#174 · Quickest way to make money in AI (as a prior business owner)

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.

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Related answers

youtube ↗Lead Generation

How can I improve view rates on my Upwork proposals when they’re highly personalized but getting 0% views?

First, check the specific proposal you’re sending—maybe it’s not resonating. A quick win: filter out any job posts that already have 20+ proposals; apply only to brand‑new listings (within the first couple of hours) because Upwork is short‑term and older posts are likely already filled. Another low‑effort fix: make sure the ‘online for messages’ bubble on your Upwork profile is green; if it’s not, you lose about half of potential responses. If you’re still getting zero views, you might be targeting outdated jobs—send more proposals to fresh posts. Remember that replies often take three to five days, so evaluate your results over a week (we do weekly retrospectives in Maker School).

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youtube ↗Lead Generation

Hey Nick, this is Ocean from Maker School. I made 3,387 from Upwork following the program. Quick plug, but I currently feel stuck mainly due to my work apps tanking despite getting 100% JSS and a much stronger portfolio. I've sent 142 over the past 30 days, only 16 reviewed with zero higher. So, you have a view rate of what's that like 8% something like that? No, 12%. The good news is I've been nailing the consistency as I'm approaching a 30-day posting streak and 22 days of five or more upper caps despite dealing with two jobs and a bunch of life issues, which derailed me initially from maker school. I've also restarted to learn cold email and scrape 2.7K from vain today. My question is, what would you do in my situation of about $1,500 in earnings from Upwork left and about 2,000 connects to spend. My goal is to make 5K per month to quit my job and be in one of your case studies when I make my first 10K a month as I believe I have quite a unique set of traits that could broaden the maker school demographic being Asian and also born in New Zealand.

You're sending about four proposals per day on average. If you increased that to 10 per day (2.5× more), you'd see roughly 2.5× more results. Your main bottleneck is the view rate, currently around 12 %; improving your CV, profile, how it stands out, and your writing to avoid generic templates could push that to 20‑25 %. Make sure the first 150 characters show you read the post, give something free, and present yourself as a professional. With a 12 % view rate, 16 viewed proposals translate to about five replies, which is rough but not hopeless. In my early days I sent 20‑25 proposals a day; I would have completed your 30‑day volume in about five and a half days, outperforming you six‑fold on views alone. Even without improving my view rate, that would have yielded roughly 90 views, around 30 replies, and three or four calls—enough to eventually land a deal. You can make up for any shortfall in volume with strategic effort, something I've done since day one. I'd still recommend you do it more effectively, but the principle holds.

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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.

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youtube ↗Cold Email

Could you make a video showing how to serve clients with a larger budget, something like $5,000 to $15,000?

Sure, I can talk about it now and, if there’s enough demand, I’ll make a full video later. The reality is that with a bigger budget you can move everything about ten‑times faster, maybe even a hundred times faster. For example, most people are limited to about nine mailboxes sending 30 emails each per day – roughly 270 emails total, or 135 new leads per day in a two‑step sequence. If you scale up to 90 mailboxes at 30 emails each, you’re looking at 2,700 emails a day, or 1,350 new leads daily, for a very low monthly cost (around $270 if you use a mailbox reseller). At a 0.02% reply rate that’s 27 positive replies, which can translate to three calls a day. With a good campaign you can convert 10‑15 calls per day, and even if 30% drop off you still get seven to ten quality calls. Assuming 45‑minute calls, you can fill an entire day’s calendar and close a couple of deals daily. If each deal is $2K, that’s $4K a day, or about $80K a month running 20 days, not counting upsells or retainers. In short, if you’re well‑resourced you can realistically schedule $80K‑plus a month with a productized offer by going all‑in on cold email, as long as you have enough leads to fulfill the volume. This means broadening your top‑of‑funnel targeting across more general niches. For a $5K‑$15K budget, $270 is only about 2.7% of the spend, leaving roughly 4% of margin for growth.

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