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Contrary Spotlight: Will Robbins

Sep 26, 2019

Will joined Contrary in 2017. Although officially an investor, he wears every hat within the firm.

Between writing apps with 100k+ downloads at age 16, working on growth at seed-stage startups, and building infrastructure at software companies, Will draws from a broad set of experiences.

To share the perspective of someone on Contrary’s full-time leadership team, we asked Will six questions:

1. Out of all things in the world… why Contrary?

I have a lot of interests. I’ve had a lot of role models too — in my family there was a therapist, investor, theoretical physicist, homemaker, Swiss-immigrant liquor store manager, and Cuban lawyer, so I grew up with every curiosity satisfied.

That’s largely why I’d be an easily-distracted founder, but just being a VC would feel a bit sterile. By working on Contrary I get a good mix of both — the gritty ups and downs of building a firm, but also the variety that comes with lots of interesting founder conversations.

Most importantly, I’ve made some really close friends here!

2. What are some frameworks you’ve learned or live by?

This could be a long post on it’s own. For starters, one piece of conventional wisdom goes something like “stay balanced”. In my view that can be dangerous thinking: the most fun, meaningful, and exciting times in my life so far have been anything but that. Maybe the trick is to make sure your direction or method of unbalance changes frequently enough.

Along similar lines, I also reject advice that sounds like “don’t care what others think about you”. I think there are plenty of people you should ignore, but you should care deeply about what your family and close friends think of you. This rule works for personal finance too. Cut mercilessly on things you don’t care about, but use that to spend extravagantly on the top few things that matter. Polarization is good in many things. Hiring, dating, whatever. I think it was Derek Sivers who coined the “hell yes, or no” phrase.

3. What’s more important than we realize?

Cold email is the Great Equalizer. It’s ridiculous that you can reach the eyeballs of nearly every relevant person in an industry without permission, context, or the burden of a reputation (or lack thereof). Sure, you may need a healthy dose of scrappiness to track down some folks. And composing a message worth responding to is an art with a surprisingly high bar. But if done right, you can quite literally build a career from scratch. I’ve seen it happen many times.

4. What’s less important than we realize?

I think most of the “learn by doing” mantras are just totally overrated, maybe even harmful. Something like “learn by shadowing the best” would make much more sense to me.

It turns out that almost all knowledge of how the world actually works is either 1) private and stored within the heads of individuals/small groups, or 2) published to achieve some separate PR or strategic goal. At the end of the day you need inner-circle access to see how the sausage is made. That is why you should get work experience, not to actually pick up skills. Some of my best learnings happened while doing completely menial labor just to be around the right situations.

This is obviously much less true for trade industries. Direct experience matters if you’re building software, for example. But in general I think people are often obsessed with certain work experience when all you need is a really high-quality mentor or unfiltered narrative.

5. What’s the last book on your shelf?

I just finished American Kingpin which tells the story of Ross Ulbricht and the Silk Road. It was one of the best books I’ve read in recent memory. The Silk Road will probably go down as one of the most interesting and novel cases of our generation. And since the whole operation took place on Ulbricht’s computer, the author had access to literally every minute detail of the operation — thousands of chat logs, images, etc. So the author wrote it like an action thriller novel in narrative format. But it’s all true.

Another favorite is Samo Burja’s Great Founder Theory. (No, it’s not about startups.) Some of the most insightful books I’ve read are less explaining things, and more creating a vocabulary to help you think. GFT is about culture, institutions, and why societies prosper or fail. It’s quite lucid and helped me think about a number of things through its lens.

6. What’s a question that everyone asks you?

I get “what do your parents think about you dropping out?” surprisingly often. My mom was convinced it was just an elaborate, dumb plot to ditch a long and boring commencement ceremony. My dad was much more on-board. He didn’t have the opportunity to do anything “risky” when he was my age, so he was glad that I had something worth focusing 100% on and the fortunate circumstances to let me go for it.

You can learn more about Will through his website. To learn more about Contrary, visit us at