Do you still have your old clients, and how is your relationship with them after experiencing massive growth?
I don't have all my old clients; I've let go of many because the profitability per unit time spent on them is lower than focusing on other things. The relationship is different now that I have 150,000 subscribers versus when I had zero subscribers and got those early clients. With the clients I still have, the relationship is pretty good—I've even negotiated a bigger partnership with one of them. Early in my community, there were questions about whether I'd still have time for them as I shifted into information products and coaching. I decided to make time because it's important to practice what I teach. Many coaches and consultants build a successful business model, then teach it as an idea, realizing they make more money selling the model than delivering the service, so they stop doing the actual work. When they stop, they lose touch with the market. In our fast‑changing industry, an outdated approach won't work in six months, making it unethical and ineffective to sell outdated methods. That's why I do live building—showing how I acquire leads and sell stuff—so I stay current. Revealing the 'sauce' (my methods) actually increases my income; every time I've shared it, I've made more money.
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.
Your content is your sales, so hiring someone to handle the most important task doesn't make sense; instead, consider delegating operations, fulfillment, or administrative work. In general, delegate any work that isn't essential to your bottom line to buy back your time—a concept Dan Martell emphasizes. Use that reclaimed time to focus on activities that have a direct one‑to‑one correlation between time spent and revenue, like high‑value sales or product development. You might worry about remaining just the sales guy while others become more valuable to larger companies, and while you're strong at marketing and getting attention, your sales still need improvement. The valuable skill is maintaining client relationships and providing daily progress updates; doing so preserves the relationship and sharpens your most valuable abilities. You're overthinking the situation—you're stuck in your head. Stop spending time on this problem; put your head down, resume the daily outreach and marketing activities that got you meetings, and repeat them all day. These concerns are largely self‑created; you are your own biggest obstacle. Getting out of your own way will unlock far greater progress. I’ve experienced this myself over the last seven or eight years: progressively removing my own limitations has been key to my success. Okay, it's Clark's as I am. Thank you.
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.
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.