Sunday marked four years since I sold iContact, a company I built based on a web app I whipped up in a few weeks time programming on my futon my sophomore year of college at UNC.
It was a decade long ride with some monumental ups and downs but the story ended just like any startup founder could dream it up—with a bunch of hoopla, a big press release and a wire transfer that still doesn’t seem real this many years later.
All that boring business stuff aside, I’ve learned since then, that when you sell a company in the new millennium there are really only three questions you must be prepared to answer.
"Did you throw a big party?"
No, I threw a very small party.
Actually, we had the trip planned before we knew the company would be sold. A week skiing at Heavenly above Lake Tahoe in one of the sweetest ski-in, ski-out houses on the mountain with a bunch of good friends, including my would-be co-founder at my next company
and his wife.
It was a great time to forget about work, reconnect with friends new and old and focus on the finer points of life, like swimming out of snow drifts on double black diamonds and striking that perfect balance required in the hot tub to keep your beer cold enough to drink but your hand warm enough it doesn’t freeze.
One of my best friends from college lives in the Bay Area and came with a buddy on short notice, throwing up from the flu on the ride up, just to make the celebration. That’s a real friend.
It was a great week of skiing, er, party.
But no, I didn’t have Florida (wait for it, below) play the after party.
When you sell your company, real life is the after party, and life is good.
"Have you bought a Tesla yet?"
F*** no. Not because I don’t like Teslas, but because too many damn people ask me this question.
I didn’t become an entrepreneur to become predictable. I did it to buck the trend, prove people wrong, fight interesting fights and surround myself with challenge.
The question is always asked with the word “yet” at the end. Like people just know I’m going to buy one.
The fact that I don’t own one now doesn’t mean anything to them. They know better.
Apparently if you’re a nerd, check, and you sell your company for a bunch of money, check, you are expected to buy a Tesla. Whoops. Sorry everyone, I realize I have let you down.
But I did buy a car, er, a truck.
I went back to my roots growing up in the mountains of North Carolina and bought a Jeep Wrangler. I added a three-inch lift kit and 35-inch mud slinging tires and I’ve had a s***-eating grin on my face ever since.
I load it up with mountain bikes and camping gear and head for the mountains any chance I can get. It’s divine. There is simply nothing better.
Truth be told, when you sell your company, your first decision is actually which financial advisor to hire. Admittedly I did originally tell mine to hold $200,000 for the purchase of a vehicle.
Two years later when I still hadn’t done it—and he got tired of asking me about it—I told him to just throw it back in the portfolio and invest it.
Screw the stock market. Maybe I should have bought the Tesla. At least I’d have some metal and a big battery I could sell now.
But I wasn’t ready to be that guy in the token overpriced sports car parked beside a Prius at one of the many Chapel Hill Starbucks. I was 30 years old for God’s sake.
I’ve got plenty of time to be old when I get, uh, old.
If I ever buy a Tesla, I promise you the NC license plate, if available, will read EXPECTED.
What do you think of Silicon Valley?
No, not the place—who cares about that? I mean, the TV series.
What character do you think you are? Can you believe he turned down the $10 million buyout offer?
Okay, before I have a panic attack… is everything okay? Are we talking about work or a TV show?
Don’t hit me with that crap when I’m trying to relax.
Yes, it’s a TV show about startups, and admittedly I talk about startups way too much as it is. So I realize it’s an easy topic to propose in conversation with me.
But, honestly, if I want to freak out about startup decisions, I’ve got plenty of scars I can drum up on demand.
Buyout offer heartbreak? Got almost 10 of those. Quirky interpersonal relationships. I can think of nothing else. Acting the part then furiously Googling all the words you didn’t understand in the investment banking meeting an hour later? Been there.
I appreciate the show takes startup culture mainstream but you have to realize all the idiosyncrasies and pain portrayed on the show are real. All entrepreneurs are living this wild ride.
Tune up, plug in, enjoy the view from your window seat, but don’t expect my sympathy when you slam your iPad screen and get to walk away. This is real life people. Be gentle.
That said, I had 17 hours to kill in the air on my way to Europe and back last week so it became time. I loaded up the entire first season and giggled and cried my way over the Atlantic Ocean, twice.
It’s a great show. But if you really like it, just start a startup.
So, that’s it. Most of the founders of the next breed of big startup hits here in NC are friends or acquaintances of mine, or I’m one of their fanboys at a minimum.
Now you all know what you’re in for. Don’t say I didn’t warn you.