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Bill Sells His Company and Interesting Places to Invest Money

May 23, 2025
Bill D’Alessandro, co-host of Acquisitions Anonymous and former owner of Natural Dog Company, shares insights after selling his company. He discusses the emotional journey of exiting a business built over 12 years and his new role in corporate development for Food Science. Bill navigates the complexities of investing his earnings, from choosing strategic options in the pet industry to tackling both emotional hurdles and market uncertainties post-sale. He also explores non-traditional investments, including real estate and BDCs, while highlighting the importance of careful planning.
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ANECDOTE

Mall Day Celebration

  • Bill celebrated selling his business by taking his kids to a mall playground and convincing his brother he bought a fancy Maserati there.
  • He values small, meaningful moments over extravagant purchases after his exit.
INSIGHT

Business Growth Phases

  • Bill finds small teams fast and strategic large enterprises fun phases to run a business.
  • The startup scaling middle phase with 10-40 employees was the most stressful and less enjoyable for him.
ADVICE

Smart Post-Exit Investing

  • Consider parceling out lump sum money by needs and invest what you won’t need for 10+ years.
  • Avoid rushing into investments post liquidity event; waiting a year before acting is advised.
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