Mentorship, Maturation, and Youthful Hubris

Posted on January 6, 2011. Filed under: startups, venture capital | Tags: |

I had breakfast this morning with Hemant Taneja. He is one of the few people in this world I would call a mentor (I’d put Ken into that category, and maybe one or two others, but that’s it).  Hemant has known me since the day I stepped foot into the startup world, and both watched and coached me through my development as an investor, a thinker, and an entrepreneur.  Many of the lessons I’ve learned about balancing confidence and humility came from him.  I remember in the first 6 months that I was at General Catalyst, I started to develop what I thought were really smart ideas and opinions about deals, investing, and what was the future.  I’d speak with authority on what was “smart and stupid” for the firm to back, and felt fortunate that the guys at the firm gave me the time and thought it worth listening.

As a young guy, who’s only previous experience was working on wall street where nobody gave me any respect or cared at all what I “thought,” this newfound microphone became intoxicating.  I was not mature enough to handle the shift in responsibility and status that I was experiencing, which was expressed in the form of a “swagger” that was not yet earned.  I remember Hemant sitting me down one day and saying “listen, you’re really smart and creative.  Your showing a ton of potential and you could be great, but you won’t know that for 5 to 7 years.”  He was referring to the fact that venture investments don’t exit for a long time, and you never know if a bet was good or not till the money comes back in.  He said, “make a spreadsheet, keep track of what you stood behind and what you passed on.  Watch how those decisions play out and measure yourself objectively.”  I internalized that advice and I believe it was one of the pivotal moments that began a practice of deeply objective and rigorous self analysis that is now core to my life.

As we ate breakfast this morning, I shared with him yet another discovery of my naïveté during the early years of my venture life that it took me 5 years to uncover.  I used to (and to some extent still do) hang my hat on an ability to see large macro trends unfolding across markets.  I used to scoff a bit at “experience” and believe that I could see the direction of a market better than most of the “old guys” at General Catalyst.  That may have been partially true, but the variable of duration of a given trend or phenomenon was lacking.  I had not been in the business long enough to see trends in the context of cycles, so in my mind every directional shift was linear and not-cyclical.  If it appeared that the world was moving from “destination” site to “distributed UX,” the future 2, 5, and 10 years out was always “distributed.”  A combination of spending a lot of time with Ken (who has seen a number of cycles in his career), and observation of the first inflection points in the trend curves I was watching five years ago, has humbled the early version of myself and warmed me to the value of experience as a complement to capacity.

It’s very strange to consciously watch yourself mature.  I can now see my former self through the lens of a more experienced investor and entrepreneur and I must have been such a pain in the ass to the Partners as GC.  Thanks for putting up with me guys.  I owe you a lot.

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6 Responses to “Mentorship, Maturation, and Youthful Hubris”

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It’s all about pattern recognition + guts Joran:

“These two qualities are in tension and inconsistent with each other.”

so true

another example of cyclicality: when i worked at GC, the future of software was “moving to the cloud” and away from downloads and installed…today apple launches the Mac App store, return to “downloaded software” (vs) fully hosted applications

No doubt that experience allows you to take a longer view and avoid pitfalls made by others. But inexperience can also be beneficial. Not following the “rules” laid out by others, or going for it in unproven markets can only be done with a healthy disregard for what the “old guys” think.

agree. read Weissman’s post in these comments. He nails the balance/tension

Great post. Thanks for sharing your experience and perspective.

Good mentors are true gems. Beyond value.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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