x

75% of people globally want unbiased news (Pew Research) but are concerned they're not getting that.

Get balanced coverage with Symby. See how stories are covered across diverse outlets and spot when one side covers a story the other skips.

PODCAST

The Road Less Traveled

Tiffany Rosenbaum

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.

business entrepreneurship

All Episodes

45:22

Ep 80 When to Scale, When to Sell: Lessons from Amy...

The Road Less Traveled ·

2026/04/07

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.

en

57:07

Ep 80 Building, Scaling, and Leading with Vision...

The Road Less Traveled ·

2026/03/31

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

en

18:17

Ep 79 Behind the Scenes of Success: Burnout, Anxiety...

The Road Less Traveled ·

2026/03/24

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

en

14:31

Ep 77 Decisions That Build Businesses with Tiffany

The Road Less Traveled ·

2026/03/10

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

en

56:13

Ep 78 The Property Management Trap: Why the Wrong...

The Road Less Traveled ·

2026/03/09

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

en

52:11

Ep 76 Wealth Is Built on Systems w/Mark Brower

The Road Less Traveled ·

2026/03/03

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

en

43:30

Ep 75 Powerful Transformation w/Jerame Mudick

The Road Less Traveled ·

2026/02/24

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

en

44:21

Ep 74 Holistic Success w/Julie Holly

The Road Less Traveled ·

2026/02/17

In this inspiring episode of The Road Less Traveled, host Tiffany Rosenbaum welcomes real estate syndicator, investor, and podcast host Julie Holly for a deep dive into building wealth while prioritizing holistic success and personal fulfillment. Drawing from her two decades in real estate and her experience as a third-generation investor, Julie shares powerful insights on moving beyond the traditional chase for financial freedom—exploring how to recalibrate life for balance, activate untapped

en

36:59

Ep 73 Working as a Couple w/Tiffany and Daniel

The Road Less Traveled ·

2026/02/10

In this candid and relatable episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with her husband and business partner, Daniel Rosenbaum, to share the real strategies they've developed to keep their marriage thriving while running a successful company together—proving you can have both a strong relationship and a healthy business without letting one destroy the other. They open up about setting firm boundaries between boardroom decisions and bedroom conversations, establishing

en

30:04

Ep 72 Specializing w/John Tilley

The Road Less Traveled ·

2026/02/03

Tiffany interviews 1031 exchange specialist John Tilley, who breaks down one of real estate's most powerful tax-deferral tools. They cover the basics of a 1031 exchange, key deadlines (45-day identification and 180-day closing periods), common pitfalls, working with qualified intermediaries, and real-world strategies for deferring capital gains taxes while upgrading properties or diversifying portfolios. Perfect for investors looking to keep more of their gains working for them—practical, expert

en

16:57

Ep 71 Achieving Success w/Tiffany

The Road Less Traveled ·

2026/01/27

In this celebratory episode of The Road Less Traveled, Tiffany Rosenbaum shares the raw truth behind recently hitting major company goals at Rosenbaum Realty Group—doubling managed doors and scaling to new heights in 2025. She dives into the real, no-fluff actions it took: mindset shifts, tough decisions, daily disciplines, identity changes, and consistent execution that turned vision into reality. Perfect for entrepreneurs and business owners ready to stop dreaming and start delivering—listen now

en

42:24

Ep 70 Gaining Visibility w/Alex and Lacy

The Road Less Traveled ·

2026/01/20

With deep industry roots (Lacy brings over a decade in property management, real estate brokerage, and local leadership; Alex adds veteran experience in business development and ethical marketing), they launched ClearLead to deliver transparent, results-driven SEO, content marketing, local search optimization, website design, and reputation strategies that actually generate qualified owner leads and portfolio growth — no fluff, just clear wins. Tiffany dives into the realities of digital marketing

en

32:24

Ep 69 Managing Expectations w/Amoura and Avery

The Road Less Traveled ·

2026/01/13

Amoura (CEO, education & strategy expert) and Avery (marketing & design veteran) share how they blend their talents to deliver full-service branding, content strategy, social media, digital campaigns, and custom professional development workshops for purpose-driven businesses, nonprofits, and entrepreneurs. Tiffany explores the realities of sibling entrepreneurship, building inclusive brands, creating high-impact marketing systems, and scaling with intention while staying authentic. Packed with

en

33:41

Ep 68 Twists and Turns w/Ben Serven

The Road Less Traveled ·

2026/01/06

Ben shares his journey from roles in property management software and high-level customer service to building a leading consulting firm that has transformed operations for over 200 property management companies across North America. Through his innovative Processes Made Simple approach, Ben helps business owners streamline workflows, implement powerful automations (especially in tools like LeadSimple), foster team accountability, and create scalable systems that reduce chaos and free owners to focus

en

27:19

Ep 67 Scaling Business w/Mindee Chidester

The Road Less Traveled ·

2025/12/30

Host Tiffany Rosenbaum speaks with Mindee Chidester, co-founder of The Plastics Clinic + Spa, a Draper, UT-based practice now powered by multiple board-certified surgeons that generates low-seven-figure revenue through a lean, referral-only model—no ads, no employees beyond essentials, and a 4–6 month waitlist. Mindee details the 2025 evolution: repositioning as a surgeon-adjacent hub with a referral flywheel replacing all marketing (90% consult conversion). Drawing from TikTok/Instagram traction

en

55:30

Ep 66 Creating w/Stephen Fox

The Road Less Traveled ·

2025/12/23

Host Tiffany Rosenbaum sits down with Stephen Fox, the founder of Upkeep Media, a remote-first marketing agency that grew from a one-man operation into an industry quiet giant serving some of the biggest names in property management—all while Stephen intentionally keeps the company lean, profitable, and 100% bootstrapped. In a warm and unguarded conversation, Stephen traces his path from burnout in corporate real estate to betting everything on content, community, and relationships over paid ads and

en

49:45

Ep 65 Discipline w/John Gillespie

The Road Less Traveled ·

2025/12/16

In a refreshingly candid conversation, host Tiffany Rosenbaum sits down with John Gillespie, partner and CIO of Gallacher Capital, a low-profile investment firm that has been managing client wealth for over 30 years. John shares the principles behind their disciplined, conviction-driven approach, how they identify opportunities, and why they prioritize alignment and capacity over growth for growth's sake. With disarming honesty, he reflects on the trade-offs of running a boutique operation in an

en

30:20

Ep 64 Aligning Ambition w/Thomas Klein

The Road Less Traveled ·

2025/12/09

In this heartfelt and transformative episode of The Road Less Traveled, host Tiffany Rosenbaum welcomes Thomas Patrick Klein, the visionary founder of The Animal Alliance—a U.S.-based 501(c)(3) nonprofit born from a raw encounter with animal suffering during global travels in 2023 alongside co-founder Maggie Chahoud. Drawing from a childhood sanctuary of rescued cats and dogs that ignited his lifelong empathy, Thomas shares how he channeled entrepreneurial grit from building Asheville's top

en

36:10

Ep 63 Breaking The Mold w/Paul Stratton

The Road Less Traveled ·

2025/12/02

In this raw episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with entrepreneur and self-described "professional troublemaker" Paul Stratton for a no-holds-barred conversation about walking away from a soul-crushing corporate career, getting canceled (twice), rebuilding from rock bottom, and deliberately building a life and multiple seven-figure businesses outside the system—often in direct defiance of conventional wisdom. Paul shares the mindset shifts that turned financial ruin

en

57:16

Ep 62 Resilient w/Kimberly Bradshaw

The Road Less Traveled ·

2025/11/25

In this heartfelt and empowering episode, host Tiffany sits down with Kimberly Bradshaw—passionate founder and owner of Flower Child Adventures, a transformative program dedicated to helping children, families, and individuals master emotional self-regulation through fun, accessible tools like yoga, breathwork, meditation, and mindfulness practices. Kimberly opens up about her inspiring journey as a single mom of three who turned personal challenges into a mission of healing and growth. From

en

81 results

Similar Podcasts

TaxTalent.com The Golden Rule Podcast

Adam Golden

TaxTalent.com Podcast

Tony Santiago

Handelsblatt Crime - spannende Streitfälle der deutschen Wirtschaft

Ina Karabasz, Solveig Gode, Sönke Iwersen

Deffner und Zschäpitz – Der Wirtschafts-Talk von WELT

WELT

Black Box - La scatola nera della finanza

Guido Brera e Gian Luca Comandini -...