PODCAST · business
The Road Less Traveled
by Tiffany Rosenbaum
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.
Episodes
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Ep 105 How to Scale a Property Management Company Without Breaking It
In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with COO Connie for a candid conversation about what it really takes to scale a property management company. They discuss how rapid growth can expose broken systems, why adding more software can sometimes create more problems,...
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Ep 104 How AI Is Changing Property Management with Peter Lohmann
AI is changing property management faster than most business owners realize—but where should you actually start? In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with Peter Lohmann, CEO of RL Property Management, to break down how AI, APIs, automation, and better data are...
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Ep 103 Why Your Property Management Processes Break as You Scale | The Road Less Traveled
What happens when your property management company grows faster than your systems can handle? In this episode of The Road Less Traveled, Tiffany Rosenbaum gets put in the hot seat to talk about the operational challenges that come with scaling a property management company. Tiffany breaks down…
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Ep 102 Want to Scale? Stop Saying You Can't Find Good People
Leadership grows over time. Building an amazing team isn't just about hiring talented people. It's about understanding your people, understanding your numbers, and being willing to adjust when something isn't working. That's why one-on-one meetings are so important. They help you understand…
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Ep 101 Beyond Referrals: Building a Business Development Team That Drives Growth
What does it really take to grow a business beyond referrals and word of mouth? In this episode of The Road Less Traveled, Tiffany Rosenbaum is joined by Dan, Rosenbaum Realty Group's business development representative, for a conversation about intentional growth, sales, leadership…
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100 Episodes Later: Why the Road Less Traveled Is Worth It
In the 100th episode of The Road Less Traveled, Tiffany Rosenbaum reflects on the lessons, struggles, mistakes, relationships, and breakthroughs that shaped both the podcast and her journey as an entrepreneur. What started with fear of judgment and uncertainty became proof that consistency beats...
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Ep 99 From 228 to 11,000 Doors: Leadership, Culture & AI in Property Management | Michael Krause
How do you grow from managing just 228 single-family homes to overseeing more than 11,000 units without losing your company culture? In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Michael Krause, Partner at Atrium Management Company, to discuss the leadership...
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EP 98 What Is Your Property Management Company REALLY Worth? | Matthew Whitaker
What makes one property management company worth significantly more than another? On this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with Matthew Whitaker, Founder and CEO of Evernest, to reveal what buyers are actually looking for when acquiring property management companies....
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Ep 97 Buying & Selling Property Management Companies: Avoid Costly Acquisition Mistakes | Deb Newell
What does it really take to successfully buy or sell a property management company? In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Dr. Deb Newell, executive consultant, acquisition advisor, and one of the property management industry's leading experts on...
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Ep 96 The Truth About Acquiring Property Management Companies with Stacey Salyer
Acquisitions can accelerate growth—but buying the wrong property management company can create more problems than opportunities. In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with Stacey Salyer, entrepreneur, acquisition expert, and longtime property management leader…
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Ep 95 Cold Calling Is Dead: 5 Property Management Business Development Strategies That Actually Work
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Ep 94 The Future of Property Management: Why AI Will Change Everything | Lindsay, CEO of Super
Artificial intelligence is transforming every industry—but nowhere is the opportunity greater than in property management. In this episode of The Road Less Traveled Podcast, Tiffany Rosenbaum sits down with Lindsay, Co-Founder and CEO of Super, to discuss how voice AI is redefining communication,...
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EP 93 Common mistakes property management companies make
In this special episode of The Road Less Traveled Podcast, Tiffany Rosenbaum takes the hot seat as Anne dives into the future of property management, real estate investing, and the systems that will define the next generation of successful companies. From artificial intelligence and automation to...
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Ep 92 What Makes a Good Real Estate Deal?
For the first time, Daniel and Tiffany are in the hot seat on The Road Less Traveled Podcast, diving into an honest conversation about property management, real estate investing, and building long-term wealth through strategic portfolio growth. They discuss how they are planning to scale within...
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EP 91 Dream Bigger: Building Wealth, Legacy & Purpose Through Real Estate
Tiffany is back in the hot seat with Anne, and once again they dive into powerful conversations around vision, growth, and leadership. They also discuss how the Remarkable notepad has been a game changer in organizing thoughts, planning, and staying focused on long-term goals. This episode…
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Ep 90 The Future of Property Management: AI, Scale & 250,000 Doors with Matthew Whitaker
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Ep 89 Building, Selling & Rebuilding a SaaS Empire
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Ep 88 Building, Scaling & Acquiring in Property Management with Ben Parham
On this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with property management entrepreneur Ben Pa to discuss the realities of growing, scaling, selling, and acquiring property management portfolios. From starting in the industry during the 2008 housing crisis to building a...
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Ep 87 Buying, Scaling & Selling Property Management Companies with Amy Hansen
What really goes into buying, growing, and selling a property management company? On this episode of The Road Less Traveled Podcast, host Tiffany Rosenbaum sits down with Amy Hansen to break down the realities behind scaling a service-based business, navigating acquisitions, and preparing for a...
