Maxed Out Mentor

There are a handful of startup world terms that I can’t stand. Sometimes that’s because the terms are confusing. Other times because they’re downright unhelpful. Other times it’s just because I’m preternaturally cantankerous. I’m not sure into which one of those my experience with the word “mentor” falls.

To rethink these old issues, start with an old example. Remember the original mentor? That’s right. It was a guy named “Mentor” and he was helping Odysseus’ son Telemachus during the Trojan War. Go back and read all about it in paperback. That mentor-mentee interaction was probably very different from the casual way the word is thrown around today.

In 2012 – 2013 when I was building startup programs in Hong Kong, I actively put myself out there to help young founders. Over that 12 month period, I had first time coffee meetings with 250 people. That’s five new people a week for a year (I didn’t track repeat meetings). The format was usually the same: 1) they contact me somehow (through a mutual connection or cold outreach), 2) we arrange a time to meet, 3) they introduce themselves and an issue they’re having, 4) I offer some suggestions or follow-up in some way. In most cases, this was a one-off conversation. The purpose of the meeting was the help during the meeting itself. In other cases, however, something else happened. From that group of 250, apart from the advice, I estimate that I connected 25 to journalists who then wrote about their startup, I connected a few to investors who put in money, and found jobs or clients for a few others. Overall, this was a very loose type of mentoring. There was no ongoing mentor-mentee relationship intended.

When I moved to Los Angeles I initially started to do the same thing but time needed for work and family prevented me from meeting as many new people. Instead I preferred to focus on a smaller number of mentees over a longer time. Even so I started to run out of time. Then a strange phenomenon started. The less time I had, the more in demand I became.

Like a stock character in a commedia dell’arte play I (or other mentors) suddenly become the last hope of the startup. From requests for meetings, coffee, to be interviewed for the (non-funded but very competitive) Incubator program I currently run, founders will bend over backwards to talk, even when I explain that they’ve got the wrong guy.

Note that this is for solicited, not unsolicited, advice. (Kevin DeWalt wrote a good post on unsolicited advice where he explains why “[u]nless you’re asking for time or money you’re under no obligation to answer anyone who challenges what you’re doing.”)

You can add lots of value if you only focus on people and situations where you are a fit, only give advice where you know what you’re talking about, don’t think that you’re running your mentee’s company, and reflect on your meetings to improve.

Don’t Make Your Mentor Mad

It’s rare, but I do get angry sometimes. It happens when I’ve put a lot into helping a founder and their company and they throw it away. I’ll give you two examples that bothered me in the last few years.

1. I helped a young team over two semesters. I coached them extensively in raising money (they followed my pitch almost exactly and it paid off in a quick raise). Coached them through the metrics they needed to hit. Repeated again and again how to analyze their data. What happened? When I asked probing questions it was revealed that their CEO was showing me and others fabricated numbers. I tore him to shreds and he never spoke to me again. When there was a well-hidden ethical problem, what was the purpose of all of the other work I did?
2. Another founder I helped raise money and get connected had the habit of spending much of his time on people problems. That is, he was not making tough people decisions. He kept people who weren’t producing and even hired new ones that didn’t produce. Over a long, painful period when nothing else of value happened in the company, he finally terminated some of them in a bridge-burning way. I reflected that the only way I could have known the extent of the situation was to be with the team as they worked. They were out of state. I should have spent more time on the rest of the team and not just the CEO. The founder’s bridge burning I chalk up to stress and miscommunication rather than malicious intent.

Today, my regular work-related repeat mentor-mentee relationships involve around 50 startups. Add to that some percentage of students in the four classes of I usually teach per year (maybe 20% of the total class population of 150 people). My goal now is to go deep on a smaller set of companies where I can make a difference.

More about that later. For now, mentors and mentees, be good to each other and be good to yourselves.