The three habits behind Jeff Pan’s cross-industry success

From running a hotel business in New York with just $5,000 to building software for Booking.com and designing mission-critical systems for SpaceX, Jeff Pan has worked across hospitality, e-commerce, travel, logistics, and aerospace. His latest venture, Belli, is a tech company focused on modernising air cargo – one of the most operationally rigid sectors in the world.

In this episode of Winning Friends, Jeff reflects on the mindset that’s guided him across industries and continents. From navigating Myanmar’s political instability to absorbing the culture of execution at SpaceX, he shares a practical approach that favours clarity over consensus, speed over polish, and learning by doing.

Look for what others dismiss

Throughout his career, Jeff has looked for systems that seem unchangeable, then questioned why they exist in the first place.

His first business was a bar, his second a hotel in New York. “I had $5,000 and no clue how hotels worked,” he says. So he did what he’s been doing ever since: reverse-engineered what was needed. “You quickly learn acquisition, distribution, operations. You pick it up because you have no choice.” Years later, those instincts carried over into his work at Booking.com, and eventually into building Belli.

What he looks for are ideas that others write off: “The best startup ideas come when you believe something that other people don’t.”

That belief shaped his early work in Myanmar, where few thought a fast-scaling e-commerce platform could succeed. “You take something that everyone assumes is unchangeable, and then you just keep asking why. The why behind the why behind the why.”

The same logic fuels Belli, where he’s working to reshape how airlines run their operations. “Nobody believed you could change the way airlines run their business,” he says. “But once you start breaking it down, it’s just legacy thinking. It’s not physics.”

Optimise for the frequency of failure

It’s not about speed for speed’s sake. “You’re optimising for the frequency of failure,” he says. “The faster you do the wrong thing, the faster you’ll figure out what works.”

He applies this approach to every new domain he enters, even learning. At one point, Jeff had spent over a million dollars on Upwork, not to outsource work, but to understand it. “I’m under the impression there’s nothing you can’t learn 60% of in 24 hours,” he says.

Learning quickly is one thing. Knowing when not to fight the wrong battle is another. Jeff has learned to spot patterns early, especially in sales. “It’s just pattern recognition,” he says. “Now I know – if the person I’m talking to is older than 65 and still using a certain legacy system, I’m not going to land that deal. I just move on.”

The instinct to test, learn, and quit what isn’t working underpins everything from product launches to hiring. “You don’t need to have the full answer,” Jeff says. “You need enough clarity to move.”

Honesty is faster

At McKinsey, Jeff told his managers exactly what he wanted: exposure to industries most founders don’t get to see. They hired him anyway.

That kind of bluntness hasn’t always been welcome. He’s been told he’s too honest, even let go for it. But in his view, if something’s not the right fit, it’s better to find out early.

He brings the same approach to hiring, where he optimises for high variance. He once spent the first 20 minutes of McKinsey interviews telling candidates why they shouldn’t take the job. “It filtered out a lot of people. But the ones who stayed – they were the ones who’d probably thrive.”

In startup hiring, he looks for signals that go deeper than CVs. “What tools would you use to build your team from scratch?” is one of his go-to questions. “The tools people choose reflect how they solve problems. If they’ve thought carefully about those things, chances are they’ll be thoughtful elsewhere too.”

That attention to character over credentials extends to client relationships, too.

One of Belli’s biggest airline deals came from a decision he made years earlier as a consultant in Singapore. Jeff had ended the project early, walking away from an easy paycheque once the work was truly done. He didn’t think much of it at the time. But that client remembered.

Years later, the same person, now CIO of a major Middle Eastern airline, came back with a contract. Not because of a sales strategy, but because of a moment of honesty.

To Jeff, that’s the real long game. “You build trust faster when people know what they’re getting,” he says. “Even if what they’re getting isn’t perfect yet.”

Beyond this episode: how e-Residency supports innovative builders in rigid industries

Winning Friends is a podcast powered by Estonia’s e-Residency, hosted by Logan Merrick and Dylan Hey. Each episode explores how relationships with co-founders, teams, or inherited systems shape the way companies are built. This conversation with Jeff Pan is about trading consensus for clarity, momentum for perfection, and how trust often starts with uncomfortable truths.

To learn more about how global entrepreneurs are scaling companies with European access, regardless of where they live, read our article on Estonia’s e-Residency programme.

Watch the full episode of Winning Friends featuring Jeff Pan below.