#36 · Should I Still Learn Programming in 2025?

youtube ↗Client Acquisition

I started learning automation in November, spent two months learning, and since January I’ve only secured two clients that are still in the process of closing. What are the top three ways to get my first two clients on board?

I think we should start by clarifying terminology: I wouldn’t consider someone a client until they’ve paid money—or at least committed to paying for something, like a software subscription. Until money changes hands or an agreement is signed, it’s not a real client. Many people think a deal is closed when the prospect says yes, but it’s not truly closed until they sign or, better yet, pay the invoice. Saying yes is different from actually paying you. You said you started automation in November, learned it in two months, and since January you’ve only got two clients in the process of closing. Over roughly 60–70 days, if you’d done a daily outreach minimum—say 10 personalized Loom videos a day via Upwork, DMs, Instagram, X, etc.—you’d have contacted about 700 people. Yet only two showed interest, which is about 0.3% (2 out of 700), or roughly 1 in 350. That’s extremely low; to get one ‘yes’ you’d need to hear roughly 349 ‘nos’. If you’d done consistent, reliable outreach using the mechanisms I show in Maker School and on my channel (daily Loom videos, etc.), even if you were terrible at it, it would be statistically unlikely to get so few results. Typical response rates are around 2%, which would be about eight times better than what you’re seeing. So you likely reached out to far fewer people—maybe around 80 total, or about one per day. To improve, first be very clear about what ‘closed’ means—wait for payment or a signed agreement. Second, set a clear daily outreach minimum, like sending 10 customized Loom videos a day on platforms such as Upwork, Instagram, X, or via DM. Third, standardize your sales process: use a repeatable roadmap (like my ‘Roadmap to $25k a Month with Automation’) that funnels prospects into a meeting, then a sales call, then a detailed proposal or scope of work, and follow the same steps each time. Doing this builds infrastructure you can iterate on—run it for 10 clients, tweak, run another 10, and you’ll see conversion rates improve. That’s what I’d do if I were in your shoes.

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Related answers

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 ↗Agency Operations

I'd love to hear more about how you went from having no clients to landing your first few, and then how you scaled to 100K months. Specifically, how did you structure long-term deals with automation clients after building their systems, and what makes clients willing to pay a retainer once the automation is set up?

Are we talking no clients in general, in any of my businesses, or specifically automation? You might be talking about automation. The way I did automation was I just started out on Upwork — applied to like 10 to 20 Upwork jobs per day along with my business partner at the time, and the vast majority of them said no to us. We used a custom Loom-video-based approach: I'd record a Loom of me talking through the problem and send out a ton of those. I got really good at explaining automation problems consistently, and we scaled that automation agency pretty quickly to $15-20K a month. We languished around $20-40K a month for a while because my partner wanted to operate it as a software consultancy taking on custom projects with a big hired team, but that didn't really work — the engineers we hired could drag-and-drop in tools like Make.com but didn't understand the business side, so the automations they built were brittle. That's when I learned how difficult hiring is for something as complicated as a software/automation project. My partner and I eventually split up amicably — he wanted to focus on the consultancy side and building resellable equity, I didn't. I kept the business, focused on high-leverage applications of systems I'd already built, scaled up Upwork applications and cold email (reinvesting most of my income into cold email), and simplified the offer down to mostly cold email systems and one-click CRM templates. Around $35-45K/month I couldn't keep scaling that way, so I started pitching a fractional-COO model: I took a few smaller clients paying $3-4K/month and gave them massive 20-30 page proposals saying, 'I want $10K/month plus 7% of your business, and here's how I'll justify it by delivering $100K/month in value.' That worked for a couple of clients, my revenue shot up, and combined with old clients coming back that same month I hit $72K in revenue (not all of it was recurring).

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youtube ↗Lead Generation

Two years into building an automation agency alongside my consulting job I have three clients generating $20K revenue—one from Upwork, one from cold email, and one referred from that cold email client. The cold email ROI is great but relying on a single client per month isn’t repeatable. I’ve built several AI tools (SEO generator, social post generator, meeting summary tool, product copywriter) and have healthy inboxes but almost no meetings. I’m considering a productized, done‑for‑you service helping CFOs get invoices paid faster. Should I scrap the current model and go all‑in on one narrow offer, or does having only three clients in two years indicate something else is broken? Also, am I not doing enough outreach?

I think the core problem isn’t the offer itself but the amount of outreach you’re doing. Based on the numbers you shared you’re probably doing far fewer outreach actions than a typical agency—maybe 24 × less than you think. If you tally every email, DM, call, or LinkedIn message you sent in the first month you’ll see you could have done many more. The growth equation is simple: more outreach equals more leads, which equals more clients. So before you scrap the model, double‑down on consistent, high‑volume outreach (cold email, LinkedIn, etc.) and track those metrics. Once you have a reliable pipeline you can decide whether to specialize, but the immediate fix is to increase outreach dramatically.

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youtube ↗Agency Operations

How do you onboard your automation clients, create the roadmap, and set expectations for retainer clients?

I start with a kickoff call where I deliver quick wins to minimize buyer's remorse, and I always take payment upfront before any work begins - never considering a client 'onboard' until the money is in my account. After receiving payment, I create a detailed proposal that serves as both a sales document and a roadmap. Roughly 60% of the proposal outlines the client's problems, demonstrating my understanding from any prior small project; about 20% covers the proposed solution; the remaining 20% discusses logistics, principally compensation. I typically pitch a large monthly fee - recently moving from $6,900 to around $12,000-$12,300 - and often add a revenue-share component to align incentives, inspired by the idea that sharing upside makes both parties more comfortable and can lead to more money. I discuss performance-based versus flat pricing, noting that beginners should lean performance-based, intermediates may go flat, and experts often return to performance-based because they have confidence in delivering results. Once the client agrees and pays, I invite them to a kickoff call to set communication expectations: I'm highly reachable via Slack (within 15 minutes) and hold daily office hours from 12 p.m. to 2 p.m. PT, plus a weekly strategy session. I ask clients to commit to the same recurring time each week for at least 50 out of 52 weeks, emphasizing consistency so they take the calls seriously and see ongoing value. During each meeting I review wins from the past week, outline what I'll do next, and address any questions or fires, ensuring I always show up with something tangible to justify the retainer. I then follow the roadmap, checking off the 45-plus tasks in order, and optionally sync with the client's project-management system (though I've moved away from using my own ClickUp board as the single source of truth). I also note that other agencies like DesignJoy use shared boards, but I prefer bringing a quick note of wins and next steps to each meeting.

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