What We Learned This Year

This was a big year for Collaborative Fund.

We raised a $100 million fund. Moved into a new office in New York. Opened a new office in San Francisco. Welcomed four new team members. We looked at more than 2,000 companies. Invested in 35 of them. We thought a lot. And we learned a lot.

Here are a few of the biggest things we learned.

Craig Shapiro: One thing I continue to learn is patience. After roughly eight years of actively planting seeds, we are on the cusp of seeing two of our early investments go public. Getting comfortable with a long feedback loop, especially when investing early, is so hard but also gratifying!

Lily Bernicker: Offering straightforward feedback on what you love about an idea or a company is just as, if not more, important than being transparent on what made you say no. There are plenty of challenges that a founder might not have any control over. And you might be wrong about the importance of those challenges. Focusing on what you find to be really strong or compelling in a person’s idea, company, or performance can help them focus on what makes them stand out.

Taylor Greene: I learned that some of the best developers are flocking to work on the blockchain. I also learned that the retail landscape is quickly changing - brick and mortar is now a core strategy for many businesses (Foxtrot, Fourpost, For Days).

Tejinder Gill: There are still plenty of exciting consumer companies being built. The very best opportunities have to be created.

Matt Lucas: Personally, I learned the importance of fear and regret in approaching risky decisions. The lesson is not to be afraid of taking risks in general, but to be afraid of not taking the right risks and regretting it later. “Good risks are those that you will both regret not taking and won’t regret if they backfire.” I also learned a ton about mechanism design and distributed decision systems (big shoutout to Princeton professor Matt Weinberg). I learned how to construct a stable matching in college admissions or dating, how to fairly cut a cake, how to run an auction, why no voting system is perfect, how cryptoasset mining incentives sans block reward are complicated, and why proof-of-stake is difficult to get right.

Josh Lubov: It is hard to maintain the culture of an organization, especially when you add new members to the group, but it is possible if you really work at it – and are aware of this priority when making decisions to hire new resources.

Stephen McKeon: I learned that public market prices and early-stage development can and often do move in opposite directions. During the last twelve months we’ve witnessed a substantial decline in the prices of cryptoassets such as bitcoin, ether, and stellar, but meanwhile a massive flood of talent entered the space to launch early-stage projects at an unprecedented pace. As these projects launch and gain traction it will power the next wave of value creation over the coming years and I’m looking forward to deploying capital into the sea change that impacts how investable assets are created, held, and traded.

Lauren Loktev: I learned that less is in our control than we tend to think. But if we learn from the detours, the preset destination is less important than we think, too. Applies to people and startups alike.

Jeff Ullrich: One thing I learned was actually more an affirmation of something I’m already a staunch believer in: the age-old adage “Teamwork makes the dream work.” With a few more lyrics and some rhythm, you’ve got yourself Collaborative’s theme song for 2018!

Nicole Diloreto: I have learned how important and invaluable it is to have a loving and supportive team around you and it never hurts to ask for help.

Morgan Housel: Things that look unsustainable can last years longer than anyone thinks. I’ve been learning this every year for about the last eight years, but each year I’m surprised at the number of things I assumed couldn’t last that remain alive and well.


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