I'm an experienced software professional and I want to go big time in AI and automations. I'm trying to obtain high-value clients and ticket services north of $150K to $1M per year per client. What kind of areas or services do you think I can offer to tap into such value?
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.
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).
Can I hit $5,000 a month with one or two clients? Absolutely. It's straightforward to do this. Hitting $5,000 a month with a client is almost the entry line to becoming a real agency owner. In the case of the person who asked this, I've had clients who paid me $20,000 to $30,000 a month for services. It's very straightforward and relatively simple: you simply need to provide a multiple on the money they are paying you. If someone is paying you $20,000 a month, as long as you're providing them $100,000, $150,000, or $200,000 a month in comparative value, they will happily pay you that amount. The reason this is difficult for people to understand is that it's at scales and scopes most find unimaginable. I first grasped this idea when my best friend Zach started working with a highly scaling content offer (some sort of automation offer). At the time I wasn't having much success, while Zach was decimating me in every way. I asked him how much money he made with this stuff; he said he made $45,000 last month. I asked how many clients he had, guessing 45, and he said he had one client paying him $45,000. I couldn't understand it because I had no experience with that. The reality is Zach was probably underpaid for the value he provided; realistically he should have been paid two and a half to three times that, given he was making the company millions per month. When you start thinking more about the value you provide and less about the sticker‑shock price, and if you can convince a client that this is true, you start being able to earn, quite honestly, unimaginable amounts of money from the right people who get it.
If you’re earning $2,500 per year, you’re essentially being robbed in broad daylight; but if you’re making $2,000 per month ($24k per year), you’re on the lower end yet not necessarily being exploited. To think about your situation, imagine you’re paid $25,000 per year while generating $500,000 in value for the YouTuber—that’s about 5% of the value you create. Most people receive only 1–2% of the value they generate, while strong salespeople earn 15–20% through commissions. My advice for contractor‑partner roles like yours is to aim for 10–15% of the value you deliver, which translates to roughly a 10× return on investment for the client. If the client is smart, they’ll happily pay you $1 to make $10 for them. The mistake many people make is realizing they’re underpaid and then demanding more money outright—a losing approach that comes across as a loss‑based demand and triggers ego or risk‑aversion in business owners. Instead, frame the conversation around growth: remind the client of the results you’ve already delivered (e.g., over $3 million generated together), share your vision for scaling to $10 million, $20 million, or $30 million, and propose a concrete roadmap (start with X, then Y, then Z). Emphasize that you want to take on more responsibility because you believe you can execute better than others, and assure them you won’t take any of their time. Then, at the close, add that you want skin in the game—more upside when things go well, and a corresponding adjustment when they don’t. Present this structure directly to the client. Because you’re leading with growth and a clear path to multiply their business, the likelihood of them agreeing to partner on a new initiative is vastly higher than if you simply complained about pay. In short, if you’re only making a few thousand dollars a year, you are being underpaid; but if you’re earning tens of thousands per month, you’re in a reasonable position. My overall approach to every job or partnership discussion is to focus on mutual growth, not to threaten to walk away unless paid more—that’s blackmail and damages trust. Successful business owners refuse to negotiate with that kind of pressure. When you approach from a desire to grow the pie together, you’ll achieve far better outcomes.
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.
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