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Ep 86 Selling the Business Without Selling Yourself w/ Nick Foster
In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with second-generation CPA and entrepreneur Nick Foster, founder of Foster Financial CPA, to discuss the realities of building, scaling, and ultimately selling a business. Nick shares his transition from corporate America and…
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Ep 85 In the Hot Seat: The Conversations That Actually Grow Your Business
In the hot seat with Executive Assistant Anne—where the hard conversations actually happen. No fluff, no bias—just real accountability, clear decisions, and taking action that moves the needle. Success isn't about feelings… it's about what you do next. *]:pointer-events-auto…
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Ep 84 From Chaos to Clarity: Building a Business Partnership That Works
Most people see the wins… not the road it took to get there. On this episode of The Road Less Traveled Podcast, we sat down with Pete & Steve to talk about what building a business partnership REALLY looks like. From managing properties in rough areas… To scaling to 30+ doors with no systems… To...
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Ep 83 Josh Huite on Mentorship, Value, and Raising the Standard
In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Josh Huite, Owner/Operator and Leadership Coach at The Tradesman Experience & Podcast. With 28 years in the trades, Josh brings a wealth of real-world insight into what it takes to succeed—not just technically, but…
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Ep 82 From 9–5 to Full-Time Flipping with Kara Beckmann
In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with real estate investor Kara Beckmann to break down her journey from working a full-time job to building a successful house flipping business. Kara shares how she navigated the early stages of flipping homes while...
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Ep 81 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,...
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Ep 80 Building, Scaling, and Leading with Vision w/Sina Shekou
On this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Sina Shekou, Chief Executive Officer of Aptly, to break down what it really takes to build and scale a company in today's world. From navigating growth and embracing risk to leveraging technology and leading teams at…
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Ep 79 Behind the Scenes of Success: Burnout, Anxiety & the Real Entrepreneur Journey
On this raw and honest episode of The Road Less Traveled, host Tiffany Rosenbaum pulls back the curtain on what entrepreneurship really looks like behind the scenes. Success often comes with pressure, long hours, and the constant weight of responsibility. Tiffany opens up about the early warning...
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Ep 77 Decisions That Build Businesses with Tiffany
In this powerful episode, entrepreneur Tiffany Rosenbaum breaks down why saying yes is often easier than being realistic—and how intentional, hyper‑focused decision‑making can completely change your business trajectory. She shares the framework she uses before saying yes to any opportunity and…
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Ep 78 The Property Management Trap: Why the Wrong Clients Cost You Everything
In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with property management expert Marc Cunningham to discuss one of the biggest mistakes professionals make in the property management industry. Many property managers believe that growth means signing every owner client…
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Ep 76 Wealth Is Built on Systems w/Mark Brower
On this episode of The Road Less Traveled, host Tiffany Rosenbaum, sits down with entrepreneur and property management expert Mark Brower to unpack what it really takes to scale a business while protecting your assets and building long-term wealth. This conversation goes beyond property...
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Ep 75 Powerful Transformation w/Jerame Mudick
In this transformative episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with breathwork facilitator, educator, and human biomechanics specialist Jerame Mudick—founder of Re|Connect Mind Body and Ayr Breathwork—for a powerful conversation on unlocking deeper healing, personal...
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Ep 74 Holistic Success w/Julie Holly
In this inspiring episode of The Road Less Traveled, host Tiffany Rosenbaum welcomes real estate syndicator, investor, and podcast host Julie Holly for a deep dive into building wealth while prioritizing holistic success and personal fulfillment. Drawing from her two decades in real estate and…
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Ep 73 Working as a Couple w/Tiffany and Daniel
In this candid and relatable episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with her husband and business partner, Daniel Rosenbaum, to share the real strategies they've developed to keep their marriage thriving while running a successful company together—proving you can have...
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Ep 72 Specializing w/John Tilley
Tiffany interviews 1031 exchange specialist John Tilley, who breaks down one of real estate's most powerful tax-deferral tools. They cover the basics of a 1031 exchange, key deadlines (45-day identification and 180-day closing periods), common pitfalls, working with qualified intermediaries, and...
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Ep 71 Achieving Success w/Tiffany
In this celebratory episode of The Road Less Traveled, Tiffany Rosenbaum shares the raw truth behind recently hitting major company goals at Rosenbaum Realty Group—doubling managed doors and scaling to new heights in 2025. She dives into the real, no-fluff actions it took: mindset shifts, tough...
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Ep 70 Gaining Visibility w/Alex and Lacy
With deep industry roots (Lacy brings over a decade in property management, real estate brokerage, and local leadership; Alex adds veteran experience in business development and ethical marketing), they launched ClearLead to deliver transparent, results-driven SEO, content marketing, local search...
