The Road Less Traveled
Tiffany Rosenbaum
Show overview
The Road Less Traveled has been publishing since 2024, and across the 2 years since has built a catalogue of 100 episodes. That works out to roughly 75 hours of audio in total. Releases follow a weekly cadence.
Episodes typically run thirty-five to sixty minutes — most land between 37 min and 54 min — though episode length varies meaningfully from one episode to the next. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Business show.
The show is actively publishing — the most recent episode landed earlier today, with 33 episodes already out so far this year. The busiest year was 2025, with 52 episodes published. Published by Tiffany Rosenbaum.
From the publisher
This podcast is about doing whats required to get to where you want to go in life and business aka "The Road Less Traveled" Tiffany takes you on a journey through her stories and others as they share THE ROAD LESS TRAVELED.
Latest Episodes
View all 100 episodes100 Episodes Later: Why the Road Less Traveled Is Worth It
Ep 99 From 228 to 11,000 Doors: Leadership, Culture & AI in Property Management | Michael Krause
EP 98 What Is Your Property Management Company REALLY Worth? | Matthew Whitaker
Ep 97 Buying & Selling Property Management Companies: Avoid Costly Acquisition Mistakes | Deb Newell
Ep 96 The Truth About Acquiring Property Management Companies with Stacey Salyer
Ep 95 Cold Calling Is Dead: 5 Property Management Business Development Strategies That Actually Work
Ep 94 The Future of Property Management: Why AI Will Change Everything | Lindsay, CEO of Super
EP 93 Common mistakes property management companies make
Ep 92 What Makes a Good Real Estate Deal?
EP 91 Dream Bigger: Building Wealth, Legacy & Purpose Through Real Estate
Ep 90 The Future of Property Management: AI, Scale & 250,000 Doors with Matthew Whitaker
Ep 89 Building, Selling & Rebuilding a SaaS Empire
Ep 89 Building, Scaling & Acquiring in Property Management with Ben Parham
Ep 87 Buying, Scaling & Selling Property Management Companies with Amy Hansen
Ep 86 Selling the Business Without Selling Yourself w/ Nick Foster
Ep 85 In the Hot Seat: The Conversations That Actually Grow Your Business
Ep 84 From Chaos to Clarity: Building a Business Partnership That Works
Ep 83 Josh Huite on Mentorship, Value, and Raising the Standard
Ep 82 From 9–5 to Full-Time Flipping with Kara Beckmann
Ep 80 When to Scale, When to Sell: Lessons from Amy Hanson
What does it really take to build and exit multiple businesses? On The Road Less Traveled, Tiffany Rosenbaum sits down with Amy Hanson to talk about scaling property management companies, navigating acquisitions, and making the tough call to move on. This episode is packed with straight-up, real-world advice for entrepreneurs who want to grow smart and build something that lasts—or sell when the time is right.