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  🙂

One Comment

  • Carole Wai Hai

    Cool post Danielle, would you give me the authorization to translate to Chinese and post it on iWeekend blog in Chinese? In China mentors have a completely different roles, they are mainly angel investor, helping just for the sake of helping is still brand new and unbelievable for most entrepreneurs here. In the industry when we hear “mentors” people think: legal advices, training providers… not role models.
    Would love to have you at iWeekend event, so if you pass by China, be sure to ping us~

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