Going Deep 2019

Supported by Greenhaven Road Capital, finding value off the beaten path.

Aaron Watson’s podcast, Going Deep, has been a consistent source of stories, ideas, and inspiration with episodes including Barry Ritholtz, Morgan Housel, and Grant Oliphant.

On March 23, 2019, Aaron was kind enough to ask me to speak at the Going Deep Summit 2.0. I talked about careers, education, changing technology, quarter-inch holes, and what kind of tools to fill our toolboxes with. It was a treat to be included alongside Tammy Thompson, Allen Gannett, Kenny Chen, Giselle Fetterman, and Joe Vennare. When I told my daughters that people thought I was funny they asked if I was sure they were actually listening.


My own notes from the event were these:

  • Conditions matter. If you live expecting that X is always true but X is only sometimes true you won’t know it.
  • Good storytelling convinces people.
  • People who attended the event are awesome.
  • Pittsburgh is awesome. Part of the weekend was spent talking to locals about why Pittsburgh might be the perfect size.
  • Starting businesses is hard but not impossible.
  • Generosity is contagious.
  • Creativity is not innate.

If ideas are nothing and execution is everything, this one-day event was a manifestation of the magic humans are capable of.

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