The Level Up Lifestyle

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May 2026

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About the show

This is The Level Up Lifestyle podcast, where we dive deep into conversations that matter for today's leaders and growth-seekers. Join host Rebekah Samuels as she unravels what it actually took for her guests to become leaders in their careers, their communities, and their own lives. Find the inspiration that takes you to the next level.

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44 recent

May 18, 20261 hr 2 min

Hired Myself Back with Brian Ross, Agency Owner

Today, Rebekah sits down with Agency Owner Brian Ross. Brian shares his journey from humble beginnings in Bangor, Maine, shaped by a father who refused to let a wheelchair define him, to building nearly two decades of sustained growth as one of Family Heritage's most enduring agency owners. He unpacks what it looks like to walk away from sixteen years of career equity, bet on yourself in the middle of a financial crisis, and find a mission worth committing to for life. Through the valleys, the self-doubt, and the moments he almost quit, Brian proves that longevity isn't built on perfect runs. It's built on showing up, staying coachable, and pouring into others the way others once poured into you. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

May 4, 202657 min

Treat It Like a Business with Tanner Frick, Agency Owner

Today, Rebekah sits down with Agency Owner Tanner Frick. Tanner shares his journey from small-town South Dakota roots, five generations deep, to building real momentum as one of Family Heritage's rising agency owners. He unpacks what it looks like to step into ownership early, navigate the growing pains that come with it, and carry forward an entrepreneurial legacy passed down through generations. Through early failures, a mindset shift, and an unrelenting work ethic, Tanner proves that success isn't about a perfect record. It's about how many times you get back up, staying true to your roots, and building something worth passing down. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

April 20, 20261 hr 1 min

The Nearly Missed Meeting with Travis Wilson, Agency Owner

Today, Rebekah sits down with Agency Owner Travis Wilson. Travis recounts his journey from working cornfields in Iowa to building one of the most enduring agencies in Family Heritage history. He unpacks what it truly takes to go from a scrappy midwestern kid with no clear plan to a Hall of Leaders inductee. Through embracing entrepreneurship early, showing up when others didn't, and leading from the front at every turn, Travis proves that legacy isn't built on where you start. It's built on faithfulness, grit, and a willingness to keep going until you have nothing left to give. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

April 6, 202656 min

From the Trailer to the Top with Terrelle Walker, Regional Director

Today, Rebekah sits down with Regional Director Terrelle Walker. Terrelle brings a remarkable journey from humble beginnings in a small South Dakota town to becoming the first agent in company history to earn both market and regional director awards. He breaks down what it really takes to climb from the bottom to the top. Through channeling raw discipline, betting on himself at every turn, and pouring into others the way his coaches and mother poured into him, Terrelle proves that real success isn't about where you start. Instead, it's about grit, relentless work ethic, and showing up every single day. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

March 23, 202645 min

Choosing Discipline Over Motivation with David Villasenor and Robin Monsky

Today, Rebekah sits down with Sales Professionals Robin Monsky and David Villasenor. Robin brings a dynamic career reinvention from forty years in sports media, while David represents the gold standard of long-term consistency. They break down what it really takes to perform at the highest level. Through embracing discomfort, holding themselves to unshakeable standards, and finding motivation in the work itself, Robin and David prove that real success isn't about talent. Instead, it's about discipline, mindset, and showing up every single day. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

March 9, 202655 min

Daily Failings to Daily Purpose with David Villasenor, Sales Professional

Today, Rebekah sits down with Sales Professional David Villasenor. David's journey began in a military family, moving from Air Force base to Air Force base, where strict rules and frequent relocations taught him to channel anger into action on the football field. Through hitting rock bottom at 25, a divine parking lot encounter in Caldwell, Texas, and becoming a father to his son Luke, David built an extraordinary career proving that the best way to level up is turning your darkest moments into your greatest purpose. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

February 23, 202651 min

Breaking Barriers & Setting the Standard with Robin Monsky, Sales Professional

Today, Rebekah sits down with Sales Professional Robin Monsky. Robin's journey began in Omaha, Nebraska, where her father built one of the country's largest car auctions and her sister trained for Olympic figure skating. After a determined pursuit of a baseball career led her to break barriers as one of baseball's first female executives, she faced the choice between staying in sports or beginning a second career later in life in financial services. Through developing standards over motivation, and learning that being different means forging your own path, Robin built an extraordinary career proving you can do anything regardless of age by being confident, and embracing new adventures. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

February 9, 202657 min

Burnout vs. Vision & Leading with Agency Owners Barry Bandera and Dillon Buck

Today, Rebekah sits down with Agency Owners Barry Bandera and Dillon Buck. Barry brings over thirty years of consistent leadership, while Dillon represents a new generation of leaders. They break down what it really takes to develop into a true leader. Through leading from the front, treating people how they want to be treated, and finding more joy in others' success than their own, Barry and Dillon prove that real leadership means being willing to do everything you ask of others. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

February 2, 202651 min

Traveling the Globe & Finding Stillness with Dillon Buck, Agency Owner

Today, Rebekah sits down with Agency Owner Dillon Buck. Dillon's journey began in Basalt, Colorado, where skiing was a rite of passage and snowboarding became his competitive outlet from age thirteen. After traveling the world on Semester at Sea, he faced the choice between a comfortable graphic design internship in Austria and eighty hours a week of rejection. Through creating ten non-negotiables for his career and learning that stillness is the foundation for showing up as the leader, husband, and father he wants to be, Dillon built an extraordinary career proving that who you want to become matters more than what you want to do. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle

January 26, 202645 min

Overcoming Poverty to Longevity & Success with Barry Bandera, Agency Owner

Today, Rebekah sits down with Agency Owner Barry Bandera. Barry's journey began in Arlington, Texas, where his parents' divorce at age 10 shifted his family from a colonial home to a three-bedroom apartment across the tracks. Through outworking everyone around him, embracing the fear of being poor, and learning that longevity means committing to something and sticking with it, Barry built an extraordinary career proving that the best way to level up is through mastering work ethic. This is the Level Up Lifestyle podcast. Make sure to follow along our journey by visiting our social channels here: https://linktr.ee/theleveluplifestyle