A Founder’s leadership lesson: when to get the @#$% outta the way

A Founder’s leadership lesson: when to get the @#$% outta the way

Ten years, I co-founded Kayak for a Cause with Scott Carlin and we grew it to an charity organization of hundreds of participants and thousands of donors.

We did a lot of good. We had some help as well.

But the critical lesson I learned this year is knowing when and how a Founder should evolve his/her role. Even though this was a not-for-profit, the lessons apply equally for start-ups (which are often less-than-not-for-profit, anyways).

Founders roles fall generally into three buckets: starters, runners and defenders of the legacy. As I learned in KFAC and at Mojiva, starters have the hunch, put a stick in the ground and by sheer force of willpower rally others around them. It’s bold. It’s inspiring. It doesn’t last all that long.

Because as the data rolls in, a starter has to evolve into a runner and runners live on data. Market data. Customer data. Stakeholder feedback. Runners use the momentum from the starter and the data from the users to keep the party going. Hunches don’t play well. Consensus rules, or at least has a greater influence.  Interestingly, my training in YEO (an entrepreneur’s organization, now called EO) helped a lot in running a charity: here were the skills I used most often:

  • Setting roles and goals: Founder and Runners both work from a set of goals, and the successful one assign roles and responsibility toward each objective. Sharing allows the rest of the team to feel part of the mission.
  • Being open to input on making it better, but firm in direction on what that means: This was a big one for KFAC. We had a logistical challenges like a modern-day Normandy invasion with wind, weather, tide, transport, launch, provisions, safety and yes entertainment all tied into one timeline. Everyone had a better idea. Precious few could be accomplished year to year, but we made a point of giving everyone a voice in making it better. Then we decided our vital factors and were firm in focussing on those few things with major impact.
  • Giving authority and resources to accomplish goals: People love to be able to make an impact and see their results. Once vital factors are in place, the team has to have the authority and the resources to accomplish their goals. Leaders look for ways to get those to the team, and it doesn’t always mean money. Sometimes it is just shortcuts or better efficiencies.
  • Making yourself obsolete by cross training your stars: this is where we truly excelled. KFAC became bigger than any one person, and every person that made it to the Committee was told to recruit their replacement from day one and prepare to make yourself obsolete. The result was a group of leaders that could jump into multiple roles. We have had our share of people move on (it’s a charity, there are no stay-bonuses!) but we have always had a backup.

This phase is where so many Founders fall down, as the skills to be a starter are vastly different from being a runner. Very few possess both talents. Very many try to hang on too long (and as major shareholders/stakeholders are able to do so, to their own detriment).

But for those that make the jump and attract another runner to their organization, a third transition awaits: leader and defender of the legacy.

While you may still be the largest shareholder, you have empowered someone else to add value to the enterprise. While your background and knowledge can be very valuable to the new team, your meddling can be equally obstructive. Knowing when is when, and passing the torch before it’s too late is another one of those Founder hunches that Founders often don’t listen to. Here’s what I learned about that phase:

  • Provide a full transition plan: no matter what you think everyone knows, you have experienced more. Passing along facts without sharing your prejudices will allow the new team a great roadmap to consult when they need it. Do it in writing.
  • Making clear the objectives (if you remain a stakeholder/owner): just because you are passing ht e torch doesn’t mean you are selling out. Make clear your legacy and what the DNA of the business means to you. It should be respected.
  • Leaving the team to do what they do best: step away from the controls. You chose them because you trust them. Demonstrate that.
  • Supporting where you can: staying in tune and in touch will allow you to point out shortcuts, dead ends and old tricks from the master. Nothing wrong with that if done in a with respect for the new team.

I have been through this transition in both the charity and the entrepreneur world, and what surprised me most were not the differences but the similarities in leadership skills. EO taught me the things that allowed me to grow KFAC, and much of the leadership team has entrepreneurial backgrounds (surprise!) . But KFAC definitely taught me the things that have allowed me to grow start-ups.

Having a great team behind you certainly helps. BTW, you can join KFAC XII here.




I mentor two kids and several entrepreneurs. Similarities are coincidental.