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#283 · every prospect has the same 4 problems

youtube ↗Client Acquisition

Should you send Upwork proposals with Looms or text, and what are examples of common problems you can assume prospects have so you can offer solutions upfront?

I always send Upwork proposals with a Loom video or a high-value personalized asset, such as a detailed Google Doc breakdown with an embedded personalized video. Giving away free, highly tailored value significantly boosts reply rates on Upwork to around 50–60%, meaning one out of every two people who view your proposal responds. As for guessing prospect problems, most service businesses within a niche struggle with the exact same core issues: 1) Reach: They lack brand visibility, so you pitch doubling their reach. 2) Lead Intent/Ads: Their ad conversion is low, so you offer to triple their ROI or reduce ad spend. 3) Conversion Process: They lack standardized sales scripts, proposal frameworks, and structured follow-ups. 4) Lifetime Value (LTV): Their Average Order Value equals their LTV because they only sell once to a client. If you help them drive repeat orders and raise LTV by 25%, you instantly increase their entire business revenue.

upworkloomprospectingoffer design

Related answers

youtube ↗Client Acquisition

I've sent 24 Upwork proposals in the past few days using Loom videos, bidding high on each. I got 4 views, 2 replies, and 1 job closed. Should I keep doing this volume, or offer a lower hourly rate? I've been accepting $30/hr at the lowest, and I feel like my reply rate isn't great.

Break the funnel into ratios: viewed/sent = 4/24 ≈ 16.6%, replied/viewed = 2/4 = 50%, closed/replied = 1/2 = 50%. The bottleneck is always your lowest ratio — here, that's the 16.6% viewed rate. A 1-percentage-point improvement there (16.6% → 17.6%) is roughly a 6% relative change, versus a 1-point move on the 50% reply rate only being about a 2% relative change — so fix the biggest bottleneck first, not the smallest number. To raise your viewed-to-sent ratio: your cover letter/proposal text is the biggest lever (clients only see the first ~100 characters, so make it hyper-relevant to the specific job, not generic), pair it with some kind of built asset specific to them (shows real effort, not just a template), respond as fast as possible after the job posts, and use Upwork's paid 'boost' feature on top of all that. No need to drop your rate — fix the funnel instead.

upworkfunnel mathconversion rateproposals
youtube ↗Lead Generation

Nick, cold emails versus Upwork. Which one helps move the needle faster to get your first win? Say you got 1K. extremely good skills, unlimited time, 18, a little social proof, and you're starting from scratch. Which of the two would be your go-to method to make a little bit more capital and get the ball rolling?

With $1,000 to bootstrap, go with Upwork. You can submit roughly 200‑300 applications (maybe more thanks to the connects refund policy). In the Maker School community, the average number of proposals needed to land a client is about 40‑60, so you could realistically secure around six clients. If the average revenue per client is around $200, that puts you at $1,200, and you can rinse and repeat. In practice, the average revenue per client is often higher—many close $1,500‑$3,000 deals—so within the first 50 proposals you could reach roughly $6,800 (or about $1,600 after the correction). Consistently scaling up from there will grow your business.

upworkcold emailbootstrap
youtube ↗Lead Generation

Please give us a detailed loom strategy for applying to jobs on Upwork.

Treat each Upwork application like a mini‑pitch video. Highly customize your outreach and record a Loom video that shows you’ve built something similar for a client. Explain why you’re the perfect fit, walk through the relevant work, and end with a clear call‑to‑action. Offer the system you’re using right now and invite the viewer to message you if they find it valuable, so you can keep delivering value.

upworkloomapplicationlead generation
youtube ↗Lead Generation

Is it the right approach to focus on Upwork, use Loom outreach to build demos, upskill by creating workflows from Upwork job descriptions, and post those systems on MakerZero for feedback?

That sounds reasonable. MakerZero is my free community where I host all my resources. Your point about doing outreach 90% of the time is spot on—if you're doing less than 90%, you're likely doing something wrong. Spending all your time rebuilding your website just spins your tires. If you have something, your core constraint is getting it out into the world. The unfortunate reality of outreach is that about 80% of people never see what you send, so you need roughly 5x more outreach than you think is reasonable. Most people think they need 15‑20% of their day on outreach, but they actually need 80‑90% like you're doing. You'll get a couple of clients, and then your reach volume will naturally drop, so just keep going.

upworkloom outreachmakerzero