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How to Avoid Status Quo Bias
Methods of Prosperity newsletter no. 140: Sheldon Adelson (1933–2021)

“Entrepreneurship is essentially identifying the path that everyone takes; and choosing a different, better way.”
Most business owners struggle with conformity to the beaten path.
They make it too safe and imitative.
They use the same incremental models their competitors swear by.
They follow the crowd rather than daring to question its direction.
Not Sheldon Adelson.
He chose the road no one else would take.
He scanned every industry for its default trajectory.
Then he veered off to create something vastly superior.
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On August 4, 1933, Sheldon Gary Adelson was born to Jewish parents. Their families came from Lithuania and the Ukraine. His Hebrew name is Sholom Gedaliah.
He was born during the Great Depression in Boston’s Dorchester neighborhood. It’s a working-class area. That’s where his mother owned a knitting shop and his father drove a taxicab and sold advertisements. Adelson sold street-corner newspapers as a boy.
He moved to New York in the early 1950’s to attend City College. He majored in real estate and finance until he dropped out. He left college without obtaining the required credits to graduate.
He served a tour of duty in the army and then went to work as a stenographer on Wall Street. Which exposed him to finance and securities markets. He monetized his Wall Street exposure and financial knowledge.
He became a millionaire by the early 1960’s.
How? By consulting with companies on how to sell their shares in the stock market. He advised them on how to access public markets and structure stock offerings.
Until something made him return to Boston. There’s no specific documented motive or “triggering event” as to why he left New York. But it was Boston where he began speculating in businesses and increasing his wealth. He went on to invest in and acquire dozens of companies. Which included a profitable tour and travel business.
In the 1970s, Adelson and partners pulled together his various ventures. They named this company the Interface Group. Through Interface, he launched computer‑industry shows starting in 1973.
Then, in 1979, he founded the COMDEX computer trade show. COMDEX grew out of Adelson’s broader convention-business strategy. He recognized that the nascent personal-computer sector needed a dealer‑focused trade show. It became one of the world’s largest computer trade exhibitions. COMDEX generated hundreds of millions in net income by the 1980s.
In 1995, Adelson and his partners sold the Interface Group’s show division. Which included COMDEX. SoftBank acquired it for roughly 862–865 million dollars. Adelson received more than 500 million from that deal.
He turned a $500 million exit into a multi-billion-dollar global empire. The opportunity he found was the imploding Las Vegas Sands resort and casino. He used that capital to expand his empire. He erected the all-suite Venetian mega-resort.
He rejected “the way things are done.”
Most casino operators treated conventions as annoying distractions. Adelson built the largest private expo center in America. He made non-gaming revenue the profit engine.
His peers clung to Vegas gambling tables.
Not Sheldon Adelson.
He bet billions on post-liberalization Macau and Singapore. That’s where he built the Cotai Strip and Marina Bay Sands when skeptics called him insane.
Notice his contrarian pivot.
He cashed out a thriving business at its absolute peak.
Why? To fund a radical reinvention in a completely different sector.
This move delivered his financial freedom.
Most entrepreneurs would have milked COMDEX forever.
Adelson sold high and bet bigger on a vision only he could see.
He identified the common path.
Then he chose a different, better way.
This works best for those destined for legendary prosperity.
And yes, you can gain true financial freedom and the profound inner peace of abundance.
Start by living this paradoxical truth:
The greatest fortunes don’t arise from following success.
The greatest fortunes arise from redefining what success even means.
I like you,
– Sean Allen Fenn
PS: The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here:

