You Have to Die Before You Can Be Reborn
Bundling and unbundling your identity
Something no one tells you about starting a company is that success can actually be just as scary as failure. It’s true for any big undertaking: failure is a disappointment, but at least it’s a return to the status quo. Success is a blind leap into the unknown. I remember, in those early days, understanding that I had signed up for something that was going to change me dramatically without knowing exactly what form that change would take. I had signed the death warrant for my current self, and I was rolling the dice as to whether whoever was going to replace him would be better.
Of course, I did end up getting replaced by a newer version of myself, and by the time we actually did fail, we’d been around for long enough that in the failure I had to get replaced all over again. Actually winding the company down—a long process—sucked, but at least while it was happening I was still technically a founder. Afterwards, I was no one.
I was lost, but it was also freeing. When you aren’t anyone, you can be anything.
“There are only two ways I know of to make money: bundling and unbundling.”
—Jim Barksdale
You wouldn’t think that one of the most famous business quotes of all time would have come from the CEO of Netscape, a company that was ignominiously crushed only a few short years after its IPO. Yet this quip turned out to have a much longer shelf life than Netscape itself. If you’re under 40 and you know who Jim Barksdale is, it’s probably because of this quote1.
The basic idea is that in almost every market, businesses either compete by packing together products or services that were previously sold individually, or they compete by taking things that were previously sold together and offering them a la carte. iTunes unbundled individual songs from albums, then Spotify rebundled all music. Craigslist unbundled classifieds from newspapers, then a million different startups unbundled each individual Craigslist section. Since Alexander Graham Bell founded AT&T in 1875, the telecom market has gone through multiple overlapping cycles of bundling and unbundling2.
These are also, I think, the only two ways to grow as a person: bundling and unbundling. We’re continually either taking on new identities or shedding old ones, sometimes by choice and sometimes because change is foisted upon us. When you go through a big life transition—or even, sometimes, a small one—you have to change your entire conception of yourself along with it.
Paul Graham has written about the benefits of keeping your identity small: it’s harder to be open-minded about ideas that are part of your identity, so the fewer beliefs you let enter that category, the more open to new ideas you’ll be. But identities have a way of latching onto us no matter how hard we try to avoid them. After all, being the kind of person who’s open to new ideas is itself an identity, as is being someone who keeps their identity small.
The only people I’ve encountered who seem to have truly small identities have all been serious meditators, many of whom report that after years of practice, the distinctions between themselves and the rest of the world seem to become a little less clear-cut. They’ve opened their minds so much, become so porous to the outside, that it’s almost like a part of them has disappeared. I admire that, but I’m not so sure it’s something I want for myself.
When I actually was a founder, I had frequent misgivings about the way that identity threatened to swallow every other part of me, but now that I haven’t been one for years, I find myself returning to that time in my life more and more, in this newsletter and elsewhere. Ironically, being an ex-founder has become more central to my public persona than being a founder ever was.
One way that manifests is in seeing echoes of the founder experience everywhere, no matter how much of a stretch the comparison may be, like a widower who thinks every woman on the street looks like his dead wife. I’m in the early stages of a new relationship right now, and a part of me feels just like I did back then: I’m signing myself up to be changed dramatically, with only a loose understanding of what those changes might be.
Being single was my identity for a long time, and shedding an old identity is always hard, no matter how badly you wanted that identity to be shed. I may never again lie awake with existential dread over not having found a partner yet, or walk home from a one-night stand’s apartment thinking about how unsatisfying it is to have sex with someone you don’t really like. Those are both negative experiences, so you’d think I’d be unambiguously glad to be leaving them behind, but it isn’t so simple. It’s hard to let go of the parts of life you’re used to, even if they sucked.
Only in retrospect is it easy to see that even those depressing experiences had a richness to them, that they were a valuable part of life’s overall texture. In saying goodbye to them, I can finally appreciate them, and we can part, if not as friends, then at least with a mutual respect. And someday, when enough time has gone by, enough cycles of my own personal bundling and unbundling, I may even look back on them fondly.
Ironically, it came in response to an investor asking about what would happen if Microsoft decided to bundle a browser with Windows.
Briefly: in the days of AT&T’s monopoly, they rented you the phone and service as one package (bundling); post-AT&T breakup you could buy the phone separately (unbundling); then with early cell phones, the phone and service came together (rebundling), but you could buy components like minutes and texts separately (unbundling); and then finally, in our current smartphone era, calls, texts, and internet are again packaged together in one subscription (bundling), but the phones are usually sold separately (unbundling).