venture capital

Thoughts on the Various Types of Entrepreneurial Mentorship


This is part of my Series on Mentorship.

I’ve been doing a lot of thinking about mentorship and mentorship programs of late.  In that I provide a fair amount of mentoring to entrepreneurs in official and unofficial capacities- I’m always thinking about what models and techniques work best for fledgling entrepreneurs and their startups. I’ll be getting into my latest thoughts on this in subsequent posts.

In the meantime, however, it occurred to me that it’s actually very important to contextualize any discussion you’re having on the subject of mentorship if your goal is to actually make any kind of progress. That's because mentorship can mean a whole host of related but significantly different activities. I’ve therefore taken a crack at classifying the various types of mentorship that I’ve seen over the years, (in the realm of entrepreneurship at least), below.

Kindly add any others to the comments if I’ve missed some!

  • Informal and unpaid entrepreneurial mentorship provided by experienced individual entrepreneurs/executives to less experienced (often first-time) entrepreneurs. These relationships often form in an ad hoc way or through a specific introduction. (Think Freddie Laker and Richard Branson).
  • More formal but unpaid entrepreneurial mentorship provided by experienced individual entrepreneurs/executives to other experienced entrepreneurs/executives on an ongoing basis. In such trusted arrangements between peers, the CEO receiving mentorship is able to “let down his or her guard” so to speak and receive the benefit of the mentor’s domain expertise.  (Think Bill Campbell's “long strolls” in Palo Alto with Steve Jobs).
  • Informal on-the-job mentorship imparted from more seasoned entrepreneur to less experienced one. Can occur within a company walls or among people in the same industry, trade or profession. Can obviously occur within legitmate or criminal enterprise. (For afficionados of The Wire think Proposition Joe, pictured above, and Marlo- who ended up turning on him. For the more refined audience, think Socrates and Plato.)
  • Informal, unpaid group mentorship sessions organized by entrepreneurs for fellow entrepreneurs in cities throughout the country. (Think TIE or Young CEO-type groups across the country).
  • Formal, paid group mentorship sessions facilitated by for-profit organizations such as the Corporate Executive Board and other similar organizations for executives and entrepreneurs alike.
  • Fellowship Programs such as the Society of Kauffman Fellows are a type of entrepreneurial mentorship organization. Kauffman's members are carefully chosen for their talents and participate in a 24-month long apprenticeship within venture capital. Thereafter they become part of a network that is constantly in contact with each other and giving back.
  • Accelerator/Mentorship Programs such as YCombinator and TechStars that take a portion of the company’s equity in exchange for a small amount of cash as well as a pre-defined period of mentorship and acceleration. Such programs have a rigorous application process and only choose a pre-defined number of promising startups to assist. Also, these programs are limited to consumer-internet/digital media type companies.
  • Groups like LaunchPad L.A. which though requiring an application, do not take equity and simply mentor companies they have accepted into the program. The overriding mission here is to strengthen the local startup community in Los Angeles by helping the most promising local entrepreneurs succeed.
  • University-based mentorship programs that do not require any kind of application apart from an affiliation with the university. There are thousands of such programs at schools around the country and they come with all sorts of nuances. Many are operated by business schools, engineering schools and other designated entities on campus. The common thread is that these services are most often provided as a free service for students, post-docs, faculty and others associated with the university who wish to try something entrepreneurial or to launch a new venture. (Think everything from the bespoke entrepreneur office hours program we're holding at Columbia Entrepreneurship, all the way to the venerable and robust MIT Venture Mentors program which has over 100 mentors).
  • SBDC's and other municipal or city-sponsored programs designed to provide assistance to people running or starting small businesses in local communities around the country.

My next post on mentorship will address what I believe to be the relative strengths and weaknesses of these sorts of mentorship activities.

For the next post in this Series, click here

Lessons from an Old Master


This is part of my Series on Mentorship.

On a frigid winter's night about seven years ago, I was challenged to a chess match by an ancient looking man with a snow white beard. We were in an old Baltic tavern that suffered from poor heating and as you can see by the photo that memorializes our encounter above, he wore his scarf, coat and hat throughout and I barely managed with a heavy sweater and scarf.

**Full disclosure: to further combat the chill, we both employed the aid of spirits- initially mild in nature and then escalating in subsequent games to a cranberry-infused vodka of his choosing.

The man spoke very little English and when he approached, merely gestured to me using the universal sign language for "play a game"? His expression was open but grave at the same time. I had been analyzing some positions and playing speed chess with some friends until that point. Of course out of respect for his age I agreed immediately, but perhaps you can see the traces of a faint smirk or bemused expression on my face as the game began. This was of course because I have been a decent tournament player throughout my life that began in earnest during my high school years when my team was twice the national champion. Over the ensuing years, I had defeated my share of masters both here and abroad. As a consequence, until this particular evening, when challenged in casual games of this nature in pubs, at parties and the like, I always approached such encounters with a fair amount of bemused indulgence, shall we say. Need I tell you by now that this particular evening was the last time I ever did so again?

In our first game, playing perhaps to the 19th century atmosphere of the place, I trotted out an old-fashioned Vienna Game which transposed into a King's Gambit. My friends, who by now no doubt sensed something was in the air began to take photos. After a half dozen moves I already realized that the man was no novice. As the middlegame arrived I could see (to my shock!) that he was in fact rather strong. As the game wore on he proceeded to beat back my attack rather forcefully- and I was only able to draw the game with a perpetual check, otherwise the advantage was fully to him. We shook hands and I looked closely at him for the first time. His ancient and dark eyes were full of light and mirth- there was no trace of mockery, just mischief- he knew he had fully stunned me. He'd been young once- and hadn't forgotten it just yet. He smiled and gestured for another. My friends were similarly stunned. The old man called out for more drinks in his native tongue.

We played a few more games. We were evenly matched- a win to him, a win to me- I forget. The vodka had arrived too and it suited him. In the last game he hit some old stride from a half-century long past- and slowly dismantled my position with a precision and inevitability that shocked us all. I eventually resigned. We all shook the old Master's hand and he gave us that great mischievous smile of his, bowed slightly and shuffled off into the night. Of course I never saw him again. 

Last night my wife and I watched a 13 year old girl shock the judges and audience on the X Factor with a stunning, soulful rendition of "Feeling Good". We looked at each other and smiled- it was amazing.

Every once in a while I meet entrepreneurs that absolutely shock me. It happened the other day yet again. I met with two massively talented young women who had ended up partnering by sheer happenstance when one complimented the other on her shoes about six months ago.  They had got to talking and well, here they were- a stunning and amazing entrepreneurial team. In the first minutes that I met them they were two incredibly humble young people and yet in the ensuing minutes during which they described what they had created- they literally transformed before my eyes. 

I thank that old Master for teaching me this great lesson. My eyes have never been the same. I wish it for your eyes, too.

For the next post in this Series on Mentorship click here