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.
Yes, you should pitch them on a sales call immediately. When a prospect replies on Upwork, they often ask follow‑up questions like, “Hey Pete, I liked your video. Can you do this for X amount? Can you do it this way?” If you give them all the information in the reply, there’s no incentive for a call—you’ve already proved everything in writing. A call lets you demonstrate how you differ from the sea of generic Upwork freelancers.
The best approach is to lightly address their questions in your reply, thank them, and then suggest a short 15‑minute call to go over details and provide a scoped price. Offer a few time slots (e.g., next hour, 4 p.m., 6 p.m.) and include a calendar link so they can pick what works for them. This way you keep the conversation moving and avoid endless back‑and‑forth.
I also provide multiple ways for them to get in touch—email, calendar link, and other contact options—so they can choose the method that’s most convenient.
Josh's approach is perfect if you're not yet in the automation industry, don't have an automation business, or aren't freelancing; your only goal should be to go from zero to one as quickly as possible. Most people in Josh's situation try to jump from zero to a hundred right away, but the strategies for going from 0 to 1 are different from those needed to scale to 100. Josh is looking for a minimum viable strategy—similar to a minimum viable product—to avoid stagnation and quit, because he values feedback loops. This is the way I approach any business model in the 2020s, given how fast everything moves. Regarding your question about minimum tools and whether to focus on Upwork until you earn money: it depends on your financial situation. The quickest path from zero to one, in my experience, is to spam three methods: Upwork applications, cold emails, and community engagement. I call it spamming like a video game because, while quality matters, the law of large numbers ensures results if you send enough outreach. For Upwork, send many applications using a customized Loom video approach—record a short video saying, 'Hey, how's it going? I just saw your post for XYZ; let me show you exactly how I'd solve this.' Highlight your relevant experience (X, Y, Z) and past results. Even if you're new to Upwork, this personalized touch boosts your chances. For cold emails, use one of my offer formulas or cold email templates, then find an audience, split‑test two or three audiences, and gauge reply rates—especially positive replies. You can personalize with AI if you wish; my Nix cold email templates are available via the four‑step cold email copying system. For communities, identify groups and niches you're interested in (e.g., videography, dental clinic managers). Post hyper‑relevant content that provides value without selling immediately. For example, in a dental clinic manager community, share a strategy like 'end‑of‑insurance reactivation' that leaves voicemails about unused benefits. By consistently giving value over time, you become an authority and can start charging for your services. These three outreach methods—Upwork, cold emails, and community posting—constitute the minimum viable strategy for landing your first client.
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.
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.