#232 · how to actually land retainers in 2026

youtube ↗Lead Generation

Should I use LinkedIn manual search or Upwork to target recruitment agencies in English‑speaking countries, and what technical credentials should I highlight in onboarding videos?

You already have enough knowledge; the problem is execution, not lack of knowledge. More knowledge won’t help—you’re just mentally masturbating listening to my voice. Thanks for the feedback, Taha. To improve execution, I focus on increasing the value I deliver and showing that value more often. My plan is to upgrade the resource library (better organization, more Claude code/skills, niche packs, open‑model templates), make sure modules reference those resources, mention the resources in posts and on weekly calls, and add them to the default welcome message for new members. I’m also pushing annual subscriptions to lower churn. The math shows that dropping churn from 20 % to around 13 % could raise monthly revenue from $220 k to over $330 k, so I’ll implement these changes to hit that target.

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Related answers

youtube ↗Marketing

I only have one case study and mostly connections with other automation builders on LinkedIn — what advice would you give for approaching LinkedIn from zero: what should I post, what themes/content, and how do I successfully interact with leads?

I treat a LinkedIn profile just like an Upwork profile — it's your own personal website, and there are a bunch of levers you can optimize like doing CRO on a landing page. Fill everything out, that's the lowest-hanging fruit: cover photo (something well-designed, even just from Canva, so it looks like you put in effort), profile picture (face clearly visible, I crop the background to white, add a little shadow, and smile at the camera), headline (a specific pitch — mine leads with being the founder of Maker School), location (I keep mine listed as San Francisco even though I'm in Calgary, just to pattern-match with people who have money), profile language set to English, a clean public profile URL, the About section, top skills, and the Featured section (that's basically the LinkedIn equivalent of an Upwork portfolio). For experience, associate yourself with something recognizable if you can — I don't technically have a company called Maker School so I've affiliated myself with 'school' to get the perceived association with a big logo people know. Then fill out every remaining field: licenses, skills, recommendations (like reviews), honors and awards, languages, interests, causes. For activity, don't make it the be-all-end-all — I'd post about once a week, but make it high-quality and specific to AI and automation, aiming for some engagement. As long as you're consistently active at some baseline level, you're probably fine.

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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.

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youtube ↗Cold Email

I’ve been doing cold outreach via email and LinkedIn but still can’t land my first meeting. What strategies do you suggest for improving my outreach and what advice do you have for bootstrapping solo founders?

When a campaign isn’t working, pretend you are a prospect on LinkedIn (or the platform you’re using) and walk through every element you control: profile picture, title, how recent your post is, and the actual message text. Optimize each piece—use a clear, professional photo that shows you as young, motivated, ambitious, and intelligent; craft a title that conveys credibility; consider posting timing (you may prefer to engage bottom‑to‑top); keep your message concise (around four lines before it cuts off) and experiment with capitals and emojis to grab attention. Treat the video or content you’re responding to as another input you can adjust. By enumerating all possible inputs and independently optimizing each, you compound small improvements (5 % here, 5 % there) into a large advantage. Apply the same logic on Upwork: use bright profile pictures, keep profiles to six lines or fewer because Upwork truncates after that, and write a tight, high‑quality CV (about 150 characters) with a strong, face‑focused image. These micro‑optimizations add up to an unstoppable edge in outreach.

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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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