On Mentorship

Please excuse the form email that I’m about to share with you, but I’ve found over the years that it helps to set a foundation for the mentor/mentee relationship. We can discuss if you have any questions.

My Info

Jonathan Beninson



My Availability

I generally reserve Fridays for mentorship and I only take in-person meetings between 10 and 4. For those in-person meetings, my schedule tends to fill up about two-three weeks in advance. If something comes up and you need to speak to me outside of the context of a normal Friday meeting, follow my 3-step guide for how to reach me:

  • Email if you’ve dropped a match and you want to discuss next Friday
  • Text if the building is catching fire
  • Call if all you see are flames

In General

I believe that the job of a mentor is to guide, not to do the work. As a mentee, this might sometimes be frustrating because it feels like I’m hiding the ball from you. The truth is that I am hiding the ball from you, but it is rarely the case that you will learn as much from hearing my answer as you will from learning your own.

There may be times where you don’t agree with my advice or don’t want to follow it. That is fine and it won’t hurt my feelings. Mentors aren’t always right and sometimes, there is no right answer. Regardless of what you do, please be honest and transparent with me about your decision. As an entrepreneur, whether you choose to listen to someone else is your privilege and your burden. Taking someone else’s advice turns that advice into your opinion and at the end of the day you must take responsibility for the outcome.

In order to keep me in the loop, please send me updates as to your progress. I prefer once a month, but less is fine if you are progressing slowly — your call. Your reports should follow this format:

  • Company Status — Company overview and updates
  • Financials — Short-form balance sheet is sufficient unless there is something more to tell
  • Team Status — New members? Issues? Conflicts?
  • Progress (Good stuff) — Including whether you’ve met/exceeded/failed to meet goals and why
  • Concerns/Challenges (Bad/Ugly stuff) — Including internal challenges, market changes, external threats, etc.

This format makes it easy for me to see, at a glance, what you’re doing and also prepares you for investor reporting down the line. Once you have set up the initial document, this exercise should take you less than 30 minutes and provide you with some good perspective. If it is taking you more than 30 minutes, you are probably writing too much or we have issues to discuss. This entire report should be able to fit on one page and should never be more than two pages.

You should also keep a “Jonathan List” of questions as they come up along with the dates. It’s best if you keep this in a shared Google Doc so you and I can see a timeline of your questions/issues. Please give me at least 24 hours prior to any conversation we have so that I have some time to review, consider, and scheme. Once we have discussed an item on the Jonathan List let me know, on the list how you resolved that item — even if you didn’t take my advice.

On Mentorship

You never need to feel guilty for receiving mentorship and you shouldn’t feel like I expect something from you. Some mentors may require compensation in the form of cash or equity. I do not. I enjoy helping other entrepreneurs and only ask that you pay it forward by mentoring someone else as soon and as often as you are able.

Finally, In the event that you ever decide that you no longer require my mentorship, please tell me so. It is not uncommon for companies to develop new issues over time and I may or may not have the experience to help you with industry-specific topics as you grow. If that day should come, I will be happy to have done my part to help guide you to that level of success.



This is the letter I’ve sent to nearly every person I’ve mentored in the last half-decade. It’s evolved a bit over time and will probably continue to evolve in the future, but I’m sharing it with you for two reasons:

  1. I want you to mentor someone; and
  2. This is a good starting point for establishing that relationship

Countless words have been written about the importance of mentorship (see Figure A), so lets move on to some topics I think should be discussed.

Figure A: Beating a Dead Horse

Mentorship Isn’t a Forever Job

“Why don’t you mentor?” I once heard someone ask in the hallowed halls of TechStars in Boulder, Colorado. “Because I don’t have time to start another company.” was the answer. Here’s the thing, that’s bullshit (see Figure B).

