Luke and Yoda

{{ story.headline }}

{{ story.subheading }}

{{ story.timestamp }}

A couple weeks ago, I called out the need within the Triangle startup scene for more of our entrepreneurs to step up and lead. I’m not saying we’re not doing it, but it’s a big job and we can’t wait for founders with gargantuan exits to turn the Triangle into the next big startup hub. We’ve got to work with what we’ve got. And furthermore, what we’ve got is more than enough.

One of the ways this theory applies is in mentoring and advising.

I recently took on a formal mentorship role after a long absence in any sort of mentoring or advising. I’ve been working with the brilliant Jamey Heit from EssayAssay, who is starting to get well-deserved buzz for an amazing technology that uses algorithms to grade papers.

Yes. Algorithms. Writing. Robot Teachers. Right in my wheelhouse.

And that fit is incredibly important, much more so than my resume or the size of my exits. I was lucky enough to have this mentorship opportunity presented to me by John Austin over at Groundwork Labs, where EssayAssay has just wrapped up their program. John knew that the technology fit was right, and he thought we’d get along.

It’s been a great ride so far. I feel like I’ve already helped, and I’m sure Jamey would agree (because I’ve asked), and we’ll more than likely remain friends once he outgrows my capability to mentor and advise. Which, if I do my job, won’t be too long from now.

That experience has been enough for me to get back into the mentorship game and take on a couple more informal mentoring roles.  And if I can do a few, I know dozens of other entrepreneurs who should be doing at least one. The Triangle, being what it is, needs a deep bench of mentors and advisors, and it doesn’t matter if those mentors and advisors are massive successes, moderate successes, or even failures.

What matters most is the experience and the involvement.

I’ve been in the startup game for a long time now, and I’ve been mentoring other startups and entrepreneurs since day one. In fact, I started my first company alongside another entrepreneur who was starting their first company. We pretty much mentored each other for about a year.

Number of exits between us: Zero.

Amount of outside money previously raised, combined: $0

Today, even though I’ve been doing startups for what seems like forever, I’m still being mentored, constantly, by people who have been at it longer than me as well as people who haven't, including people I’m mentoring, like Jamey.

Shh. I’ve learned a few things from him. Don’t tell him. It’ll make me look bad.

Mentoring is a tough concept to wrap your brain around for any first-time entrepreneur. It’s help. It’s hard to ask for, it’s hard to know who to ask, and it’s hard to know what to ask for.

So how do you get started? How do you make sure your mentor is the right mentor for you, with all the right knowledge, experience, and wisdom to get you and your fledgling company where you need to be?

You don’t. Because no one can do that. Anyone who tells you they can do that is full of it.

I’ve heard all the horror stories. Early-stagers with a great idea and no clue how to move forward being told they need to create complex financials and a detailed investor deck. Late-stagers with profitable businesses being advised to pivot into the hot meme of the day (social, gamification, etc.). Co-founders being told to cut the other co-founder loose after one meeting because, according to the mentor, they’re dead weight.

Any of this sound familiar?

Unless you have someone like John Austin and Groundwork doing the matchmaking, you’re going to need a couple meetings to know if there’s a fit.

But I can tell you this. If your proposed mentor comes in hot with a 12 step program to get your business in order -- if they bring a template or assessment or some kind of spreadsheet to the first meeting, pay for their coffee and show them the door.

There's a difference between mentoring and consulting, and a lot of people confuse the two. A mentor or advisor isn’t there to help you make incremental improvements to your bottom line or your company growth. Mentoring is organic. It’s listening. And then it’s dropping the four most important words in the mentor toolkit.

Here’s what I did.

The best advice always comes from personal experience. And the best way to impart that advice is always anecdotally. There's no way to prove causation from one experience to the next. My context will always be different than yours. And I'm not on your board. The decisions, well, they're still going to be yours to make.

And if I can't tell you what I did because I've never done what you're doing, I should be offering up the next best thing.

Here's what I would do.

Not: Here's what you should do.

And if I can't do that. You need to check me.

Mentoring, whether formal or informal, should be a part-time, volunteer proposition. This means that entrepreneurs should be constantly double-checking their mentors and said advice, a little like getting a second opinion from a doctor before undergoing a major procedure.

There should also be a weeding out every so often. Even the good ones. Yeah, you might have a mentor for a good long time, but at some point, you should have stopped referring to them as your mentor and started calling them your drinking buddy.

I could always use more of those. The cool thing is, so could you.