The Road Less Traveled

Tiffany Rosenbaum
  • 5.0 (41)
  • Entrepreneurship

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.

  1. 9h ago

    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 valuations, mergers, and operational growth. Drawing from years of experience helping companies scale, acquire, and successfully exit, Deb shares the biggest mistakes buyers and sellers make, how businesses are truly valued, and why emotional attachment can derail even the best deals. She also explains what buyers should look for during due diligence, how to prepare a company for sale, and why team capacity and operational readiness matter just as much as the purchase price. Whether you're preparing to sell your company, actively acquiring portfolios, or simply planning for future growth, this episode provides practical insights to help you make smarter business decisions. In this episode: The biggest mistakes buyers and sellers make during acquisitions Why emotional attachment can impact company valuations How property management companies are actually valued EBITDA vs. SDE vs. per-door pricing explained Seller financing and structuring acquisition deals Hidden costs buyers and sellers often overlook Preparing your company before putting it on the market Managing team capacity during rapid growth Due diligence strategies that protect both sides Building a business that's attractive to future buyers If you're serious about growing through acquisitions or maximizing the value of your property management company, this conversation is packed with actionable advice from one of the industry's most respected acquisition consultants. 👍 Enjoyed this episode? Like this video Subscribe for more conversations on leadership, property management, and business growth Share this episode with another property management professional Comment below: What's the biggest lesson you've learned about buying or selling a business? #PropertyManagement #BusinessAcquisitions #BusinessGrowth #Leadership #RealEstate #PropertyManagementBusiness #Entrepreneurship #DebNewell #TiffanyRosenbaum #TheRoadLessTraveled #BusinessValuation #MergersAndAcquisitions

  2. Jul 28

    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 with more than 22 years of industry experience. Stacey shares lessons from building her own property management company, completing acquisitions, selling to a national organization, and working in corporate development on property management M&A deals across the country. Tiffany and Stacey break down what property management owners need to understand before pursuing acquisitions—from defining your buy box and evaluating the true cost of a deal to preparing your team for what happens after the contract is signed. They also discuss the future of the property management industry, including consolidation, AI, changing management fees, and why smaller companies may face increasing pressure to scale, adapt, or consider selling. You'll hear insights on valuation methods, seller financing versus SBA financing, integration challenges, leadership development, and why the hardest part of an acquisition often begins after closing. Most importantly, Stacey explains why owners need to get clear on one question before chasing their next deal: Why do you want to acquire in the first place? Whether you're considering your first acquisition, actively buying property management companies, or preparing your business for future growth, this episode offers a practical look at what successful acquisitions actually require. #PropertyManagement #Acquisitions #MergersAndAcquisitions #BusinessGrowth #RealEstate #PropertyManagementBusiness #Entrepreneurship #Leadership #BusinessAcquisition #TheRoadLessTraveled #StaceySalyer #TiffanyRosenbaum

  3. Jul 21

    Ep 95 Cold Calling Is Dead: 5 Property Management Business Development Strategies That Actually Work

    *]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-WEB:1fb72576-b818-45c1-8b28-c44553bcf800-0" data-turn-id-container= "request-WEB:1fb72576-b818-45c1-8b28-c44553bcf800-0" data-testid= "conversation-turn-2" data-turn="assistant"> Want to grow your property management company without relying on cold calls? In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with international business development expert Deniz Yusuf, founder of BDM Coach, to break down the proven strategies that helped him sign 925 property management agreements in just four years—all while maintaining full management fees. You'll learn why referrals outperform cold calling, how to build a business development system that generates consistent leads, and why becoming the trusted expert in your market is the key to long-term growth. In this episode, you'll discover: Why cold calling is no longer the most effective growth strategy How referrals create higher-quality clients who already trust you The first phone call every BDM should make How strategic partnerships can become your biggest lead source Building authority through social media and educational content Why video marketing is essential for property managers The importance of Google Business Profile for local growth How storytelling and data help you close more business The role of client retention in sustainable growth Practical business development strategies you can implement today If you're a property management business owner, business development manager, or real estate professional looking to grow your portfolio, this episode is packed with actionable advice you can start using immediately. 👍 If you enjoyed this episode: Like this video Subscribe for more property management insights Share with your team or fellow property managers Leave a comment with your biggest business development takeaway #PropertyManagement #BusinessDevelopment #RealEstate #PropertyManager #SalesStrategy #LeadGeneration #Marketing #Entrepreneur #TheRoadLessTraveled #PropertyManagementBusiness #BusinessGrowth #ReferralMarketing #DenizYusuf #TiffanyRosenbaum

