At Next Big Sound we have been incredibly fortunate to have world class mentors. I count Troy Henikoff and Jason Mendelson as the two most impactful. Instead of talking about them in particular this post I’d like to pass on what I’ve learned about finding and engaging mentors overall.
I’ve had people ask me explicitly to “be their mentor.” It’s not like a thesis advisor, or any formal position, it’s a relationship and like any relationship, it needs to be two ways. But what could a 40-year-old serial entrepreneur or venture capitalist possibly learn from a 22-year-old, first-time entrepreneur? And with hundreds or thousands of people reaching out to them each year for money or advice, why would they spend an inordinate amount of time and energy with any one of them? A feedback loop. Closing the circuit. Let me explain.
I’m sure I get 1000x less inbound requests than Jason or Troy but now that I have a lot of people reaching out to “pick my brain” I can get a sense of what happens even at my scale. I’ll have one 30 minute, first time, meeting with someone who connected with me via a warm introduction. The 30 minutes are slammed in the middle of an afternoon between my calls with customers, investors, current team members and prospective hires etc. I spend the first 10 minutes orienting myself to their situation - trying to subtly remind myself how we were connected, where they came from, where they are going, what they hope to get out of this meeting etc. We dive into a few areas and I will go into whatever relevant areas they want to talk about. We usually end the last few minutes with me prescribing something I’ve said before: time-gating; pre-mortem analysis; or don’t ask for money, ask for advice. Or I’ll make a few introductions. And then just as quick as the relationship started, it ends.
Here is where the feedback loop comes in. Right here, where 99% of people fall off the face of the earth, right here is where the relationship can become bi-directional and start building towards something beneficial for both sides. A quick note that says what happened!!#@&!
Did you use time-gating and it blew up in your face? Was the pre-mortem supremely helpful? Why? Did the introduction lead to the job you wanted? Or was it a waste of time? Even if you did literally the opposite of my advice, and it worked like a charm, that would be incredibly useful for me to know so I can stop blindly recommending something and can adjust my world-view.
If I wanted to find an amazing group of people who could be in my corner, give me advice along the way, and mentor me through a dynamic time in my life here is what I would do:
- Set a calendar alarm 2-4 weeks after my first meeting with the person with a reminder of the distinct piece of advice that was given or introduction that was made.
- Send them a short email that day with the implementation of the advice, what happened, and any other articles, video or reading on the topic that is relevant (this last one is just a bonus).
- I would set a second calendar alert for that person 4-8 weeks after that to ask for another quick call or email with hopefully a new, specific challenge I was facing.
- Rinse and repeat.
This obviously has to be paired with continual progress, sincere professional challenges you are facing, and solid interpersonal chemistry, but this is one of the surest ways I know to “find a mentor.”
For avoidance of doubt - I was far too clueless to do this with Troy or Jason, Troy was a professor of mine at Northwestern so we had forced interactions every week for 12 weeks. Jason was a warm intro and then lead mentor during Techstars for 12 weeks. My recipe above is trying to manufacture something like that in the wild and I’ve ended up using it with success myself.