GP Interview: Andy Weissman

Andy Weissman is a managing partner at Union Square Ventures in New York City. This is his Emerging Manager interview.

👉  Big Learnings Up Front (B.L.U.F.): Publishing public investment memos forces clear and open thinking. Checklists create better prepared pitch meetings. Having reserves is a many-sided advantage.

Andy, tell us about yourself

My family consists, on both sides, of New Yorkers. Some member of my family has lived continuously in New York City for 120 years. I am part of that tradition. Started with a career in media transactional law, stumbled into technology at AOL in the mid 90s, fell into venture capital in the 00s, bumped into an old colleague and started a company around 2006, lept back into venture in 2012 or so.

Describe your fund

Union Square Ventures is a thesis and process driven fund. This means a few things:

  1. We invest according to a thesis. We publish this thesis (and its variations and ideas surround and relating thereto). This is meant to be a dynamic process or conversation with the market.

  2. The funds are small - generally $200M.

  3. We publish our investment memos as blog posts. There is no other internal record of an investment than that public facing writing. I like to think of this as a forcing function of sorts.

  4. We don’t vote, instead making decisions collaboratively. 

I have written a bit about this here and in a recent post I also wrote:

As always, we remain committed to our way of practicing venture capital and finding those companies that believe we can be great partners. Our funds are small. Our focus is thesis-driven. Our website is a compilation of ideas from ourselves and others, constantly evolving yet always open and public. We publish our investment memos as blog posts. We are active partners to all the companies we invest in at all times. And our decision making is collaborative (we don’t vote). 

Share one process improvement you’ve used individually or as a team which has made you a better fund manager

A few things: as above, the publishing of investment memos as blog posts and the forcing function that results from that.

Secondly, we created a one page “checklist” with 10 questions we use for each company coming to present to us - the idea was how to internally get 11 people  in the same factual mindset before an investment. These questions include:

What does the business do?

Is this a non-obvious idea

What is the two-sentence thesis for this investment? 

How is this company market expanding?

What are the key risks we need to be comfortable with to do this?

What is our thesis for the long term defensibility of this business?

What are the strengths of the team with regard to the company’s strategy?

How diverse is the founding team?

And third, we are obsessive about doing reserves analyses for each of our funds, often. This ensures we have the capital we need to support our companies and their changing conditions.

Which founder from your portfolio has had the greatest impact on you and why?

A founder of a recent investment that we havent announced so I am not at liberty to say who it is. But her career is an inspiration. She is a first time founder yet it feels like everything she has done has led to this moment.  

What’s one thing you wish you knew before you became a VC?

How long the average hold periods are, and would become.

Tell us the story of a rabbit hole you recently fell deep into

Jerry Seinfeld recently said: 

That's the paradise of standup comedy. Standup comics receive a score on what they are doing more often and more critically than any other human on earth

Which has continued a long-standing attempt by me at understanding how comedians work. For, as captured in that quote, the feedback loop for stand up comedy is instantaneous. I feel like I have so much more to learn from that. Related: Steve Martin’s Born Standing Up is the best book about an entrepreneur's journey that I have ever read.   

Name one GP and one LP everyone should learn from -- and whom we should feature next

GP: Caroline Kassie, Metrodora Ventures (I am only interested in learning from first time managers these days)

LP: Beezer Clarkson

Finally, what are the 3 best emojis?

🎶 🎸 🤟🏼

Andy Weissman is now on the EM roster at << View all these EMs, learn from them and then teach me some new things. 

Andy’s contacts: @aweissman or Thank you, Andy, for being open to sharing your time — Reilly