Should I start with broader freelance work on Upwork to build relationships and upsell later, or focus solely on selling a specialized productized service from day one when I have no clients?
I used to be super into strategy and building the most productized solution before taking it to market and trying to figure everything out on day one. Unfortunately, I made next to no money. When I did win a client, it was very difficult because my total addressable market was pretty low. I over‑qualified clients, seeking only those with very high leverage who would let me scale using my little productized template and pay me $10k–$30k. I found it hard to scale because I was making opinionated decisions based on what was in my own head—what I thought was the best business model and the right way to pitch it. Nowadays you can't make decisions just in your head; you have to make decisions in the market. If I could go back in time, I would have taken on broader freelance work from day one instead of spending years building packages and pitching them a certain way. Doing the math, I could hit $40k MRR with five clients and then upsell a portion of them. I wish I could just go back in time and raw dog it—caveman max it—because I would have gotten a lot farther. Everything I've learned from the market has been thousands of times more valuable than what I thought I knew and what I learned from strategy. So, that's my answer to that question.
Instead of selling custom builds or one‑off projects, switch to productized services. Create a simple, repeatable deliverable—like a basic CRM setup—so you don’t have to go through a lengthy scoping phase, learn new platforms, or do extensive revisions. You can price it lower (e.g., $2,000) and deliver more of them each month. Five $2,000 projects equal $10,000, which is double what you’d make from a single $5,000 project. The trade‑off is higher leverage: you either keep the old model and grow slowly, or you redesign your business to run on repeatable, smaller projects. That’s how many freelancers and solo agencies now hit $20‑$40k months.
So, if you've closed four clients, I feel you—and nice job being offered two jobs and showing simple builds is almost always enough. I entirely agree with you; you’ve probably internalized some sales skills that don’t come easily to many younger people or those without corporate experience. Recognize that you have a unique angle: you’re good at explaining things to people, not just stumbling upon an amazing trick. Anyway, for sure: if clients want to hire you for a fixed number of weeks, let them pitch ideas and quote hours per task. Initially they’ll need to pitch the ideas and tell you what they want, but you should move into a partnership role as quickly as possible. Do a couple of jobs at this fixed‑pricing level for a few months—I did it at $11.75 an hour, then pushed to $15 an hour. That was cool for a while, but remember the hourly rate involves more than just the number. Move to fixed price for sure. Since you’ve already shown you can close clients easily and quickly, fixed price is just a small curveball to handle—not a big deal.
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.
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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