The Road Less Traveled

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 LeadSim...

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 refer...

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 i...

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...

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 life...

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—ofte...

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...

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 CE...

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 creati...

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 se...

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 o...

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 c...

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...

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...

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 Chr...

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...

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, Cra...

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 ex...

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 insightfu...

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 discus...

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 financi...

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...

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,...

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 Tiffan...

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 a...