#186 · How to *Actually* Sell High-Ticket Retainers for Any Service
I’m not selling web design right now because I don’t think it’s as good or cool as automation, which may just reflect my current skill set.
You don’t have to choose just one—you can do both digital and local. Run a side‑by‑side experiment for about two weeks: target local businesses across the US and South Africa in one test, and digital businesses in the same regions in another. Measure how many people say yes in each, how difficult it is to scrape leads (using time as a metric), and what average order value you can pitch for digital versus physical offers. Let the data tell you which works better.
No, as a beginner you should not target local businesses first. There’s a big list of things to target before going local—always start with digital, and consider hybrid or high‑cost‑of‑living countries before local. Local businesses are much harder to scrape leads for; you usually need to pull data via Google Maps API or address‑based scraping, which is hyper‑limited and raises the bar significantly. You’d have to invest far more money than for digital businesses, yet the pay is low, so the return isn’t worth it. Generally, these businesses have a high barrier to entry and offer little pay. If you want context, I’ll link a video about niches; three automation‑agency niches come with criteria I use, one of which is that they tend to be digital. For newcomers, that means definitely not targeting local businesses—it’s just a lot easier to pull the digital lever. If you’re experienced and see a genuine market opportunity with a particular type of local business, then I might consider it.
Small businesses often have a generic info email that routes directly to the person in charge, though it may be filtered through junk folders. While this approach typically yields lower response rates compared to more targeted methods, it can still be viable, especially if it's the only data you have. Gathering email data is cheap and easy: you can search Google for relevant terms, scrape the resulting websites, and extract email addresses via simple HTTP requests. This can quickly generate thousands of contacts for just a few cents, making it a low‑barrier entry point despite the competition.
Upwork works well for beginners who lack sales‑marketing experience—it’s a simple paid‑access to a pool of people who already want what you sell, so you don’t need to be a strong salesperson. Cold email gives you access to the whole world, but your ability to explain, justify, and sell the problem becomes the big differentiator. Cold email is typically more scalable and makes more money over time than Upwork, though Upwork is easier to start with. I actually use both in tandem.