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

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)

Mentions: 


Empire Flippers Podcasts


Empire Flippers Marketplace


Create an Empire Flippers account


Subscribe to our weekly newsletter


Dividend Watch


Semrush


Uber Suggest


Google Keyword Planner



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