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. 1D AGO

    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 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.

    37 min

  2. APR 7

    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, real-world advice for entrepreneurs who want to grow smart and build something that lasts—or sell when the time is right.

    45 min

  3. MAR 31

    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 a high level, Sina shares the mindset and strategies every entrepreneur needs to hear. This episode dives into the realities behind entrepreneurship—decision-making, adaptability, and staying ahead in a competitive market. If you're a business owner looking to grow, scale, and lead with purpose, this is a conversation you don't want to miss.

    57 min

  4. MAR 24

    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 signs of burnout—the stress, anxiety, and emotional toll that many business owners quietly carry while trying to lead, grow, and provide for others. She shares why recognizing those early signals matters and how building the right support system can make the difference between breaking down and breaking through. From mentorship and learning from other entrepreneurs to staying active through workouts and running groups, Tiffany talks about the importance of finding ways to reset, recharge, and stay grounded. Entrepreneurship can feel isolating, but the truth is everyone has knowledge and perspective to offer. Listening, learning, and surrounding yourself with the right people can help you push forward even when the pressure feels overwhelming. This episode is a reminder that rest is important—even if it's hard to find time for it when you're carrying the weight of a business.   If you're an entrepreneur navigating stress, growth, and responsibility, this conversation will remind you that you're not alone on the road less traveled. Connect with Tiffany on Instagram: @TiffanyMRosenbaum and share your takeaways!

    18 min

  5. MAR 10

    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 the raw truth behind recently hitting major company milestones. If you're an entrepreneur ready to move from dreaming to delivering, this episode gives you the unfiltered roadmap to start smashing your own goals. Connect with Tiffany on Instagram: @TiffanyMRosenbaum and share your takeaways!

    15 min

  6. MAR 9

    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 they can, especially in the early stages of building their business. But Marc explains why chasing numbers—whether it's 10, 20, or 30 clients—without the right expectations and alignment can actually create more problems than profit. Drawing from years of experience in the property management space, Marc shares how failing to properly vet clients or set clear expectations often leads to stress, operational issues, and long-term regret. Instead of focusing purely on hitting client count goals, successful property managers must learn which owners to bring on—and which ones to walk away from. In this conversation, Tiffany and Marc break down: The #1 mistake property managers make when growing their portfolio Why saying yes to every client can hurt your business The importance of setting expectations with property owners early How the wrong clients can create operational chaos How to build a healthy, sustainable property management business If you're in property management—or building any service-based business—this episode offers powerful insight into why the right clients matter more than the number of clients Connect with Tiffany on Instagram: @TiffanyMRosenbaum and share your biggest takeaway from the episode!

    56 min

  7. MAR 3

    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 management—it's about leadership, systems, and thinking like a true business owner. Mark shares how proactive operations, strong communication, and preventative strategies don't just protect properties—they create leverage, free up your time, and allow you to grow without chaos. If you want to step out of the day-to-day technician role and into the CEO mindset, this episode is packed with real-world insights. Whether you own one property, multiple investments, or you're building a company from the ground up, you'll walk away understanding how structure, delegation, and foresight are the real drivers of sustainable success. If your goal is to scale smarter, protect what you've built, and operate like a high-level entrepreneur—this episode is a must-listen.

    52 min

  8. FEB 24

    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 growth, and inner freedom through intentional breath and mind-body reconnection. Drawing from his years of guiding global clients, corporate events, retreats, and online sessions, Jerame shares how breathwork serves as a fast-track tool to release stored trauma, shift out of numbing patterns, break through mental and emotional ceilings, and reclaim control over your nervous system in ways traditional therapy often can't reach. Tiffany and Jerame explore practical techniques for everyday integration, the synergy of breathwork with practices like cold therapy, mindset shifts for sustainable well-being, and why true transformation starts with moving the earth within—offering listeners actionable insights to elevate their mental, emotional, and physical resilience. Whether you're new to breathwork or seeking next-level personal development, this episode delivers raw, inspiring wisdom to help you heal, grow, and live more fully.

    44 min
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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
    82
  • Rating
    Clean
  • Copyright
    © 2024
  • Show Website
    The Road Less Traveled