Fantastic Builders and Where to Find Them, 5th Installment
A nugget of wisdom from my walk with Sahil Lavingia
Catch up on previous “Fantastic Builder” spotlights with this running catalog.
Builder Spotlight #6: Money, Mormons, and A Life Well-Lived (Sahil Lavingia)
Principles on display: The builder’s mindset as a third way; your life as the measure of all things; we build ourselves by building
A few weeks ago I went for a walk with Sahil Lavingia in San Francisco (in an affirming self-demonstration of the fact that you can just meet people). In case you haven’t heard of Sahil, he’s the CEO and founder of Gumroad, author of The Miminalist Entrepreneur, painter, and influencer who first built his massive following by telling the honest story of his failure to grow Gumroad into a billion-dollar company. That “failed” company has since helped creators earn over $1 billion dollars on its platform, by the way:
Anyway, as we walked and talked, Sahil filled me in on a piece of the story that didn’t make it into that viral essay, but that struck me as pivotal from a builder’s mindset standpoint.
After the disappointment of having to lay off his entire team to make Gumroad a sustainable business—which, by the Silicon Valley “go big or go home” startup ethos he had internalized, felt like a massive failure—Sahil retreated from the Valley for a while. He sought refuge in creative pursuits like painting and fiction writing, and even moved to Provo, Utah, to take a writing class at Brigham Young University with Brandon Sanderson (a fantasy author he admired). And he noticed that the people he met there were beholden to a very different sort of ethos than the one he had absorbed in the Valley—but they were beholden to it just the same.
The other students in his creative writing class stressed out about their performance in the class and whether it would sufficiently impress Sanderson, in much the same way Sahil had stressed out about his startup’s performance and whether it would sufficiently impress SF’s highest-status investors. His new friends in the Mormon community showed no concern for the growth of his startup, but showed great concern for the fact that he was not yet married. Where Sahil’s inner drill sergeant had been pushing him to fall in line with the Valley’s default template for success, their inner drill sergeants were pushing them to fall in line with BYU’s or the Mormon church’s default templates for success.
In smiling at these people’s obeisance to their culturally received templates, I suspect Sahil was able to see that his obeisance to his own culturally received template—the “build a billion-dollar venture-backed startup” template—was not the only nor the obviously best template for living a great life. And in seeing this, he likely developed a healthy skepticism of the notion that any given template could warrant blind obeisance for its own sake.
Thus inoculated against his inner drill sergeants, Sahil was free to consider what sort of life he actually wanted to build for himself, and then define his standards of success accordingly. Here is how he went on to describe the subsequent shift in his success criteria for Gumroad:
For years, my only metric of success was building a billion-dollar company. Now, I realize that was a terrible goal. It's completely arbitrary and doesn't accurately reflect impact.
I'm not making an excuse or pretending that I didn't fail. I'm not pretending that failure feels good. Everyone knows that the failure rate in startups—especially venture-funded ones—is super high, but it still sucks when you don't reach your goals.
I failed, but I also succeeded at many other things. Gumroad turned $10 million of investor capital into $178 million (and counting) for creators. Without a fundraising goal coming up, we're simply focused on building the best product we can for our customers. On top of all that, I'm happy creating value beyond our revenue-generating product (like these words you're reading).
In rethinking his metrics of “success” for Gumroad, Sahil grounded his criteria in what mattered to him, not just for this specific venture, but his life as a whole. For some ambitious builders, “building a billion-dollar company” is a valid goal, given the kind of value they thrive on creating and the kinds of dents they want to make in their world. As Sahil puts it in that same essay, “There’s nothing wrong with trying to build the next Microsoft” (and indeed, Bill Gates remains Sahil’s “all-time hero,” as he is one of mine). But Sahil is not Bill Gates; he is a creator who loves to write and paint and walk around discussing ideas (lucky me!) as much as he loves to code. And the company he has built, a platform for creators by creators, is perfectly suited to both express and support these values. (The same is true, by the way, of the new venture he’s building now). For instance, from his 2021 essay “No Meetings, No Deadlines, No Full-Time Employees”:
Instead of having meetings, people ‘talk’ to each other via GitHub, Notion, and (occasionally) Slack, expecting responses within 24 hours. Because there are no standups or ‘syncs’ and some projects can involve expensive feedback loops to collaborate, working this way requires clear and thoughtful communication.
Everyone writes well, and writes a lot.
There are no deadlines either. We ship incrementally, and launch things whenever the stuff in development is better than what's currently in production.
From 2011 to 2016, building Gumroad was my singular focus in life. But today, it is just a part of my life, like a hobby might be. For example, I paint for fun, and every once in a while, I sell a painting.
At some point, it clicked: Creators make money so they can make stuff, instead of the other way around. Why not adopt this framing at Gumroad, too?
This is what working in the creator economy should feel like.
If you follow Sahil on social media or read his writing, you’ll know he applies this level of fresh thinking and intentionality not only to his business but to the design of every aspect of his life. For instance, here he is responding to an interview question about his morning routine:
The first thing I do is either drop my girlfriend off at work and head to the gym, or shower.
I can’t function if I haven’t showered. I can’t go to the gym if I’ve already showered.
And here he is, in another interview, talking about his approach to painting:
One of Lavingia’s favorite hobbies is painting: he spends about 18 hours a week doing it. “If I have a really great painting, I celebrate it. If I don’t, I celebrate it,” he says. “It’s about this multi-year journey for me, improving my ability to paint.”
And, on what painting has helped him understand about building tech products:
There’s nothing that’s gonna teach you how to build stuff faster than building stuff. It’s just like painting.
This insight, as Sahil’s story so beautifully illustrates, scales all the way up to life as a whole. There’s nothing that’ll teach you how to live your life faster than living it—that is, living your life, undeterred by whatever local drill sergeants might try to pressure you into living someone else’s.