#293 · AI gets you into a market but destroys you

youtube ↗Client Acquisition

I've struggled to get clients on LinkedIn due to inconsistency and not knowing what to sell or how to outreach. Should I try Upwork instead, or am I just coping? What would be the monthly cost to acquire a client within three months on Upwork?

Well, Ziad, you won't know what you're doing until you've done it; it's unreasonable to expect a beginner to have perfect outreach skills on LinkedIn. Your initial results will likely be the worst you'll ever get, and judging future performance by those early results is a losing game. Early LinkedIn outreach will have low view and reply rates, but after a year of practice those metrics will improve significantly—don't judge by chapter one, judge by chapter 100. Yes, you should try Upwork and other freelance platforms; there's nothing wrong with that, and you can use multiple platforms simultaneously. In Maker School we spend 70‑80% of our computer time on sales, marketing, and outreach because that's what gets clients; without clients you just have a hobby. Regarding cost to acquire a client within three months on Upwork: many students land a client after 10‑20 applications, with a median around 40‑50 applications. If your average cost per application is $5‑$6, that's about $200‑$300 spent. For a $500 client, that's a 40‑60% marketing cost on the first deal—high, but typical; early deals are usually the worst financially. As you upsell and gain experience, your marketing cost as a percentage of gross drops, often to 10‑15% of total gross. Don't stay on Upwork forever; use it as a crutch to reach more scalable platforms like cold email.

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Related answers

youtube ↗Client Acquisition

I've been on LinkedIn for months trying to get clients and failed — a mix of inconsistency and not knowing what to sell or how to do outreach properly. I've been considering starting on Upwork instead. Is that a good idea, or am I just coping? How much would it cost monthly to land a client within 3 months? I always thought I should stick to LinkedIn since I know the platform, but the deeper I get, the more I realize I don't know what I'm doing.

You won't know what you're doing until you've actually done it — it's unreasonable to expect polished outreach skills as an absolute beginner. Your results right now will be the worst they'll ever be; don't judge your future potential by your current 'chapter one' results, judge by 'chapter 100.' Yes, you should be doing more outreach broadly, including Upwork and other freelance platforms — ideally simultaneously. In Maker School, people spend 70-80% of their computer time on sales, marketing, and outreach, because that's what actually gets clients; without clients, you have a hobby, not a business. On cost: plenty of people land their first client within 10-20 Upwork applications, though the median is more like 40-50. If your average cost per application is $5-6, 40 applications is roughly $200 — which against a $500 first client is a high ~40% marketing cost, but your first deal is always your worst deal financially. As you build a track record and start upselling, your marketing cost as a percentage of revenue drops significantly — most people settle around 10-15% of gross spent on marketing via Upwork over time. Don't plan to stay on Upwork forever though — treat it as a crutch to get you to something more scalable, like cold email.

upworklinkedin outreachcost per clientgetting started
youtube ↗Lead Generation

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
youtube ↗Lead Generation

If I have zero budget but plenty of time, can I land my first client in under 48 hours and generate $10k monthly revenue quickly?

With no money, you double‑down on time. Scrape LinkedIn or Upwork profiles for first names and contact details, then manually reach out with a concise pitch that showcases your AI skill and offers a quick solution. Aim for 10‑minute outreach slots; in 48 hours (assuming you sleep 16 hours) you have 32 slots, which translates to about 192 potential prospects. Even a single positive response can land a $5k‑$10k client. If LinkedIn isn’t an option, be relentless on any platform—spend every waking second on outreach. These prospects are pre‑qualified because they’ve already expressed a willingness to pay for a problem solved. You can also farm social media for signals of need and contact those users directly.

zero budgetcold outreach48 hoursclient acquisition
youtube ↗Agency Operations

If I start an automation agency solo, how different would that be from what I'm doing now (contracting with IT consulting under my registered corp)?

He explains that starting an automation agency solo under your existing registered corporation is essentially the same as what you're already doing—providing services as a person under your corp. The registered corp is your business entity; you're not becoming a sole proprietor or independent contractor, you're just offering services through it. This matches the business model he recommends: targeting Microsoft 365-based companies, where you have the most experience and authority. If you can deliver scalably, the model works. For cold outreach, he suggests linking to your personal LinkedIn instead of an agency website because LinkedIn provides social proof and you can't share past client work due to NDAs. Make sure your LinkedIn is optimized. Regarding Maker School, if you're not after automation templates, tools, referrals, or learning Maker Naid, the main benefit is mainly breaking limiting beliefs—but if you're already making 20,000 dollars a month you likely don't have many of those. For you, the real value would be networking and direct access to him (questions answered within 24 hours versus 5-7 days elsewhere). Most members want templates, referrals, sales training, their first customer, and emotional support; you don't need those. What remains is the community of about 2,600 people and his personal access, which can be valuable to the right person, though average earnings in Maker School are around 2,000 dollars per month.

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