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/

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Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.

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In this episode of JackQuisitions, Jack sits back down with Chris Barr to talk about what real leverage looks like in a self-funded search: building systems instead of just refreshing BizBuySell, working your broker network, and turning your geo + niche into an actual acquisition brand.

They break down how Chris is rebuilding his search infrastructure after round one, why tech leverage (CRM, scraping, cold outbound) matters more than you think, and how conferences, LinkedIn, and local presence (hello, West Palm Beach) quietly generate real deal flow. They also dig into ETA conferences like Harvard’s, the value of boards and mentors, and why most first deals go wrong when searchers are desperate to escape the slog.

If you’re a year into a search, stuck in a niche or geography, or wondering if you should start a business instead of buying one… this one’s for you.

🔍 What You’ll Learn

• How Chris rebuilt his search with tech leverage: CRM, scraping, and cold outreach running in the background.
• Why broker relationships still matter—and how to use them for both first look and “last look” on older listings.
• How to use LinkedIn, conferences, and DMs without feeling like a guru—and still generate real opportunities.
  
  

💼 Shoutout to Quick Staffers LLC

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💼 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

Host

Jack Carr

Guest

Chris Barr

Send us a text

Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.

🖊️ Sign up HERE for more insights


📢 Enjoyed the episode?
✅ Like, Comment & Subscribe for weekly insights on business acquisitions, deal flow, marketing, and growth strategies!

📌 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.

Buying a septic company is one of the highest-ROI moves in home-service M&A… if you know where to look.

In this episode of JackQuisitions, Jack breaks down exactly where real septic deals come from — from the obvious online marketplaces to the off-market gold mines almost no one talks about. If you’re serious about buying your first septic business (or adding one as a high-margin tuck-in), this roadmap will save you weeks of searching and tens of thousands of dollars.

Jack covers why septic is one of his favorite industries to acquire, why so many buyers overlook it, and the simple outreach strategy that consistently uncovers motivated sellers long before they hit BizBuySell.

Whether you're running an SBA search, building a route-based portfolio, or just trying to get into home-service acquisitions in 2026, this one gives you the playbook.

What You’ll Learn

• The 3 real channels for finding septic companies for sale (and which one beats the others every time).
• How deal aggregator sites really work—and why the “clean books” come with a premium price tag.
• Why local business brokers can be useful… and why they rarely have septic deals ready to go.

💼 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

🔗 Connect

Jack Carr

Keywords:

JackQuisitions, septic acquisition, route-based business, home service acquisition, off-market deal sourcing, SBA acquisition, residential service, trades entrepreneurship, business brokers, BizBuySell, deal flow, customer lists, route-based valuation, environmental services, well drilling, state permit lookup

Hashtags:

#JackQuisitions #HomeServices #BusinessAcquisition #SmallBusiness #Entrepreneurship #Trades #HVAC #Plumbing #Septic #ServiceTitan #Nexstar #GrossMargin #RouteBasedBusiness #OffMarketDeals

Send us a text

Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.

🖊️ Sign up HERE for more insights


📢 Enjoyed the episode?
✅ Like, Comment & Subscribe for weekly insights on business acquisitions, deal flow, marketing, and growth strategies!

📌 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.