Just as nobody who marries spends their wedding day planning their divorce, almost nobody starts a business contemplating what rocks it will eventually splinter and break upon, and how to build a life raft for themselves.
I take that back. Some folks I know, who played pivotal roles in the evolution of the web, actually started their businesses with a clear goal of selling them to somebody bigger. Like Typekit was designed to sell to Adobe. Or Blogger was designed to sell to Google.
Such folks, several of whom are now post-economy wealthy, lived in the Bay Area in the 1990s and early 2000s, where building to flip was widely discussed and accepted.
Meanwhile, in NYC…
I, on the other hand, live in New York. So I started my web businesses (like Happy Cog™ design studio) to serve clients, as NYC creatives have always done, and with no understanding that I would one day need to leave the company and should have an exit plan. Why would I exit? Why would I ever stop doing work that brought excitement and meaning to my life?
Similarly, I started my personal site with its “Ask Dr. Web” tutorials in 1995, and co-founded my web design publication, A List Apart, in 1997, for the sheer joy of sharing knowledge, with no concept of making money, let alone of one day selling the business.
Eventually, despite my naivete, and mostly thanks to Jim Coudal and Jason Fried, A List Apart began making money by running one carefully screened ad per page. I used that money, as you will expect, to pay our writers, editors, and producers. And when it came time to stop running ads, I slowed our publication schedule, paid writers out of my own pocket, and worked with a small crew of fellow volunteers, who published ALA because we believed in the mission. (Still do.)
If I had come of business age in San Francisco, I likely would have sold A List Apart to somebody like O’Reilly, but that was never my plan because I make toys to play with, not to give away.
An ecosystem apart
In spite of A List Apart’s running at a loss, in the early 2010s I co-founded two businesses that spun out of it: An Event Apart design conference with Eric Meyer, and A Book Apart with Mandy Brown (later replaced by CEO Katel LeDu) and Jason Santa Maria. And during those first years, business was great.
We published HTML5 For Web Designers the day after Steve Jobs, waving an iPhone on the world’s biggest stage (okay, sitting at his desk), announced that Flash was dead because HTML5 would bring app-like dynamism to the web using open standards instead of proprietary code. It (our first book, I mean) sold brilliantly. “Gee, publishing isn’t that hard” I naively told myself. (No, I knew it was hard. My favorite publishers had been laying off my favorite editors for ten years before my partners and I took the plunge. But the early success did make me think the books we published about web design would always find a large, eager audience. In time, I would learn otherwise.)
And while we began the publishing house by relying on the best writers we knew personally to write about the topics they were most passionate about, I’m proud to say that, as we went along, we also discovered brilliant first-time book authors, helping them create perfectly polished, fluff-free manuscripts that made genuine contributions to our readers’ understanding of UX and all it entails. (And not just to our readers. The insights they brought to their work after digesting our books rubbed off on their colleagues.)
In giving these brilliant writers a platform, we not only helped them take their careers to the next level, we also helped people who create web content think and work better, which in turn helped the people who used the websites, applications, and products our readers designed and built. Of that, I am proud.
Stay hungry
An Event Apart (RIP) was also a damned fine early success. Web designers liked our innovation of a multi-day, single-track conference, with a holistic approach to web design, code, and content, and unifying themes between the individual talks. Our freaking-amazing speakers debuted Huge Ideas including Mobile First and Responsive Web Design—ideas which, like perfect contextual menus in UX, arrived at the very moment designers needed them.
Not only that, but these humble geniuses also sat in the auditorium with our audience for all three days of each conference event: listening to each other’s presentations, and updating their own presentations to better bounce off each other’s ideas and the evolving themes of that particular show.
I could spend hours telling you how our producer Toby M. made miracles happen at every show, or how person-in-charge Marci E. brought joy to our community. How many of our speakers became authors. How some “graduated” from An Event Apart as newcomers replaced them. How the diversity of our speaking line-up, which wasn’t terrific in 2008, improved greatly each year. (Not that we ever said, “We need another black speaker” or “We need a trans speaker” or what-have-you. Just that we learned to swim outside the pool we came from, and discover great talent everywhere.) Our speakers were also almost uniformly Just Nice Good People, which doesn’t always happen when you’re collecting the greatest minds in an industry.
That’s not even to mention the incredible people who attended our shows, some of whom became lifetime friends for me.
So why, given the joy these businesses brought to everyone connected to them, including me, would my partners and I have even conceived of an exit strategy? We wanted the Good Times to roll on forever.
But of course they never do.
Things end
COVID did in An Event Apart. Some conferences survived, of course. Different priorities, different overheads, different business models. Some that survived do not pay their speakers. Others, where the conference is an adjunct to a bigger business, laid off or reassigned conference staff while the pandemic made live events impossible. Others that survived mostly rely on volunteer labor, whereas we had paid staff. They were worth their weight in platinum, and we’d have paid them more (because they were worth more) if the pandemic and six-figure hotel contracts hadn’t made continuing the show impossible. My partner and I earned nothing during the business’s last five years, and got personally stuck with a six-figure debt when the event closed. It is what it is.
Although books should be COVID-proof, multiple financial problems eventually beset our publishing house as well. For most of the run of the business, my partner and I earned nothing beyond the glow of contributing to our community’s knowledge. We paid our CEO, authors, and editors, kept nothing for ourselves, and tried, oh how we tried, to keep the business going as its revenues tanked.
Speaking only for myself, I’ve learned that I am good at starting businesses and keeping them going creatively, as long as somebody else figures out the money. I suck at that, and I’m obsessed with the notions of fairness and self-sacrifice that were drummed into me by a narcissistic family that valued me for taking on the roles they were emotionally incapable of handling—such as bringing up my baby brother in my father’s absence, which no child is equipped or should be asked to do, and yet it happens all the time. Growing up this way made me put my own self-interest last. Which is also why it never occurred to me to plan an exit. And by the time I needed to do so, the businesses were not in shape to sell.
Closing a conference is bad, but attendees can go to other conferences, and speakers can speak at other conferences; closing a conference doesn’t end a community. It sucks for the business but doesn’t strand participants.
But closing a publishing house hurts like hell, and you feel you let everybody down. I know how much our closing hurt some of our authors, and I think about that, instead of the good we achieved, when I look back.
No doubt when my partner and I write the large personal checks to cover our deceased business’s outstanding debts, we’ll be regretting the harm our closing caused, not basking in the warm glow of how many careers we changed for the better. Like the standup comedian who obsesses about the guy who’s frowning at table 3, and doesn’t hear the laughter of the rest of the crowd. We also, hopefully, won’t focus too closely on our financial wreckage. Just pay the bill, and move on.
Anyway, I hadn’t publicly addressed the endings of these businesses, so I figured it was time to do so. I’m sharing my experience only. If you ask any of the people I worked with on these projects, they might have a different story to tell. And that would be their story, and it would be every bit as valid as anything I’ve said here.
I also didn’t ask permission of my partners, speakers, or authors before sharing these thoughts. Probably I should have. But, hey. As I’ve said. I’m speaking here only for myself.
So, anyway.
Parting gift
Is it worth the risk of starting a web-related business that isn’t a venture-backed startup? I still think it is, and I applaud all who try. Heck, I might even do so myself someday. If you’re doubtful because of (((gestures at everything))), it might be worth noting that I started Happy Cog™ during the dot-com crash, when studios were closing all around me. And we launched A Book Apart during the world financial crisis of late 2008. Don’t let (((all this))) deter you from trying something bold. Let me know when you do. I’ll keep watching the skies.
P.S. Under swell third-party ownership and management, Happy Cog is still going strong. Check it out!
