Success in Venture Capital comes down to getting an entrepreneur to pick you.

And getting lucky.


Success in sourcing is about seeing a large number of potentially interesting companies. This is mostly about having high activity. Like sales, sourcing is a numbers game. And the harder you work, the more companies that you meet. The more companies you meet, the more likely you are to find great ones.

Additionally, if people like you, you’re more likely to get referred interesting companies.


Differentiating good from great is about miles. You can’t tell if a company is one in ten, one in a hundred or one in a thousand until you’ve seen a thousand companies. And you want to invest in “one in a thousand” companies. You’ve got to put in the miles, and see enough companies to be able to judge greatness. This happens with time, and once again with work ethic. More miles per day builds your mileage faster.


Getting Selected

Winning competitive deals is by far the hardest part of venture in the long term. Most great deals are competitive. These days, co-leads are uncommon, so there is typically only room for one new lead investor. If the founders don’t choose you to lead the round, there is no prize for second place. I came in second to Peter Fenton on Yelp in my first year of venture, and watched it go public from the sidelines six years later. That was a wake up call for me. Winners are grinners and everyone else goes empty handed.

— Building expertise in a domain that few others have,

— Investing earlier than others,

— Going to a geography that isn’t well covered by others, or

— Tapping a network that others do not.

You need to think hard about what that advantage will be. “Being smart”, “working hard”, “caring for my companies” or “being likable” are not differentiators in venture today. These are table stakes.

Getting Lucky

Luck is the final ingredient to being a good VC. It doesn’t get enough credit. Luck is always part of the game, whether as an investor or founder. Looking back we tend to tell stories about how it was all inevitable, and how this decision or that factor was what caused the success. But that is survivorship bias writ large.

“Luck = preparation + opportunity”.

To some extent you can make your own luck, or at least you can put yourself in the path of where luck may be more likely. Seeking upside volatility is a winning strategy. In any investment, there are always lots of reasons to say no. Good investors listen to all those reasons but also find the key reason to say yes.

Success in VC

Success in VC is path dependent. Once you have made good investments, sourcing, sorting, getting selected and shepherding all become easier. And luck comes your way more often as well.


Alex Taussig’s interview with The Twenty Minute VC

Nicole Quinn’s interview with Girlboss Radio (referenced above)

Semil Shah’s interview with Recode Decode

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