Startup Founders: 5 Tips for Engaging New Mentors


Writing by Matt Menietti. Matt is the former Executive Director of GlobalHack, a St. Louis-based nonprofit that organizes civic-focused software competitions and youth coding programs. Before GlobalHack, Matt ran day-to-day operations for SixThirty and Capital Innovators, two nationally-ranked startup accelerator programs that provide early-stage tech companies with seed funding, mentorship, and valuable industry connections. He is an alumni of the Coro Fellowship in Public Affairs, an intense, cross-sector, experiential learning program based in St. Louis, Missouri and currently serves on the Board of Directors for FOCUS St. Louis, a civic leadership organization. Originally from Iowa City, Matt is an avid champion and advocate for the St. Louis startup community, and has organized several volunteer-led hackathons, meetups, and events.

I’m not an expert mentor by any measure. And while I don’t have any exits under my belt, I did help launch a social enterprise with a small group of civic-minded rockstars (GoodMap) and I’ve worked with dozens of entrepreneurs over the course of two accelerator programs (Capital Innovators and SixThirty). That qualifies me to give some advice, right?

More specifically, my experience with these two accelerator programs provided me with a unique perspective of observing founders’ interactions with mentors. Quality mentorship was one of the biggest reasons founders gained value through the program. Effective mentors poked holes in business plans, asked tough questions, gave relevant timely advice, and made meaningful connections for our portfolio companies.

Wanting to try this for myself, I started having monthly office hours at Venture Café, where I meet with 3–4 entrepreneurs for 20-minute “speed mentoring” sessions. I’ve had really great conversations, and some horrid ones where within two minutes of the conversation, I was already checking my watch, asking myself, “Is this over yet?”

I suppose some of that can be attributed to the nature of startup founders — some will be outstanding, and others will leave much to be desired.

Given this, I thought I would share some of my observations and suggestions for engaging new mentors.

Have your pitch down

This is a no-brainer. I was so amazed at how many founders I met who had trouble communicating their business or value proposition in less than two sentences. I would spend most of the 20-minute session just trying to figure out what the company did, instead of offering advice or making connections. You need to be able to explain what your business does and who it serves in less than two sentences, and at a 5th grade reading level. If you can’t answer the question, “We do [X] for [Y]”, then you’re in big trouble.

Take notes

One of my biggest pet peeves during these mentoring sessions is when founders don’t take notes. Not only is it really hard to remember everything that you discussed, it makes the mentor feel like their advice isn’t worth writing down. Don’t get me wrong, I’ve interacted with my fair share of sub-par mentors, but you should always have a pen and paper handy for these types of situations, especially when following up for connections after your initial meeting. Invest in a nice moleskin notebook and never leave home without it.

Come prepared with questions

Without question, I can tell founders who are prepared for a 20-minute mentor meeting and those that aren’t. I’m impressed by those that have the wherewithal to do a simple Google search — who I’ve worked for and what I’m interested in. With only 20 minutes (some mentors may give you less!), you can’t spend it on small talk or getting familiar with the other person’s background. It helps hasten the conversation in a way that makes it an efficient use of everybody’s time. Even better, write (10) questions that you want answered during your meeting. You don’t have to ask all of them (and chances are, you won’t get to), but at least you’ll be prepared. Write them down in that notebook I told you about!

Be specific with your requests

Mentor meetings can cover a lot of ground, from team formation, business model validation, pricing, and marketing strategy. If time isn’t on your side, I suggest you focus on 1–2 items you’d really like to get out of the meeting. If you’re meeting with a person with a background in enterprise sales, it would be wise to focus your line of questioning on his/her expertise. For example, “We’re thinking about opening up a new distribution channel with this partner and these are the terms of the deal. What would you recommend we do?” This is even more applicable when asking for introductions. Mentors (even the good ones) aren’t going to do the thinking or legwork for you.

Always send a follow-up email

Unless the mentor is being paid through a formal program (like an Entrepreneur-in-Residence, or EIR) most startup mentors aren’t being compensated for their time. Regardless of the quality of the advice you’re given, write a follow up email within 24 hours of your meeting (so it’s fresh in their head) explaining how much you valued their time and insight. Be sure to mention any follow up items that the mentor is responsible for — most likely introductions or suggestions for other resources.

If you follow these tips, mentors will be more likely to re-engage with you and be advocates for you and your company in the future.

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