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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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What happens after you build a company, sell it for millions, and realize you're not done yet?

In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Sina Shekou to discuss the realities of entrepreneurship, acquisitions, failure, identity, and starting over.

Sina shares the story behind building Propertyware from the ground up, growing it into a multi-million-dollar SaaS company, and ultimately selling it to RealPage. He opens up about the emotional side of entrepreneurship, the challenges of due diligence, lessons learned from shutting down businesses, and why success is more about relationships than revenue.

Topics include:

• Building Propertyware from a real-world need
• The process of selling a company and navigating due diligence
• What entrepreneurs get wrong about exits
• Life after selling a business
• The emotional impact of failure and starting over
• Why team and relationships matter more than ever
• AI, innovation, and the future of business
• Lessons from AppFolio and entrepreneurship
• The importance of focus, patience, and long-term thinking
• Sina's favorite business book: The Alchemist

Whether you're building, buying, selling, or scaling a business, this conversation is packed with insights from someone who has experienced every stage of the entrepreneurial journey.

#TheRoadLessTraveled #Entrepreneurship #BusinessGrowth #SaaS #PropertyManagement #Leadership #BusinessOwner #StartupLife #AI #Acquisitions #BusinessSuccess #TiffanyRosenbaum #SinaShekou #AppFolio #Propertyware

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 multi-state brokerage managing nearly 450 residential units, Ben shares the lessons learned through every stage of the journey.

Ben opens up about leaving the family business, launching his own company from the ground up, surviving the early entrepreneurial grind, and why he made the difficult decision to sell part of his portfolio to regain balance and refocus his business. He also gives an inside look at acquiring over 200 doors in Jacksonville, including how acquisitions are structured, what due diligence mistakes to avoid, and why knowing your numbers is critical before making any deal.

Topics covered in this episode include:

• Scaling a property management company from scratch
• The emotional and financial realities of entrepreneurship
• Selling part of a property management portfolio
• Acquisition strategies and due diligence tips
• Managing staff transitions during acquisitions
• Understanding clawback provisions and deal structures
• Why systems, profitability, and culture matter in growth
• Recommended books and resources for business owners

If you're a property manager, entrepreneur, or business owner looking to grow strategically while protecting your time, family, and sanity, this episode is packed with real-world insights you won't want to miss.

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 successful exit.

Amy shares how she accidentally entered the property management industry in 2006, grew her first company from 90 to 250 doors, and later sold the entire operation. After relocating to Dallas and building a second company from the ground up, she completed another major transaction in 2025 by selling her accounts to Berkshire Hathaway PenFed Realty — where she now serves as Vice President of Property Management for Texas.

In this episode, they discuss:

• Buying and scaling property management companies
• Selling accounts vs. selling an entire business
• Due diligence mistakes buyers and sellers make
• Why culture fit can make or break an acquisition
• Preventing employee and client churn during transitions
• The importance of E&O insurance and tail policies
• Why documentation and systems matter more than ever
• The long-term reality behind successful exits and acquisitions

If you're a property manager, real estate entrepreneur, or business owner thinking about growth through acquisition, this episode delivers real-world insight into the challenges, risks, and opportunities that come with building a company worth buying.

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 a CFO position into entrepreneurship, driven by a desire for greater freedom and work-life balance for his family. He opens up about the strategic way he built his company—working as a fractional CFO while slowly growing his own client base—and the lessons he learned along the way.

The conversation dives into:

• Why net profit matters more than flashy revenue numbers
• When business owners should hire accounting help
• The hidden stress and "brain damage" behind scaling a service business
• Selling business assets while maintaining consulting freedom
• How to reduce client churn during acquisitions
• The importance of vetting buyers and their systems before selling
• Mindset shifts around gratitude, stress, and staying present

Nick also shares books and philosophies that transformed his thinking, including Rich Dad Poor Dad, Think and Grow Rich, and The Untethered Soul.

This episode is packed with honest insight for entrepreneurs navigating growth, burnout, acquisitions, and the emotional realities behind business ownership.

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.

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Entrepreneurs and business owners always think they can do it better—I did too. Early on, I tried correcting everything and everyone. Reality check: as long as policies, procedures, and laws are followed, you've got to let your team bring their personality. That's how you build a dynamic team that actually scales.

In the beginning, survival mode is real. Your KPIs? Messy. Raw. It felt like running a corn maze blindfolded—no clue what the numbers meant, just trying to stay alive. I didn't even know what key performance indicators were. Finally went to a mentor and said, "I'm lost—I need to know if I'm moving forward or falling behind."

Starting from zero as an entrepreneur in property management, here's the truth:

• Know your cost to acquire a client (and yes, that might mean knocking doors yourself).
• Track your delinquency rate like your business depends on it—because it does.
• Understand days on market—vacancy is costing you and your clients more than they realize.
• Get clear on your vacancy rate vs the market—are you better, average, or behind?

Most owners ignore vacancy because they think it's just "time"… it's not. It's lost revenue, trust, and momentum.

Your goal? Don't just exist in the market—beat it.

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 literally driving around collecting rent on the 1st…

It was chaos.

Until they got clear on roles, structure, and accountability.

Because the truth is— Partnerships don't fail from lack of opportunity… They fail from lack of clarity.

🎙️ If you're building a business, especially with a partner—this one hits different.

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 as a leader and business owner.

Josh shares how a pivotal mentorship early in his career transformed both his personal life and professional trajectory, equipping him with the tools to grow a thriving business in a crowded, often undervalued industry. Today, he's on a mission to pass those lessons forward—helping tradesmen elevate their leadership, build stronger teams, and create lasting value in the marketplace.

From the power of mentorship to the art of authentic leadership, this conversation dives deep into the mindset and strategies needed to raise the standard and reshape the perception of the trades. If you're looking to grow, lead, and make a meaningful impact in your field, this episode delivers practical wisdom and inspiration from someone who's lived it.

Explore more from Josh at: https://www.thetradesmanexperience.com

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 balancing a 9–5, what gave her the confidence to go all in, and the key lessons she learned along the way. From understanding today's market to avoiding costly mistakes, this conversation is packed with real, practical insights for anyone looking to break into the flipping industry.

One of the biggest takeaways? Insurance is not optional. Kara dives into why proper coverage is critical in real estate and property management—and how skipping it can cost you everything.

We also explore:

• How to get started in house flipping with little experience
• The realities of managing projects and properties
• Lessons learned from deals that didn't go as planned
• Why networking is one of the most powerful tools for success
• How building relationships can help you avoid expensive mistakes

If you've ever thought about flipping houses or scaling in real estate, this episode gives you a real look at what it takes—and what to watch out for.

🎧 Tune in and learn how taking The Road less Traveled can lead to real success.

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.