Why Buying Digital Businesses Beats the Stock Market With Nathan Hamilton [Ep.180]

Jun 19, 2025

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The golden age of affiliate sites may be behind us, but can affiliate sites still make good money? And are websites in general still a good investment?

In this episode, Greg speaks with Nathan Hamilton, a former equity analyst who shifted into buying and growing online businesses. Nathan recently acquired dividend.watch, a dividend investing platform that helps users discover stocks, track income, and manage their portfolios in one place.

Nathan explains how Google’s algorithm updates and the rise of AI have reshaped the affiliate landscape. While many content sites have struggled, he shares which strategies still work and what kinds of online businesses are best positioned for success today.

He also walks through his acquisition process, what he looks for in a deal, how he evaluates growth potential, and why he moved away from affiliate sites in favor of more product-driven platforms. As a non-technical buyer, Nathan offers helpful lessons on managing a tech-heavy site without technical expertise.

Drawing from his financial background, Nathan compares investing in online businesses to buying stocks, weighing the risks, rewards, and potential ROI of each.

Finally, Nathan flips the script on Greg, asking how he’s seeing affiliate site owners adapt to today’s SEO challenges and what strategies successful operators are using to diversify their traffic and revenue streams.

If you’re wondering whether content sites still have a future, or you’re a would-be investor trying to choose between stocks and digital businesses, this episode is packed with firsthand insight you won’t want to miss.

Topics Discussed in this episode:

Nathan’s background and how he ended up flipping sites (02:19)
What Nathan looks for in an acquisition (05:47)
How the algorithm updates affected Nathan’s sites and how to thrive moving forward (07:32)
Nathan’s growth plan for his newly acquired business (12:35)
The best online business models to invest in right now (21:10)
Nathan’s experience taking over an existing business (22:36)
Nathan’s advice for non-technical buyers looking to acquire a business (24:28)
The ROI of buying digital businesses vs buying stocks(27:12)

Nathan’s Questions for Greg

How is Greg seeing affiliate sites manage the current SEO and AI environment (30:42)
What strategies are people using to diversify beyond SEO? (42:08)

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Sit back, grab a coffee, and discover whether investing in affiliate sites is still worth it.