The Active Duty Passive Income Podcast

The Army’s ‘Perfect Soldier’ Walked Away — and Built His Own Empire with Cheyenne Wachtendorf | Ep 383

Episode 383

Markian sits down with Cheyenne Wachtendorf, a new ADPI member whose path runs from military service to creative deals—live-in flips, seller finance—and a 106-acre VA loan purchase. Cheyenne shares the mindset behind taking calculated risks, learning from setbacks, and his vision for Walk Squad Haven: real estate development, experiential recreation, and community mentorship.

Time Stamps

00:00 Introduction and Conference Recap

 01:30 Guest Introduction: Cheyenne Wetten

 02:23 Cheyenne's Unique Real Estate Journey

 06:36 Military Background and Personal Struggles

 10:47 Transition from Military to Real Estate

 19:12 The Importance of Mentorship and Community

 49:55 Cheyenne's Vision and Future Plans

 52:36 The Puzzle of Real Estate Vision

 53:14 Mapping Out the Dream

 53:41 Leveraging W2 Income

 55:49 First Real Estate Investments

 01:01:02 Facing Setbacks and Learning

 01:05:05 Rebounding with New Strategies

 01:11:16 The Big Vision: W Squad Haven

 01:17:17 Final Thoughts and Future Plans

Key Takeaways

  • Start small, build momentum: early creative wins compound into bigger plays.
  • Use VA loan creatively: structure matters more than “standard.”
  • Failures become playbooks: debrief, systemize, and iterate.
  • Mission first: purpose makes persistence possible.

Connect with Cheyenne

WachSquad Haven on Facebook:

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