F|R: The 9 Signs of a One-hit Wonder

Many entrepreneurs fear being a flash-in-the-pan success — achieving an exit once, but never again. (Some might call this being lucky rather than good.) But while the allure of success inspires us to do great things, achieving it can have an ugly aftereffect: complacency. Vigilance, my friends, is the only path to serial-founder bliss. Here, in descending order, I offer nine leading indicators that you’re headed for one-hit wonderdom.

9. You went and got all tricked out.
I mean with your next business, not your fashion sense. But remember how you got your first hit — with a kindergarten-level UI that any neophyte could comprehend. Sure your friends called you Forrest Gump and sneered that you were lucky; that’s their problem. Trying to prove to your friends that you’re really, truly smart isn’t good business. Delivering a simple, usable concept that solves problems and makes money is.

8. VC meetings go a little too well.
During your first run, half the VCs shooed you out of their offices, while the other half spent as much time looking at their BlackBerrys as they did you during your presentation. But now VCs call you and when you do take a meeting, all you hear is praise. No matter that a VC doesn’t understand your pitch, you get a term sheet anyway. (And who can fault you for co-investing with OATV-Sequoia-KPCB?)

7. You have hobbies that require special outfits.
Your hobby used to be promoting your company six days a week. Now when anyone asks you what’s new, you talk toys, not shop. You’re proud that you “only paid” $1.4 million for that catamaran parked on Catalina Island, but there are hidden costs — like the time you spent shopping for it, and the clothes you doff while sitting on it (you can’t sail it, remember?). You know what they say about big boats: Every extra foot of length equates to another diminishing asset — your shareholders’ value.

6. Every weekend is a 3-day affair.
Your workweek used to be six days. Now you work four days because Mondays you have jetlag and Thursday nights you host pool parties. Cut your three-day weekends down to one per month.

5. You have an entirely new “crew.”
When your star was just starting to rise, hanging with other nerd founders and bloggers was your idea of a good time. Now you have a contact list filled with party hangers-on. Nothing says one-hit wonder like a circle of friends you don’t really know.

4. You sign the dinner bill without reading it.
At your first hit company you never even expensed airport parking, so concerned were you with impressing your investors by coming in under budget. Today you have a private car service and don’t even see the dinner bill. If you’re eating at Evvia’s table 50 twice a week, you’re hurtling toward one-hit wonderdom.

3. You confuse junkets with networking opportunities.
Experienced people know the difference between an authentic business-building event and just another excuse for a corporate-sponsored party. I can say this, because I go every year: The Super Bowl is not a networking event. Figure out which events are which. And if you can’t seem to do that, go find a cave where you can build your next arc reactor.

2. You’ve uttered any three of the following five lies:
That wasn’t my first startup.
Well, money’s not that important to me.
I have no regrets selling to [Google, Microsoft, Yahoo, IDG or that PE firm].
I would never consider buying it back.
I’m going into venture capital to share my experience.

And the No. 1 indicator you’re at risk of becoming a one-hit wonder…

1. You’ve lost your stomach for mistakes.
Business in Startupville is defined by ebbs and flows — one step forward, two steps back. Now you’re so concerned with preserving your new success, you’ve lost the ability to tolerate the ebb of a negative blog post, a business model rehash, or the need to issue pink slips. Business success is the result of being able to adapt to and tolerate temporary failures.

Larry Chiang is the founder of duck9.com, which helps college students improve their credit ratings. He is a frequent contributor to Found|READ.