A Practical Guide to Business Acquisitions for First-Time Buyers With Matt Raad [Ep.197]

Dec 17, 2025

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Buying an online business can feel overwhelming, especially if you are new to acquisitions. In this week's podcast episode, we sit down with Matt Raad, a seasoned digital business buyer and coach who has helped countless first-time buyers navigate the acquisition process with confidence.

Due diligence takes center stage as Matt explains what really matters when evaluating an online business and how skipping this step can turn a promising deal into an expensive mistake. For beginners, he breaks down the types of businesses that are best suited for first-time buyers and why simpler models often outperform flashy ones.

We also cover beginner-friendly deal structures, including how to reduce risk and preserve capital when buying your first site. After the deal closes, Matt shares practical post-acquisition growth strategies for smaller websites that don't require huge teams or budgets.We also dig into a topic many new buyers underestimate: why you should never sell a business yourself and instead work with a broker who understands deal structure, negotiations, and risk.

Finally, we address a common myth head-on: online businesses are no longer as passive as they once were, and Matt explains what buyers should realistically expect today.

If you're thinking about buying your first online business or refining your acquisition strategy, this episode is packed with practical insights you can use immediately.

Topics Discussed in this episode:

Pivoting from buying brick-and-mortar businesses to digital businesses (01:53)
Never sell a business yourself; always use a broker (09:54)
The importance of doing good due diligence (14:04)
The best kind of businesses for newbies to buy (15:46)
Deal structures for beginners (30:41)
Post-acquisition growth strategies for small sites (35:50)
Online businesses are not as passive as they used to be (42:05)

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Sit back, grab a coffee, and learn how to buy your first online business with confidence!