Caveat Mentor: Armchair vs. Real-World Advisors

(click on the photo just above to play the video)

This is part of my Series on Mentorship.

In previous posts I have touched on the importance of first-time entrepreneurs having an experienced mentor at their side.  I'd like to elaborate a bit on what qualities I believe this person should and should not have. Before reading any further though, do watch this hilarious video snippet above from the classic movie Back to School and you'll know what I'm talking about.

Your Mentor should be:

  • An experienced serial entrepreneur with a big network he/she can reach out to on your behalf when the time is right, ie. prospects, customers, partners, investors, potential hires
  • A person who is trustworthy, loyal, respected and well-liked in the entrepreneurial community
  • Someone you greatly respect who is ready to roll-up his/her sleeves and really help you

Your Mentor should NOT be:

  • Someone who has never been an entrepreneur but likes to tell people what to do
  • A bureaucrat, a service provider to you or a broker-dealer
  • A person with no relevant expertise or real-world experience with start-ups
  • A substitute for hard work and for getting your product, first customers and partners in place

For the next post in this Series, click here

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

Lessons from a Young Master

Sorcerers apprentice
Sorcerers apprentice

This is part of my Series on Mentorship.

I recently wrote about some enduring lessons I was privileged to learn from that great Old Master I told you about. I'm happy to say that of late I've been receiving some additional lessons, this time from some younger Masters.

A few weeks ago I started teaching our young son the game of chess. He is just a little over 2 years old but he is already learning what to call each piece, how to set them up on the board and now every night after dinner he says, "Daddy let's play chess" and we set up the board together, play a move or two and then he typically is ready to move on to another game or toy. I don't overdo it with him, but I can already see the enthusiasm he is developing for the idea and camaraderie of the game. Seeing him encounter chess with his fresh eyes has been something of a revelation for me. It has made me understand how precious the opportunity to teach something special to another human being can be. I've also come to understand just how much the teacher has to both remember and un-learn all at once. You have to constantly ask yourself questions like "what is he seeing that I no longer can", "what should I have been taught early on that took me years to realize on my own?". Imagination and creativity are paramount. You hope that in its purest form teaching is a gift to both the student and teacher. Each learns a great deal from the other and from the process as well.

I'm also teaching at Columbia Business School this year where I was appointed as an adjunct Professor of Entrepreneurship. I teach the Launching New Ventures class and we have 70 students with us, some of whom are dead-set on launching companies and becoming entrepreneurs. It's a huge challenge and you want to do your very best for them- not just to inspire them but to give them every practical advantage they can possibly have. Again I believe understanding how they see the landscape in front of them is paramount. You must understand how they think and the prism through which they're evaluating the world. A lot of this requires the teacher to unlearn and remember at the some time. One student was shocked when I told him how to approach a certain meeting. He said "I'm allowed to speak that way?" It was a powerful moment where he realized for the first time that there were no limits on him. I wish someone had told me that when I was in school twenty-five years ago!

As a teacher you feel an awesome responsibility to do right by each and every student. Amidst all of this, you also gradually realize not just what a privilege it is to guide them on their journey- but just how much the teacher is learning from all of his students along the way. It's quite stunning.

So here's to the young masters- to their success both in business and in life- and to all that they in turn teach us about ourselves along the way.

For the next post in this Series on Mentorship, click here

Death of a Mentor: Reflections

This is part of my ongoing Series on Mentorship.

Yesterday was Thanksgiving and I was thinking about the many things for which I am thankful. I won't list them here as they are many. But my mind kept returning to memories of a great mentor of mine who passed away earlier this year and I was filled with both gratitude and profound sadness. The intervening months since his passing have really done nothing to ease my grief and I'm sure it's much the same with his family members as well as the legion of loyal friends he made during a truly remarkable life. 

Upon reflection I believe this is because he was a person with an enormous capacity for friendship along with an immense store of wisdom and life experience that he was always happy to draw upon for the benefit his friends. In our increasingly fast-paced and surface-oriented society, he struck many of us as a walking anachronism- always organizing gatherings of friends from the many remarkable chapters of his life and often presiding over celebrations or roasts or fireside conversations that typically lasted late into the night. He was a world-class raconteur, a master of roasts and toasts alike, as well as a formidable prankster and joke-teller. 

