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How Unpopular Ventures' Founder Built a $50 Million Startup Portfolio
Discover the unconventional story of Peter Livingston, founder of Unpopular Ventures, who has invested over $50 million in 300 startups across the world.
Andrew Logemann
Andrew Logemann
Head of Marketing
min read

Meet Peter Livingston. The Founder and GP of Unpopular Ventures has invested over $50 million in 300 startups across the world, including one fintech investment, Jeeves, that's already returned 112x in two years.

For Peter, every important decision of the last ten years has been shaped by a single mantra: "go where it's quiet." In his quest to go where others are not, Peter found himself in Istanbul talking to a stranger about marriage six days after they met. Twelve months later, this stranger became his wife. Then, after seven years of travel, they sold their house and everything they owned to become digital nomads.

Inspired by his own unconventional experience, Peter formed Unpopular Ventures with the thesis that the best opportunities – in life and business – come when you go where no one else is going. Adam Nathan, CEO of Almanac, sat down with Peter to discuss his decision to build a life and business off the beaten path. Here's their full conversation.

Why 'who you're with' shapes the next two most important decisions in your life

Adam Nathan: Thanks for being here, Peter. Let's get right into it. What was the biggest question you've had to decide in the last 10 years?

Peter Livingston: I recently spent a lot of time thinking about this. I kept going back to something that Naval Ravikant said: the three most important decisions in your life are where you are, who you're with, and what you do. And I kept cycling through those three because I've made really big and important decisions in each of those three areas over the last 10 years. But I realized that it all actually ties back to one: who I'm with.

To begin that story – my wife and I met nine and a half years ago in a hostel in Istanbul. I was there during spring break of my second year of business school. My wife's from Ukraine, but she had lived in Turkey for a while and was back visiting some friends. We met in this hostel and immediately fell in love. On day six of spending time together, we were already talking about getting married.

How an openness to adventure led us from strangers to fiancés in under six months

Adam Nathan: How did that take off so quickly and were you considering other options? Ultimately, what made you say yes?

Peter Livingston: Well, yes and no. I'd had a number of relationships before, but I was single at the time. The chemistry was so good. We quickly discovered we had a lot in common, like our love for travel and adventure. One of the things that was pretty neat: on day two of being in Istanbul together, I left for another part of Turkey to meet up with some of my friends. I invited her to come with me, and she said yes. I think it was that openness to adventure and taking risks together that really helped us bond initially.

I'll expand into this next part now. So we had spent those six days together, but I had to go back and finish business school and she had to go back to Ukraine. But we kept talking almost every day on Skype. We decided we wanted to try to be together, but the big issue was she couldn't come to the U.S. without us getting married. There was no way around it just because of the visa restrictions. So she actually proposed that we go live somewhere else for as long as necessary to figure out if we really did want to get married. We ended up picking the Dominican Republic. I finished business school and a couple days after that, we both flew to the Dominican Republic and lived there for four months together. At the end of that we decided we wanted to be together, so we came back to the U.S. and got married.

Why we sold our house and have no possessions other than what's in our suitcases

Adam Nathan: That's an amazing story. So it sounds like location has played a big role in your marriage. I'm curious, how do you think about location now and as one of the big decisions that you've had to make throughout your life?

Peter Livingston: Long story short, it has been a wonderfully successful decision. We've been together for nine and a half years, and have been married for eight and half. We have two kids, ages five and seven, and we couldn't be happier. One of the things that I really love about my wife is her sense of adventure, love for travel, and gypsy soul. She's never happy in one place for very long. And because of that, we've always been on the move.

It started with when we came to the U.S. We went back to San Francisco, which is where I'm from, and spent a year there. Although I had spent my whole life there–my family's there, my friends are there, I went to Stanford a couple times, I'd been through several startups there – we both realized that for the next stage of our lives it wasn't the right place us. And that led us on another journey.

First, we ended up going to Miami for five years. We loved being in Miami – it felt really refreshing to be in this new place figuring things out again for the first time. And it led us on this path where we came back to the Bay area briefly, but then Covid hit and we realized that we can really be anywhere we wanted. We ended up going to Germany for six months, came back, and tried out living in Nashville for six months. And after all these moves we realized we loved to be on the move. We didn't ever want to be in a single physical place all the time.

