How Regular People Get Rich Buying Boring Businesses - JackQuisitions Feed Drop
Owned and Operated - A Plumbing, Electrical, and HVAC Business Growth Podcast
Mass Outreach vs Personalized Touch
Chris and Jack debate mass-mailing strategies versus personalized phone calls, emphasizing persistence and selective automation.
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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.
More Ways To Connect with O&O
John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC
📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.
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