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Non-Athletes Can't Be The Best Coaches
You cannot learn without getting your hands dirty. You cannot coach without training first.
I recently grabbed coffee with a friend, Shawn, who is running his own fund, who's got a really interesting background– starting as a lawyer, in huge publicly traded corporates, and now operating a VC, working with the small fish (startups.) In between, he worked an operator role at a huge investment firm, helping turn around & grow business.
Quick side note: I’d like to grab coffee with more interesting individuals over the next few weeks. I’ll be in Lisbon, & London, and would love to get in touch with interesting people. Drop an email to email@example.com, or message me on twitter / linkedin
It was a really interesting chat, particularly his perspectives on:
Why VC is a terrible career starting point, even if you want to become a VC
Fund management & investing are entirely different skills → this relates to a broader separation of business/operation skills vs. the ‘art’ of what you do
If you want to be the best coach, you at least have to have been in the position of an athlete at some point, for some significant period of time. This was an analogy I made to his point, about why VC isn’t a place he recommends to start careers.
In junior capacities in VC, second what he told me, you spend most of your time either doing grunt work for new deals, or trying to help grow existing portfolio companies. The thesis of his point, though, was that it’s virtually impossible to help a company grow when you’ve never done anything of that sort yourself– sure, text book theory is great for exams, but when the wheels hit the road, that stuff flies out.
Through my analogy, this is effectively like reading all about how to do push-ups, and exercise, and then trying to be an effective personal trainer from that. Sure, perhaps it’s not impossible, but you certainly aren’t likely to be the best at what you do. It’s hard to be among the best.
TL;DR: If you want to become a personal trainer, then train yourself first.
He suggested that even if you want to do VC, it’s more useful to try act in some kind of operator role, whether as a part of a larger company, or perhaps in a venture of your own, before trying to teach, coach, or talk strategies with portfolio companies. His equivalent to this was helping as an operator at the large investment firm he worked at.
Granted, though, I still think the teacher ultimately learns twice– this is an important note I want to attach to the above thought. If you then start training people, you will very quickly learn much more about how training works, or doesn’t work, on different people. You can extrapolate that analogy to VC work, or other domains.
This is a large part of why I chose to start a business by myself, without investors or co-founders– it’s going to force me to learn how to grow my own business first, run my own team, etc. I have come to learn that’s a very different skillset to development, and not as trivial as I thought from an outsider perspective.
This arcs off into the second point, around how fund management and investing are skills often conflated as being similar, and on a broader basis, how a business skillset is vastly different from the ‘art’ or whatever is being sold.
In the case of VC, Shawn pointed out many young VCs cropped up during the crypto bull market, who later crashed & burned when realising fund management was not what they’d hoped for. He pointed out fund management is really more a mix of knowing legal & accounting structures, and managing teams & stakeholders, much like managing a business. Investing is just the thing you’re selling.
This is something I intellectually recognised for a long time, but have come to internalise it much more, as I’ve realised just how vast the business skillset is. It’s very versatile, but equally, very hard to master.