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).
You're going to want to focus on partnerships in a situation like this. You're going to want to focus on big retainers where a percentage of your compensation is tied to the growth of the business. There are a few people in my life that make far more than this right now. One of my best friends is making around $1M-$1.5M every year with a single client. The way he did that is he came into the organization pretty small based off a referral. He proved his ability to do that one thing super well. He then built some systems for that one thing and said, "Hey guys, I actually just built a system that automated a fair chunk of the work I'm doing on a daily basis. I think I could make you guys way more money if you let me do this for other roles." They said "Yeah, absolutely." He started doing that. Eventually he moved into automating growth roles, and now he's taking a cut of whatever money he makes for the company, which is obviously a lot of money. So some sort of growth partnership, some sort of fractional COO-style gig, some sort of fractional CTO-style gig can be good if you want to juggle multiple, or you can just go balls deep like my buddy did with one — I think that's totally workable too. $150K-$1M per year per client logically speaking is just like $12K-$15K per month, so that's not that big of an ask. $1M per year per client is obviously bigger. That's probably the simplest and easiest way to do it. The sorts of businesses that are good to do this with are typically young people that do a highly scalable backend service — something like an information product, some sort of coaching, some sort of e-commerce thing that's highly scalable, where you can take a chunk of the revenue and the revenue tends to be quite large.
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.
The biggest one-time contract I sold was mid $220,000 for a project I called 'Uber for lumpers'—a system connecting companies needing lumpers (people who load/unload ships) with lumper workers. My business partner and I built it, but it was a total pain and not worth the time; it was one of the first projects we sold, so I took on custom work, but I don't recommend doing custom projects more than a couple times early on because there's little ROI on your time—my hourly rate is about $50. After that, I did a proposal generator system project that paid $1,500 and took only about 5–10 minutes to fulfill (plus ~30 minutes selling and a 30‑minute kickoff call). That gave a huge return on investment and unlocked the leverage idea: I could either make $225,000 in month‑one revenue from a big custom project, or I could create templates and sell the need, then spend five minutes copying a template I already built. Regarding agency requests, I get about 10 genuine agency inquiries per month; most want to invest $15K–$20K and work with me on a three‑month subscription at $5,900/month ($17,700 up front). I haven’t finalized my agency dynamics yet. The businesses that reach out most are high‑earning industries: fintech, software, financing/investing (e.g., underwriting firms that need automated financial data and email replies), and companies installing power grids that take a cut of hundred‑million‑dollar projects. My agency currently makes about $25,000 a month; from the $128,000 profit I mentioned, that’s roughly 20% of my income. Monthly profit isn’t the only metric—enterprise value matters. Info products are hard to sell because they’re tied to me; agencies have low multiples, whereas a SaaS product can achieve much higher multiples. I’m therefore building templates and done‑for‑you services, continuing to scale the agency for enterprise value and to stay connected to what I teach, because in coaching, when a system works, people often abandon it to teach it, which makes it outdated. I want to avoid that.
biggest contractuber for lumpersproposal generatoragency
Cool man, I know you already have a full-time job, which is fantastic. You're probably working 6 to 8 hours on that job and then spending time on lead generation, client calls, and fulfillment. You're doing a lot, and it's natural to wonder if it's time to bring on help. Here's what I'd do: first, set a near‑term realistic income goal—for example, $25,000 a month. Add up your salary, income from custom projects, and any other income. See how far you are from that goal. Then calculate your current internal hourly rate (maybe around $100/hour). If you need an extra $10,000 to reach $25k, that's about 100 additional hours. Ask yourself if you have 100 hours in your schedule. If not, you don't necessarily need to hire; you could raise your prices or pursue higher‑paying clients. Doubling your rates would double your income for the same time, getting you a large share of the way there. You could also increase lead volume—more leads give you more opportunities to pick the best‑performing projects instead of settling for low‑rate work out of scarcity. My decision‑making mindset is based on expected value: I evaluate the expected value of taking on a client or making a decision and choose the option with the highest expected value at that moment. Regarding hiring, my experience shows it's not easy to post a job, review candidates, interview, and hire quickly; you add a daily management time sync. The equation for effective hiring is whether the daily management time plus the cost of paying someone is less than the value they create by doing the work. Early in a hire, you're often not profitable until they're onboarded, trained, and up to speed. So, unless you have a much higher goal—say $50k, $100k, or $200k a month—you probably don't need to hire right now. As for scaling an agency model, I do think it gets harder to scale beyond a certain point. It was harder for me at $72k/month than at $25k/month. After a certain point you're no longer just an automation agency; you become a niche‑specific service or system‑providing agency. For example, one community member scaled to $80k/month by pivoting from automation services to selling cold‑email systems—a lead‑generation focus. If you start as an automation agency but find a super‑high‑ROI CRM project, you'll quickly shift toward being a recruitment‑agency‑style CRM provider. If you stick with the pure AI‑automation‑agency idea, you'll likely plateau around a $1M annual run‑rate, because that's when you need to hire managers to manage people, which is tricky.