by - Dexter Zhuang left the 9-to-5 world to pursue a portfolio career with multiple income streams.
- The most effective way he has found money is through a service-based gig, such as coaching.
- He recommends reaching down and leaning into your network to succeed with coaching or advice.
Dexter Zhuang spent a decade in the corporate world, working at large companies like Dropbox and smaller startups, before calling it quits on his own in 2023.
At that time he had been experimenting with his printing business for years. His first attempt at making money on the side was an e-commerce business selling sampler tea boxes. He lived in San Francisco at the time and worked at Dropbox as a product manager.
“I learned a lot about, OK, what’s it actually like to build something on the side?” Zhuang, 33, told Business Insider. “I also learned that e-commerce wasn’t something I was particularly interested in doing much afterwards. I’d 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 year-long travel sabbatical.
“For much of my life up until that point, I felt like I had been some sort of chronic high achiever. 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 a milestone that was important to me, but I felt burned out and I was struggling to to decide what I actually wanted to do next.”
Zhuang met his wife while traveling the world.
Thanks to Dexter Zhuang
He decided to tap into some of his savings and live out a dream he had put aside: traveling the world.
Zhuang didn’t necessarily need to bring in income while traveling — he budgeted enough to last a year — but he had the time and missed work, which led to his next side Hustle: Remote Career Coaching. Unlike e-commerce, coaching clicked for Zhuang and “really opened my eyes to what’s possible with a service-type side hustle.”
Transition to a ‘portfolio career’
Zhunag’s traveling 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 pursuing what he calls a “portfolio portfolio.”
A portfolio career involves multiple income streams. In its simplest form, it’s a full-time job plus a side job, which Zhuang has been doing for years; For him, this currently means working on various side projects instead of a full-time role with one employer.
Its revenue streams include three main categories: services such as Consulting and Advising, a cohort-based course derived from its newsletter fees abroad, and affiliates for various financial software and services.
Among its revenue streams, “the most lucrative is the consulting and consulting — 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 corporate space, Zhuang noted; What is often glossed over is How Niche down, which starts with fully understanding your market.
“You have to know exactly what all the niches are,” he said. “In my consulting and coaching experience, I didn’t know exactly about the market at first, so I started broadly to test different hypotheses and learn about the market before narrowing my focus.”
Its broad market was series A and B startups. After testing different industries in that space, over time, he found his niche: “I found that the type of companies that reach out to me in general are fintech startups – there are a lot of them where I add a lot of value .”
Zhuang’s main income stream is coaching and consulting, which he can do remotely.
Thanks to Dexter Zhuang
2. Lean into your network to land your first client. Zhuang said 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 immediate network.”
His fourth was his first inbound customer – a founder who contacted him through his website.
“It’s definitely not just me experiencing this. I interviewed over 20 other side hustlers, and what I found is that about 50% of them get their first client from referrals or their direct network as well,” he said.
He noted that his data is “not statistically important or anything,” but the point is: “Tap your referrals or your network for that first client.”
3. Win ‘The Game of One.’ When Zhuang first meets clients looking to grow their side business, he often 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 works and what doesn’t. Whereas if you just launch with one offer, then the Then Validation is a lot easier because there is only one offer to accept or decline.”
Start with what you think is your strongest product, test it on your first customer and then repeat, he said, “Then test that same offering with the second customer, repeat and test it again with a third customer and iterate.