Coach 2 Player (C2P)

I have a saying, “the lifespan of a mentor’s advice is the same as milk.” In a world that is moving as fast as as ours is, what worked last year is highly unlikely to work this one. It is only those who constantly seek to have new experiences who can have lasting value to those that they advise.

Time on the Bench

I have been fortunate enough to hang around the startup world for two(?) bubbles and close to two decades.  I have been the person writing checks, helping others get checks and working with founders fix problems that checks don’t.  I have spent countless hours on in coffee shops, bars, conference rooms and airplanes talking to founders and offering whatever perspective, experience and advice that I could.  I have no illusions about the wisdom that I “dropped”.  All I can hope is that it was a net positive.


For the last 14 months I have gotten myself back into the ring.  Yes, I know I shifted my sports metaphor, but I really don’t care and if you think that growing a company is not similar to getting punched in the face then you haven’t done it. As CEO for VL Group I have become the very leader that I have been advising; passionate, idealistic, visionary, action-focused…and stupid.  Really.

One of my most recommended authors is Ryan Holiday.  His two books, The Obstacle is the Way and The Ego is the Enemy, are now on my annual re-read list.  In Obstacle he outlines three core pillars; perspective, action and will. As mentors we often focus on the steps that our mentees need to take (action) or how they should be prepared for a marathon not a sprint (will).  Sometimes we forget that our very perspective is different from theirs.  This is a benefit but also a curse. It is easy to suggest cutting features from a MVP when you hold no emotional attachment to them. It is fine to suggest a team change when you haven’t spent weekends working with someone to make the company come to life.

Spoiled Milk

As mentors we should really all work to remember the perspective of the founder.  Like an Instagram filer it is is easy to remember our times as founders and business leaders in a more beautiful way.  Building a business isn’t easy and it isn’t pretty.  Remember firing a friend, being embarrassed in your community or having your mortgage company call?  Now talk to a founder about why they didn’t have time to build a pitch deck or build a financial model.

I am fortunate to have known the pool which I chose to jump into the deep end of.  Many don’t. Being a player (not in the rap “you go playa” sense, just in the continuing sports metaphor sense) has reminded me how I can be a better coach.  Perspective, the founder’s, can almost always be a better place to start than from yours.



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