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