How Regular People Get Rich Buying Boring Businesses

Should you stay sector-agnostic in ETA (entrepreneurship through acquisition) or plant a flag with a clear buy box brokers, CPAs, and attorneys can remember? After a month sidelined by a home flood, searcher Chris Barr returns to his acquisition entrepreneurship journey—refining a small-business acquisition thesis around B2B services, GovCon janitorial contracts, and Florida/Palm Beach deal sourcing. We dig into search fund tactics, on-market and off-market pipelines, broker outreach, list scraping, AI-assisted follow-ups, and how to position for SBA 7(a) financing, LOIs, diligence, and close.

From tier-1 vs. tier-2/3 service models to residential vs. commercial focus, Jack and Chris get tactical about building a repeatable deal flow engine in a tight geo, crafting a memorable buy box (ticket size, customer type, contract length), and using light automation without sounding like spam. If you’re refining your acquisition criteria—B2B/government contracting, janitorial cleaning services, niche add-ons (e.g., AeroSeal), high-margin home services, or local trades—this episode hits playbooks for valuation, negotiation, seasonality, staffing, and lender selection so you can source better deals, faster.

💡 What You’ll Learn
 • How to create a “tight buy box” brokers/CPAs/lawyers can remember and route deals to
 • The case for B2B and GovCon janitorial (set-asides, contracts, and people leverage)
 • Tier 1 vs. Tier 2/3 plays (e.g., niche add-ons like AeroSeal) and which fits a “nice-wage, simple, local” plan
 • Residential vs. commercial: ticket size, sales motion, and capacity caps
 • On-market vs. off-market engines: re-engaging brokers, list-scraping, and thoughtful personalization
 • Using AI for workflow and follow-ups—without sounding like a bot
 • Why timelines slip (and that’s normal): guilt, resets, and staying in the game
 • Picking the right SBA lender for trades acquisitions

💼 Special Thanks to First Internet Bank!

Looking to buy or expand a business? First Internet Bank is a National Preferred SBA lender specializing in acquisitions for the skilled trades. Their SBA loan program offers up to 90% financing for business acquisitions, partner buyouts, and commercial real estate—plus optional lines of credit to fuel future growth. Unlike traditional lenders, they take a “how can we” approach, making deals happen for both first-time buyers and experienced operators.

👉 Special Offer: Mention Owned and Operated for a reduced good faith deposit and a complimentary deal review + buyside prequalification.

Connect with Alan Peterson from First Internet Bank here 

💼Shoutout to Avoca AI!

Looking to train your call center and improve technician performance? Avoca AI helps teams identify issues, improve call quality, and drive results from start to finish.

 🔗 Schedule a demo

🎙 Host: Jack Carr

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