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Ep 69 Managing Expectations w/Amoura and Avery
Amoura (CEO, education & strategy expert) and Avery (marketing & design veteran) share how they blend their talents to deliver full-service branding, content strategy, social media, digital campaigns, and custom professional development workshops for purpose-driven businesses, nonprofits, and...
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Ep 68 Twists and Turns w/Ben Serven
Ben shares his journey from roles in property management software and high-level customer service to building a leading consulting firm that has transformed operations for over 200 property management companies across North America. Through his innovative Processes Made Simple approach, Ben helps...
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Ep 67 Scaling Business w/Mindee Chidester
Host Tiffany Rosenbaum speaks with Mindee Chidester, co-founder of The Plastics Clinic + Spa, a Draper, UT-based practice now powered by multiple board-certified surgeons that generates low-seven-figure revenue through a lean, referral-only model—no ads, no employees beyond essentials, and a 4–6...
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Ep 66 Creating w/Stephen Fox
Host Tiffany Rosenbaum sits down with Stephen Fox, the founder of Upkeep Media, a remote-first marketing agency that grew from a one-man operation into an industry quiet giant serving some of the biggest names in property management—all while Stephen intentionally keeps the company lean,...
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Ep 65 Discipline w/John Gillespie
In a refreshingly candid conversation, host Tiffany Rosenbaum sits down with John Gillespie, partner and CIO of Gallacher Capital, a low-profile investment firm that has been managing client wealth for over 30 years. John shares the principles behind their disciplined, conviction-driven approach,...
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Ep 64 Aligning Ambition w/Thomas Klein
In this heartfelt and transformative episode of The Road Less Traveled, host Tiffany Rosenbaum welcomes Thomas Patrick Klein, the visionary founder of The Animal Alliance—a U.S.-based 501(c)(3) nonprofit born from a raw encounter with animal suffering during global travels in 2023 alongside...
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Ep 63 Breaking The Mold w/Paul Stratton
In this raw episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with entrepreneur and self-described "professional troublemaker" Paul Stratton for a no-holds-barred conversation about walking away from a soul-crushing corporate career, getting canceled (twice), rebuilding from…
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Ep 62 Resilient w/Kimberly Bradshaw
In this heartfelt and empowering episode, host Tiffany sits down with Kimberly Bradshaw—passionate founder and owner of Flower Child Adventures, a transformative program dedicated to helping children, families, and individuals master emotional self-regulation through fun, accessible tools like...
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Ep 61 Jumping In w/Chris Springer
In this powerhouse episode, host Tiffany welcomes Chris Springer—a decorated U.S. Army veteran, West Point graduate, former economics professor at the academy, strategy instructor at the Command and General Staff College, Ranger-tabbed officer, and Senior Jumpmaster—for an unforgettable crossover...
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Ep 60 Building Dreams w/Corey Taylor
In this engaging episode of the podcast, host Tiffany sits down with Corey Taylor, founder of Copper Sky Construction, for a candid conversation about the world of high-end home remodeling and design-build projects. Corey shares his journey from flipping historic homes in Sonoma County to…
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Ep 59 Conquering Chaos w/Clate Mask
In this electrifying episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Clate Mask—co-founder and CEO of Keap (the force behind Infusionsoft), NY Times bestselling author of Conquer the Chaos, and one of Arizona's most celebrated tech founders—to unpack the raw, unfiltered...
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Ep 58 Rising Above Tragedy w/Ashlynne Miller
Step into the world of calculated risks and heartfelt protection with host Tiffany Rosenbaum on The Road Less Traveled, featuring Ashlynne Miller, the dynamic Texas-based insurance professional who's turning policies into peace of mind one client at a time. Hailing from the heart of the Lone Star...
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Ep 57 Building Legacies w/Brandon Martino
Tune in to The Road Less Traveled as host Tiffany Rosenbaum chats with Brandon Martino, the Texas native and managing partner of Orison Holdings, whose vision has reshaped the Denton County landscape. Growing up in small-town charm, Brandon cut his teeth in construction before teaming up with...
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Ep 56 Back for more w/Heath Treasure
Welcome back for part two of an unmissable deep dive with Heath Treasure, the Blue Collar Millionaire and founder of Ultimate Blue Collar. In their first conversation, Heath shared his raw origin story—dropping out of college to bootstrap a trucking empire from scratch in 2000, growing it into a...
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ABOUT THIS SHOW
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.
HOSTED BY
Tiffany Rosenbaum
CATEGORIES
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Frequently Asked Questions
How many episodes does The Road Less Traveled have?
The Road Less Traveled currently has 105 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is The Road Less Traveled about?
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.
How often does The Road Less Traveled release new episodes?
The Road Less Traveled publishes regularly with 105 episodes available. Check the episode list for the typical release schedule.
Where can I listen to The Road Less Traveled?
You can listen to The Road Less Traveled on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts The Road Less Traveled?
The Road Less Traveled is created and hosted by Tiffany Rosenbaum.
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