Reese Cooper asks: I have an 8‑hour job paying $500/month, I’ve already spent that month’s money, and Upward connects cost money I don’t have. Should I double down on other outreach methods or just give up?

#110 · "I make just $500/m at my job—how do I grow an AI agency?"

Reese Cooper asks: I have an 8‑hour job paying $500/month, I’ve already spent that month’s money, and Upward connects cost money I don’t have. Should I double down on other outreach methods or just give up?

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.

cold emailupworkcold dmcommunity posting

Related answers

youtube ↗Lead Generation

What is the most straightforward path to reach $20,000 per month without using cold email outreach, given I have two engineering jobs earning $3,000 a month and a few hundred dollars from freelancing, plus a $500 monthly learning budget?

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.

upworkincomecold-emailscaling

youtube ↗Cold Email

Does cold email outreach still work? I want to start Maker School, but applying to Upwork jobs seems like the main effort—five apps a day would cost about $400/month, which I can't afford. I know it takes money to make money, but I want to retain control.

Yeah, well, I think you hit the nail on the head. It does take money to make money, but it doesn't explicitly require money—you can make it work with zero dollars, though it takes longer and is harder. The high‑leverage approach is to invest a little money at strategic pressure points to ease burdens like mundane outreach. So yeah, cold email outreach definitely still works. There are dozens of people posting wins about their cold outreach every day; if you check Maker School or the wins tab, about a third are cold outreach. The reason more aren’t cold outreach is that after most people get their first win they stop posting, and cold outreach is super scalable, so those who win tend to get many wins. In contrast, with Upwork you’re excited about the very first customer, which over‑represents Upwork wins. Anyway, the math: 400 bucks a month for 18‑credit applications at $1.50 per 50 credits per 10 equals $2.7, then you said 150—actually you’re right, it’s $400 a month. Most people don’t actually do five Upwork apps a day, and you’re amortizing the cost across the whole month. I recommend beginners do this because, compared with many other methods, you spend a little money each day instead of a large lump sum, and you see returns quickly, though the gap between investment and return is smaller and shorter. The way Upwork works is you spend a little bit of money daily—about $12 a day for 30 days—so you start seeing results pretty quickly, though the returns aren’t as big because Upwork is more competitive and has limits on job size and client acquisition. You notice the gap between starting and making money is shorter and smaller, which is why many people use Upwork. So yeah, it does take money to make money, but you don’t have to do it this way; you could send cold DMs, send cold emails manually, or try a million other things. Just don’t let the possibility of failure stop you from pursuing success.

cold emailupworklead generation

youtube ↗Lead Generation

Hey Nick, after I joined Maker School, what would be the rough monthly budget that I should have considering all the tools and upper connects can add up quite a bit? Sorry, I didn't mean to down thumb you. If you give a specific number range, thanks a lot.

Your monthly budget varies mainly with outreach volume. Many people find sending 10 Loom videos daily overwhelming, but I never considered it hard when starting out. Think of it like coal miners who just accept mining as their job—your baseline for effort. Not everyone does 10 Upwork applications daily (my month‑one recommendation); we usually taper to 3‑2 per day later. Upwork connects average about $3 each; after boosting and view‑rate adjustments, assume roughly $4 per day if you send four applications daily, totaling ~$240 monthly if done 20 days a month. The idea is that by the time you’ve spent that amount, you’ll likely have landed a client who covers at least that cost, ideally 5‑10×. Add fixed beginner costs of $100‑$250 for Upwork. You’ll need a cold‑email system: I recommend services costing $55‑$60 for mailboxes/domains in month one, then $35/month thereafter (e.g., Instantly, Smartlead). Lead‑scraping services run about $1‑$1.50 per thousand leads; targeting 3,000 leads adds ~$5/month. Putting it together: ~$40 for cold‑email, $50‑$60 for mailboxes/domains, and $100‑$250 for Upwork connects, giving a realistic monthly range of $350‑$400 for a total beginner doing moderate outreach. The biggest variable is how much outreach you actually do.

outreach budgetUpwork connectscold email cost

youtube ↗Agency Operations

How many hours per day should I dedicate to Maker School while working full-time and interning, and how much money should I allocate besides subscription fees?

Well, you ended up joining anyway—just kidding. For anyone else here, I'd recommend a couple of hours, maybe two to three hours per day. The first couple of days might be a bit heavier: day one could be three to four hours, day two two to three hours, then from day three onward it settles to about two hours a day, maybe a little more. Some people take longer at the start, but that's okay. The reason this works quickly is that lead generation and outreach strategies become fast with practice because I make you do a lot of them. Regardless of initial timing, you'll eventually gravitate to a two‑to‑three‑hour daily workload, which most people can fit in. A core part of the program is daily accountability and habit tracking—not just learning a specific lead gen tactic or setting up automations. It's like going to the gym but for money: you show up daily, track your habits, and build consistency. Regarding money, it's hard to give a fixed number because it scales with how much outreach you do. My suggestion is about ten Upwork applications a day and roughly two thousand cold emails in the first month. In practice, most people end up spending an extra $100‑$150 per month on things like Upwork fees or cold‑email tools, due to limiting beliefs that hold them back. The beauty of Maker School is that the capital outlay is low: you spread the cost over three months, and the time to see results is short compared to typical businesses that require a big upfront spike with uncertain payoff. You also get discounts via coupon aggregators and my affiliate links, so give it a try.

maker schooltime commitmentcostagency