Mentors 17/18: Be Challenging/Robust, but Never Destructive

Brad Feld
Brad Feld
Feb 6 · 3 min read

I wrote 16 posts detailing each item of the Techstars Mentor Manifesto. However, there were 18 items and, for some reason, I never got around to writing the final two.

Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up. I kept saying “I’ll get to it” but never did. So, he did it for me, with the added motivation of getting it up prior to the kickoff to this year’s Boston program. Following is item #17 of the Techstars Mentor Manifesto, in Jay’s words.

This item on the list might sound very similar to #4, “Be Direct. Tell the Truth, However Hard.” But, it’s different. This item (#17) has to do with you, not the companies.

You have been asked to be a mentor at Techstars because you’ve been successful as an entrepreneur and/or a leader. The managing director for your cohort trusts that you’ll help the founders. And those founders are betting — with stock in their company — that you’ll be good for them.

Because of your expertise, you are likely to quickly spot areas in their businesses that need work urgently.

Because you’ve read all the posts here about the Techstars Mentor Manifesto, you dutifully start by being socratic and digging into the fundamental thing that is broken. You are direct, telling the hard truth that you are deeply concerned about some area.

But at some point, you sense the entrepreneur isn’t simply following your lead. They aren’t changing some element of their business to align with your direction. So, you are more direct. You push harder and more forcefully because you think it’s important. But the entrepreneur continues to “not get it”.

And, just like that, you’re irritated. You shut down, you quickly end the meeting, or you push even harder. After the meeting, you vent to the Techstars managing director that this company is in real trouble because the founders aren’t paying attention to this element you find important.

We’ve now reached the point of this post: Never Be Destructive.

The moment you go beyond trying to get your point across to the entrepreneur and do something outside that moment that is less-than-supportive, you’ve stopped being a mentor. You are now simply a judge. Or, worse, a detriment to the company.

You have let your desire to succeed as a mentor become paramount. Your actions can easily shift from being helpful as a mentor to being hurtful to the entrepreneur.

If you let this state persist, your frustration will leak outside the safe space of Techstars. It might be something you say to an investor; which means you’ve now affected the company’s ability to raise capital. If you vent to another founder, you either hurt your own reputation or the mentee’s reputation. At worst, you may end up affecting their relationships with potential partners or future hiring candidates.

Being a Techstars mentor does not mean being 100% dedicated to being a successful mentor. It means being 100% dedicated to helping founders build great companies.

So, be robust if you have to in making sure they hear what you’re trying to make them aware of.

But when you leave the room, make sure you flip the switch and remain 100% dedicated to making them successful, whether or not you think they heard what you had to say.

Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.


Originally published at Feld Thoughts.

Brad Feld

Written by

Brad Feld

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade