#278 · upwork vs cold email: which gets your first client faster?

youtube ↗AI & Automation

Nick, I'm considering offering or selling AI to businesses. I want to start to some small businesses before aiming for bigger clients. How would you tackle this given they have different needs and situations or problems? Do you build a setup per business or do we build a set of services that could work like a general AI service? Also, for approach, direct messaging or in person.

Don't overthink the exact method—pick a few approaches and test them. Choose three different ways of reaching people, set a minimum daily outreach for each, and stick with it for a month or two (30‑60 days). See what works, then double down.

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Related answers

youtube ↗AI & Automation

Is selling broad AI implementation tailored to each business valuable, or should I niche down into specific solutions like marketing and use AI within those?

If you’re making $0‑$20 k per month, keep selling broad AI implementations and use AI to create the perception of a highly customized service. Once you want to go beyond that revenue level, you need to productize and template your offering; that part of the market hasn’t changed even as AI models have advanced.

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youtube ↗Offers

What offers could I sell, and can my existing AI systems be used as leverage? Which type of business owners should I target and where are they? Should I sell a service and use AI to fulfill it instead of selling AI directly?

You’ve already built a DM qualification skill that let you charge 40% more on a client deal, plus LinkedIn content automation that generates one to two inbound leads per day. That gives you solid social proof, but you need to frame it in concrete, dollar‑sign metrics. Instead of talking about the system itself, talk about the results it can deliver – for example, 20 to 40 meetings per month and an estimated pipeline value of $25,000. Position yourself as helping small‑to‑medium business owners who aren’t massive enterprise CEOs – think a 30‑something running a three‑person agency who wants to relax a bit. Provide clear value to that audience. As for offers, you can sell virtually anything: the DM qualification skill, LinkedIn and content automation systems, management services, social‑media brand growth, niche video editing, AI‑enabled video editing, or even content edited with tools like Hyperframes or Remotion. Lead sources are typically scraped from LinkedIn Sales Navigator where prospects voluntarily share a lot of information.

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youtube ↗Offers

Hey Nick, quick question if you don't mind. So, of course, this will depend on the niche you're getting into, but about how many and what kind of services would you recommend offering as you're starting out? Seems like you wouldn't want so many of the potential clients you're overwhelmed, but also not so few that you're seen as a non-option, if that makes sense. But I could definitely be looking at this from the wrong angle here. Truly appreciate all you do, my man. God bless. Thank you.

I recommend offering services that solve money-based needs for people who have money and are willing to spend it. Compliance-related needs are money needs but not as direct a path as getting more leads, converting leads, talking to more people, or solving administrative issues costing a company $1,000–$2,000 a month. Focus on money services. As an AI-enabled business, you have many options; anything that solves a need and can have AI sprinkled on top is a good bet. AI doesn't create possibilities; it makes pre-existing solutions faster and easier to implement. The key is knowing how to solve money needs for real businesses, not just knowing about AI. Don't worry about having too many or too few services; start with three offers, put them in front of people, see what they say. If they like the offers and ask for more, naturally create another and upsell to the most sensible offer. Avoid trying to get everything right from the start; don't put the forest before the trees.

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youtube ↗Client Acquisition

What types of businesses or clients should a beginner target on Upwork (or similar platforms) when starting with AI automation?

Accept any and all work on Upwork—think of it as an elevator that instantly connects you to large businesses you’d never meet otherwise. Even as a total newbie, you can land a client doing $10–$20 million a year within a week, giving you a powerful case study like 'I helped a $10 million/year business achieve X, Y, Z.' At this stage, don’t worry about qualifying or tightening the funnel; go broad to bootstrap experience, collect case studies, and start making money. The creator shares a personal example: a friend who jumped on Upwork while he was door‑to‑door went from zero to a legitimate $30 000/month income in three‑to‑four months by maximizing opportunity and landing a big‑ticket client whose needs matched his skill set—something the creator missed while grinding door‑to‑door for $5 000/month.

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