He had this great adventuresome spirit and was a complete original in every way. He loved the sea, was a great sailor, practiced maritime law and was involved with a number of other businesses over the years. Right after college he'd signed up with the Marines, ultimately leading his platoon onto the shores of Da Nang as part of the first official combat troop deployment in Vietnam in '65. He'd boxed in his day, acted here and there, traveled extensively and played his share of competitive rugby and squash.  Everyone who knew him had their own stories about him- the legendary cross-country trips he would take aboard his restored and un-airconditioned XK Jaguar 140, the raucous and debauched parties he'd thrown over the years, the elaborate and memorable roasts, pranks and toasts, the cigar nights replete with his decorative fez and on and on.

This is not the place to eulogize him, that has been eloquently done by friends more capable than myself. What I'd like to reflect upon here though, is what qualities made him such great mentor to me over the more than two decades I knew him: 

  • First, I am struck by the fact that he took his role immensely seriously and prioritized it. 
  • He always made time and when we met was never in a hurry. 
  • In our discussions he always got to the core of the matter somehow by asking the right questions and listening carefully. 
  • He never hesitated to directly challenge either me or my assumptions, no matter how difficult it might have been for me.
  • When he gave advice he didn't mince words either- he wasn't afraid to give counsel and direction when he knew you needed it. 
  • Similarly, he knew when you needed to figure things out for yourself. 
  • He had no agenda other than to help you. 
  • Enormous wisdom and understanding of human affairs & motivations.

When he learned he had Parkinsons he accepted it, and, like everything else in his life would face it head-on. He bore its ravages with great stoicism and his huge personality and indomitable spirit burned bright until the very end.

After his funeral yet another story floated back to me. It was from the companion of his later years, a lady-friend he had known since his youth. She'd told the story that a few weeks before he passed they were picnicking beside a river beneath a clear, unbroken summer's sky of the deepest azure, his favorite kind of day. Suddenly, after some time, she saw him somehow wriggle his Parkinsons-ravaged body into an innertube he'd brought along. In an instant he'd slid down a hill into the water and she watched in amazement as he then effortlessly navigated down the river- eventually beaching himself much further downstream. As she approached he flashed that immense smile he was known for and told her "these are the halcyon days of my life".

For the Next Post in this Series on Mentorship click here

Mentorship Gone Wrong: Three Things to Watch Out For

This is part of my Series on Mentorship.

It occurred to me that no series on mentorship would be worth much if I didn't make mention of the various forms of bad or faux mentorship I've seen out there. In fact, from what I've observed over the years, the worst advice is actually well-intentioned.

In a startup context, bad advice is particularly devastating and can actually kill you before you even get started.

So here's a list of some stuff that amounts to "mentorship-gone-wrong":

The "Mentor" Has No Concept of what Mentorship Actually Means:

An entrepreneur I know once told me he was having some "issues" with a team member. He told me he'd tried to "mentor" him and it "wasn't working". I checked into the situation- basically he'd had a few phone conversations with the other guy amounting to a cross between a beration and a pep-talk. This is so far from mentorship it's almost comical. Nevertheless, the profundity of his lack of understanding of what basic mentorship involves was stunning.

The "Mentor" Has Zero Experience or Understanding of the Startup World:

Often I see fledgling entrepreneurs seek out advice from well-intentioned people who are not in the startup world but have been successful (or perhaps not) elsewhere, (ie. lawyers, bankers, executives, accountants, etc.) Inevitably these folks always feel as though they have a lot to share. Rarely do such folks say: "you really ought to talk to someone in the startup world who knows what they're talking about". These interactions often lead to the worst and most damaging advice I see. They often, for example, make introductions to people they think are "venture capitalists" who are usually unscrupulous broker-dealers. With one single careless introduction they can ruin an unsuspecting person's entrepreneurial life.

The Delicate Category of Certain Lawyers who Fancy Themselves to be Mentors             

This one's a delicate issue because there are definitely a couple of individuals out there in the startup world who make great mentors and also happen to be lawyers. But make no mistake, this is the overwhelming exception rather than the rule.

If you're an entrepreneur you really should be mentored by an entrepreneur, not by someone billing you by the hour.

In fact, I see loads of easily resolvable transactions destroyed by lawyers who try to insert themselves way too aggressively on the business-side of issues and get into their clients' heads in a big way, especially those clients are new to entrepreneurship.

Nature (and lawyers) abhor a vaccum.

Remember, you are the entrepreneur- you make the deals happen- the lawyer you pay alerts you to legitmate issues and papers the deal. That's how it should work.

That's it for now. If you think I've left anything out please by all means leave a comment.