A couple of times each month I see questions pop up in different forums about the ideal founding team size for new ventures.

The answers are typically framed from the point of view of a venture capital or angel investor who is (correctly) concerned about de-risking the business. Often times this will be described as an appropriate mix of quality technical and business development skillsets matched by the founders’ ability to balance workload and deliver on a hiring plan to match growth ambitions.

There are those that say ventures can have a single founder (that was me once) and the same people, including Fred Wilson at Union Square Ventures, note that it can be done but it’s a lonely existence. Experience tells me that the optimal number of founders in a new venture is three but it turns out that this is (at best) a second order consideration. The primary consideration is who your co-founders should be.

Your future co-founders must be on your work bucket list.

That’s the bottom line.

My work bucket list is a very short list of (at the moment) eight people who I would love to work with before it’s too late. Whether through an existing relationship or via their own admission (because I only know half of my bucket list personally), each person:

  • Is insanely curious
  • Uses empathy and compassion to lead
  • Is at the top of their game
  • Has a great sense of humour
  • Loves learning

Gautam and Opher were on my work bucket list when I formed AirShr because they each have these qualities in spades.

But here’s the thing, the true awesomeness of these guys has really only been revealed when the going has gotten tough like when pressure mounts because raising capital is taking longer than expected or life is a bit overwhelming because you haven’t slept properly in two years.

This all might seem obvious but it seems to me that when founders are out seeking partners they tend to lead with a function-first approach (i.e. I need a chief technology officer or a VP business development). In doing so their first step is to look at a candidate’s ‘on-paper’ track record and give little consideration to qualities that really matter, particularly when the going gets tough.

If you haven’t done this before, perhaps give some thought to your work bucket list and why people would earn the right to be on your list.

I don’t know when and I don’t know how but I also look forward to one day working with Jeff Weiner and Emily Ma.

Now you know half of my work bucket list. Who’s on yours?