Co-CEO

I love starting companies.

I don't regard anything quite as professionally rewarding as setting foot on that journey with an old laptop, a head full of ideas, some wits about me, and at least a bit of anecdotal evidence that this could be "big". It's an absolute blast! And as in most journeys (other than spiritual quests - onesomes :) it is good to have someone along for the ride equally up to the challenges ahead, unbridled in their enthusiasm, and complementary in skill.

Because as much as I love the experience, starting a company is hard as hell. There is a dogged uncertainty kept at bay with the constant push towards value. There are pressures and deadlines: pressure to complete the product, pressure to sell the product even before it has fully materialized as living proof that value exists (see, they bought it). Adapt, adapt, adapt. There are pressures exerted by employees past, present, and future, that most human aspect of the business dictated by individual needs, struggles, and desires. There are pressures from investors to move the ball forward to make it to the next stage of the game. There are networking functions to attend, constant meetings with venture capitalists, investment bankers, and other interested parties. There are sales calls, vendor relationships to manage, and a frenetic challenge to be everywhere at once.

In my last three companies I have been the Chief Technology Officer and have had the good fortune to have started the last two with my good friend and CEO Don Springer. Don and I have always co-managed the company and I was reminded of the healthy aspects of this model by the founders of MadKast who told me they were co-managing their company. We've always operated in this model and in fact debated in the first few weeks before starting Collective Intellect which one of us would hold the CEO title. The debate went something like this:

Don: Tim why don't you be CEO this time around
Tim: I don't think you're getting off the hook that easily. No way. You should be CEO.

My advice is to find someone you have professional and emotional balance with. I deeply understand the technology. Don can sell and has an innate ability to put together multi-page cap tables with no circular references. I am a big picture guy who pursues ideas, and Don is more detail oriented. Don will put together a presentation with 40 slides where I will use 5. We can finish each other's sentences, drink our scotch, have fun, vehemently argue a point without offending the other, and still get the presentation done in time. The bottom line is that we hold a lot of mutual respect for each other. Enough to actually listen.

Being able to lean on someone else to help make the hard decisions and steward the company is priceless in bad times and incredibly rewarding in good times.