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Lessons from a Lost Investment: Trust, Syndications, and the Real Risks of Passive Income

Lessons from a Lost Investment: Trust, Syndications, and the Real Risks of Passive Income

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In this episode, Josh (@thelifestylecrna) and Colin (@colinfrompdr) get brutally honest about what happens when investing doesn’t go as planned.

Josh opens up about losing money in a real estate syndication — what drew him to the deal, how the numbers didn’t add up, and the hard lessons learned about trust, due diligence, and chasing “potential.” The two dig into the difference between guaranteed returns and “projected” ones, what it means to invest with people you actually know, and why most of the wealthiest people have taken big losses before finding success.

They also touch on balancing family, business, and burnout — from late-night calls and hospital shifts to figuring out when enough is enough. It’s equal parts investing, parenting, and self-awareness — all wrapped in the usual mix of humor and honesty that makes The Lifestyle CRNA so relatable.

🎧 Topics include:

  • Why even “trusted” syndications can flop
  • Spreading risk and reading between the projections
  • Personal guarantees vs. passive promises
  • Balancing family, freedom, and financial goals
  • The importance of real relationships in investing

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