Author Archives for Mike

How to think about advisors vs. mentors (Oversubscribed Weekly #11)

January 24, 2019 by

When building your startup, mentors/advisors can help you fundraise, and investors can later become mentors/advisors. Therefore, it’s important to understand these roles when thinking about fundraising.

The words “mentor” and “advisors” are often used interchangeably. However, I’d argue that there’s a critical difference, and understanding that difference can help you get the most out of your mentor/advisor relationships.

Mentorship helps you navigate ambiguity and the things you don’t know you don’t know (e.g. “what’s the most important thing I should be focusing on”). Advice helps you address a specific challenge you’re facing (e.g. “what’s the right way to set up my supply chain?”).

Some folks are really good mentors, some are good advisors, and some can do a little of both. Entrusting someone to give you mentorship or advice is not to be taken lightly. Good mentors and advisors can make you a better entrepreneur and make a tremendous impact on your business.

Make sure you’re thinking about how to get the most out of your mentor/advisor relationships, and let your mentors/advisors play to their strengths.For example, Micah Baldwin is one of the better startup mentors out there. While he has certain domain expertise he can tap into for specific startups facing specific situations, he’s a great mentor for any startup because he does this:

If you’re looking for mentorship but the other person is doing most of the talking, then they’re not a mentor (but they could still be a good advisor!)

Fred Wilson also talks about the dichotomy between mentorship and advice in his blog post, What Kind Of Coach Do You Want. He talks about how his partner, Andy, listens and asks more questions (mentorship), whereas he is more direct with what to do (advice).

My colleagues and I are asked all the time for recommendations for coaches, mostly for the founders and CEOs we work with, but often for others on the senior team. I am a huge fan of coaches. I think they can be game changing for leaders and their teams.


I always ask a bunch of questions to find out what kind of coach someone wants before making suggestions.


A key question is whether you want answers or questions from your coach.


My partner Andy wrote a bit about this, in a very different context, the other day.


I’ve spent a large portion of my career investing in early-stage companies. Part of that job is to advise and counsel, to assist a company in reaching its potential. I try to ask for feedback on how I am doing in that job. A constant thing I hear is to provide more direct answers to problems posed to me. Typically, I am told, I answer their questions with further questions.  

Yet, I think it’s important to tolerate ambiguity. Maybe there isn’t a direct answer. Maybe I don’t know the answer. Maybe I want to assist others in coming up with their own answers.

I have to confess that I am more of a “why don’t you try this?” sort of advisor.

Andy is more of a “why do you want to do that?” sort of advisor.

Both can be very valuable but it really depends on what you want/need in an advisor. Getting answers when you want questions can be frustrating. Getting questions when you want answers can be equally frustrating.

So think about what it is you want from a coach before going out and finding one. Getting the fit right is important.

If you were a Union Square Ventures portfolio company, hoping for Andy to provide direct advice and hoping for Fred to provide mentorship wouldn’t have the best possible results.

Make sure you think about your mentors and advisors like you would employees or cofounders – understand their strengths and let them do what they do best (and don’t listen to advice from people who aren’t good at giving it).If you’re looking for more detailed advice on how to build a team of advisors and the different ways to engage with them, read the article Snag the Best Advisors for Your Startup, from Best-selling Authors to Fortune 500 CEOs, profiling Amy Chang and how she build a rockstar team of advisors.