• by William Mougayar
    Venture advisor, 4x entrepreneur, marketer & strategist. I live in Toronto, curate a lot, blog a bit, and help startups.

Revisiting Mentorship: Diversify your Mentors as you Grow your Startup

mentorshipIt’s a generally accepted common practice that startups benefit from mentoring, especially while in their early stages of development. There is no shortage of mentors in startup communities and mentor networks among accelerators who pride themselves on such value-added, and it is a good thing during these startup stages.

In this post, I’d like to first segment the types of potential mentors, then suggest evolutionary mentorship sources for more mature startups.

So where do mentors come from?

  • Peer entrepreneurs
  • Role models
  • Corporate employees
  • VCs
  • Angel investors
  • Board members
  • Advisors
  • Accelerators program managers
  • Expert consultants
  • Pundits


Each one of these segments has their strengths and weaknesses. The strengths are typically obvious and they depend on how much the mentors know about your particular situations, and their own experience in the mentoring process. [The Techstars Mentor Manifesto is a good refresher.]

But their weaknesses are more invisible, and they are the kinds of things that a startup CEO needs to either discount, or be aware of.

Peer entrepreneurs may not have experienced what you are going through.

Role models sometimes have a better image than substance.

Corporate employees may be unrealistic about startup realities.

VCs will most often see things according to their own thesis and agendas, and if you are getting mentored by VCs who have invested in you, they can be too emotionally attached, and more forgiving.

Not all angel investors have had broad operational experience.

Sometimes you end-up with the wrong Board member, and that creates tension when listening to them.

The advisors you pick initially may be useful then, but if they don’t evolve with you, their value may diminish over time.

Program managers in accelerators are typically junior and don’t have depth or breadth.

Expert consultants will tilt on advising you more than mentor you.

Pundits may be more visionary, and sometimes not so relevant to your immediate priorities.

This diversity in mentorship choices is a good thing for early stage startups, but as a startup matures, I suggest they should re-think who their mentors are.

As a startup grows and finds product/market fit, there is less and less ambiguity about their business. With less ambiguity,  you need less ambiguous mentoring and support. The mad, fast and furious moments of early stages gradually becomes less mad, less furious and more measured and structured, as the startup grows. Therefore, the type of mentoring required becomes more prescriptive and less suggestive because several situations and issues will have more clarity to them.

I recently advised a startup to consider vesting an advisor package to 1-2 years, not 4 years, because you can’t really predict the value of the same advisor over 4 years. If they are great, renew them yearly.

Take a page from Brian Chesky who expanded his mentorship horizons, and went really high by picking some legendary role models and asked them for specific mentorship and learning advice. It is a bold move, and I’m not suggesting that any startup CEO could have easy access to these types of people, but the point is to aim high and try to go out-of-the-box when it comes to mentoring support.

Screen Shot 2015-08-25 at 6.30.07 PMSource: The Education of Airbnb’s Brian Chesky (Fortune).

What’s so interesting about getting advice from successful CEOs of bigger corporations or larger startups?
They have honed in their execution capabilities, and know well how to manage people and objectives. And they know how to be strategic while at the same being operational, so you can learn from them how they manage that balance. Each seasoned CEO has a few unique tricks and rituals, and maybe one them will click with your needs or personality. I wrote a blog post titled Managing a Startup Isn’t Different – Don’t Re-invent Everything, because I saw first-time startup CEOs trying to reinvent management in their own ways. My suggestion is to go back to first principles of management, and read a couple of old-fashioned books on being a first time CEO, then discount what doesn’t apply, but take what applies. But don’t discount the basic principles of managing people. Or read Matt Blumberg’s Startup CEO book.

So, my advice is to think about re-evaluating your mentors, role models and advisors at every successive funding round or stage of growth that you reach.

Your needs are changing, so why not change who you are being surrounding with and influenced by?