P58: From Commercial Real Estate to Bankruptcy… & Bouncing Back in the Boating Industry (🔐 A Continuation of EP 225 🔓)

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Background:

Welcome to the second part of the Rob Hannah interview, the CEO and Owner of Chicago Yacht Works located in Chicago, Illinois. For our listeners who want to check out the first part, please visit Episode 225 – Rob Hannah interview. During the 2009 downturn, Rob filed for personal bankruptcy and both his personal and entrepreneurial life was in shambles. However, 2011 turned out to be a great year for Rob because he was given the opportunity to start all over again by creating Chicago Yacht Works. He assumed control of the Chicago Yacht Yard, which is a full-service marine and storage facility that is located in the river in downtown Chicago. The business quickly grew and became an industry leader with its boat services and storage catering to everyone. Through the years, they have added brokerage and new boat sales to their business line.

Before Chicago Yacht Works, Rob was extensively involved in commercial real estate. His real estate background spans from design and build to acquisition and disposition. He has created an ownership structure that can comply with the IRS Section 1031, which enables investors to acquire fractional interests in real property, while deferring capital gains and related taxation. He became an expert in 1031 allowing him to teach attorneys and accountants and giving him the opportunity to speak at ABA, AICPA, and other professional certification conferences. Rob is also a featured lecturer at the MIT Center for Real Estate, Kellogg School of Management, and DePaul University.

Time-Stamped Show Notes:

  • [4:15] Rob used to teach Section 1031 to the American Bar Association and the AICPA, as he was completely immersed in it.
  • [6:04] In 1997, Rob and a tax attorney had a Private Letter Ruling request submitted to the IRS.
  • [10:47] Rob explains in detail what a private letter ruling is all about.
  • [17:19] Working for the Tax Deferred Services made Rob 1.1 million dollars in a year. However, it was only on paper and he did not get paid, which is why he left the company.
  • [19:38] After leaving his previous company, Rob started his own company called Tax Strategies Group.
  • [21:52] In 2001, The Tax Strategies Group was supposed to have its first TIC deal in Miami but 9/11 happened.
  • [25:11] Rob talks about how they earn in the Tax Strategies Group.
  • [27:37] Another TIC deal in Michigan turned out great, which allowed Rob to buy out his partner in the business.
  • [31:49] When it comes to his personal life in the earlier days, it was immensely challenging for Rob.
  • [34:57] Rob offers a more detailed explanation of Real Estate Arbitrage.
  • [36:25] Insight Real Estate is the second company that Rob created.
  • [37:42] During the 2009 downturn, Rob filed for personal bankruptcy.
  • [41:34] Rob shares what it’s like to be bankrupt.
  • [44:59] Leveraged buyout gave Rob the opportunity to start Chicago Yacht Works even though he had filed bankruptcy.
  • [47:52] Over the last ten years, Rob’s personal life became a lot better.

Key Point from the Interview:

  • “As an entrepreneur, we tend to only look through the windshield cos we’re trying to go 100 miles an hour and every once in a while, we kinda look back and see where you’ve been is a valuable thing.”

Resources Mentioned:

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