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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

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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47:12

Ep 53 Building to the Next Level w/Bjorn Johnson

The Road Less Traveled ·

2025/09/23

Join host Tiffany Rosenbaum on The Road Less Traveled for a compelling conversation with Bjorn Johnson, Chief Operating Officer of H4U Construction and former tech executive. In this episode, Bjorn shares his inspiring transition from a tech-driven career to leading H4U Construction, a premier Scottsdale-based remodeling and construction company. Drawing from his diverse background, including his early days as a wildland firefighter in southern Oregon, Bjorn discusses how his passion for people,

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01:22:58

Ep 52 Learning w/Craig Breinholt

The Road Less Traveled ·

2025/09/16

Join host Tiffany Rosenbaum on The Road Less Traveled for a captivating conversation with Craig Breinholt, an innovative entrepreneur and visionary leader. In this episode, Craig opens up about his unique journey, sharing the bold decisions, unexpected challenges, and defining moments that shaped his path to success. From navigating uncharted business ventures to embracing risk and resilience, Craig’s story offers powerful insights for aspiring trailblazers. Tiffany and Craig explore the mindset

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59:36

Ep 51 Take a Shot w/Derek Price

The Road Less Traveled ·

2025/09/09

Join host Tiffany Rosenbaum on The Road Less Traveled for an inspiring conversation with Derek Price, former NFL player, jiu-jitsu brown belt, and founder of The Faction Foundation. In this episode, Derek shares his remarkable journey from the football field to entrepreneurship, revealing the challenges and triumphs that shaped his unconventional path. With candid insights, he discusses how his experiences as a student-athlete and professional in the NFL influenced his leadership style and fueled

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44:16

Ep 50 Connected w/Travis Brady

The Road Less Traveled ·

2025/09/02

In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Travis Brady, a dynamic entrepreneur and visionary leader who has forged an unconventional path to success. Travis shares his journey from humble beginnings to building a thriving business, revealing the bold decisions, innovative strategies, and resilient mindset that propelled him forward. With Tiffany’s insightful questions, the conversation dives deep into overcoming challenges, seizing opportunities, and embracing

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01:10:10

Ep 49 Failing Up w/Steve Rozenburg

The Road Less Traveled ·

2025/08/26

In this episode of The Road Less Traveled, host Tiffany Rosenbaum interviews Steve Rozenberg, an accomplished entrepreneur, international airline pilot, and business coach. Steve recounts his pivot from a career in aviation, disrupted by the 9/11 attacks, to building and scaling Empire Industries, a property management company overseeing over 1,000 properties before its successful exit. He discusses founding The Rozenberg Group, where he helps businesses accelerate sales and growth through

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36:21

Ep 48 Getting Back Up w/Bill Walsh

The Road Less Traveled ·

2025/08/19

In this episode of The Road Less Traveled, host Tiffany Rosenbaum sits down with Bill Walsh, a renowned business coach, venture capitalist, and founder of Powerteam International. Bill shares his journey from humble beginnings to becoming a global leader in entrepreneurial education, detailing the strategies that helped him build a multimillion-dollar empire. He discusses overcoming early financial struggles, leveraging mentorship, and navigating high-stakes investment decisions in competitive

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48:20

Ep 47 Traveling w/Rob Lee

The Road Less Traveled ·

2025/08/12

In this episode of The Road Less Traveled, host Tiffany Rosenbaum interviews Rob Lee, CEO and co-founder of Swift Passport and Visa Services. Rob shares his journey from a corporate background to launching Swift in 2008 with his wife, Laurie, driven by a gap they identified in the travel document industry. He discusses overcoming early challenges, such as navigating complex government regulations and building trust with clients, while detailing strategies that grew Swift into a leader in expedited

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56:29

Ep 46 Innovation w/David Borden

The Road Less Traveled ·

2025/08/05

Join Tiffany for an inspiring conversation with David Borden, CEO of Rentvine, a trailblazing property management software company. Tiffany and David dive into the entrepreneurial journey, exploring how Rentvine is going to revolutionize the property management industry. David shares insights on the mindset required to scale a business, the importance of data sharing in disrupting industry norms, and the strategies that fueled Rentvine’s rapid growth. With Tiffany’s passion for unlocking human

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54:29

Ep 45 Welcome Back Lior Abramovich

The Road Less Traveled ·

2025/07/29

Tiffany dives deeper into Lior’s remarkable journey of resilience and innovation. Lior opens up about the lessons learned since their first interview, sharing fresh perspectives on scaling businesses, overcoming setbacks, and seizing new opportunities in an ever-changing market. From bold pivots to building a legacy, Lior’s story is a masterclass in adaptability and strategic thinking. Join Tiffany and Lior for a dynamic conversation packed with wisdom and inspiration for anyone looking to blaze

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01:01:44

Ep 44 Self Discovery w/Ryan Sandstorm

The Road Less Traveled ·

2025/07/22

Tiffany sits down with Ryan Sandstrom, a dynamic lawyer and entrepreneur who has carved a unique path in the world of business. Ryan shares his inspiring journey to becoming a trailblazer in his industry. With candid insights, he discusses the pivotal decisions that shaped his career, the challenges of navigating competitive markets, and the innovative strategies that fueled his success. Tiffany and Ryan explore the mindset required to take risks, adapt to change, and seize opportunities on the road

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57:58

Ep 43 Financial Independence w/Sam Knickerbocker

The Road Less Traveled ·

2025/07/15

Join host Tiffany Rosenbaum on The Road Less Traveled for an inspiring conversation with Sam Knickerbocker, a dynamic entrepreneur and visionary leader. In this episode, Sam shares his unconventional journey to success, revealing the challenges, triumphs, and pivotal moments that shaped his path. From bold career pivots to innovative strategies for building wealth, Sam’s story offers actionable insights and motivation for aspiring entrepreneurs. Tune in to discover how embracing the road less

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59:52

Ep 42 Hope and Resilience w/Damon West

The Road Less Traveled ·

2025/07/08

Join host Tiffany on The Road Less Travelled, a podcast that dives into the inspiring stories of individuals who have forged their own paths, defying convention to pursue lives of purpose and impact. Each episode features in-depth conversations with guests who share their unique journeys, challenges, and triumphs, offering listeners insights into what it means to take the road less travelled. In this compelling episode, Tiffany sits down with Damon West, a former college quarterback turned

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57:04

Ep 41 Accidental Entrepreneur w/Mitch Whiting

The Road Less Traveled ·

2025/07/01

Join host Tiffany as she sits down with Mitch Whiting, an innovative entrepreneur shaking up the business world. In this compelling episode, Mitch shares his bold journey, from tackling early setbacks to building ventures that combine vision with impact. Tiffany and Mitch explore actionable strategies for overcoming self-doubt, forging meaningful professional networks, and capitalizing on unique strengths to achieve business success. Mitch’s story delivers practical insights for listeners eager to

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50:54

Ep 40 Blazing Trails w/Aaliyah Heine

The Road Less Traveled ·

2025/06/24

On this episode of The Road Less Travelled Tiffany interviews Aaliyah Heine, a dynamic professional making her mark in the creative industry. In this engaging episode, Aaliyah shares her unconventional career journey, revealing how she overcame early challenges to secure roles that blend creativity with strategic impact. Tiffany and Aaliyah dive into practical strategies for overcoming imposter syndrome, building authentic professional relationships, and leveraging personal strengths to drive career

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59 results

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