Every once a month, I receive a notification to remind me of talking to my mentors. More frequently than not, I don't need to call them or email them anyways. More and more I have been interacting with them informally, on specific topics that come and go.

Mentors are great to help you make decisions, but more so to act as a sounding board. Kind of a low frequency Feedback mechanism. They are my permanent board.

This is very subjective, but this is how I pick them (People), how I interact with them (Process) and what I get from them (Tools).

  1. A mentor is an accomplished figure that promotes honesty and optimism
  2. A mentor provides advice by listening to your developments and asking soft questions, often unrelated to what you talked about
  3. A mentor eliminates blindspots in long term strategic decisions. 

A mentor is an accomplished figure that promotes honesty and optimism.  This is my test to recognize them. With few exceptions, my mentors are on average 10 years older or more. They've all been recognized by their peers as the best at what they do. They are extremely sensitive to what's going on in the world and around them and they voice it. The ones which aren't so close personally can be quite diplomatic, but rarely do I sense they hold any sacred cows. They provide detailed critic of what they see as wrong and can provide endless actionable options of solutions. More than anything usually they have this fun and senator-like optimism that "everything will solve itself, at its own pace".

A mentor provides advice by listening to your developments and asking soft questions, often unrelated to what you asked. He or she doesn't generally question your specific pricing or marketing activities. They mostly listen. And usually try to see if you are overreaching, if you're happy, if you're conflicted about something, and act there. When I was at, I showed all my mentors my strategy, which was polished and logically congruent. I sent full reports of all the details I had. One of the comments I got was something like "Can you really go international with this kind of funding (300k€)? How would you raise more? You're an entrepreneur for HBS, but no one cares. Remember this is Portugal". While I had smart answers, the reality was more complex. Raising money for Ecommerce in Portugal in the midst of the crisis with a complex investor configuration was not going to be easy. Investors don't care if you're smart or your ideas looks promising. We did grow, we did get interested parties, but the whole thing was long and painful and sucked my energy away from daily growth. While my enthusiasm was obvious, at the onset the setting didn't pass the smell test for him, and I appreciate now these types of comments.

A mentor eliminates blindspots in long term strategic decisions. Its usually impossible and also very stressful to predict how things play out in the long term. A mentor has been through many cycles and can recognize some "do's" and many "dont's" before you actually get there. Example: a professor at HBS once told me to not start businesses part-time or reward part-time'ness. I resisted this idea and have tried to put resources in small prototypes, waiting that something would happen and then I'd jump. Or assigning an even more junior person to run the business while I provided guidance. It just doesn't work. When in the past I committed 100% to a startup, at or now at, was when I became the most successful. When I tried to do it part-time, my ideas became nice expensive hobbies. I always learned something, but overall I spent money and time which could have been poured in my main activity.

While the informal number varies, I currently have 10 mentors on call. My father, brother, two former senior clients, three former bosses, a pair of colleagues and a former professor. This includes scientists, engineers, finance people, lawyers, current or former CEOs of companies as big as several billion in valuation, consultants. Most of them are or have been entrepreneurs. 

I haven't asked them to be my mentors or chased them. I just historically reached them for this or that, and eventually I realized they were my core set. I couldn't do it without any of them!

Call up yours frequently! Don't forget.