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

youtube ↗Lead Generation

What strategies can I use to integrate my automation services with local small‑to‑medium‑sized businesses via cold DMs?

Nick advises Jake to stick with packaged automation services rather than moving to custom projects, because custom work suffers from scope bloat and inefficiencies. He suggests leveraging Jake’s existing mortgage‑originator network: compile a list of all B2B clients and leads from that work, plus any other network connections. In a spreadsheet, put clients in column A, ways you could help them in column B, systems you could build or sell in column C, and pitch price in column D. Then warm‑pitch each contact by referencing your automation work and asking if they know anyone who might need it. Start with existing clients and leads, then expand to your wider network for referrals. This approach uses your proven problem‑solver reputation, making outreach far more effective than cold outreach. After exhausting warm contacts, you can still add a scalable outbound mechanism (e.g., B2B cold email) to reach strangers, but the warm path is the fastest route to revenue.

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Related answers

youtube ↗Niches

Can you give examples of automation you’ve built for the real‑estate niche, and should I target freelancers, individuals, or companies and agencies?

I recommend targeting businesses with 1‑10 employees, so you can serve both freelancers/individuals and small agencies without making it exclusive. As for examples, I’ve built a cold‑email system for a brokerage that flips under‑priced homes. They had a list of about 50,000 contacts; the system pulled personal data, crafted personalized cold‑email campaigns, and generated massive responses—some reports suggest $50‑150 K in the first day. I also created automated property‑assessment tools that ingest a property’s square footage, regional price per square foot, distance to schools, crime rates, and other factors to output an instant valuation. These tools run on a custom platform (omake.com) and automate the entire assessment workflow. Both solutions have real value for real‑estate professionals and demonstrate the kind of automation you can sell in that niche.

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youtube ↗Client Acquisition

After building an AI automation invoicing system for a creative agency (27 freelancers), I've spent 4 months trying to find similar clients without success; lost direction. What advice do you have for finding clients for this AI automation service?

Use a tiered outreach approach. First, pitch to people who have already paid you—past clients give you about 10× the results per hour compared to cold outreach. Next, go to those who have paid you before, then to prospects who almost paid but didn’t, then to people you’ve already reached out to, and finally to completely cold audiences. Each step down the tier cuts the expected return (≈5×, 2×, 1.5×, 1×). It’s analogous to retargeting ads: validate your offer with a warm audience before spending time on cold leads. In your case, start with the agency you built the invoicing system for, show them the ROI you delivered, and ask for referrals or additional work.

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youtube ↗Lead Generation

Two years into building an automation agency alongside my consulting job I have three clients generating $20K revenue—one from Upwork, one from cold email, and one referred from that cold email client. The cold email ROI is great but relying on a single client per month isn’t repeatable. I’ve built several AI tools (SEO generator, social post generator, meeting summary tool, product copywriter) and have healthy inboxes but almost no meetings. I’m considering a productized, done‑for‑you service helping CFOs get invoices paid faster. Should I scrap the current model and go all‑in on one narrow offer, or does having only three clients in two years indicate something else is broken? Also, am I not doing enough outreach?

I think the core problem isn’t the offer itself but the amount of outreach you’re doing. Based on the numbers you shared you’re probably doing far fewer outreach actions than a typical agency—maybe 24 × less than you think. If you tally every email, DM, call, or LinkedIn message you sent in the first month you’ll see you could have done many more. The growth equation is simple: more outreach equals more leads, which equals more clients. So before you scrap the model, double‑down on consistent, high‑volume outreach (cold email, LinkedIn, etc.) and track those metrics. Once you have a reliable pipeline you can decide whether to specialize, but the immediate fix is to increase outreach dramatically.

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youtube ↗Lead Generation

How would you automate customer acquisition for a plumbing business?

Use a mix of automated inbound and outbound methods. Inbound: run PPC ads (Google Ads), list on aggregators like Bark.com (they sell leads), and invest in local SEO to rank for service searches. Outbound: compile a list of property management companies in your service area, then pitch them a preferred‑vendor package with 24/7 emergency service, discounted trials, etc. Leverage tools like Appify for scraping leads from Indeed/LinkedIn, enrichment with Clay, and AI‑personalized outreach via Instantly or Smart Lead. Track metrics, iterate quickly, and aim for low cost per meeting ($5–$10). Focus on revenue‑driving activities; after a few projects, bootstrap social proof and case studies.

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