Do you think it's a good idea to spend about $50 a month on Upwork Connects until I get my first client, and if so, should I use the overbidding strategy you’ve mentioned?
If I were you, Theo, I’d be very specific about the jobs you target. You probably won’t need to spend $50 a month; aim for around 15‑20 Upwork applications a month. Set an hourly timer and check Upwork once an hour for new postings, and be quick to apply to jobs posted in the last few minutes. Bid a reasonable amount and cap your Connects spend at about 30 Connects (roughly $2) per job. Focus on recent listings to increase the chance your bid gets seen, rather than throwing hundreds of Connects at older jobs. Use this sniper‑rifle approach with your limited budget. Also supplement Upwork with free outreach like LinkedIn DMs. Hopefully that makes sense.
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.
He says it’s realistic—most people get a gig every ~15 apps. Upwork connects cost $1.50 for 10 connects ($0.15 each); to stay at $2.50 you’d need about 16 connects. Typical jobs need 11‑14 connects, and boosting (pay‑per‑click) adds ~0.9 per app, bringing average cost to ~$3. He advises aiming for ~$3, finding cheaper/more viable platforms, and testing.
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
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.