From Dropbox to Side Hustles: Ex-Employee Reveals Keys to Portfolio Career Success
Staff Editor Former Dropbox Employee Transitions to Portfolio Career, Shares Insights on Successful Side Hustles
Dexter Zhuang, a former corporate professional at Dropbox and various startups, has successfully transitioned to self-employment in 2023, embracing a “portfolio career” approach. This shift comes after a series of life-changing experiences, including a travel sabbatical and achieving Coast FIRE (Financial Independence, Retire Early).
Zhuang’s journey began with an e-commerce side hustle selling sampler tea boxes, which, despite not achieving financial success, provided valuable lessons. In 2018, feeling burnout and seeking to redefine personal success, he left Dropbox for a travel sabbatical that spanned 20 countries. During this time, he met his wife and began remote career coaching.
After moving to Singapore in 2020 and working at a fintech startup until 2023, Zhuang achieved Coast FIRE, allowing him to pursue a portfolio career. This approach combines multiple income streams, including consulting and advising services, a cohort-based course from his newsletter Money Abroad, and affiliate partnerships.
Zhuang emphasizes the importance of service-based side hustles, particularly coaching and consulting, as the most lucrative income streams. He advises aspiring entrepreneurs to start broad and then niche down, drawing from his own experience of initially working with Series A and B startups before focusing on fintech startups.
For those looking to launch a service-based side hustle, Zhuang recommends leveraging personal networks to land initial clients. He stresses the effectiveness of referrals and existing connections in the early stages of client acquisition.
Another key piece of advice from Zhuang is to “win the game of one” by perfecting a single offer before expanding to multiple products or services. He suggests testing and iterating on one offer with initial clients to ensure clarity and success.
Zhuang’s transition and insights offer valuable guidance for professionals considering a shift to self-employment or looking to diversify their income streams through side hustles.
