Riding Solo or Better Together?

What Everyone Says

Choosing a co-founder is like getting married. You find someone who shares the same views and ideals as you. He or she is privy to all of your private information and your inner workings and secrets. You celebrate your union and both profit from any successes. And separating could be a messy and expensive ordeal.

Conventional wisdom says that startups should have two or three founders.

People tend to have very strong opinions on the issue, although I doubt they have definitive evidence or proof to back up their opinions. Some investors won’t even invest in single founders at all — so understandably for entrepreneurs this is a big issue.

Most “business-focused” single founders are told right from the get go that they need to find a technical co-founder. But lately, firsthand experience in the field has got me challenging that conventional axiom.

Why Is It Better Together?

For me, at least what I take away from it all, it’s about the camaraderie and partnership that emerges when two (or more) people decide to go on such an incredible journey together. And when the going gets tough (and it always does), it’s nice to have someone sitting beside you in the dark who knows exactly what you feel. [Isn’t this reading as a marriage?]

There’s a comfort in that. Multiple founders — if the relationship is good — means an automatic and very close support group. Of course, founders don’t always get along, and a lot of startups fail because of founder disagreements, so the support groups/camaraderie/partnership comes with a big asterisk or contingency.

A good partnership between co-founders usually means a good division of labor and thing can be a little less overwhelming for each individual. That’s a good thing. Each founder has his or her own thing to focus on, with his or her own laundry list of to-dos, and ideally (key word — ideally) each founder has complete confidence in the other one to deliver. But that cofounder relationship takes constant work to maintain, and it can go sour surprisingly quick.

Why Is It Better Alone?

A single founder has an advantage when it comes to ego clashes. Humans nurture big egos by nature — especially in a field dominated by those spewing ideas for the next big thing with each passing moment — and these egos can grow bigger as the person ‘grows up.’

Sharing from his experience, Bowei Gai, a serial entrepreneur who sold his company last to LinkedIn shared, “Two member founding teams encounter an impasse many a times when nobody is willing to budge from their stand. There hardly seems a way out.”

As entrepreneurial communities grow all over the world, it’s becoming a lot easier to find other people with similar experiences. A single founder doesn’t have to sit in a room by his or herself and despair — he or she can go out for beers with other founders in equally difficult situations and commiserate. That’s a huge thing. I would encourage more founders to do that and not stay locked up in a dark room alone. Sometimes foudners just need to vent, but sometimes they can get constructive advice and input too.

Single founders have another advantage in that they don’t need to build consensus with other founders. They don’t need to work on the delicate co-founder relationship, and can just plow ahead. They may need to bring in additional senior talent, often on the technical side (which has its own challenges), but they’re 100% in control. There’s just something simpler about it overall.

So, Who Wins?

I don’t see a definitive answer.

People have their opinions based on their own experience. I’ve seen good and bad co-founders come and go. It all comes down to being situationally dependent. Decide if you’d like to be fully in control of a situation, or if you want someone to jump off that cliff with you.

Just make sure of one thing — SIGN A PRENUP.