How I Try to Mentor Startups (And Hopefully Add Value)

Fred Destin wrote a fantastic blog post recently on how to be a good startup mentor. It made me think a great deal about how I mentor startups, where I’m effective, and where I could improve. As Fred notes, “good mentoring is hard.”

He’s absolutely right.

I’m currently mentoring a number of companies inside of FounderFuel (a Montreal-based startup accelerator.) I also work with the companies that graduated from Year One Labs (Localmind, Massive Damage and HighScore House.) I recently agreed to be a mentor for a new accelerator in Washington, DC called Acceleprise, which focuses on B2B startups. And I mentor a couple other companies as well.

Hopefully I’ll have the capacity and ability to continue mentoring startups for many years to come. It’s an incredibly rewarding experience. So in thinking about how I like to mentor, how I think I mentor, and how I try to add value, I’ve come up with a bunch of thoughts below. Hopefully they’ll prove helpful to entrepreneurs looking for mentors (and trying to understand what to expect), and to other mentors trying to figure out how to get involved in startups.

Side note: If you’re an entrepreneur looking for advice on how to pick a quality advisor, I wrote this post: Promises and Platitudes – The Dangers of Low Quality Advisors.

The Lean Canvas
If you’ve read my blog before, you know I’m a fan of Lean Canvas. Here are some blog posts related to Lean Canvas that I’ve written.

As a tool for presenting to advisors and mentors, it’s perfect: clear, simple and to the point. I rarely work with a startup now that isn’t using a Lean Canvas. And one of my first questions when someone asks me for advice is, “Do you have a Lean Canvas we can look at together?”

Asking “Why?”
Mentors are in the enviable position of not being “blinded by love” for your startup. Entrepreneurs get blinded; mentors shouldn’t. The simplest way of cutting through the blindness is to ask “Why?” It’s not any more complicated than that. Keep asking “why” over and over and you’ll cut through the blindness very quickly.

I’m probably too soft
Entrepreneurs don’t need sugarcoating (although once in awhile we all need a solid ego boost!) I’m too soft, but I’m trying to be more and more critical, without being a complete ass about it. Mentors only pop in occasionally, entrepreneurs live and breathe what they’re doing, so it’s not fair to be insanely critical without understanding everything that’s going on. Still, it’s hard to be completely honest all the time.

Introductions don’t flow freely
I genuinely enjoy connecting people, but I’m also cautious with introductions (more so than I used to be.) If I make too many introductions and they don’t go anywhere, people will value my introductions less, and that’s going to negatively impact everyone I work with. There has to be a genuine purpose for an introduction, the timing has to be right (for everyone involved), and expectations have to be clearly set.

I value learning a great deal
Along with the Lean Canvas, I’m a big advocate of Lean Startup. I’ve made so many mistakes in the past; I definitely put a premium on learning as a measurement of progress. It’s not the only measurement, but it’s absolutely critical in the early stages.

You don’t have to agree with me
I’m there to help if I can and provide advice. But that doesn’t mean you have to agree with me. If you disagree with me and go down a different road, I’ll still support you, as long as you’re demonstrating genuine progress. I’m there to keep you honest (and a little less blinded and overwhelmed by everything that’s going on), not make sure you do everything I think you should be doing.

I can’t chase you
If you want my assistance, I’m available (as much as I can be), but I don’t have time to chase people around. I think this is universal for mentors (and people in general) – everyone’s busy with their own stuff. So if you don’t ask for something, you’re not likely to get it.

I want to work with people I like
It’s important for me to work with people I like, people I want to hang out with. Life’s too short to spend it with people you don’t really want to be with.

But that doesn’t mean the relationship is always perfect and friendly. Mentors and founders should be comfortable enough to disagree, have open discussions, and get into each other’s faces (within reason). As long as it remains reasonably constructive and civil, I’m OK with (and want to see!) people’s passion emerge. Don’t be afraid to get in my face and tell me what you think.

Mentors have to devote serious time
I take the commitments I’ve agreed to very seriously, and I genuinely care about what happens. You can’t be a good mentor without agreeing to devote serious time to it, and when called upon, be able to respond and dig in. Mentoring isn’t something you can do flippantly; the people you’re helping are depending on you.

Mentoring is hugely rewarding for me
I can’t stress this enough. I’m fairly certain I get as much ut of mentoring startups as they get from my efforts. I learn a ton. I meet great people. I get to explore tons of different ideas, tackle interesting problems and try to connect dots where there weren’t any connections before. I love it.

And here’s the thing — in writing this post I’ve realized that “mentoring startups” is actually incorrect.

You don’t mentor startups, you mentor people.

It’s the same reason why an advisory board should be dedicated to the founders, not the company (or others involved in the company.) Companies come and go, they change many times over before they succeed (if at all) – but the people are the same. I’m not mentoring startups, I’m mentoring people. And there have been times when I’ve provided advice to founders that isn’t necessarily in the “best interests” of the startup. That’s because I care about the founders above anything else. And if a startup fails and the founders go on to other adventures, but our relationship remains good and valuable, then I’m ready to jump in again.

Want more content like this?

Signup for free and you'll get new content as soon as it's available. Thanks!

  • Pingback: Mentoring Startups | SGEye Eyes the World()

  • Mark MacLeod

    Gret advice Ben. And you have made a big impact on Founderfuel. The program relies on contributions from people like you. Thank you

  • Benjamin Yoskovitz

    Thanks Mark. I’m really enjoying my time w/ FounderFuel…

  • MatchLites

    This is stellar Ben. I have not asked you to be a mentor, but I remember asking you two or three questions within the last two years and you replied back ASAP. Of course you did not have to, but that is the kind of person you are. Btw, I have used your wise advice everytime :) Thanks! Also, thanks for the awesome sit down with Tech Hustlers :)  Just in case anyone wants to hear your brilliance, here it is :-)

  • Jordan

    Great article.  I won’t be a mentor anytime soon but I might be one in need of mentoring.  This is great to see what help I can look for what resource to use, thanks.  

  • Benjamin Yoskovitz

    Thanks Jordan. Glad you enjoyed the article.

  • Startupmentor

    Ben, Please continue being vocal about this topic Your insights are very helpful..Exactly we are mentoring people not startups and its about better journeys not ‘shinier destinations!’

  • Pingback: How to Maximize the Value of Mentors in Accelerators()

  • Pingback: How to Maximize the Value of Mentors in Accelerators | | EspadaSoftEspadaSoft()

  • Pingback: 7 great articles about mentoring startups… « Ercan Yilmaz()

  • Pingback: The Technical Side of the MVP for Non Techs – Why You Need a Tech Team Member :: Launch America()

  • Pingback: Advising vs. Investing()