“Do you know where we are?” asked Milo.

“Certainly,” he replied, “we’re right here on this very spot. Besides, being lost is never a matter of not knowing where you are; it's a matter of not knowing where you aren't – and I don’t care at all about where I’m not."

In The End It’s All Guesswork

…So investors generally work with people they like. (A great comment from Naval on Venture Hacks.)

The past year at Penny Black, a new venture capital firm in New York, has been a fantastic and eye-opening experience. As I learn more and more about the VC side of the table, however, one thing that continues to nag at me is the difficulty in learning what makes a good startup investment in a sea of great ideas and great entrepreneurs.

It doesn’t help that the traditional exit horizon (when you learn if you have succeeded or failed) for a venture capital investment is generally 3 to 5, or even 7 to 9 years, making it very difficult to quickly learn from your mistakes. My only consolation is that it seems like this issue plagues much of the venture capital world, as evidenced by the poor returns the industry has faced over the past decade.

I can see many reasons for this: Defining Pia broader asymmetry of information in young companies, a lack of data in new markets, and the fact that there are too many variables and not enough hard numbers in startup companies. I’m not complaining though - if you were able to make a science out of venture capital, the profession largely wouldn’t exist, at least not in its current form.

Though lately I feel like due diligence on a startup is similar to trying to define pi – you keep getting endlessly closer to an answer with more and more data and research, until finally you’re forced to make a simple gut decision.

Given this, if you want to be funded I’m convinced that it’s most important to just be a generally nice and friendly person. Everything else is simply signaling.


Juventas Fugit  is designed and written by Justin Wohlstadter, who, when not writing in the third person, can be found in a coffee shop talking about startups, thinking about the future of education, and generally procrastinating something important.

  • Passions: startups that positively affect the world, education innovation, good design, learning, and meeting those with an equally insatiable curiosity.
  • Play: building new ways for people to connect and explore knowledge at Wayfinder.
  • Previously: was director of product design at Enterproid (acquired by Google). Before that I built the early-stage venture arm of Penny Black and co-founded BOLDstart Ventures, where I was lucky enough to invest in some awesome startups including Rapportive (acquired by Linkedin), Blaze (acquired by Akamai), GoInstant (acquired by Salesforce), Klout (acquired by Lithium), Enterproid (acquired by Google), IndieGoGo and many more. And before all of this I was involved in a bunch of other crazy, less successful startup ventures involving fire extinguishers, measuring philanthropic impact, and creative spaces.
  • Pedantry: most of the important stuff I taught myself or learned from friends, but I’m fortunate to have also (barely received) degrees from Harvard and Oxford. At Oxford I wrote my dissertation on how internet innovation will disrupt access to higher education.
  • Procrastination: can be found on Twitter, Linkedin, AngelList and other web spaces, and be reached via email at my first name at this domain.
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