How do you do cold outreach for a school community geared toward peer support and masterminding, and is cold outreach mainly suited to selling services?
Yes, you can do cold outreach for a school community, but I don’t recommend it. Communities are usually low‑ticket; the typical model is a monthly fee (e.g., $184/month for Maker School) for 3–6 months, whereas achieving similar accountability elsewhere might cost $4,000. I can deliver it for around $120, and people stay longer because they’re paying ongoing, which helps me project revenue. However, selling a mechanism that demands a lot of your time and energy for a $50/month product doesn’t make sense—you’d spend five to ten hours building campaigns and jump on five sales calls for just $50 in return. It only works if the product is high‑ticket (e.g., $5,000/month), which is rare in school communities. In general, I’d say no. If you want to run a successful school community, base it on inbound rather than cold outreach. Okay, all right—hopefully you found this valuable.
No problem, you should definitely double down on other forms of outreach. There are two ways to get clients: money‑intensive methods, where you spend money to acquire clients fast, and time‑intensive methods, where you spend time instead of money. In Maker School I focus on money‑intensive tactics, but the amount of money needed is actually very low compared to most businesses. For example, cold email might cost around $220 a month (software, mailboxes, leads), which is about 44% of your $500 take‑home — still a lot when you also need to pay rent. Upwork Connects cost about $2.50 per application; using the Connect strategy 20 days a month adds roughly $250, bringing your total outreach spend to about $470, or 94% of your income. Clearly, spending that much on paid outreach isn’t realistic. If you don’t have money to spend, you trade your time for what that money would have bought you. Start with cold DMs: combine the best of my cold email and Upwork approaches, and send them on LinkedIn, X (Twitter), Instagram, and Reddit — about 20 per platform each day. At three minutes per message, that’s roughly four hours a day, yielding around 1,200 outreach attempts per month. Even with a modest 5% reply rate and a 25% booking‑to‑close rate, you could land a few clients and start generating income. As you reinvest those earnings, your outreach becomes more scalable and your hourly effective rate improves. Another time‑intensive tactic is community posting: join relevant Slack, Discord, LinkedIn, Facebook groups, answer questions daily for two weeks, then start posting your own value‑driven content. When you gain visibility and authority in those communities, people will DM you for help, letting you pitch your services and turn those interactions into leads. The core idea is to trade time for money early on; as your earnings grow, you can gradually shift back to money‑intensive methods and reduce the time you need to spend.
I would absolutely just keep doing what you're doing—it's clearly working, so just do more and better of it. But I wouldn't allow that to stop you from experimenting with other approaches. Spend 80% of your time on the two models that have been working for you so far, and 20% on something else, like cold outreach or email. I would also significantly improve my prices: in Maker School, people sign $1,500 for one project in their first two weeks, then the next product is $3,000, then $5,000. So, just price more with every deal.
No, not really. The whole idea is that you're going to want to sell services here. If you're not going to sell services, Maker School probably will not deliver the return on investment. To be honest, my whole game is that I want you to deliver a return on investment, because then you'll be likely to pay me more money over the long run — versus somebody who joins for a month or two, finds the program superficially interesting, but doesn't get a return on investment. Ultimately I'm here because I want things to work. I want them to work for you, and in working for you, I want them to work for me.
You can absolutely hit $17‑$20K a month without cold email, but you need to focus on the platforms and outreach methods that actually move the needle. The biggest issue right now is that you’re not targeting the right places. While cold email is the simplest and most scalable channel, you can still generate high income through Upwork and community‑based outreach. For example, sending about ten high‑quality Upwork proposals a day can give you a 4‑6x return on your connect spend, which translates to roughly $7‑$8K a month after accounting for marketing and platform costs, leaving you with a healthy 75% gross margin. To improve beyond linear growth, decouple inputs from outputs by building reusable outreach templates and leveraging platforms that let you automate large‑scale, yet personalized, communication. Cold email is one such lever: invest a fixed amount of time in a high‑quality campaign, target precisely, and let it run without daily manual effort. Community outreach works similarly—become a recognized figure in a niche community, create evergreen posts that solve problems, and let those assets generate leads with minimal ongoing work. The same principle applies to cold DMs. All these strategies are layers of leverage; even the lowest‑leverage method—consistent Upwork activity—can get you to $17K if you execute well.