#306 · how to get clients from free communities in 2026

youtube ↗Niches

What are your thoughts on selling AI enablement (e.g., AI medical scribes) to clinicians and physicians in the medical space?

That sounds like a great idea; I think you should pursue it. Having seen firsthand how bottlenecked many medical organizations are just from taking medical notes, I believe AI medical scribes are a solid move. Your main concern will be navigating HIPAA and other regulations concerning personal identifying information (PII). Often you must store data on-premises or ensure it never leaves the country, which can be tricky—if data accidentally crosses a wire outside the country, it could end up somewhere like Tajikistan in 0.1 seconds, creating serious compliance issues. The point is there are security hurdles to overcome, but working in a regulated industry has advantages: it's harder to enter, and once you're in, your moat isn't just the solution—it's also the regulation itself.

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Related answers

youtube ↗Niches

Why do you recommend avoiding regulated industries like healthcare when selling AI automations?

Regulated niches like healthcare are significantly harder to build simple automation systems for and even harder to offer guarantees in. Regulated industries often have strict legal limits on marketing claims and guarantees. Furthermore, healthcare compliance requirements like HIPAA, data residency rules, and PII anonymization create massive sales friction and long procurement forms before you can even begin work.

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youtube ↗Niches

I want to sell business AI implementations to help businesses save time and maximize earnings. How would you pitch it, and who is an ideal customer?

In general, the best niches for an AI service are high ticket, so these are services that themselves get a lot of money when they close a deal. They also tend to be digital, meaning services that you can scrape online fairly easily. And finally, they tend to be really low compliance need — services that don't require you to check a bunch of HIPAA boxes or do a bunch of SOC 2 compliance in order to enter the space. The reason why: high ticket means if you get them a single client, you pay for yourself for a long time. Digital means it's really easy to scrape, so low friction. And low compliance needs means you're not going to screw anything up — there are a lot of hidden risks that people constantly consider before accepting a project with an outside vendor if they are in a compliance-heavy industry.

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youtube ↗Niches

Which businesses should I target for my AI automation agency, ideally high‑ticket, online‑focused companies, and what else should I consider?

You want three things. First, target niches with high lifetime value (LTV). The higher the LTV, the more you can spend to acquire a client and still make a profit. For example, a shoe‑shine service might generate a few hundred dollars per year, whereas a personal injury firm could bring tens or hundreds of thousands. Second, choose industries where the prospect data is easily scrapable or digitally acquirable—LinkedIn Sales Navigator, keyword searches, etc.—so you can find decision‑makers who can sign checks. Third, consider compliance: heavily regulated sectors like healthcare or government‑related services are hard to automate with AI and carry legal risk. Also avoid platforms that could ban you if you automate them. In short, focus on high‑LTV, digitally reachable, low‑regulation niches.

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youtube ↗AI & Automation

In your experience, what are the limitations of using middleware/serverless automations (chaining tools like Make, ClickUp, OpenAI, etc.) in highly regulated industries like healthcare or finance — are the regulations too tight to provide the kind of flexibility and value you'd offer smaller businesses?

The regulations aren't too tight to do it, but they're definitely tighter than other situations, and honestly I just don't like dealing with it. In practice, if you want to do these automations in US healthcare you can't just use Make because it's not HIPAA compliant — you need a final compliance filter/check, and the same applies to financial regulations; it makes your life way harder, forces you onto alternative platforms, and requires things like anonymizing customer data. As a business owner you get to choose your niches, and in my case the juice usually isn't worth the squeeze, so I stay away from highly regulated industries and stick to less-regulated, typically smaller businesses (though I've worked with 8-9 figure companies too). It's a tradeoff: regulated/enterprise healthcare clients mean bigger ticket sizes, longer contracts, and slower-moving business, but also a whole new tech stack to learn, unfamiliar applications, data anonymization work, and real legal/regulatory risk. I can get the same benefits working with other kinds of businesses without those cons, so that's what I choose to do — though I could see situations where someone's genuinely set on going after that market anyway.

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