Episode 138: Tom Rubens – The Biggest Problems That Bring Down a Business

Episode 138: Tom Rubens – The Biggest Problems That Bring Down a Business


Over the last 40 years, Tom has founded, bought, sold, and managed businesses in industries as diverse as a commodity trading company, a real estate brokerage, investment groups, and minor league baseball and basketball franchises.

Tom’s four decades in business have taught him a painful yet profitable lesson — to address the biggest problems that drag down an organization (and the owner’s health and sanity with it), you need to look beyond the Balance Sheet.

From intra-management bickering, to employee apathy, to products that should sell themselves but don’t, nearly every challenge he encounter in business is a symptom of the real problems: human nature, poor communication & great ideas with terrible execution

In my chat with Tom, we start off by digging deep into his first foray into being his own boss, a trader at the Chicago Board of Trade. After a terrible day on the trading floor, Tom called it a day and decided to buy a minor league basketball franchise…without ever having employees, let alone experience in the sports ownership world. The key to Tom’s success was that he was willing to put himself out there and learn from others. He took the time to speak with all of the owners, figure out what wasn’t working and did the exact opposite. After a wild ride in owning minor league sports teams, Tom now leverages his experience to help other business owners crush it.


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