The Road Less Traveled

Publicly listed emails

tiffany@rosenbaumrealtygroup.com

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Ep 105 How to Scale a Property Management Company Without Breaking It

October 06, 2026

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, and how AI can help teams become more efficient without replacing the people behind the business. Tiffany also shares how her company grew from roughly 560 units to 1,200 units in a year—and why that...

Ep 104 How AI Is Changing Property Management with Peter Lohmann

September 29, 2026

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 ...

Ep 103 Why Your Property Management Processes Break as You Scale | The Road Less Traveled

September 22, 2026

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 als...

Evernest Property Management Show · Medium booking difficulty · 1,000 - 10,000 listeners

Property Management Business · Low booking difficulty · 1,000 - 10,000 listeners

The Property Management Show · Medium booking difficulty · 1,000 - 10,000 listeners

How do I get in touch with The Road Less Traveled?

The Road Less Traveled is hosted by Tiffany Rosenbaum. Its publicly listed email is tiffany@rosenbaumrealtygroup.com. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.

What is the email for The Road Less Traveled?

The publicly listed email for The Road Less Traveled: tiffany@rosenbaumrealtygroup.com.

How many listeners does The Road Less Traveled have?

Podseeker estimates The Road Less Traveled reaches 100 to 1,000 listeners per episode. Only the publisher has exact numbers.

Who is an ideal guest for The Road Less Traveled?

The Road Less Traveled typically books industry leaders. Typical guest background: Property-management company founders, executives, real-estate operators, acquisition advisers, valuation specialists, and corporate-development leaders with substantial operating or transaction experience. Common among recent guests: Scaled a property-management portfolio or company substantially; Founded or led a property-management business; Completed or advised on acquisitions, mergers, or company sales. Recent guests include Michael Krause, Matthew Whitaker, and Deb Newell.

How hard is it to get booked on The Road Less Traveled?

Medium. Guests usually need solid credentials in the topic and an idea that fits the show.

What topics does The Road Less Traveled cover?

Recent episodes cover Property Management, Real Estate, Acquisitions, Leadership, and Entrepreneurship. Pitch an idea tied to one of these topics and mention a recent episode.