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. 6d ago

    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 transforming the property management industry. Peter explains why having an API doesn't necessarily mean your software is AI-ready, how property managers can connect their systems to tools like ChatGPT and Claude, and why clean, centralized data will become increasingly important. They also dive into real-world AI applications, including predicting owner churn, automating leasing conversations, improving owner disbursements, reducing manual work, and helping teams become more efficient without simply replacing employees. Peter also shares three important ways property management companies can prepare for AI: • Consolidate the number of software tools you use • Choose platforms with strong API capabilities • Avoid storing the same data across multiple systems Whether you're already experimenting with AI or you're overwhelmed and don't know where to begin, this conversation is a practical look at how property management companies can start using AI one problem at a time. The biggest takeaway: you don't have to understand everything about AI—you just have to stay curious and start experimenting.

  2. Sep 22

    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 why maintenance is one of the most important parts of property management, how communication impacts both owners and residents, and why documented processes have to evolve as your company grows. She also shares lessons from scaling her company, including why processes broke during rapid growth, the importance of departmentalizing your team, creating accountability around outcomes, tracking KPIs, reducing owner churn, and building systems around the customer experience. You'll learn why great processes still need a human element, why leaders need feedback from the people actually doing the work, and why having a clear vision is essential if you want your team to grow with the company. If you own or operate a property management company and want to scale without losing efficiency, team culture, or client experience, this episode is packed with lessons you can apply to your business.

  3. Sep 15

    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 what's actually happening with your team. Is someone overwhelmed? Is something happening at home? Have they lost interest in their role? Do they want to grow but don't know what their next opportunity looks like? But conversations only tell you part of the story. The data tells you what's actually happening inside the business. When you have dashboards showing daily numbers across departments and multiple offices, you can identify problems faster. You can see where performance is slipping, where someone has too much on their plate, and where one office is outperforming another. Instead of waiting months to realize something is broken, you can see it, pinpoint it, and pivot. Great leaders need both: people and data. Someone can tell you, "I'm fine," but the numbers might show something different. Your responsibility as a leader is to figure out how to have that conversation, understand the individual, and help them grow into the right position. And if you want great people to stay, leadership starts with you. You can't complain that "good people are impossible to find" while showing up late, avoiding accountability, or expecting your team to put in an effort you aren't willing to give yourself. Your team will reflect your leadership. I learned this the hard way. Early in business, we had a great CFO leave with two weeks' notice. I felt defeated and immediately went into panic mode. My mindset became: "We just need a butt in the seat. It's accounting—how bad could it be?" That was a mistake. The lesson wasn't simply that we needed another person. We needed to understand why the system broke, what the position actually required, and who was truly the right person to fill that gap. Property management is difficult. Business is difficult. Leadership is difficult. But instead of asking, "Who can we blame?" Start asking: "What's breaking, what is the data telling us, and how do we fix it?" That's how better leaders build better teams—and better teams build companies that can actually scale.

  4. Sep 1

    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, relationships, and building a business development department that can scale with the company. Tiffany shares why one of the biggest turning points in her business was realizing that she couldn't do everything alone. Building the right team—and protecting the culture of that team—became one of the most important parts of growing the company. They dive into what intentional growth actually looks like, why every hire and decision should connect back to the company's larger vision, and why business owners can't simply say they want to grow without understanding where they're trying to go. Tiffany and Dan also discuss: Why business development needs clear ownership The difference between networking and actual business development Why Tiffany prefers training over rigid sales scripts How relationships can take years to produce opportunities The KPIs every business development team should track Why sales becomes predictable when you understand your numbers How AI will change business development and customer expectations Why growing too fast can actually chokehold a business The importance of hiring and training ahead of growth Why being busy isn't the same as moving the company forward Building a multi-state business development team Why growth should ultimately be about impact—not simply becoming the biggest company One of the biggest lessons from the conversation is simple: growth without infrastructure can break a business. The goal isn't just to generate more leads. It's to build the people, processes, technology, culture, and relationships necessary to support where the company is going next. For Tiffany, that means thinking years ahead, using data to make better decisions, embracing AI, developing leaders, and building a team that believes in the vision just as much as the owner does. If you're a property management company owner, entrepreneur, sales leader, or business owner trying to move beyond referral-based growth, this episode is packed with practical lessons on building a scalable growth engine.

