I once admitted publicly that I have sex with my co-founder, Kass.
Since then, I can confirm that we have had more sex. And we have sold our business. So I thought it was a good time as any to go back and revisit the cofounder relationship.
Choosing a worthy cofounder is one of the hardest decisions you will ever make in business. Like in marriage, making sure that you go into it for the right reasons is crucial.
Happy cofounders make happy companies, just like happy parents make happy kids.
I founded Buddy Media, and my other companies, with Kass, my wife, business partner and best friend.
Early on, many investors told us they didn't fund husband-wife teams. These meetings were very short as we had no plans to change our relationship status to accommodate their arbitrary rules.
We’re not in the market for funding, as we are happily employed by Salesforce. But I imagine the reception will be quite different this time around.
While I can't find any official data showing aggregate results of businesses with married, or romantically-involved, co-founders, I can point to many well-known babies of these unions, including Cisco, comScore, Marvell, and VMWare. These companies alone are worth more than $125 billion!
Before you jump on the bandwagon and call us weird, let me point out that when you start a business with someone, you marry that person.
She’s the first person you talk to in the morning. She's the last person you talk to at night. She’s the shoulder you cry on as you worry about running out of money. She's your roommate as you share hotel rooms, or your aunt's living room pullout, in a bold attempt to preserve money. You're inseparable.
Paul Graham of Y Combinator has written that having a co-founder is “like we're married, but we're not f***ing.”
Instead of signing a marriage certificate presented by a rabbi, priest, or other official, cofounders sign another binding agreement, the incorporation documents. Both legal documents bind them together for better or worse, in corporate sickness, and in health.
Working with my wife is easy, far easier, I imagine, than working with someone I barely know. Our skill sets are perfect complements.
I focus on the ideas, sales, raising money, and the strategic direction of the company. Kass handles all operations, finance, HR, marketing. She's the Tom to my Jerry, the Beauty to my Beast.
Before launching a business with someone, you should ask the following questions. Try to get all the emotion out of the room (I know, it’s hard, as all you see are the great times ahead). Be honest with yourself. Brutally honest, as you answer each of the questions.
Does she complete you?
Not to go all Jerry Maguire on you … but you should start a company with someone whose strengths are your weaknesses, and whose weaknesses are your strengths. Divide and conquer together.
If you know how to sell, find a programmer. If you are a techie, find someone who understands business. Are you creative? Find a logical thinker who feels at home in a world of spreadsheets. Are you an introvert? Take improv comedy lessons—and find a networker.
Do you trust him? Would you leave your baby with him?
Intelligence is relative. How hard you work will change over time. Trust is constant. Cofounders who trust people implicitly will stick together. I’ve seen cofounders fall out of trust with each other. Each time, the company suffers, as does the long-term relationship between the cofounders.
Is she in it for the long haul or a quick hit?
If you want to have fun, get a date. If you want to get rich quick, buy a lottery ticket. If want to really live and experience the highs and lows of entrepreneurship, then start a company. And make sure your cofounder feels the same.
It’s going to take twice as long to accomplish all that you want to do. And take twice as much money. So make sure the person you are starting the company with has the same time horizon as you.
It’s easy to get drunk on the concept of starting a company. The money, excitement and freedom sound awesome at the beginning. But it’s just as easy to get beaten down by the world.
At the beginning, the possibilities are endless. When you’re running out of money and need to figure out how to make the next payroll, the possibilities don’t seem so endless. Actually, the end seems disastrously close.
It’s a dark feeling I hope you never have to experience. But if you do, you want a cofounder who is in it until you reach the goal line, or death’s doorstep.
Does he thrive on chaos?
The only constant in start-up land is chaos. You want a cofounder who can work with you to navigate the crap sandwiches served up fresh daily.
It's not how well you get along with your cofounder. It's how well you get along when the bottom falls out. Getting through the good times is easy. Weathering the bad times is not. And remember, there's no makeup sex with your co-founder (unless you're married or dating!)
Solid relationships are built on trust, clear communication and compassion over an extended period of time. The same is true of marriages.
If you can raise three kids with someone, and still make time for date nights and enjoy each other's company, chances are you can start a company with that person.
So don’t be afraid to start your business with someone you truly love. I haven't tried the alternative. But starting a business with someone you don't like makes no sense at all. Life is just too short.
If you like what you just read, please follow me on LinkedIn here. There's more to come.
(PHOTO: Flickr)