This morning I posted a link on Twitter & Facebook to How I Mentor Startups & Entrepreneurs. After it went out, I realized it doesn’t tell the full story. Where are the details of how this whole thing works. I knew I’d written it down at some point, so I dug up this email I wrote to the 500 Startups list. New personal rule: emails longer than 4 paragraphs might need to be blog posts. Enjoy!
As a mentor who has gotten involved in ~12 companies and ended up writing checks to 3, so far, I want to share a little about how I think about the whole process. First of all, I love mentoring and it is one of the most rewarding things I’ve done with my free time. Its teaching me a ton about myself, things I’m interested in that I don’t always get to think about in my day-to-day work, and I get paid back with data — either the advice I give helps the startup or it doesn’t.
However, I don’t work with every start that approaches me. For other startups/mentors here’s my process:
0: I get an inbound request/intro from a founder/startup/investor/etc. — my first question is, “can I help these folks?”. If they have a startup in an industry or problem space that I don’t know anything about, or can’t find excitement for, or think is a dumb idea then I tactfully decline. Those things make it impossible to become a “true believer” and every time I have gone against this I have regretted it.
1: I agree to meet up for coffee and find out my about the team, their vision, their execution so far, and how they think I can help them. Usually they come to me for my broadly advertised skills in marketing, but often they find Ican help with a bunch of other stuff too. I can usually tell if I am likely to invest in them after my first meeting, and this sets how much time I want to commit.
2: Usually I find that there is a period at the beginning where the startup needs a lot of time and attention, and has a specific use for me as a mentor. I like to commit to meeting a few times over the next 3 months for 2-3 hour working sessions, and if things are going well then I’ll usually write a check in the next 8-12 weeks. If not, then I’ll usually wrap things up after the 3 month period and move on. Some startups just stop using me, whether its because they’re busy or because I’m not helping I don’t know, but I am laissez faire about it. If you keep asking me for my time you will get it… but don’t expect me to pursue you too much.
3: Writing the check. Usually $5k and really I don’t worry about the valuation or think I’m going to get the money back (or care) - I’m paying to be at the table for the long term. Its a way to have skin in the game. I also have companies where I have a small % equity in return for my time… which is usually only something the really early stage ones can offer. And yes, if one of these companies had a moderate return I would super happy — but the reality is that I’d probably just invest it in more companies (or maybe my own one day).
4: The ongoing relationship - I block out time for my investments/mentorships on my calendar. Sunday is my 500workday I host an office hours at a local coffee shop doing 20 minute lightening mentor sessions, and I meet withstartups at their offices or at my house if they don’t have an office yet. I work on them even when I don’t meet with them, doing research or catching up on their news. They probably don’t even know how much I stalk them.
And that’s how it works for me, I spend about 6 hours a week on it… so it will take me about 32 years to hit my 10,000 hours of mastery. That’s cool, because my 58 year old self will be a really quirky and fabulous angel investor. Here’s hoping