20 Years In: Incomplete Reflections on Entrepreneurship

I found an interesting—some may say insane—letter in my junk drawer of a document box. You know, that box that goes everywhere with you and progressively fills up with “important” documents you believe you need to keep, like tax returns and Staples receipts for printer paper and pens purchased in 2001.

My family and I are in the process of moving (thank you NYC, hello Denver!) and because my box had nearly reached capacity, I decided to clean it out. I mostly spent my time shaking my head at the fact that I actually kept all this stuff to begin with, but I did come across this gem: An LOI to acquire my first business, FunGrams.com, dated May 2000. Almost exactly 20 years ago.

If the acquisition had gone through, I would’ve been a millionaire at 16. It didn’t, and you can probably guess why given the date of the LOI (interesting aside: The potential acquirer, eUniverse, successfully pivoted away from greeting cards, weathered the dot-com collapse, and incubated MySpace in 2003).

While the acquisition didn’t happen, I did fall head-over-heels in love with technology, the Internet, and devising ways to make it work for me. I’ve had three “real” companies over the last 20 years, but there’s not been a moment that I haven’t had something going. Even if it was a simple side-project or two. Never a time, that is, until now.

I stepped down from Contently after nine years just before Thanksgiving, and CashCrate, a company I started in 2006, hummed along for a cool 13 years—including the 9 I was at Contently, thanks to an enduring business model and a talented team—before succumbing* to legal trouble wrought on by bad third-party software and a subsequent data-breach, also in 2019.

The point is, 2020 is the first year since 1998 that I haven’t had my hands in something, and I’ve decided the best thing to do is keep it that way—at least for six months, maybe longer. My son just turned three, my wife and I are in the midst of our aforementioned move, and I’m getting some badly needed rest and recovery. Because of pounds of flesh have been extracted, make no bones about it. It’s not an easy way to live.

Last week, Tim Ferris wrote a piece called “Reasons To Not Become Famous”. It’s a great read insofar as it’s not something people typically talk about. Not because fame is without it’s own unique set of challenges, but because it’s something most people don’t feel they’re allowed to talk about. Superficially, it’s the epitome of a “first-world problem”. Who doesn’t want to be famous?

Similarly, being (or appearing as) a successful entrepreneur is culturally “in” at the moment. And to be sure, there are great things that come with that (both entrepreneurship and being culturally in). But there are also a host of negatives. Real trade-offs. And when talking about them is perceived as whining, it creates a pervasive sense of stigma that results in real damage. The numbers don’t lie: A recent-ish study found that 49% of entrepreneurs say they suffer from mental health issues, compared to just 7% of the general populous.

It’s a problem, one I’d really like to help with while I’m in a position to do so. Maybe a series of interviews, maybe a podcast. I’m not sure. But I do know every time I get too deep in ideation about this or any other project, I find myself on a path back “to the kiln”, to use Jerry Colonna’s words, and I force myself to back off. At least for now, at least for another few months.

* CashCrate is still alive, but the heart of the company–our rewards program–has been sold off and the site no longer requires day-to-day maintenance.