#186 · How to *Actually* Sell High-Ticket Retainers for Any Service

youtube ↗Client Acquisition

How long does it typically take students to get their first client, and what additional investment is needed beyond the subscription fee?

On average, students take about a week and a half to two weeks to land their first client. Beyond the subscription fee, you’ll need Upwork Connects, instant-instant mailboxes (which are important but not huge in cost), and software platforms like Appify, Make.com, or NM. The biggest first‑month expense is usually the Connects. With consistent effort, you can land your first three or four clients in the first month, and cost per acquisition can be as low as around $100.

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Related answers

youtube ↗Lead Generation

How should I spend $1,000 to start getting clients? I considered buying a bulk of inboxes and a premium instantly plan to increase sending volume, but do you have other suggestions?

If you haven’t had a client yet, allocate part of the $1,000 to Upwork to buy your first job—it’s the simplest way to get started. Also invest in Maker School to learn the automation framework and get the curriculum. With the remaining budget, buy a modest number of mailboxes (around 20–21) and domains (about $50 for domains plus $70 for mailboxes, totaling ~$120). Use leftover funds to purchase leads. This approach lets you cover education, outreach tools, and lead acquisition while positioning you to land your first client through Upwork, provided you stay consistent and follow the program’s advice.

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youtube ↗Pricing

How much should I expect to spend before getting my first client after joining Maker School?

Industry averages suggest you’d spend around $200 to $300 before landing your first client. The Maker School fee is about $184, but you typically receive $2,000 to $3,000 in discounts and credits upon joining, which offsets the cost. You can use those credits on platforms like Upwork, cold email, LinkedIn DMs, or community outreach to acquire your first client. Upwork is often the simplest route because clients already have budget and are ready to hire. Cold email is high leverage but takes longer to master, especially for beginners who lack sales process understanding. Other methods include cold DMs on platforms, LinkedIn outreach, and engaging in communities like Reddit or LinkedIn groups to solve problems and get on calls. Overall, you should expect to spend at least a couple hundred dollars; if you’re not willing to invest that amount, joining paid products may not be worthwhile since you’ll need to recoup the investment after landing a client.

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youtube ↗Client Acquisition

Den Fleser asks: As a developer wanting to switch to a contractor‑based B2B solution provider with a target of $20K a month, how much daily time is needed to complete the course and how many hours daily are required to get the first client to earn $4‑6K a month?

How much time is needed daily to complete the actual course? On average, when people join, assuming you have no automation experience, your first few days are pretty long. You'll usually spend somewhere between 3 to 5 hours a day just taking the automation courses because we now have a bunch of automation courses. After that, the amount of time you spend per day tends to go down. The first week or so will probably take you like 3 hours a day. The reason is you're figuring out how to do things like outreach, setting up the systems, and also doing outreach the same days. After about a week, most of the systems are set up because you've done the work before, and then it's just pure outreach along with some administrative steps that you have to do every day. That's maybe 2 hours a day. Eventually you get down to maybe an hour and a half a day. After about a month into the program, you're spending a consistent hour and a half a day on that to grow your business. You can certainly spend more and many people do, but that's what the program minimums are. Second question: how many hours are needed to get the first client? That's really tough to say because there's a lot of luck involved. Some people get their first client after sending 20 pieces of outreach, others after 200, and in my early door‑to‑door days I got my first client after around 2,500 pieces of outreach. You don't have to do that physically; you can sit at your computer, use voice transcript tools, and the availability of opportunity is higher. As long as you follow the program, the guarantee is that within 90 days you'll have at least your first automation customer. If you charge $2,000 a month, you need two of those to hit the 4‑6K a month requirement. The lowest charges can be $100 to $500 for some people, while others making $25,000 on their first client. Income varies depending on how you acquire them. Upwork tends to be lower cost and lower income ($100‑$500), while cold email can bring $2,000‑$5,000.

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