How can I acquire more upmarket or mid-market enterprise clients—should I use direct response or focus purely on content?
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.
Debs Automate asks how to find clients. I explain that despite frustration, we are in the greatest era for client acquisition. There are two main buckets: inbound, where you create valuable content and monetize attention via a funnel (selling a service or product), and outbound, where you reach out to people with something valuable and try to sell them one-on-one. I started with outbound, door-knocking to sell marketing packages. Outbound is harder than inbound, but learning outbound makes inbound easy. If you can sell to a stranger and convert them into a paying customer, virtually all business becomes straightforward, especially for those making $0–50k a month. To do outbound, start with a data source of people who may need your product or service—such as LinkedIn, Instagram, X, Reddit, or Google. Find a deficiency in what they are currently doing and offer to resolve it upfront for little or no cost, then provide a strong guarantee on the back end. The person who initially asked about finding clients hasn't explored all possible outreach opportunities; there are more ways to get clients now than ever before, which is an interesting challenge to crack.
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.
We already work with any industry on anything they need—AI systems, business software, automations. The simplest way to start productizing is not to invent a new service, but to look at what you’ve already delivered that clients liked and double down on that. Make a list of every project you’ve done over the past year, pull the email threads, project files, and note the industries and types of work. Patterns will emerge: you’ll see which systems you built most often and, more importantly, which ones generated the most revenue. Use that data to decide which services to package. Then, reach out to the clients you built those high‑value systems for, remind them of the results, and ask for referrals and repeat business. Reactivating past clients is a low‑effort way to generate upsells—typically a 3‑4% uptake rate, and I’ve seen 15‑20% when I first started. Identify the most profitable, least time‑intensive product you’ve created—often an automated follow‑up agent or similar—and turn it into a repeatable checklist or product. Streamline the delivery: ask if you really need three discovery calls or if a single call or a form will suffice, reducing time investment and allowing you to raise prices, which is pure leverage. In short, catalog your past work, find the high‑margin, low‑effort services, market them to similar clients, reactivate old customers, and refine the process into a sellable product.
I would invest it entirely in lead generation. If you're not investing your money in lead generation, what else are you investing it in? Sure, marginal expenditures will happen for things like client fulfillment and growing your team, but if you're a beginner, the only thing that really matters is how many people see your brand, book meetings with you, and decide to close. So your priority is maximizing the top of the funnel. Three simple ways to do that: First, spend some money on Upwork applications—it's a vetted marketplace where people have raised their hands saying they want to pay for someone good at this. It's easy to stand out; you don't need to compete with thousands. Just ask yourself what makes you different and how you can show that differentiation makes you better suited than the other 50‑ish people they'll scroll through. Reply rates are around 10–20% in Maker School, which is high. Second, run a cold email campaign sending high‑quality, templated but AI‑customized outreach to people in your target market who have a higher‑than‑usual probability of needing what you offer. Think of it as a soft version of putting your hand up: these folks aren't raising hands yet, but they might soon, and you'll catch them as they do. Third, use an inbound approach like joining communities, becoming an authority in your niche (home services, HVAC, digital, PPC, etc.), which helps fill gaps your outreach methods might miss.
lead generationupworkcold emailinbound communities