Who is behind *unranked? | Ep. 2 - Jamie Finney

As interviewed by Jonathan Bragdon

Why founders?

Founders are the ones that can fix the most things the quickest.

In more human terms, I believe it is extremely healthy for a society's shared mental state if people feel like they can create something out of their own volition. Personally, if I believe in my agency, I am more likely to pick my head up and try to improve what I see. If that plays out across an entire population, the optimist in me believes we'll start to find the capacity to care about issues bigger than ourselves.

How did you learn about building companies?

I've built a lot of things, but I honestly can't take credit for "building a company" like the ones we invest in. I've built two venture capital firms and numerous events and programs that have had decent impact and continue on today. But I've never gone for the full founder ride like the founders I support. I think this distinction is important.

That said, I would like to think that I've gained some helpful breadth of perspective through investing in 70+ companies and digging in with countless along the way. Or that I'm at least someone worth 'digging in' alongside when things do come up.

How did you learn about funding?

I remember living in Boulder and becoming privy to the entrepreneurial ecosystem that was exploding there. It was a source of so much energy and action, but the headlines were often, as is the case for the startup ecosystem, all about funding. It was the only milestone people could demarcate.

From there, my curiosity led me to try to understand what venture funding was. The more I pulled on the thread, the more it gave. I first interned with the Impact Angel Group which was run by Elizabeth Kraus, now founder and Chief Investment Officer at Mergelane. That helped me understand what the job of investing really is. Later, I audited a "Venture 360" class at the CU Law School which Brad Bernthal taught with Jason Mendelson from Foundry Group. It was my favorite class I ever took.

About a year after college, I started Kokopelli Capital with my brother Cory and our friend Fletcher Richman. We realized that we had great dealflow through our community roles, wanted to keep working together, and wanted to keep working with founders. It seemed absurd at the time, and still does, but we just selected the simplest strategy possible, fundraised, and executed it. Being a tiny fund and just three of us, we had to learn everything ourselves. "What does a quarterly report look like?", "What are the right performance metrics to ask our companies for?", all of it. So that was my venture funding education. I think we'll get into later how that wasn't the entire picture.

What do you do effortlessly?

I see dead people. Not really, but I do really resemble that actor.

I see and diagnose systems easily.

What did you not learn from a book?

How to weight things for importance. Assuming we're talking about textbooks or 'business books', they make everything seem like it will show up in a test as evenly weighted questions.

Mastery is rarely a matter of knowing everything down to the last detail and rather knowing what is important in a given situation. What expertise is actually required (whether or not it is yours)? What is actual progress in this situation?

What is taken as a fact that you don’t believe is true?

Doing anything ambitious and self-directed (aka entrepreneurship) requires extra-long hours and supreme sacrifice.

One could spend a lifetime learning how to turn their brain off during the "off" hours. When you can't do this, you're often inadvertently sacrificing those hours. Entrepreneurship is all-consuming, and part of the art is knowing how to create and be present for downtime.

In contrast, I don't believe you win at entrepreneurship by being "clocked in" for the most hours. Very few people can execute an efficient 80 hour week, and they usually are sacrificing something pretty important in their lives to make those inefficient 80 hours possible - family time, hobbies, health, etc.

Entrepreneurship takes work ethic and focus, but that isn't the same as working the most hours.

What do most people overlook?

How their to-do list actually gets them where they want to go (or does not).

What do you see that is broken? (How did you learn about it?)

How we get funding to sound business models and capable entrepreneurs. It should be a meritocracy, but company-funding is still the tail wagging the dog if you ask me.

As for how I learned about this...

...Throughout the journey to starting a VC fund (mentioned above), I was suspicious that venture capital as we know it (preferred equity, SAFE, convertible, etc) was the singular answer.

I loved the startup scene in Boulder, but it just wasn't the culture I grew up in. I understood what risk capital was and that it had an important role for audacious risky startups, but was on the prowl for VC alternatives. Funding seemed like a fulcrum for progress, but no one had applied it to a non-startuppy context, like the small town I grew up in.

Then came the first Indie VC term sheet. I hardly knew what I was reading, but I knew it had potential. So I kept pulling on that string. Back then, I felt like I couldn't be the only person pondering this stuff. I had a dream of starting a conference to find others questioning funding like me and see who knew what. And three or four years later, I landed the right job to get away with this, and that became the Alternative Capital Summit. I suppose I've just kept trying to meet people and learn in public since then. And here we are...

But it is still so damn broken.

What isn’t working?

Funding a company should be like eating a healthy diet as a human.

Right now we basically start with a heavy breakfast and a bloody mary (VC) or piece of toast (think bank loan). And then we tell founders to go make a day out of that - not even taking into account what their day holds.

Except in businesses and funding, the days are years and it is our life's work.

Food is an input so you can have great output, and funding should be the same for companies.

What do you get impatient about?

Skiing powder. I've been told I'm hard to be around when I'm trying to make powder skiing happen.

And big problems that seem totally solvable. I don't get worked up about much in a day-to-day sense, but when it seems like no one is doing the work to fix it, I've been known to get impatient in seeking solutions. This can come out in rants or, ideally, well-thought-out writing (hence *unranked).

What problems do you, specifically, want to work on over the next 10 years?

Funding and means of wealth creation.

Where do you start?

Here.

Who would be good allies in that? Who do you want to be working with?

You.

And honestly too many other folks to name. So many people whom I've connected with over these funding problems are exceptionally smart, grounded, and nice.