My Wisest Mentor: My Grandmother


This is the inaugural post of my Series on Mentorship which appropriately, given my subject, is written on Mother's Day.

Although I advise a healthy number of founders on a regular basis as a friend and/or in my roles at Columbia University, I also have the privilege of playing the role of very involved mentor to a few select entrepreneurs at any given time. It is a role that I take very seriously as I believe it to be an indispensable need for fledgling entrepreneurs. Properly carried out, it can be incredibly rewarding for both mentor and mentee. 

Mentorship of course comes in many forms and I will eventually get into its many manifestations through the course of this Series. But let me say that when I think about the rare and special people who have truly given me this gift of mentorship I am always deeply humbled.

My wisest mentor of all was my paternal grandmother, pictured above with my brother and me on the porch of her Brooklyn home. She was a remarkable woman of immense wisdom and experience and a legendary figure to those who knew her throughout her long life. (She lived to the venerable age of 104!) Entrepreneur, community organizer, immigrant, sage advisor, trusted friend, mother, wife, daughter, sister, landlord, great-grandmother, benefactor to many despite her modest means- she was an unforgettable figure that touched many lives.

One of eleven sisters, she had come to this country by ship in 1921 from a small village in Russia with no education and no knowledge of English. After some years she and my grandfather started their own luncheonette with the little money they had assiduously saved and over time became beloved staples of their community. They worked incredibly hard and always treated everyone around them with respect and kindness. Their customers loved them and as a result of their immense efforts and indefatigable character their business thrived. In time they were blessed with two sons that they raised with these same values.

During these years my grandmother somehow found time to organize the old-world equivalent of a social network comprised of all the people from her home village that had come to the New York area and I remember how she would host frequent gatherings of these countrymen in her home, cooking for 20+ guests at a time with great enthusiasm. The organization was literally a moveable feast of great characters. Anyone new to America from her village was treated like family by her and she made it her special mission to look after them until they were settled here with a job or with some means of supporting themselves. Her sense of fairness transcended her humble station in life and when the City failed to make good on a promise having to do with the zoning of a commercial property she and my grandfather had purchased, she went to see the Mayor herself unannounced and after four hours of waiting he finally agreed to see her. He could not resist her great charm and profound sense of right and wrong and took care of the matter within a week's time. She was a staunch patriot- deeply grateful for the opportunities the freedom here afforded her family. When the time came, her oldest son went overseas to fight in World War II, island-hopping in the pacific theater. Like so many families during the war years, hers too listened intently to the radio reports nightly throughout those years all the while wondering if their son would come home and if America would prevail.  He was to be decorated for his service and returned with his fellow soldiers- victorious.

I remarked throughout my childhood and through all the years that I knew her that she was always helping people. People from her village, people from the community, her family and her friends, relatives who had fallen on hard times. I remember too, that when my grandfather became incapacitated with Alzheimers she never even considered bringing him to some kind of assisted facility though many encouraged her to do so. She spent a decade or more feeding him, moving him from bed to chair to bed, talking to him and caring for him herself though she was well into her seventies by then. People who visited them were in awe of her strength and devotion.

I remember too how much she advised me when I started out in business, how many stories she would tell me, each of which carried such meaningful lessons. She understood human beings deeply and never forgot a face, a person's life-story- it all was so important to her- she cared immensely. She taught me the meaning of customer service, of reputation, diligence, integrity, attention to detail, humility, hard work, authenticity. And she taught me to work only with people who embodied these qualities and not to waste my time with those that did not.

All this is what I learned from her by watching, by listening. She was my wisest and dearest mentor.

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

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.