Should I start as an agency or freelance on Upwork? I’m in my last year of high school, preparing for university, want to pursue entrepreneurship but have circumstances preventing me from going now—what do you recommend?
He advises starting as a freelancer on Upwork as quickly as possible, not forming an agency there because proposal reply rates suffer and clients prefer working with a person rather than a faceless corporation. Use freelancing to generate initial revenue, then hire team members but still brand the work as yourself, avoiding a corporate facade until you’ve reached around $50 k in earnings. After that you can scale the team and rebrand as a company. He also encourages the high‑school student, noting that pursuing entrepreneurship now is great.
Most clients on Upwork don’t want to work with agencies. I recommend not using Upwork as a primary agency growth channel; treat it as a way to get an initial foothold while you’re still freelancing. When you’re selling yourself, you want the client to feel they’re hiring you, not an agency. Avoid agency language on your profile—use “founder” if you like, and bring up any consultants only during calls after you’ve secured the project. Start as a freelancer, deliver a high‑quality first project, get a great review, then gradually introduce others or a consultant on later projects. Don’t say you’ll hand the work off to an agency; keep the work yourself initially. In short, don’t label yourself as an agency on Upwork—position yourself as an automation specialist or similar, because Upwork users dislike the word “agency.”
Yes, freelancers should start a one-person agency for branding and sellability reasons. A freelance outfit earning $200k can't be sold because the business relies entirely on you. Forming a company gives you the opportunity to sell it later, even if it's a one-person entity, because you can use the company as a branding vehicle and open the door to equity-building steps. While branding yourself as an individual (e.g., 'I'm Nick Zerbe') can lead to faster growth because clients prefer working with a human, creating an agency separates the corporate worker-bee job from freelance work and makes the transition to a full agency easier when you hire help. In short, the advantage is primarily equity-based: building an asset, investing time, energy, money, and risk, then selling it to capture capital gains and avoid high taxes.
If you're early in your career and need experience and to pay down debt, take every opportunity—including agency work—to build skills and cash flow. Once you're earning $10–$20k/month as a solo freelancer, saying yes to everything spreads you thin and prevents skill accumulation; you'll plateau. At that point, niche down to one or two core offerings so your revenue can keep growing. Early stage: say yes to everything. Later stage: focus and specialize.
I understand the perspective, but I don't think most people here already have the business experience to launch and run an agency from scratch. Starting as a freelancer — doing the bulk of the work yourself early on — actually makes sense, because you need to learn how to deliver the service before you're capable of running a real business around it. Diving straight into hiring and infrastructure before you've learned to sell usually means losing the forest for the trees. The sequence that works: learn to sell first, then learn the service, then worry about business infrastructure once those are solid.