#24 · $139,000 in February 2025

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.

regulated industrieshealthcarefinancehipaamiddleware

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.

healthcareregulated nicheshipaaai automation
youtube ↗Niches

I'm a nurse practitioner transitioning into automation. I have limited knowledge and experience in SEO, copywriting, and marketing, which poses a huge obstacle. I'm stuck looking for a niche in healthcare and have landed on building adowered claims and education workflows for health insurers. What are your thoughts? How concerned about profitability should I be? Do you think regulations and HIPPO will pose a huge threat?

I wouldn't recommend a beginner go into a compliance-heavy industry like healthcare. Even with experience, case studies, or knowledge of how it works, building claims adjudication workflows for health insurers is a sticky business. If you want to build good systems for that market, you'll likely need to target mid-market to enterprise or government-affiliated organizations. The hoops to get your first deal will be much tighter, further away, and harder to reach. My recommendation: focus on a smaller audience to start, get a couple of wins, learn client management, how to service other businesses, and handle common business problems. Then use that experience to attack the mid-market level more adeptly, backed by actual experience rather than just reading or watching videos.

healthcare nichecomplianceprofitability
youtube ↗Agency Operations

How do you make sure the client's data is secure and private?

I mostly work with industries that aren’t heavily regulated—creative agencies, SEO agencies, ad agencies, digital marketing businesses, consultancies—where security isn’t a big concern and clients care more about growth. I avoid highly regulated fields like medical, legal, health, tech, finance because of top‑down regulations that make handling customer data complicated. If a client does care about privacy, I address their concerns as best I can: I explain where their data is stored, note that it’s purged every 30 days, and share relevant legal statutes. I don’t self‑host or build on‑prem solutions; for enterprise‑level needs like HIPAA‑compliant automations, you’d need alternatives such as Caragon, which come with higher costs (e.g., $400/month for 2,000 workflow runs plus 7¢ per run). That’s outside my current business model, so I focus on the lower‑friction, high‑ROI market.

securityprivacydata protection
youtube ↗AI & Automation

What are your thoughts on implementing Finance and Accounting automation solutions for businesses, and are there any known limitations?

You can automate many finance and accounting tasks—like categorizing transactions, variance analysis, and building dashboards—but if you’re creating a regulated financial product you must comply with relevant regulations (though I don’t recall the exact U.S. body). I avoid highly regulated industries like medical or finance because I don’t want to deal with that compliance burden; I stick to the B2B agency space where it’s more ‘wild west’. For most businesses, the limitation isn’t the automation itself but data‑security concerns; however, the onus of due diligence is on the company hiring you, not on you as the provider. You can still add value by using AI to spot large expenditures or strange transactions in QuickBooks or Xero exports, or to categorize bulk transactions, without trying to compete directly with those platforms.

finance automationaccountingregulationsdata security