  4. Jul 14

    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, automating repetitive tasks, and creating a better experience for property managers, owners, residents, and vendors. From why traditional portals are becoming obsolete to how AI can reduce workload without replacing human relationships, this conversation explores what every property management company needs to know as technology rapidly evolves. Lindsay also shares why successful AI implementation starts with clear processes, strong leadership, and a willingness to embrace change—not just new software. In this episode, you'll learn: Why communication is still one of property management's biggest challenges How voice AI is changing the customer experience Why AI is only as good as the processes behind it The importance of training your team before implementing new technology How property managers can use AI to eliminate repetitive work while improving service Why owner communication is becoming more important than ever The future of portals, dashboards, and customer interactions How to prepare your business for the next wave of AI innovation Why competition and technology make the entire industry stronger Whether you're a property management company owner, operator, or technology enthusiast, this episode will help you think differently about AI and how to leverage it to build a more scalable, efficient, and customer-focused business. 🎙️ Subscribe to The Road Less Traveled Podcast for conversations with industry leaders who are shaping the future of property management, leadership, technology, and business growth. #PropertyManagement #AI #ArtificialIntelligence #VoiceAI #PropTech #Leadership #BusinessGrowth #Technology #CustomerExperience #Automation #PropertyManagers #TheRoadLessTraveled #TiffanyRosenbaum #SuperAI

  5. Jul 7 ·  Video

    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 customer obsession and relationship-driven leadership, Tiffany shares why the property management industry is undergoing one of the biggest transformations it has ever seen. She explains how AI should be used as a tool—not a replacement for people—and why meaningful relationships will become the greatest competitive advantage in the years ahead. The conversation also explores what separates an average property management company from an exceptional one, why investors need more than rent collection, and how strategic asset management helps owners build lasting wealth and generational legacies. Whether you're a property manager, real estate investor, business owner, or entrepreneur, this episode is packed with practical insights on leadership, innovation, scaling a business, and preparing for the future of the industry. Topics Covered: The future of AI in property management Why relationships will always outperform automation Common mistakes property management companies make How to build scalable systems and teams What investors should expect from a great property manager Creating generational wealth through strategic real estate investing Why the best companies are customer obsessed—not transaction focused If you're looking to stay ahead of where the industry is headed, this is an episode you won't want to miss.

  6. Jun 30

    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 their business, why building investment portfolios has become a major focus, and the challenges that come with finding the right opportunities in today's market. One of the biggest obstacles investors face is simple: finding good deals. But what actually makes a deal good—or bad? Daniel and Tiffany break down how they evaluate opportunities, what red flags they watch for, and the key factors every investor should understand before making a move. From growth strategy to deal analysis, this episode offers valuable insight for anyone looking to scale in property management or real estate investing.

  7. Jun 23

    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 centers around Tiffany's bold vision of reaching 22,000 doors over the next 10 years—a goal many would call unrealistic or even crazy. But as Tiffany shares, big dreams are rarely understood by everyone around you. For Tiffany, this vision goes far beyond door count. It's about impact. It's about helping 5,000 families build generational wealth and creating a lasting legacy through real estate. The conversation explores the importance of having purpose, especially on the hard days when quitting feels easier than pushing forward. Tiffany reflects on how real estate changed her life and gave her the ability to support her family during difficult times, fueling her passion to help others do the same. She also opens up about one of her biggest leadership lessons: learning to let go. Early on, Tiffany believed everything had to be done her way, but over time she realized that mindset was limiting the growth of the business. Learning to delegate and trust others became a critical part of scaling. With a goal as massive as 22,000 doors, planning matters. Tiffany has mapped out everything—from projected churn to hiring needs and team growth year by year. But she also recognizes that the roadmap will evolve because growth at that level comes with challenges no one can fully predict. One powerful moment in the episode comes when Tiffany shares how a trusted advisor challenged her entire plan, tearing it apart and poking holes in every detail. Initially, it felt defeating. But she later realized the feedback wasn't meant to discourage her—it was meant to strengthen her. They could clearly see where she wanted to go, even if the exact path to get there is still unfolding. This episode is a powerful reminder that big visions require courage, adaptability, and the willingness to keep moving forward—even when the path isn't perfectly clear.

  8. Jun 9

    Ep 90 The Future of Property Management: AI, Scale & 250,000 Doors with Matthew Whitaker

    *]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-WEB:079c093b-beaf-495c-a77a-316c465feab8-0" data-turn-id-container= "request-WEB:079c093b-beaf-495c-a77a-316c465feab8-0" data-testid= "conversation-turn-2" data-scroll-anchor="false" data-turn= "assistant"> In this episode of The Road Less Traveled, Tiffany Rosenbaum sits down with Evernest founder Matthew Whitaker to discuss his journey from real estate investor during the 2008 recession to building one of the largest property management companies in the United States. With over 15,000 units under management and a vision for 250,000 doors, Matthew shares how technology, AI, acquisitions, and operational excellence are reshaping the property management industry. Key topics include: Scaling a property management company across multiple markets How AI and automation are transforming operations The future of property management fees Acquisition strategies and calculating returns on purchased portfolios Reducing churn and improving customer experience Building proprietary software versus using third-party platforms Why great people remain the most important asset in any business Matthew's vision for the next generation of property management Whether you're a property manager, real estate investor, or business owner looking to scale, this episode is packed with insights on leveraging technology while keeping people at the center of growth. Connect with Matthew Whitaker: Find Matthew on LinkedIn to follow his insights on property management, technology, and business growth.

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5
out of 5
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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.

Information

  • Creator
    Tiffany Rosenbaum
  • Years Active
    2024 - 2026
  • Episodes
    97
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    The Road Less Traveled

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