Do you need to start out on Upwork?

#83 · How Broke Beginners Are Winning With AI Agencies

Do you need to start out on Upwork?

No, you don't need to start anywhere else. Upwork is by far the easiest place to start for a number of reasons. As a beginner, sales is hard and consists of three parts: understanding the client’s problem, pitching a solution, and standing out enough for the client to pick you. Upwork handles the first two parts for you; you only need to pay for connects and a fee (now between 10‑15%) when you deliver a project. This means you only have to focus on being the best pick among freelancers, which is roughly one‑third of the sales work. It also minimizes capital outlay because you don't need to spend large amounts on cold‑email tools, ads, or other lead‑generation platforms. As a beginner you might spend around $200 on tools and see no results for weeks, whereas with Upwork you can start seeing ROI in a few days, making the gap between spending and earning much shorter.

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Related answers

youtube ↗Pricing

If you're starting on Upwork today with a strong skill set and portfolio, how should you approach pricing? Should you temporarily price below your previous industry rates to build reviews and momentum?

Yes, you’ll need to lower your rates to get clients on a new platform. Treat Upwork (or Fiverr, etc.) like digital real estate—you’ve just bought a rundown house. You have to do some head‑trimming, break out the paint, and take low‑paying work to improve the property. Most people’s first gigs are $250, $500, maybe $1,000. My first door‑to‑door client paid me around $7, after refunds it was maybe $5‑10. The point is you’ll start small, earn $250, $500, $1k, $2k, and eventually trade that for dollars earned. Initially it’s just about trimming the hedges and putting a fresh coat of paint on the house.

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youtube ↗Lead Generation

How should I spend $1,000 to start getting clients? I considered buying a bulk of inboxes and a premium instantly plan to increase sending volume, but do you have other suggestions?

If you haven’t had a client yet, allocate part of the $1,000 to Upwork to buy your first job—it’s the simplest way to get started. Also invest in Maker School to learn the automation framework and get the curriculum. With the remaining budget, buy a modest number of mailboxes (around 20–21) and domains (about $50 for domains plus $70 for mailboxes, totaling ~$120). Use leftover funds to purchase leads. This approach lets you cover education, outreach tools, and lead acquisition while positioning you to land your first client through Upwork, provided you stay consistent and follow the program’s advice.

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youtube ↗Client Acquisition

Does your roadmap to getting your first client involve Upwork, or is it more personalized per trade?

Yes—Upwork is the straightest line to your first customer when you’ve never sold anything before. It lets you get into conversations, learn basic sales, and earn an initial return on investment while paying down client‑management and skill debt you didn’t know you had. However, relying on Upwork long‑term is a crutch because most projects are custom, forcing you to rebuild the wheel each time and making templated delivery impossible. After you’ve cleared that debt, transition to more scalable outbound methods like cold email. Only after a couple of months do you begin exploring scalable inbound or social‑media approaches. The early phase is strictly Upwork‑focused to bootstrap the business.

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youtube ↗Lead Generation

Nick, cold emails versus Upwork. Which one helps move the needle faster to get your first win? Say you got 1K. extremely good skills, unlimited time, 18, a little social proof, and you're starting from scratch. Which of the two would be your go-to method to make a little bit more capital and get the ball rolling?

With $1,000 to bootstrap, go with Upwork. You can submit roughly 200‑300 applications (maybe more thanks to the connects refund policy). In the Maker School community, the average number of proposals needed to land a client is about 40‑60, so you could realistically secure around six clients. If the average revenue per client is around $200, that puts you at $1,200, and you can rinse and repeat. In practice, the average revenue per client is often higher—many close $1,500‑$3,000 deals—so within the first 50 proposals you could reach roughly $6,800 (or about $1,600 after the correction). Consistently scaling up from there will grow your business.

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