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.
Upwork works well for beginners who lack sales‑marketing experience—it’s a simple paid‑access to a pool of people who already want what you sell, so you don’t need to be a strong salesperson. Cold email gives you access to the whole world, but your ability to explain, justify, and sell the problem becomes the big differentiator. Cold email is typically more scalable and makes more money over time than Upwork, though Upwork is easier to start with. I actually use both in tandem.
But anyway, how do you acquire more upmarket clients? I mean, I wish I could say there's a special system for upmarket clients. A lot of them tend to be more referral-based and gated. They won't take you seriously unless you can accomplish the first hurdle: finding a plausibly deniable reason to reach out to them. That means perusing the network of the people you want to get in touch with, making preliminary introductions or leveraging relationships, then using those connections to find your way to an intro. That's a big thing, but it's very manually intensive and not something you can automate. Aside from that, it's really just the same thing: sending cold emails and working your way up a decision-maker chain, delivering exorbitant value upfront. They're more bureaucratic, with longer sales cycles, but that doesn't mean they're impenetrable. Many cases exist of people in Maker School with zero experience who throw enough outreach to get the attention of a mid-level SVP or similar, then use that to ramp themselves up to a $25–$50 million per year business. It's uncommon, but it occurs.
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.
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.