In this episode of JackQuisitions, Jack sits down with Stephen Olmon to unpack one of the spiciest ETA questions out there: should you buy a business or build one first? Stephen shares his non-traditional path into entrepreneurship—from a pastor/teacher household to telecom consulting, then into the world of software, NewCo businesses, and eventually acquisitions.

They dig into Stephen’s early failed independent sponsor deals, how those bruises shaped his approach, and why he ultimately went the SBA route to acquire and scale Alarm Masters, a Houston-based fire & life safety company now rolling up competitors across Texas. Along the way, you’ll hear what Stephen looks for in alarm/security acquisitions (RMR mix, attrition, commercial focus), how they balance organic vs acquisition growth, and why self-awareness is the most underrated skill in buying businesses.

If you’ve ever wondered whether you’re actually built to buy a company—or if you should build first, buy later—this one’s for you.

🔍 What You’ll Learn

• Why “buy vs build” isn’t a strategy question—it’s a self-awareness question.
• Stephen’s path from NewCo entrepreneurship to acquisitions (and what changed his mind).
• A clear breakdown of the independent sponsor model and why most deals die in diligence.

💼 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: [https://alanfib.com/]

🔗 Connect
Jack Carr — X (Twitter): https://www.x.com/thehvacjack

Stephen Olmon — https://www.linkedin.com/in/stephenolmon/

Send us a text

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