Advice,  Startups

500 Details: The Process of Mentoring Startups

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  🙂