Latest / The Side Hustle Career Podcast with Fexingo: Second Income, Freelancing While Employed / How a Freelancer Built a Virtual Assistant Agency Side Hustle
Transcript
- Lucas: So there's this moment that a lot of side hustlers hit — you're making decent money, but you're also working every evening and Saturday. You've basically built yourself a second job. Luna: Right. The classic 'trading time for dollars' ceiling. I've definitely been there. Lucas: Today's guest — well, case study — is someone we'll call Jenna. She was a retail associate at a department store in Phoenix, making about thirty-five thousand a year. In 2023 she started offering virtual assistant services on the side. By early 2025, her side hustle was bringing in seven thousand dollars a month. By June 2026 — this month — she's turned it into a full-fledged agency with five subcontractors. Luna: And the key detail: she didn't quit her retail job until the side hustle was consistently hitting that five-figure mark. She worked both for about eighteen months. Lucas: Exactly. That's the part I find most instructive. She started with the most basic VA tasks — calendar management, email filtering, data entry. Charging fifteen dollars an hour on Upwork. Pretty quickly she realised that if she wanted to scale, she couldn't stay in that commodity pricing zone. Luna: So what did she shift? Did she niche down into something specific? Lucas: She did. She noticed that the clients who paid the best — and were the least annoying — were busy executives and solopreneurs who needed what she calls 'executive-level admin support.' Not just scheduling, but proactive inbox management, travel booking, even light project management. She rebranded her offering around that. Raised her rates to forty-five dollars an hour. Luna: Three times her starting rate. And she still got clients? Lucas: More than before. Because the messaging changed. Instead of 'I'll help with your email,' it became 'I'll keep your calendar and inbox so organised you can focus on the work that actually grows your business.' That's a value proposition that commands higher rates. Within three months, she had a waitlist. Luna: So at that point she's making maybe three to four thousand a month on her own. How did she make the leap to agency? Lucas: She hired her first subcontractor — a former coworker from retail who had admin skills but didn't want to hustle for clients. Jenna trained her on her exact systems and handed off the lower-tier tasks. That freed her up to focus on client acquisition and high-touch relationship management. The subcontractor got paid twenty dollars an hour; Jenna kept the twenty-five-dollar spread. Luna: That's the classic agency arbitrage. But a lot of people fail at that because they don't have the systems in place to train someone else. Lucas: That's the underrated part of her story. She documented everything. She had SOPs — standard operating procedures — for every recurring task. How to triage an inbox. How to book travel. How to prep a weekly agenda. She built a small knowledge base in Notion. So when she onboarded a new subcontractor, they could be somewhat productive within a week. Luna: That's something we've talked about before — the side hustle that scales is the one where you can eventually step back from the day-to-day. Jenna seems to have done that intentionally from the start. Lucas: Totally. And the numbers are pretty clean. She started with one subcontractor, then added a second when the workload justified it. By the time she quit her retail job in late 2024, she had three subcontractors and was grossing about eight thousand a month. After paying subcontractors and covering her small overhead — about four hundred a month for tools and software — she was taking home around five thousand. That was more than her retail salary. Luna: And now she's at seven thousand net, with five subcontractors. That's a real business, not a side hustle anymore. Lucas: Right. And she's still the only one who talks to clients directly. She calls herself the 'client experience layer.' The subcontractors do the execution, she does the relationship management and quality control. That model means she can keep growing without becoming a bottleneck. Luna: One thing I'm curious about — what tools does she actually use? Because a lot of people think you need expensive software to run a VA agency. Lucas: Her stack is surprisingly simple. Google Workspace for email and docs. Notion for the SOPs and client notes. Calendly for scheduling. A dedicated virtual phone line through a service called OpenPhone. And for project management, she uses Trello — nothing fancy. Total monthly cost: about a hundred and fifty dollars. She passes some of that through to clients as a small technology fee. Luna: So the barriers to entry are really low. But the barrier to scaling is the systems and the willingness to delegate. Lucas: Exactly. And Jenna had to learn delegation the hard way. She told me that her first subcontractor made a few mistakes — double-booked a client's flight, sent a wrong attachment. Jenna's instinct was to take back control. But she resisted that urge. Instead, she improved the training and the checklists. She realised that perfectionism was the enemy of scale. Luna: That's such a common trap. You start a side hustle because you want control, and then to grow you have to give up control. Lucas: It's the paradox. But she worked through it. Now she's at a point where she's thinking about adding a sixth subcontractor, and she's exploring white-label partnerships with other agencies that need overflow capacity. Luna: White-label — meaning she does the work under another agency's brand? Lucas: Exactly. A larger VA agency might have more clients than they can handle, so they subcontract to Jenna's team. Jenna's team works under that agency's name, but Jenna handles the staffing and quality. It's a way to get a steady stream of work without having to market constantly. Luna: That's a smart growth strategy. And it diversifies her revenue — she's not dependent on just a handful of direct clients. Lucas: Right. Her direct clients are about sixty percent of revenue, the white-label work is forty percent. She's aiming to flip that ratio over the next year so the white-label work is the majority — steadier, less relationship management. Luna: You know, hearing stories like Jenna's — it really reinforces something we've said on this show before. The side hustles that work best are often the ones where you're solving a boring, painful problem for someone who has money but no time. Lucas: Exactly. And if you've been following along with these episodes, we hope they've helped you think differently about your own career or side hustle. If they have, and you've gotten some real value out of them, a couple of dollars a month is genuinely what keeps these going — buy me a coffee dot com slash fexingo, if that's something you've gotten something from. Luna: Yeah, it's a small way to support the ad-free model, and it really does make a difference. Lucas: Alright. So back to Jenna — one more thing I want to highlight is how she handled the transition from employee to full-time entrepreneur. She didn't just quit one day. She gradually reduced her retail hours over six months, testing whether the side hustle income was stable. Luna: That's the smart way. She used the side hustle to de-risk the leap. Lucas: Exactly. She went from forty hours a week in retail to thirty, then twenty, then zero. Each step was contingent on her VA income covering the difference. By the time she left, she had six months of living expenses saved, plus a growing client base. Luna: I think that's the most practical takeaway for anyone listening who's thinking about starting a VA side hustle — or any service side hustle. You don't have to jump. You can ease in. Lucas: And you don't need a fancy background. Jenna had no prior admin experience. She learned on the job with her first few clients. She just had good organisational instincts and a willingness to figure things out. Luna: So for someone listening right now who's thinking, 'I could do that,' what's the first step? Lucas: Jenna's advice is to pick one service — just one — and offer it for free or at a steep discount to a friend or former colleague who runs a small business. Do it for a month. Document everything. Then use that experience to build a simple portfolio or case study. Then start charging. Luna: That's concrete. And it lowers the barrier to starting — you don't need a website or a business license on day one. Lucas: Exactly. Jenna's first client was her cousin's real estate agent. She managed his calendar for two months for free. That gave her the confidence and the reference to start charging. Luna: And now she's running a seven-thousand-dollar-a-month agency. It's a great example of starting small and thinking big. Lucas: Yeah. And it's a reminder that the side hustle doesn't have to stay a side hustle. For Jenna, it became a career. Luna: Thanks for listening — we'll be back next week with another story.