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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

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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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59:28

Ep 61 Jumping In w/Chris Springer

The Road Less Traveled ·

2025/11/18

In this powerhouse episode, host Tiffany welcomes Chris Springer—a decorated U.S. Army veteran, West Point graduate, former economics professor at the academy, strategy instructor at the Command and General Staff College, Ranger-tabbed officer, and Senior Jumpmaster—for an unforgettable crossover of military precision, leadership mastery, and cutting-edge proptech innovation. Now at the helm as CEO of Property Manager Websites (PMW)—the industry-leading builder of SEO-optimized, lead-converting

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43:32

Ep 60 Building Dreams w/Corey Taylor

The Road Less Traveled ·

2025/11/11

In this engaging episode of the podcast, host Tiffany sits down with Corey Taylor, founder of Copper Sky Construction, for a candid conversation about the world of high-end home remodeling and design-build projects. Corey shares his journey from flipping historic homes in Sonoma County to building a reputable firm specializing in kitchen and bath renovations, whole-home transformations, and creative additions that blend modern luxury with timeless charm. Dive deep into the challenges and triumphs

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39:58

Ep 59 Conquering Chaos w/Clate Mask

The Road Less Traveled ·

2025/11/04

In this electrifying episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Clate Mask—co-founder and CEO of Keap (the force behind Infusionsoft), NY Times bestselling author of Conquer the Chaos, and one of Arizona's most celebrated tech founders—to unpack the raw, unfiltered journey of bootstrapping a garage-born idea through six near-death experiences into a 9-figure empire serving over 200,000 entrepreneurs worldwide; from the brutal pivot to customer-obsessed automation and

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48:15

Ep 58 Rising Above Tragedy w/Ashlynne Miller

The Road Less Traveled ·

2025/10/28

Step into the world of calculated risks and heartfelt protection with host Tiffany Rosenbaum on The Road Less Traveled, featuring Ashlynne Miller, the dynamic Texas-based insurance professional who's turning policies into peace of mind one client at a time. Hailing from the heart of the Lone Star State, Ashlynne's journey began far from the boardrooms of big agencies—in the unpredictable terrain of everyday challenges that taught her the true value of security. Whether it's navigating the wilds of

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34:21

Ep 57 Building Legacies w/Brandon Martino

The Road Less Traveled ·

2025/10/21

Tune in to The Road Less Traveled as host Tiffany Rosenbaum chats with Brandon Martino, the Texas native and managing partner of Orison Holdings, whose vision has reshaped the Denton County landscape. Growing up in small-town charm, Brandon cut his teeth in construction before teaming up with industry expert Lee Ramsey in 2012 to launch Orison Holdings—a powerhouse portfolio blending commercial construction, real estate investment, and development. From revitalizing downtown Denton with projects

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53:01

Ep 56 Back for more w/Heath Treasure

The Road Less Traveled ·

2025/10/14

Welcome back for part two of an unmissable deep dive with Heath Treasure, the Blue Collar Millionaire and founder of Ultimate Blue Collar. In their first conversation, Heath shared his raw origin story—dropping out of college to bootstrap a trucking empire from scratch in 2000, growing it into a 200-truck powerhouse that employed hundreds, and orchestrating a multimillion-dollar exit at 7x EBITDA to Red Bull's parent company. Now, Heath returns with fresh fire, unpacking the gritty realities of his

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47:09

Ep 55 Taking Risks w/Barak Shamir

The Road Less Traveled ·

2025/10/07

Join host Tiffany on The Road Less Traveled for an inspiring conversation with Barak Shamir, CEO of Showdigs, an AI-powered leasing automation platform revolutionizing property management. Once a dedicated basketball player in Israel from age 7, mentoring his younger brother on the court, Barak’s path took a bold pivot in 2016 when a scout—his coach’s brother—spotted his potential and launched him into a global modeling career with top agencies like Select Model Management and Next Management

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21:55

Ep 54 Unique Calling w/Rebecca Jones

The Road Less Traveled ·

2025/09/30

Join host Tiffany Rosenbaum on The Road Less Traveled for a heartfelt conversation with Rebecca, a certified birth and postpartum doula and the heart behind Beloved Motherhood AZ. In this episode, Rebecca shares her inspiring journey as a wife, mother of four, and compassionate caregiver, driven by her mission to support mothers through the sacred seasons of childbirth and postpartum. From her Christ-centered approach to hands-on doula care in Maricopa, AZ, Rebecca discusses the challenges and joys

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73 results

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