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#51 · How to Start an AI Automation Agency In High School (2025)

youtube ↗Agency Operations

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.

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Related answers

youtube ↗Lead Generation

I have a question on Upwork: many clients request not to work with agencies. What is your experience with this?

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.”

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youtube ↗Agency Operations

Should I accept an agency offer to create systems and do direct response ads, or continue seeking cold email clients via Upwork, given I have no experience and want to stay focused on cold email?

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.

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youtube ↗Agency Operations

Isn't teaching everyone to run their own agency just producing a bunch of glorified, commoditized freelancers?

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.

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youtube ↗Pricing

What budget should I start with when joining Maker School, and should I focus on freelancing to save money or jump straight into the program?

You're definitely overthinking it. Roadblocks appear when you can't generate revenue quickly enough to bootstrap. A $500‑a‑month freelance income is reasonable, but you don’t want to be in a scarcity mindset where you feel forced to make Maker School work at all costs. Think of it like sprinting: going 100 % all the time burns you out, while operating at about 85 %—a relaxed competence—lets you stay effective. My recommendation is to save up for a month, then look for the most cost‑effective options. You don’t need to submit a huge number of applications; focus on quality. Lean heavily on cold email and community‑based outreach that don’t require any money. That 80/20 blend of starting now with limited funds and waiting for a larger budget later will give you the best chance of success without hitting roadblocks.

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