How to Find a Mentor

Everyone Should Have At Least One


Last week, I wrote this very well-received article for ExitEvent about how any startup community needs a deep bench of mentors. While that was my main point, I also got into what makes a mentor great and how to go about choosing one.

I made it clear that a great startup mentor doesn't necessarily have to have one or more large exits. They just need to have experience with -- and passion for -- what you're trying to do.

Their main goal is to impart to you what they did to get to where they got.

I got mostly these two questions back:

1. Can you mentor me? (Appreciate the thought, but no, I've got a few right now)

2. How do I go about finding a great mentor for me? (Uhhhh…)

Good question.

Here you go.

Now, I'm not talking about JUST startup mentoring here, I'm talking about success in any discipline. Yes, that mostly follows a startup or small business or career theme, because those are what you most need mentors for.

You want to get in great shape? You need a book and/or the Internets. You don't need a mentor for that. If you have to have one, they charge about $50 an hour at your local gym. I don't recommend that, but whatever is going to get you off the couch. It's your money.

So this is about finding the right person to advise you on getting your business or your career or your life's passion in order. And for that last one, I'm not talking about your personal life. For that, you need a whole other thing. I like the church, but that's me. I went to Catholic school.

Start At The Top

This might seem a little odd, but start out by shooting for the most successful people in your field. Admittedly, you're going to have to reach way out of your depth, and if you aren't, you're not reaching far enough. The odds are going to be stacked way against you, but don't let location, status, or your own lack of network get in your way.

This is how people “get lucky.” They make their own luck. However, luck being what it is, don't spend a ton of time doing this.


Spend a ton of time doing this. Go to stuff in your field. Anything. Conferences, trade shows, speaking engagements, meetups, whatever. Worst case is you learn something. Meet everyone there. Like I said, your mentor doesn't have to be the most successful person in the room, just someone with more experience than you. Preferably, way more.

Stay within your field, and don't assume that someone who is a massive success in selling books or T-shirts or is the CEO of a major corporation is going to know how to get your app off the ground. Or vice-versa. Or any versa.

Be Persistent, But Be Pragmatic

If they're not into you, let it go and move on. Life is not the Karate Kid. If they're a crotchety d-bag who is too important for you or too jaded by their journey, how much help are they going to be? Wait, let me answer that for you. They will be Negative Help.

Most people are actually open to mentorship, provided the fit is right and you're not an ass about it. And that means, if you're getting a lot of no, you're either going to the wrong places or you're using the wrong approach. Check yourself often.

Ask For Help

Know what you want them to do for you. Nothing is more frustrating than someone asking me to coffee or beers (although I like beers) with nothing more than a generic request for advice. Have an end goal in mind, and make that clear and quantifiable. Also give a closed time-frame.

“I'd like you to mentor me for a few months to help me find my first hire and break into the yarn sales market.”

Something like that.

Be realistic as well. If we've never met, there's no way I'm getting you funded, but I can help you plan your fundraise.

Offer Something In Return

You've got talent. Use it. At the very least, your mentor should be able to learn something from you. I've also done straight-up trades before. Again, you're not offering to paint their fence or wax their car, but if the fit is right, there should be something you can do for them.

“In return, I'll tell every new prospect I talk to how awesome your sewing machine business is.”

You get my point.

Be Selective, But Be Open

Rule one is never take on a mentor that can't help you. Mentoring is not consulting, and unless that person has either sold or built something a lot like your product, they're not right.

But if you find someone who is in the ballpark who you really get along with, play it out. You never know when the right advice is going to come along and from where. Mentorship comes in varying degrees and you can have one mentor or a dozen.

My best friend? He's a mentor. My dad? Still a mentor. That one founder whose business has nothing to do with mine and who I only see every three or four months at startup events but I love his takes. Mentor/drinking buddy. My wife? You better believe she's a mentor.

But I'm still seeking them out. Constantly. Back when I was starting out I had three or four at any given time. These days, outside of those from my personal life whom I've mentioned above, I've got at least one, sometimes two.

And shh, some of them don't know they're mentoring me. That's cool too.

But keep in mind there are literally dozens of other people I've met with in the past, including some I thought would be a home run for me as a mentor, who I just don't see in that way anymore. You have to weed them out, some because you've grown past them, others because they were never right in the first place.

Keep them close and return the favor when you can. Even the ones that sucked.

There really are no hard and fast rules to landing a mentor, but finding them is just like finding investors, employees, partners, even customers. It takes a lot of research, a lot of networking, a little trial and error, and plenty of due diligence.