As I’ve gotten older I’ve become increasingly reflective on the seemingly random twists and turns in my life. Most of this consideration has gone towards my professional life, as I was blessed with meeting my life partner in college and, therefore, my personal life has largely been “up and to the right” since meeting the person of my dreams. But oh, that career… As I’ve thought deeply about exactly how I arrived at my current circumstance, there is a common element that has influenced each twist and turn I’ve taken: trusted mentors. While there is no doubt that I’ve done the work, taken the risks and pushed myself to the brink, it would be both disingenuous and inaccurate to say that I’ve done it completely on my own: I’ve been influenced by many great people who have, and continue to have, a marked impact on my thought process and decision-making. It actually boggles my mind to think about the generosity and helpfulness provided by these individuals, whether advice and counsel on a specific issue, hugely valuable contacts they’ve made or just a kick in the ass to say “keep it up,” they’ve without question had a material and positive impact on my outcomes (for which I feel incredibly fortunate). So, this message is both a call to action to the ambitious, curious and those hungry for guidance and a shout out to mentors everywhere who have positively impacted the destinies of their acolytes: because you rock. And I regularly try and give back in this same way, as I know the power of the mentor role and how beneficial it can be for the right person thirsting for such coaching and empowerment.
During my time on Wall Street, I was young, green, yet hungry for knowledge. I started in M&A, and personally found it to be pretty dull. After a few years, I identified a mentor who helped me transition from M&A to Capital Structuring, which may sound boring to you but was pretty cool to me. Designing new financial instruments. Solving complex problems. I was psyched. I did this for a few years, at which point I felt I wanted a break to consider other options in my career, principally on the buy-side. I went to grad school while consulting part-time, and settled on a transition to money management as my post-graduate school objective. I received some offers and was excited, but was then asked my my original mentor to meet with the Global Head of Derivatives at my original employer. Let me say, however, that derivatives, trading, etc. were nowhere in my thought process. I was going buy-side, period. I had it all figured out. Well…
After my mentor recommended the meeting, which of course I took notwithstanding the “certainty” of my thought process, I spent several hours with the head of derivatives and his team. Long story short, they sold me on my unconventional corporate finance background as being a true competitive advantage in the future of the derivatives world, circa early-1990s. But, I said, I’ve never taken a course in options or futures. No problem, they replied, we can teach you that. You’re a mathy guy. But I don’t know the first thing about advising large corporations on risk management strategies. Well, they retorted, you understand how to speak to large corporations about solving complex problems. Corporate risk is a complex problem. Well, I already have these cool buy-side offers and I’m outta here. But are you really sure you want to do that, after the six years of relationship equity you’ve built up here and the greenfield opportunity we’re offering to you? Uh, uh, uh….ok. I consulted with my mentor who said the following: give it a shot. It may not feel like the easy or comfortable thing to do, but you’re already a respected member of the firm, we know you well, and we’ll put you in a challenging position but one where we’re confident that you’ll be successful. Why not give it a shot? I was 27, ready for a challenge, and chucked my buy-side aspirations aside because the opportunity sounded interesting but also because my mentor introduced it to me and sold it to me through their wisdom. I took it. And it was one of the best business and life decisions I ever made.
After the firm went through a merger and the culture markedly changed (for the worse), I decided to leave. It was a terribly hard decision but I knew within myself that my learning had stopped a new and exciting challenge was in the offing. I was recruited to help re-build a new business after its decimation in the wake of a tough merger. I joined a group of super smart, super motivated mercenaries whose goal was to kick the crap out of the Wall Street incumbents and to do so with intellect, aggressive risk taking and a shared mission of making money between Sales and Trading (which is a huge cultural barrier to overcome). It was a magical time and one which started out as a long shot but quickly turned into reality. We did rock it and moving myself out of my comfort zone in my original firm is exactly what I needed to grow. And I found a set of new mentors to help me manage this transition and chart the next phase of my career. After helping to build Equity Derivatives at my new firm for three years, I was ready for a new challenge. My most senior mentor helped me transition into the leadership of a massive quantitative trading business, the learnings from which have had a dramatic impact on my career ever since.
I decided to leave Wall Street after I felt my learnings (and fun) had run their course, and left to pursue a new career with passion and intensity: seed stage technology investing in data-intensive businesses. It started in 2004 and has continued unabated. It has been an amazing metamorphosis from Wall Street leader to angel investor to venture capitalist. And each step of the way I have been aided by trusted mentors. Whether it was key connections, perspectives on how to best help entrepreneurs or terms concerning my fund, my mentors have been essential elements of my thought processes and de-risked my decision making at every turn.
I’ve spoken about mentors in the abstract. But how should one best engage a mentor and secure their support?
- Be clear when articulating your objectives. Targeting a mentor for assistance is fine, but without focus the relationship will fall flat. Most great mentors are extremely busy in their own right and you owe them a clear story with a clear ask and a clear purpose.
- Make sure it is a two-way relationship. While there is generally a power imbalance in the mentor relationship, there is no reason why one being mentored can’t deliver value to their mentor. It can be small stuff, like referring investment opportunities, presenting ideas, or showing in potential recruiting candidates. Or it can even be taking their advice and keeping them posted. Whatever it is, the point is that you should be considerate of the mentor and their sacrifice and be helpful however you can be. The great mentor never asks for such things; you just deliver it.
- Sweat the little things. Always say thank you. Never burn a relationship that the mentor has initiated for you. Be considerate when something the mentor has done yields great gains for you. The mentor gets great satisfaction from hearing of their acolyte’s wins. Make sure you share the victory with them.
- Remember the “karma boomerang.” If you are successful identifying and benefiting from great mentors, remember the value they have brought to your life and give that to others. The greatest gift is to learn how to give; a great mentor has shown you the way. Now it is your responsibility to teach another. Though you are surely busy, be sure you carve enough time out for select mentor relationships and always remember the power you have to impact the lives of others.
Words are inadequate to describe the benefits to one who does a good job identifying, soliciting and working with great mentors. Life in all its aspects is complex, and having the coaching and support of those more experienced than you can be the difference between making smart, well-informed decisions and poor decisions. And these relationships can follow you throughout your life. Take control. Admit your weaknesses. And build lasting relationships to help augment that “white space” in your experience base. It will pay dividends the magnitude of which is hard to comprehend.