A Millennial Quit His 9-to-5 And Built A 'portfolio Career' Of Side Hustles. He Shares His Most Lucrative Revenue Stream — And 3 Strategies Anyone Can Use To Capitalize On It

Dexter Zhuang, founder of Money Abroad, quit his job at Dropbox and took a yearlong sabbatical to travel to 20 countries.

Courtesy of Dexter Zhuang

• Dexter Zhuang left the 9-to-5 world to pursue a portfolio career with multiple income streams.
• The most effective way he's found to make money is through a service-based gig, such as coaching.
• He recommends niching down and leaning into your network to succeed with coaching or consulting.

Dexter Zhuang spent a decade in the corporate world, working at large firms like Dropbox and smaller startups, before calling it quits to work for himself in 2023.

At that point, he'd experimented with side hustles for years. His first attempt at making money on the side was an e-commerce business selling sampler tea boxes. He was living in San Francisco at the time and working at Dropbox as a product manager.

"I learned a lot about, OK, what is it actually like to build something on the side?" Zhuang, 33, told Business Insider. "I also learned that e-commerce wasn't something that I was particularly interested in doing a lot of afterward. I would say it didn't work out, but it was a good lesson learned for future side hustles."

He quit Dropbox in 2018 to take a yearlong travel sabbatical.

"For much of my life up until that point, I felt like I had been a chronic high achiever of sorts. I had grinded hard in my career to pursue what I thought was my definition of success at the time: to become a high-paying tech executive or the founder of a unicorn startup," Zhuang said.

When Dropbox went public in 2018, "I felt like I had 'made it' to some extent. I felt like I had checked off a milestone that was important to me, but I felt burned out, and I struggled to decide what I actually wanted to do next."

Courtesy of Dexter Zhuang

He decided to tap into some of his savings and live out a dream that he'd tucked aside: traveling the world.

Zhuang didn't necessarily need to bring in any income while traveling — he'd budgeted enough to last a year — but he had the time and missed working, which led to his next side hustle: remote career coaching. Unlike e-commerce, coaching clicked for Zhuang and, "really opened up my eyes to what's possible with a service kind of side hustle."

Transitioning to a 'portfolio career'

Zhunag's travel sabbatical took him to 20 countries in Southeast Asia, East Asia, Europe, and Latin America. On one of his trips, he met his wife.

The couple moved to Singapore in 2020, and Zhuang jumped back into the workforce. He worked for a fintech startup through 2023, at which point he hit Coast FIRE and quit to pursue what he calls a "portfolio career."

A portfolio career involves multiple income streams. In its simplest form, it's a full-time job plus a side hustle, which Zhuang has technically been doing for years; for him currently, it means working on various side projects rather than having a full-time role with one employer.

His revenue streams include three main categories: services such as consulting and advising, a cohort-based course that derived from his newsletter Money Abroad, and affiliates for various financial software and services.

Among his income streams, "the most lucrative is the consulting and advising — the services piece — for sure," he said.

How to make money with a service-based side hustle

Zhuang has followed three principles to scale his coaching and consulting business.

1. Start broad and niche down. "Niching down" is fairly common advice in the business space, noted Zhuang; what often gets glossed over is how to niche down, which starts with fully understanding your market.

"You need to know exactly what all the niches are," he said. "In my experience consulting and coaching, I didn't know exactly about the market initially so I started out broad to test different hypotheses and learn about the market before narrowing my focus."

His broad market was Series A and B startups. After testing various industries within that space, over time, he found his niche: "I discovered that, generally, the type of companies that tend to reach out to me are fintech startups — those are ones where I add a lot of value."

Courtesy of Dexter Zhuang

2. Lean into your network to land your first client. Zhuang said that his first three clients came from his network: "Client one was a referral from a VC friend of mine, client two was a referral from a colleague at work, client number three was someone in my direct network."

His fourth was his first inbound client — a founder who contacted him through his website.

"It's definitely not just me that experiences this. I've interviewed over 20 other side hustlers, and what I discovered is that roughly 50% of them get their first client from referrals or their immediate network as well," he said.

He noted that his data is "not statistically significant or anything," but the point stands: "Tap your referrals or your network for that first client."

3. Win 'the game of one.' When Zhuang first meets with clients looking to grow their side business, oftentimes he finds that they want to sell multiple products or services. He always advises them to "win the game of one offer first."

It makes it easier to validate, he explained: "If you launch four offers and then it doesn't work, you may not have a clear idea of what's working and what's not. Whereas, if you just launch with one offer, then the validation is a lot easier because there's only one offer to accept or decline."

Start with what you think is your strongest product, test it on your first client, and then iterate, he said: "Then, test that same offer with the second client, iterate it, then test it again with a third client, and iterate. The point is really on focusing, and resisting the temptation to add unnecessary complexity when you don't have to."