How to Cultivate a Generation of Mentors and Angels

The entrepreneurial blogs were on fire this morning with posts from notable thought leaders Scott Kirsner, Jeff Bussgang and Bill Warner.  All of them focused on the issues at hand in our local entrepreneurial community.  Bill used baseball as a metaphor to our situation in our community and as a method to measure success for our community.  I think it's quite accurate and is a great extension of the "major league" and "minor league" problems Scott Kirsner wrote about previously. 

Bill arranged a call with myself and Fan Bi to discuss our thoughts on the issues at hand from those posts.  Bill sees problems at all the stages and wanted a fresh perspective to balance out the heavy hitters he had already spoken to.  I'd like to share a few of the things we talked about and then a set of ideas Bill wanted me to post that I shared in our conversation.

First, if you haven't read Jeff, Scott and Bill's posts, you need to. You can click their names at the top of this article to get to each person's blog.  The basics is that we are defining Massachusetts companies by how great their success has been by baseball hits: singles are successfully in their market, doubles are any company with sales over $10M, triples are any growing company with sales over $100M, home runs have a >$1B market cap and a grand slam >$10B market cap. They all argue we don't have enough home runs and grand slams and that we need to work to change the culture to promote more of them.  

But how do we get more of both? I think it's all about incremental steps. Here's my theory: 

How to Cultivate a Generation of Mentors and Angels

Everyone can help each other in this system.  If you're in the major leagues, it means you've got at least a little success under your belt.  You could definitely help those that are out there for the first time.  As you gain more experience, you can help later stage companies and potentially become more involved if your schedule permits.  

Meanwhile, as a "minor leaguer," you need guidance when you're starting. Often a short conversation with a veteran can have a huge impact, which is why I suggest 1-2 hours a month likely in the form of quick meetings or a couple phone calls a month.  Your insights as a mentor often reveal things a first-timer doesn't recognize but are obvious to you.  Never underestimate the simple value of that. 

As the "minor leaguer" develops his company, he's going to have more questions and likely need a bit more help. Hopefully if he has a few "light mentors," one is becoming particularly interested and can become more involved as the business launches and grows.  Eventually that business will become a single and the entrepreneur is officially a major leaguer.  This major leaguer has now had help through his early stages and should "give back" to help the next group.

Meanwhile, looking back at the "Major Leagues" track, I believe that if you have entrepreneurs involved in early stage companies and mentoring that it is much more likely that they will become Angels after they have a liquidity event.  

Setting up this structure of helping one another and "paying it forward" is a great way for helping the whole ecosystem. Every experience you have along the lifespan of a company from ideation to development to launch to investment to exit is a stage that someone else has yet to experience. This means virtually everyone in the ecosystem can be a mentor to someone else who is earlier in their entrepreneurial career.

So, that's my theory. Get everyone mentoring and helping each other and the whole ecosystem will benefit. Get entrepreneurs who are hitting doubles, triples and higher to be involved in the process, and I bet they'll be more likely to become angels.

I challenge you to go out and identify 1 or 2 people to provide "light mentoring" to and see where it goes. If you're past the stage of a "potential founder," there's someone you can help.

What do you think? How do we get more angels? How can we spark more mentoring?