So we got rid of everything we owned and we became digital nomads. So for about a year and a half, we have owned nothing. We have no home, no possessions other than what is in our suitcases, and we live in Airbnbs. We've been all over the world with our two kids–spent most of the year in Europe and Australia – and we just love living this way. I don't think I would've found this lifestyle without my wife.

Why every success I've ever had comes from going off the beaten path

Adam Nathan: That's pretty amazing that you're doing the nomad life with two kids. How does that relate to what you do with Unpopular Ventures?

Peter Livingston: So that's the third thing. We've done who I'm with and where we are, now it's what I do. Unpopular Ventures is a venture capital entity that's both a syndicate and rolling fund hosted on AngelList. We named it Unpopular Ventures because all of my best business outcomes, investments, and life experiences – including finding my wife and living all around the world – have come when I went off the beaten path and looked for what no one else was doing.

I founded Unpopular Ventures with the thesis that we were going to invest in the very best founders from all over the world in all kinds of industries and markets. We just have to make the case that they're a little bit off the beaten path and non consensus. So about half of our portfolio is outside the US – particularly in emerging markets. A big part of that has been in Latin America, which I learned a lot about because of our five years in Miami.

And we've also been very active in Europe, Africa, India, and the Middle East. A lot of that has also been spurred by my experience living around the world. We've been really fortunate that we've been incredibly successful – I think because we've had this new wave of globalization in remote work.

As an example, one of our best investments is a company called Jeeves. We were the biggest investor in the first two seed rounds starting at a $10 million valuation. It's become a global business bank. It basically provides credit, credit cards, financing, and a whole suite of financial services for startups around the world that operate in more than one country. They help startups navigate all the regulatory requirements and challenges that come with running a business financially across borders.

I found that investment when we were living in Germany for six months. I think the founder partially chose me as an investor because of my global focus and outlook. They're building a global company – I'm a global investor. I became very immediately aware of the potential of the business because we had to set up a bank account in Germany and I saw how messed up the financial systems are for anyone that is crossing borders or doing anything in more than one country.

We invested in Jeeves at a $10 million valuation and they were last valued at about $2.1 billion, so, as far as I know, that was one of the highest multiple investments that's been done by an angel syndicate in the last few years. The only one that's higher was OpenSea, but our Jeeves investment is up 112x in two years.

That, among many other investments of ours that are on a great trajectory, all ties back to marrying my wife, living around the world, and being open to this idea that there are really amazing opportunities, amazing founders, and tons of underserved customers that need better solutions.

Why you should forget following your passion and go where it's quiet instead

Adam Nathan: Great. So looking back on your story, what advice would you have for others?

Peter Livingston: There are a couple things. There's a saying that goes follow your passion. It's very controversial. I think the better saying is to follow your interests and always be open to new things. You don't want to be reckless. But I think that when you know, you know. And you should chase that despite whatever people around you are saying.

A lot of people had doubts about me going to live in the Dominican Republic with this girl that I had just met. A lot of people had doubts about us moving to Miami and then becoming digital nomads. It seemed really crazy and risky to a lot people. But in each case, it felt like the right thing to me.

With my wife for instance, I didn't need to spend a lot of time doing due diligence. I knew right away it was a good fit. I think that as long as you know that it's the right thing, regardless of what everyone else says, you should run toward it.

One of my professors in business school, Irv Grousbeck, said something like go where it's quiet. And I kind of took that to mean: be willing to go into places that are not well known or well documented. Don't go where lots of other smart people are going, because very often the places where no one else was looking was where the opportunity was. I found that to be true both in Miami and in our global outlook of looking for great opportunities. So go where the quiet is.

Adam Nathan: Well, that's great advice. Thank you for sharing your story. It's an inspiring one and hopefully we'll get some people to follow in your footsteps and go to the many other places where it's still quiet.

Peter Livingston: Thank you so much, Adam.

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