Figure B — Bullshit

I have three levels of mentorship. Not in a bronze, silver, gold sort of way, but in terms of my time commitment:

  1. Coffee — This is the bulk of my mentorship. 30–60 minutes of listening and responding with some follow up email introductions as needed. I might even look at a deck. Total time in: 1–2 hours
  2. Friendship — This covers most of the rest of my mentorship time. 1–2 calls or coffees a month for 3–6 months. This is a little bit of a bigger investment, but for the VAST majority of entrepreneurs, it’s all they will ever need from me. After this amount of time, they know as much as I can teach them about how to not fuck up their companies. After that, I may hear from them 1–2 times a year with progress updates or questions where they would like my feedback. Total time in: >15 hours in first year
  3. Relationship — The holy grail. I do this rarely (usually no more than one at a time) and only in cases where I feel like I have something truly additive for the right entrepreneur. What is the right entrepreneur? Big ideas, small ego, thoughtful listener, investable company. This looks like an advisor role or a board seat. My phone is always available and I’ll show up for first hires, big meetings, indictments, etc. Total time in: Generally >40 hours a year (less over time)

If you’re doing the math with me, that’s easily 50 entrepreneurs a year working a few hours on a Friday. I know a guy named Brad who meets people at a coffee shop in 15 minute increments, one right after the other. Drinking coffee for an hour a day, he could easily help over 300 entrepreneurs in a month.

Point is, you have time to be a mentor.

What Mentorship Isn’t

Mentorship isn’t answers. The stepping stones to my success each have miles of foundation beneath them; which is to say that I could never tell someone how to be successful. No part of the path to victory is axiomatic and the best anyone can say starts of like this “Well, in my experience…” In many cases, qualifying statements like this are used to indicate expertise, but not in this case. Most entrepreneurs are scared, uncertain, looking for answers. They want you to tell them what is right, to prescribe a path for them. One can never say this often enough to an entrepreneur:

I can only tell you what has worked or not worked for me in the past. I can’t tell you why it worked or didn’t work, because I don’t know what other forces were at play. It’s up to you to take this information and use it to make your own decision.

Entrepreneurship is the process of learning yourself through building a business. It’s a lot like being a parent in this way. One can never fully step into either role if one does not accept authority and then engage with love, concern, and less than adequate sleep. A mentor must not steal from the entrepreneur the opportunity to step into his or her own authority.

On Being Mentored

Do you need answers you can count on? Do you need someone to tell you how to solve a problem? Do you need to know the right way to get to where you want to go? Chances are, you should go home. You’re probably not ready yet to be happy or successful as an entrepreneur and that’s okay, you might be soon enough.

If you want to be an entrepreneur you should seek mentors and learn how to be with them.

  1. Be respectful — This doesn’t mean grovel and this doesn’t mean do everything your mentor tells you. Being respectful means making good use of the time you’re given by being prepared. Being respectful means asking for and working with communication preferences (I learned this one the embarrassing way). Being respectful means saying “Thank You.” I can’t tell you how rarely I’m thanked in a way that goes beyond “Thanks for your time” in an email or at the close of a conversation. I don’t do it for the gratitude, but it’s nice to be appreciated. Finally, being respectful means respecting your mentor’s desire to mentor you. It is unlikely that you have anything of value to offer your mentor by way of quid-pro-quo services. Your mentors are being rewarded other ways for helping you: maybe they get to stay current on new tech, maybe they feel good when they help, maybe they’re paying it forward. Don’t take their reward by trying to make mentorship transactional. On that note:
  2. Be respectful — No, this isn’t a typo, it’s just a different type of respect. Be respectful of yourself. You’re doing something that matters. Your mentor agrees. Don’t apologize for yourself and don’t think that you have nothing to offer your mentors in return for their assistance. You have gratitude and you have your business. If you’re making a good attempt at both, your mentor should be truly very happy.
  3. Be honest — I cannot tell you how many times it has happened that a mentee of mine hid the truth from me or tried to soften it. Whether you shit the bed, didn’t listen to your mentor’s advice, or you’re really stuck on something that you and your mentor have already covered a bunch of times, just be honest. If your mentor doesn’t know where you are, your mentor can’t help you. By the way, this is true for investors as well.
  4. Work hard — Nothing is more frustrating than giving your time to someone who isn’t putting in the work. If you’re not getting along as quickly as you like, keep going, pivot, ask for help. Whatever you do, do something and let your mentor know.

That’s it. Have I missed something? Let me know in the comments.

psst… Like this post? Click the heart!