  5. Aug 25

    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 perfection. Over 100 episodes, Tiffany discovered that everyone has a story, every entrepreneur faces struggles, and success often comes down to how quickly you get back up after being knocked down. Tiffany shares some of the biggest lessons she has learned along the way, including why success compounds through consistent action, why discipline will always outperform motivation, and why the hardest conversations often create the biggest breakthroughs. She also dives into leadership, building the right team, protecting company culture, learning from failure, maintaining high standards, and understanding that business ultimately comes down to people. The episode also gets personal as Tiffany shares the struggles that shaped her—from difficulties with reading and speech as a child to financial hardship when she first moved to Arizona and the journey that eventually led her into real estate and property management. Her message after 100 episodes is simple: the easier road may offer comfort today, but the harder road creates growth for tomorrow. Your story isn't finished. Make the call. Start the business. Have the difficult conversation. Take the opportunity. Choose growth over comfort. Because the road less traveled can lead to the life most people only dream about.

  6. Aug 18

    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 philosophies, culture, systems, and technology that fueled one of the industry's most impressive growth stories. Michael shares the lessons learned from scaling through acquisitions, building high-performing teams, leveraging AI, and creating a business that puts people first. From starting as a maintenance technician to helping lead one of the Southeast's fastest-growing property management companies, Michael explains why vision, mentorship, and strong company culture outperform strategy alone. In this episode: How Atrium grew from 228 homes to over 11,000 units Why company culture beats strategy over the long term Hiring for core values instead of resumes Building leaders instead of creating employees The importance of mentorship and mastermind groups Why bigger isn't always better—and how to define success for yourself Practical ways AI is improving operations and customer experience Leveraging dashboards, automation, and custom AI tools to scale The power of relationships, gratitude, and memorable client experiences Leadership lessons learned from mistakes, tough conversations, and continuous growth Michael's favorite books on leadership, business, and personal development Whether you're a property management company owner, entrepreneur, or business leader looking to scale with intention, this episode is packed with actionable strategies on leadership, culture, innovation, and building a company designed for long-term success. 👍 Enjoyed the episode? Like this video Subscribe for more conversations with industry leaders Share this episode with another entrepreneur or property management professional Comment below: What's the biggest leadership lesson that's helped you grow your business? #PropertyManagement #Leadership #BusinessGrowth #CompanyCulture #ArtificialIntelligence #AI #Entrepreneurship #MichaelKrause #TiffanyRosenbaum #TheRoadLessTraveled #BusinessPodcast #ScalingBusiness

  7. Aug 11

    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. Matthew breaks down Evernest's acquisition process—from the first conversation with a seller to valuation, due diligence, the LOI, closing, and the critical first 30 days after the acquisition. But valuation isn't just about your door count. They dive into the factors that can make—or break—a deal, including units per owner, average rent, market density, client concentration, management agreements, trust accounting, financials, and how dependent the company is on its owner. Matthew also reveals why some acquisitions have actually made Evernest worth less, why sellers often overvalue their companies, and what owners should start fixing 12–24 months before they plan to sell. Plus, they explore how AI is changing Evernest's acquisition strategy and why Matthew believes density equals profitability as property management continues to consolidate. If you own a property management company, are considering an acquisition, or want to build a company someone would actually want to buy, this episode is packed with insights you need to hear. The Road Less Traveled — with Tiffany Rosenbaum

  8. Aug 4

    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

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5
out of 5
41 Ratings

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
    104
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    The Road Less Traveled

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