5 Things I've Learned About Mentorship

Two days ago, in a post about my mentor, someone commented that it is hard to find a mentor. I asked the person if I should write a post about ways to find a mentor and another person chimed in with a broader suggestion. He wrote that it'd be more valuable for me to answer questions (or set expectations) on working with someone with my mentor's profile and time constraints. I'm going to try to keep it simple here with five questions answered:

1. How did I meet my mentor(s)?

I believe you can only accomplish what you believe is possible. Often times, the best way to feel something is possible is to see someone else do some version of it. This is one of the best things about mentorship: the ability to learn from people who have done what you're attempting to do. For me as a black CEO in tech, I'm looking for other people of color and women to advise me often because their experiences are likely more similar to my own. For a young Michael Jordan, that meant looking at David Thompson’s success in college basketball. For Barack Obama, that may have meant looking at Nelson Mandela’s or Abe Lincoln’s journeys to the Presidency. For me, as an entrepreneur and CEO, it often means finding other entrepreneurs or CEOs for insight and advice. Routinely, I find myself learning from peers like Jason Mayden, CEO of SuperHeroic, Joshua Kissi, co-founder of TONL, and Eugene Kan, co-founder of Maekan.

When I exited my last business, I did so knowing I wanted to take a job working at Bazaarvoice (then the hottest startup in Austin) where I’d learn directly from people like Heather Brunner (then-COO) and Brett Hurt (the founder and then-CEO), and open myself up to them as potential advisers down the road when I started my own technology startup. I'm thankful to call both of them advisers and investors in Localeur, today. Similarly, when I worked in public affairs in D.C. at the start of my career, people like Joe Householder and Dick Keil were instrumental in helping me understand the industry. These two men, along with a few others from my DC years, are invested in Localeur as well. Needless to say, the best way to make a mentor is to put yourself in a position to learn from others over time, whether in an official capacity or not. Far too many young people come up to me after talks I give at colleges and conferences and say, “I have an idea for an app” or “I’m going to be an entrepreneur.” So many of these individuals are greeted with harsh realities soon after they begin launching a business because they’ve never worked for someone else who founded a startup or ran a business. Working with and for someone you admire and respect is a phenomenal way to find a mentor, even if that means in a some type of volunteer capacity.

2. How did I get the person(s) to agree to mentor me?

I have never once in my life asked someone outright, “will you be my mentor?” Not once. For those who go around on LinkedIn sending messages to people they’ve never met asking for advice or mentorship, my recommendation is to stop immediately. Instead, put yourself in a position to be mentored. Take a job where you’ll learn. Attend conferences or events where the people you admire are speaking so you can ask questions. Volunteer for the nonprofits where your (hopeful) mentors are board members. Only after demonstrating a genuine interest, desire to learn and true sense of patience (rather than giving off the instant gratification vibes that have become the bane of managing people in the millennial generation and explain why something like Fyre Fest was such a disaster for the attendees and founder alike) will someone in a position of leadership and influence truly take note of the benefits of mentoring you. I’ve found this to be true over and over again, from high school teachers and college professors who’ve taken an interest in me to bosses who’ve mentored me even more actively once I became a former employee and they could embrace my full range of interests more than when they were working to optimize me for a particular role I was hired for at their company.

3. How often do I meet/talk with my mentor(s) and what are the conversations like?

Everyone is different, but generally there doesn’t need to be any kind of scheduled cadence in my experience. Sometimes, it’s a breakfast or lunch meeting once every 4 to 6 months and other times it’s the occasional phone call. Regardless, the most important sign of mentorship to me isn’t frequency of communication, but the authenticity of the communication. Is this someone who is really listening to you and what you’re thinking/experiencing/working toward and sharing feedback/thoughts/advice or is it someone who is simply using their own experiences to tell you to do things just as they did. I once met a VC in Austin who started telling me how I should run Localeur before I even had a full minute to share my vision for Localeur. That’s not an investor I’d want much less mentor material. Instead, I’ve always sought out people who lead with empathy, listen as much as they speak (something I’m constantly working to improve myself) and are always sharing advice and feedback from the point of view of someone who has a set of experiences that may or may not help me in my situation(s) rather than someone who presents their experiences as fact to be followed sun up to sundown by every person on the planet. My high school track coach and his wife probably don’t consider themselves mentors of mine because they aren’t entrepreneurs or CEOs (he’s an AP history teacher and she’s a nurse), but they certainly are because of their having listened to my situations over the last 20 years and always giving me honest, nonjudgmental feedback.

[I want to make a note here that I recently had one of the most amazing and powerful conversations with Heather about white privilege, and her ability to "go there" with me and share her feelings and listen to my experiences was probably one of the five most important "professional" conversations I've ever had. Further proof she's a badass person and mentor.]

4. Do you apply any type of measurable goals or is it just advice?

There are so many things in life worth measuring. Grades on a report card. Points in a game. Box office results for a sequel. Funds invested in minority founders for Silicon Valley VC firms (though few actually do). I could go on and on, but I don’t put mentorship in there.

For me, mentorship is about relationships not goals. The intent of the relationships I have with my mentors is to become a better version of myself, not only as a business leader, but as a human being. I could care less if a potential mentor is the CEO of the biggest company in the world if that same person does little to give back to others, is a terrible spouse/parent/friend/boss. I am solely interested in relationships that feed the full version of me, not just the CEO or entrepreneur. For this reason, the only measurable part of mentorship for me is longevity. Case in point, I have 100 investors in Localeur and dozens of them are people who’ve known me since high school, college, my time in DC, previous jobs and businesses. These are people who've helped me reach my potential. To me, the longevity of those relationships and the people who I seek advice and mentorship from is testament to the value I continue to receive from them and they continue to receive from me.

5. How do you return value to a mentor?

This is probably the single most important question involving mentorship. If you have a great understanding of how you’ll provide value to a mentor, you’ll have a much better chance of actually getting the high-level mentors you seek and keeping them in your personal board of directors (a broader group of people whom you rely upon over time to provide feedback and counsel at various stages of your life and career). For me, I’ve always known I bring two distinct things to the table as a mentee:

1. I am a connector. I am constantly making introductions for people and also sharing information with others that puts me in a position for people to view me as both a human and information connector. From media/press relationships I've shared to books I've recommended, connecting people and information is a big part of who I am.

2. I am a promoter. Routinely, I am acting as a cheerleader and promoter of my mentors and their respective businesses, endeavors and milestones. I'm paying it forward over and over again. Something as simple as sharing a news article on a mentor on Twitter or Facebook can make a big difference in helping that person realize how appreciated and valued they are to you (and others whom see the things you share). 

Ultimately, the give of mentorship is far more valuable than the get because the more you give to mentors (and others in general), the more experience you’ll have figuring out how to ask others to give to you. Mentorship is perhaps one of the best “train the trainers” systems in history. It’s not just about giving someone fish. It’s teaching them how to fish and how to have the people you teach to fish go on to teach others to do the same. 

I'll end with one final note. Several of my friends happen to be black and female founders, creatives and business owners. They are photographers, musicians, tech startup founders and more. Many of them have started the businesses they run today and had some of their biggest professional milestones because they had the confidence to start and felt they could succeed after watching my journey and limited success. To me, the greatest gift of mentorship is the feeling of knowing that whether or not someone calls you their mentor everyday or not, you have played a positive role in shaping someone else's personal and professional journey and unlocking that person's full potential as a person and leader. I try to give my mentors that feeling and public acknowledgment because they've done that for me.