Mistakes you can make in finding a technical co-founder, or your CTO

Finding the CTO for your company is really, really hard.

I have had to do it every single time in starting 5 companies. Some of them got really big like Virgin Mobile USA or moderately big like Peek (so far) and some just got nowhere.

These guys make lots of money in ‘non-startup’ jobs and as engineering personalities are often less adventurous. And since it’s *your* idea they are often less passionate/smitten by the obvious rightness of your amazing invention.

So it’s hard.

Here is a mistake many people make, and I have made many times: hire somebody from the industry you are attempting to attack.

Your dream candidate when making this mistake is 10-20 years of experience in the industry. A director or VP with experience managing millions of budget and dozens of staff. This person has delivered big projects over time. They have poise and can talk business with you like a real veteran. They think strategically. On paper they have managed all the technologies you need, know how business is done inside the beast you plan to slay, and on top of it can explain stuff in plain english.

I have hired such people many times already, and always regretted it. You hire a gray haired CTO with his entire team or some top lieutenants, the board loves it, the business partners are like “wow”, and you feel safe.


These guys in every case have been really hard to deal with. Their evident success inside big organizations has come from skills you don’t want or need

  • talk english = great at bullshitting ignorant business folks
  • management experience = expertise at budgets and project plans
  • loyalty = protecting their people from ‘business guy’ pressure
  • experience/sobriety/Five 9s = clueless about new technologies
  • senior = expensive
  • accomplished = risk averse

Thought experiment: would you hire the marketing guy at this person’s company to replace YOU? Of course not! That guy is a bozo! Commutes from an expensive house in Connecticut, plays golf, reads Fast Company for ideas, has a Twitter account with 4 posts… Well your amazing tech hire is probably the tech version of that guy. Watch out.