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#138 · How to Sell AI Automation for First Timers (Step-by-Step)

youtube ↗Client Acquisition

How do I gain trust with social proof, handle delivery, agreement, and payment after a first client, and find initial clients?

To gain trust, show concrete results: use the format 'I generated X for Y using Z'—for example, $153,821 for a B2B SaaS company via CRO, or $92,000/month for a content writing business via content‑production systems. Collect three or four of these one‑line case studies and post them on your website, Upwork profile, and keep them top of mind. Delivery means building the solution in the client’s own workspace. I avoid lengthy agreements; instead I send a brief proposal that includes minimal legal language and the payment terms, so the client handles the legal side and the proposal, I receive payment, and we move forward—all in one exchange. Finding clients is simple in theory but hard in practice; client acquisition is the toughest part of the business, so focus on the fundamentals rather than looking for shortcuts. If you’re truly starting from scratch, you can bootstrap by building a small result (like a cold‑email system that does X, Y, Z) for yourself and using that as proof.

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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 ↗Client Acquisition

How do I find clients in the really early stages of your AI automation agency? I tried Discord and Reddit at no success for three weeks only 50 bucks per automation. 50 bucks per automation. Any advice? And um, how do I even ship them if I got one?

Thanks for the question. Shipping an automation isn't really needed—you don't need to ship it at all because the shipping happens during the building process. You start by talking with somebody who likes what you have to offer, get them on a call, discuss the problems and solutions, do quick math to see how much the problem is costing them, and pitch your solution at a fraction of that cost—usually around 30%. Once they agree, you send a proposal, they sign it and pay you a little money. I like doing a 50/50 upfront and then upon delivery structure for a small intro offer, then transitioning to a retainer fully paid up front at the beginning of each month. After they sign, you need to get them on a kickoff call to walk through expectations, scope, timelines, and confirm the scope again before starting work—this is your point of highest leverage. If there are project problems, deal with them now while you have some of their money and haven't done work yet, rather than at the end when they're holding money out on you. On the kickoff call, you also have them sign up to the necessary platforms (like Make.com or N8N) so they have everything they need upfront and you never have to bug them again for access; the only messages you'll get are positive happy updates. As a Make.com partner and NN verified creator, I get preferential treatment like a thousand free operations via affiliate promo codes, which adds 3‑5% to your margin because they use your affiliate links and trust you as an authority. You have no liability for recurring payments—they take that on. Before the end of the call, you have all the credentials so you never have to bug them again. That's how you actually go about doing the shipping. To find clients in the really early stages of your automation agency, join Maker School.

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youtube ↗Client Acquisition

How to overcome the chicken-and-egg problem of selling first vs building later when starting with zero case studies?

You don’t have to choose strictly between selling first and building later; you can do both. On platforms like Upwork, propose to build a small draft system for a client as part of your application, build it quickly, then offer it for free just to get in the room and show what you can do. When the next client asks for something similar, you already have a system you built recently that you can share—again for free—to build credibility and move the conversation forward. Over time you accumulate a library of demo systems. You can also sell confidently without prior builds by offering a guarantee or by framing your pitch around the value you’ll deliver, and you can use cold email to propose building a free prototype to get a foot in the door.

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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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