Hells no. But man, it’s a tough place to leave.” Five Questions on Startups, Newsletters & Life Post-Airbnb w Lenny Rachitsky

Our friendship began as many do – in a bar a few days after I’d been told that Lenny (a) just left airbnb and (b) was smart. Upon receiving the tip I clicked over to his Twitter profile where I saw that indeed he had left airbnb and that he was clearly super duper smart because he already followed me. A DM-slide and poof! cocktails and product management war stories ensued. In the time since he’s written some really wonderful posts and now a newsletter that’s going paid subscription, so seemed like an opportune time to ask him Five Questions...

Future’s So Bright….

Hunter Walk: So like, we’ve been friends for a year now. I went back and checked and it looked like I Twitter stalked you when you left Airbnb. Before we jump into Present Day Lenny, can you share how you initially got involved with Airbnb and, leading the witness, had you intended to stay as long as you did?

Lenny Rachitsky: I have this memory I’ll never forget of sitting in an early Airbnb all-hands looking at a big ass Airbnb logo (the old one) projected on the back wall, and thinking to myself “wait, how the hell did I end up at Airbnb??”

I was CEO of a little startup (Localmind) which we started in 2011, and things were going great. Growth was up, we were regularly getting featured in the App Store, and we were just about to kick off our seed round. But when Airbnb can knocking, we quickly realized that our most likely long-term outcome was going to be an acquisition, and that we couldn’t think of a single better company to end up at. So we sold.

When our team came on board, I quickly moved into product (I was an engineer up to that point), and held on for dear life for seven years. 

One of my favorite memories from the early days is of Joe talking to an engineer/designer who was working on an update of the homepage literally a few days before a major launch. She was asking for feedback on what she thought was a complete homepage. Instead, Joe offered, “build something the internet has never seen before.” 

And the funny thing is that she did (a sweet parallax’y hero image deal). That moment is actually a great microcosm of Airbnb. Never settling for good enough, always looking for ways to push further, and expecting the very best from everyone.

Did I intend to stay there for seven years? Hells no. When I started, I gave it a few years tops. But man, it’s a tough place to leave.

HW: What’s your decision framework for how you choose to spend time these days? I know you’ve done some advising and angel investing. But there have been some fun side projects too with regards to personal interests.

LR: My simple strategy for this year of exploration (which I’m so incredibly fortunate to have) has been to spend as much time as possible on things that give me energy. And as little time as possible on things that don’t. That’s it.

Though my original plan after leaving Airbnb was to start a company again, through this process, I discovered two things:

  1. What I don’t want to do: Specifically, become a full-time VC (no offense Hunter), write a book, or start a product management training course. These are things that folks keep suggesting I do, but I do not enjoy them and am trying hard to avoid sliding into these default paths.
  2. What I do want to do: I’ve discovered the things I enjoy most, at least for now, are writing, angel investing, and advising. So I’ve been trying to build a life where I can do those things.

As a result, these days, I spend about a third of my time advising, a third investing, and third writing.

HW: Ah yes, your writing. I’ve loved the newsletter and am glad to see you’re really committing to it with a paid subscription tier. I’m sure it was already opening doors for you professionally so what was behind starting to charge? Starting to build an income again? Signaling worth for the content? Challenging yourself to up your game?

LR: Folks seem to think I’ve had a well-thought-out plan with this newsletter. Honestly, I’ve been figuring it out as I go along. 

I first started writing as a way to get learnings out of my head, before I forgot them. Then, as people started asking me smart questions about things I didn’t have great answers to, it gave me an excuse to go learn more myself (and have better answers). So I embarked on some in-depth research projects (e.g. marketplace growth), looped in smarter people on topics I have little experience on, and collaborated with other great publications to reach new audiences.

Why’d I decide to start charging? For a very simple reason: I want to avoid getting a real job. I’m trying to see if I can make a real living doing this eclectic combination of writing, investing, and advising. It’s a life experiment! Plus, there’s a really neat flywheel between these three things that’s become a huge bonus.

HW: Does this also mean you’ll have a budget to get some custom illustrations from your wife? Along this same timeframe I’ve gotten to know you, she published a best-selling book. What has riding along that experience been like?

LR: If only budget was the reason she doesn’t help me with my newsletter design 😂 She’s definitely got better things to do, plus she tries to avoid the tech world as much as possible.

But, I’m glad we’re clear that Michelle is the real star of our family. She’s as talented as she is modest, and I couldn’t be more proud of her. If readers don’t already follow her on IG, you’re making a big mistake.

Watching her publish her book (excellent reading for the sheltering lifestyle btw) was an illuminating experience. It’s partly what convinced me NOT to write a book. For her, it was a life goal, but the economics are ridiculous, and I’m convinced that for what I’m doing, investing that time in a paid newsletter is a much higher ROI use of time.

HW: I’m sure there are new grads and folks early in their tech careers for whom you’re a role model. What’s the advice you’d give someone now – and has any of that been changed by what’s currently going on with COVID19 and what the world might look like on the other side of this?

LR: This may be the first time anyone has called me a role model, so I have to let that process for a few days.

Some timeless advice I come back to when wondering what to do:

  1. Do great work, create value, and good things will happen.
  2. Spend as much time as possible on things that give you energy.
  3. Work at the intersection of (i) things you enjoy doing, (ii) things you’re good at, and (iii) things that other people want.

Beyond that, for people early in their career, I would suggest optimizing for “variety of experiences.” Do as many different kinds of things as you can. Not only does trying a bunch of things help you find what you enjoy doing most, but also later in life you’ll find that many of the things you learned early on will be essential puzzle pieces in the work you end up doing. I’m pretty sure Steve Jobs said something similar, so it must be true. Explore, tinker, and take risks!

And finally, for the post-COVID19 world, my general take is that it’s going to further accelerate software eating the world (if that’s even possible), and so there’s even more reason to guide your career towards tech. At least the early part of your career. That decision early on for me, to get into software development, was the one thing allowed me to have this freedom to take time to explore and new paths. I’ve been so unbelievably lucky.

Thanks Lenny! I’m a happy paid subscriber to Lenny’s Newsletter and recommend you check it out as well (there’s a free tier too).