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November 3, 2025 18 mins

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You can’t out-hustle broken systems. You can’t outwork bad strategy. You can’t out-grind poor leadership.

In this episode, Tiffany High shares the truth most people don’t want to hear: busyness isn’t the same as progress, and freedom only comes after mastering the fundamentals and building the right systems.

Through personal stories, hard lessons, and real examples from their own business, Tiffany reveals how to stop being the bottleneck, document what’s working, and build a business that runs without you.

You’ll Learn How To:

  • Escape the “broke and busy” trap that keeps investors stuck
  • Build real systems instead of constantly chasing new tactics
  • Earn the right to delegate and automate your business
  • Move from operator to true business owner

What You’ll Learn in This Episode:

  • (01:06) Why most investors stay busy but broke
  • (02:07) The difference between a job and a business
  • (02:31) People confuse motion with progress
  • (03:54) Tiffany’s lessons from calling every seller herself
  • (05:02) A phase in every business called 'swamp'
  • (05:49) Understanding skill debt vs. management debt
  • (07:02) From stressed-out operator to business owner
  • (07:34) The handwritten mailers story
  • (08:28) The secret to keeping a personal touch at scale
  • (10:31) Don't worry about scale, worry about building your skill sets
  • (11:33) The “Done For You → Done With You → Do It Yourself” framework
  • (12:23) The step-by-step formula to finally get unstuck
  • (13:58) What real freedom actually feels like
  • (14:23) Operator vs. owner
  • (16:01) The exact systems and tools Tiffany and Josh use today.

Who This Episode Is For:

  • Real estate investors who are tired of doing everything themselves
  • Business owners who want more control
  • Anyone feeling stuck in “hustle mode” without real progress
  • Entrepreneurs who are ready to build a scalable, self-running business

Why You Should Listen:

Tiffany shares the mindset shifts and step-by-step strategies that helped her and Josh move from burnout to real freedom. You’ll walk away knowing what’s holding you back and how to fix it for good.

Follow Tiffany and Josh here:

Download the free resource Tiffany built. www.rdebook.com                                    26 Mistakes I Made as a Real Estate Investor

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