My Career Mistake: Not Cultivating Enough Mentorship

The error of omission.

In a previous Venture Upward post about plotting your next career move, I recommended proactively seeking out and fostering senior VC co-investor relationships at other firms as soon as you begin your first VC job.  The primary tangible benefit of this activity is to lay the groundwork for finding your next role in the business.  However, this endeavor is also beneficial for career advancement, as these relationships can yield valuable mentorship.

Early in my venture career, I was fortunate to have two direct bosses at two different firms. Both were exceptional investors, and each employed drastically different investing styles. I learned a tremendous amount from these leaders, which I incorporate  into my daily practice today.  And yes, I did establish relationships with partners at other firms who were much more senior.  I believe I did it quite well, actually, likely better than many of my peers.  As a result, some of those people have been incredibly helpful over the past 15+ years I’ve worked in venture, especially when my now partners and I were starting NextView. Most notably, a handful of them went absolutely out of their way to help us, including warmly introducing us to LPs and even investing their own money into our first fund. To those people, I am and will always be extremely grateful.

All of this being said, my career mistake was that I didn’t take the relationships with more senior VCs one step further.  I found exceptional, wise teachers and unyielding supporters.  However, it seems true mentorship goes beyond those roles.  I suspect that I didn’t open up myself to becoming a real mentee as I didn’t show genuine vulnerability.  I didn’t want to exhibit weakness.  I didn’t ask for help when I didn’t know what to do, or when I was facing unexpected challenges.

Venture is a lonely game, and even though you’re constantly interacting with people, your ultimate success depends on a one-person track record.  I didn’t want to share my concerns or my mistakes with anyone, out of fear of looking inept.  Given the competitive nature of VC, it’s challenging to know who to trust, out of concern that potentially damaging information will leak or worse, result in losing your seat.  Reflecting back, however, I could have benefited from counsel on navigating the political landscape of my (former) firms, encouragement earlier in my career to think about LP relationships, and critical feedback about which investments I should pursue.  In retrospect, I was too naïve and idealistic about the path towards building a track record in this business, and would have benefited from guidance about approaching it.

The benefits of the first step — establishing authentic relationships with more senior folks including those outside your firm — are clear and with little downside.  While these efforts establish a foundation for landing your next gig, I encourage you to not stop there.  Identify relationships which may have the capacity to be uniquely special and risk some vulnerability.  Sharing current challenges and struggles with a sincere ear for advice provides the opportunity for something even more valuable than your next job.  Real mentorship can help positively shape your career as an investor, accelerating even faster.