Payoneer’s CEO Says the Best Entrepreneurs Are ‘Unemployable’ — Here’s Why That’s a Good Thing

I’ve talked to a lot of entrepreneurs over the years, but John Caplan might be the first one to tell me, flat out, that the best entrepreneurs are basically unemployable. As CEO of Payoneer, John runs a company that quietly powers the global economy — a financial services platform serving two million customers around the world, moving roughly $100 billion a year for entrepreneurs selling on Amazon, Shopify, Etsy, and beyond. Since taking the reins, he’s helped grow Payoneer from a $500 million business into a billion-dollar one. Here’s his playbook.

Dan Bova: Can you give us the elevator pitch for Payoneer?
John Caplan: Payoneer’s an incredible company. We are 22 years old, and we provide all the financial tools an entrepreneur who operates their business cross-border needs. Think of us, in some ways, like a bank alternative. If you’re an entrepreneur in Vietnam and you’re selling products to Latin America and hiring talent across the Philippines, you use Payoneer’s multi-currency wallet to really run your financial operations. We have two million customers in 190 countries, just about $100 billion of activity in the Payoneer accounts around the world, and we’re over a billion-dollar revenue business and nearly $300 million of adjusted EBITDA.

What’s something about crossing borders that entrepreneurs aren’t thinking about that you’re solving for?
There’s a bunch of things — the first thing is holding multiple currencies. If you sell in one currency and get paid in another, having a multi-currency wallet is not easy, because your local banks around the world don’t provide that capability. The second thing we solve is providing everything in the palm of your hand — using your mobile phone as your financial command center. And I think the third primary benefit is all of the accounts receivable and accounts payable tools an entrepreneur needs. Maybe it’s cards that they give their employees when they go on business trips with limits on them, or being able to send an invoice and a link to get paid quickly. A very simple set of tools that make running a business globally easy from day one. If you’re at Procter & Gamble, you have a whole finance department that does that. But if you’re a 100-person company in the Philippines, banks aren’t really built for you. We exist for the entrepreneurs of the world — really the backbone of the global economy.

What is it about entrepreneurs that makes you want to help them?
I am an insatiable entrepreneur myself. And, in a funny way, the best entrepreneurs are really unemployable at some level. We rebel against authority, and we want to make the world a better place. I’ve often thought of entrepreneurship and leadership as two different things. Entrepreneurs are driven by passion and vision and sometimes naive hope, and leaders are driven by trying to build systems to turn those ideas into economics and a reality. I’ve spent my career doing both — starting things from scratch and scaling them. The thing I enjoy most is coming into a company like Payoneer and running it with the entrepreneurial passion I’ve had my whole life.

Can you talk about the steps you took that allowed you to grow to a billion-dollar company?
This is the fourth or fifth big-scale transformation I’ve led, and I really have a transformation playbook. It starts with cutting all the noise out, talking to customers, and actually listening to their needs instead of looking at your competition. That’s thing number one. Recognizing how they create value so you can help them create the value they’re trying to deliver is the second. The third is building a culture and a community of executives with a shared passion for the mission to make other people’s lives better. And then a rigorous, data-driven decision-making process, so the numbers tell the story and we make decisions out of that data. At the end of the day, I act fast and I act fair, and people who work with me know I’m committed to the results and the team delivering those results.

Do you have any advice for leading someone who’s smart but really risk-averse — afraid to make a mistake and almost paralyzed by that fear?
I think it depends on the capacity. If fear is paralyzing someone, that can be a leadership issue — you’ve got to create psychological safety for the people on your team. But some of it is a chemical thing — if someone’s too risk-averse, they shouldn’t be an entrepreneur. It feels good to me to wake up every morning and try to earn my job again. I start with zero credit in the morning, try to earn some, go to sleep exhausted from what we built, and try to get up tomorrow and do it again. At the end of the day, I think my job is to remove the biggest obstacles standing in the way of our next growth unlock.

Working on an international level, are there cultural norms you’ve had to learn about working with people from different countries?
That’s an awesome question. We’re 2,500 employees on staff and 4,000 people in total, on the ground in 30 countries — every culture you could imagine. I was on a Zoom this morning with a colleague in Mumbai, a colleague in Dubai, a colleague in Tel Aviv, me in New York, and somebody in London, all of us with different backgrounds. The great unifying principle behind all of us was that entrepreneurs around the world are the same. There’s a common DNA — a restless desire to improve the world around you, take care of your kids, and create wealth and impact. The problem-solving skills and leadership approaches aren’t always the same — some people are command-and-control, others are more collaborative, some use a lot of data, others move on instinct. But at the end of the day, the viewpoint is: Can I make something the world needs? Can I treat my customers fairly? And will I get paid fairly for it?

For an entrepreneur wondering if they can trust a company like Payoneer with their business, what questions should they be asking?
I think first — you know it when you see it. There’s no amount of glossed-up marketing that can get in the way of an organization that authentically has your best interests at heart and is trying to do the right thing. So trust your gut would be the first thing I’d suggest. In a space like ours, there are lots of great financial services firms, and entrepreneurs have plenty of choices, but very few of them are actually built by entrepreneurs and for entrepreneurs — that’s what we’ve tried to do here. We built the capability to pay contractors and employees around the world compliantly because, by talking to our customers, it was clear that an insurance firm in Louisiana has people all over the world and needs a way to pay them compliantly — because if they don’t pay them, they won’t do the work, and they can’t scale their business.

Any behind-the-curtain stories from your business or background that might be fun to share?
When my grandfather came to the United States in 1904, he and his brother started a business in 1912 that is still in our family — Oscar Heyman and Brothers, a luxury jewelry manufacturing firm. He and his brothers worked in the Fabergé factories in Russia and brought that capability to the US. What runs in my veins is this idea that if you really want the dream, it’s hard work, but you can do it if you’re willing to make the sacrifices and create real value and put your mind to it. I’ve lived my whole life sort of obsessed with helping people build companies. My barber — I helped him open a barber shop on 85th Street because he was too smart to be working for anybody else. At 55 years old, I’ve finally got to the place where spending Saturdays with my barber, figuring out how he can grow his business, is actually fun for me. I’m not sneaking off to play golf — I’m helping him figure out how to set up his Square so he can get paid and do his marketing.