Fred Wilson, a VC (Venture Capitalist) I quite like and admire, talks about Mentors, in particular about the two mentors that shaped his professional life. Here’s two important passages (bold is mine):

Angela Merkel, LeBron James, Oprah Winfrey, Jeff Bezos … Nobody gets somewhere on their own. Everyone has help.

And then, further down in his blog post:

The thing about mentors is you can’t really ask someone to mentor you. It kind of happens organically. Someone takes you under their wing. They see something in you and want to bring it out, develop it.

I agree. But I think Fred’s post is missing a crucial element: most of us can’t have lunch with Bliss McCrum Jr, and therefore most people can’t have him as a mentor (that lunch is how Fred got a job at Euclid Partners, and eventually Bliss became one of the most important mentors of his life).

Mentorship is great… If you can have it. But what about the rest of us?

Most of us can’t have lunch with Bliss

He’s one out of maybe 1,000 people that would have deserved that privilege. But the other 999, unlike Fred, weren’t in the position to even try to get it. They were not born in the US, or they aren’t white, or male, or couldn’t go to MIT or to Wharton.

This is not to say that Fred didn’t earn his career. And I’m happy for him! But when talking about mentors, I feel that you SHOULD say something about the rest of us. Because the rest of us would think: that’s true for you, Fred. But what about me?

My mentors

I feel thankful for the career that I had so far, despite it being nowhere near as successful as Fred’s one (TL;DR: started a few companies, one of which was acquired; CS professor; Evangelist at AWS; CTO at VMware, tens of startup investments (me and M14T), now in the VC world somehow). And perhaps it’s a good opportunity to publicly recognize the role that my mentors had in enabling it. Here it goes.

My mentors

And yet it wasn’t easy at all to find them, or to create the opportunity for that special sparkle that happens when someone more experienced feels the desire to help a less experienced one.

But where, and how, did I manage to get mentors to help me? And more importantly, where NOT, and how NOT?

I grew up in Assisi, a small town in Italy. Beautiful, small, and not ideal for a career in tech, unless by “in the Cloud” you mean something holier (Assisi is an important religious place — St. Francis, etc.)

The first real mentor was my (older) brother Marco. We started a consulting business together in the year 2000, and worked together for about 8 years. It was painful for me, but I went from “truly hopeless” to “maybe there’s a chance to survive” thanks to him (and I had no idea how green or inexperienced I was). He gave me what he could, but we were both heavily limited by the environment around us. Thankfully, I didn’t stay in an Italian small town forever.
In this case, the mentorship happened because we are brothers, and I was so “green” that you didn’t need someone from Silicon Valley to help me get to the next level.

Then, on January 18th, 2007, I presented Beeseek (the prototype for an open source search engine) at Communia, an Italian tech conference in Turin. Stefano Quintarelli was in the audience. He took me under his wing, and never left me, to this day.
It happened because, despite Italy not being a great place for tech, I spent hundreds of hours on a project that never made me any money; but it was interesting enough to get me a speaking slot at that conference. Yes, you create the opportunity and then roll the dice.

At Amazon Web Services, two of my managers (I had four/five in total) had an impact on me. One, Martin Buhr, was the first manager that ever cared about me and my professional growth. I almost couldn’t believe that he didn’t want to take advantage of me and screw me and squeeze me and then throw me away (my past experiences). I wouldn’t go as far as calling him a “mentor”, though, because our frequent travel prevented us from interacting often. By the way, this is the story of how I got hired by Amazon.
Instead, the one that truly was a persistent, high energy manager, AND the one I’d fully consider a mentor, was Shane Owenby, during my time in Singapore from 2010 to 2012. Shane CARED. Shane wanted me to succeed. Shane was stubborn, opinionated, and (let me say it) often wrong on all things evangelism. Yes, he was, and eventually he would admit it. But you couldn’t NOT love him. When the AWS team grew, I started to realize how precious and privileged my relationship with him was. Few others had the access I had. Probably none enjoyed his feedback and support as much as I did.

Dulcis in fundo (latin for: dessert at the end), when I left AWS to join VMware in 2014, my manager was Riccardo Di Blasio, a fellow Italian. We met in 2010 when AWS wanted him to leave EMC to run AWS Europe. Joe Tucci made him an offer he couldn’t refuse and kept him at EMC, but our paths crossed again when we found each other in Silicon Valley four years later. I was tired of AWS (a long story), and he was leading sales for VMware’s cloud division, and needed a CTO. Bingo!
Riccardo had a peculiar management style which wasn’t for everybody, but he was a really effective sales leader, and most importantly he truly was a mentor to me: he took this “seasoned” technical manager (me) and tried to transform him into an executive at a public company. A big jump if you ask me. I spent two years at VMware, learned a lot, did a few important things, but failed to leave a mark. Riccardo left 18 months after I joined; and I left a few months later. The cloud division faded away (not because of our departure) in a few more months, and nobody remembers vCloud Air today.

It kind of happens

But Fred is right on this, too. It kind of happens. But you need to create the opportunity for that thing to happen.

Tech, startups and investments. Global life. Italian heart.