Inzo Technologies — When you acquire a business, you inherit its accumulated IT and cybersecurity problems too. Inzo helps acquisition entrepreneurs evaluate technology risk during due diligence and manage cybersecurity, IT, and voice after closing, including a complimentary IT risk audit of your target company. Learn more at https://www.inzotechnologies.com/eta Quiet Light Brokerage specializes in helping entrepreneurs buy and sell businesses with experienced operators as brokers. They offer a free valuation clarity call to help owners understand what their business is worth and how to increase its value before selling. Learn more at https://quietlight.com/ In this episode the hosts talk about a highly profitable, third-generation Caribbean infrastructure construction business generating $23 million in revenue and $6 million in annual cash flow, but its government relationships, political connections, and questionable $35 million project pipeline could make it nearly impossible for an outsider to buy. Business Listing – https://www.vikingmergers.com/listing/40-year-infrastructure-construction-business-1926/ Welcome to Acquisitions Anonymous – the #1 podcast for small business M&A. Every week, we break down businesses for sale and talk about buying, operating, and growing them. Looking to build a professional website in minutes? Try Wix: https://wix.pxf.io/c/6898629/3115214/25616?trafcat=template HubSpot is the backbone for how businesses scale without chaos. Try them out here: https://go.try-hubspot.com/OeG9Vr Subscribe for more episodes: https://www.youtube.com/@AcquisitionsAnonymousPodcast?sub_confirmation=1 Subscribe to our Newsletter: https://www.acquanon.com/newsletter What would you pay for a Caribbean construction company generating $23 million in annual revenue and $6 million in cash flow? Michael Girdley, Mills Snell, Bill D'Alessandro, and guest Alex break down a 44-year-old, third-generation family business specializing in bridge construction, airport runways, highway paving, and major infrastructure projects across the Caribbean. With more than 70 professionals, its own asphalt and concrete manufacturing facilities, and a reported $35 million project pipeline, this business boasts an impressive 26% cash flow margin. But with no public asking price and a potentially complicated ownership structure, is this a hidden gem or a deal that's too risky to touch? The hosts dig into the challenges of acquiring a government-dependent construction business in an unfamiliar market. How much of its success depends on decades of family relationships and local political connections? Is the $35 million pipeline actually contracted backlog, or just potential work? And how transferable are those contracts when a new owner takes over? The conversation explores project-based revenue volatility, foreign ownership risks, and why a business potentially worth 5–6x earnings in Miami might command a much lower multiple in the Caribbean. The debate gets especially interesting when the hosts discuss creative deal structures, seller equity rollovers, and the type of buyer who could actually make this acquisition work. Bill also shares a wild story about Cuba's government-run ice cream factories and black-market economy, illustrating just how differently business can operate across the Caribbean. While some hosts quickly pass on the opportunity, others see the potential for a locally connected entrepreneur to acquire a highly profitable infrastructure business at an attractive valuation. Key Highlights: - $23M Revenue, $6M Cash Flow: A 44-year-old Caribbean construction business with 26% cash flow margins. - $35M Project Pipeline: Are these signed contracts or just potential deals? - Political Connections: Government relationships could make ownership transfer risky. - 3x vs. 6x Valuation: Caribbean risks could significantly lower the company's value. - Who Should Buy It? A locally connected buyer using creative financing and seller involvement. Subscribe to weekly our Newsletter and get curated deals in your inbox Advertise with us by clicking here Do you love Acquanon and want to see our smiling faces? Subscribe to our Youtube channel.Do you enjoy our content? Rate our show!Follow us on Twitter @acquanon Learnings about small business acquisitions and operations.For inquiries or suggestions, email us at contact@acquanon.com
