The Level Up Lifestyle

The Level Up Lifestyle

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.

Episodes

Hired Myself Back with Brian Ross, Agency Owner

May 18, 2026 • 62 mins
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...
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Treat It Like a Business with Tanner Frick, Agency Owner

May 4, 2026 • 57 mins
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 ...
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The Nearly Missed Meeting with Travis Wilson, Agency Owner

April 20, 2026 • 61 mins
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 pro...
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From the Trailer to the Top with Terrelle Walker, Regional Director

April 6, 2026 • 56 mins
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 coache...
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Choosing Discipline Over Motivation with David Villasenor and Robin Monsky

March 23, 2026 • 45 mins
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 pro...
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Daily Failings to Daily Purpose with David Villasenor, Sales Professional

March 9, 2026 • 55 mins
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 th...
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Breaking Barriers & Setting the Standard with Robin Monsky, Sales Professional

February 23, 2026 • 51 mins
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 f...
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Burnout vs. Vision & Leading with Agency Owners Barry Bandera and Dillon Buck

February 9, 2026 • 57 mins
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...
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Traveling the Globe & Finding Stillness with Dillon Buck, Agency Owner

February 2, 2026 • 51 mins
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 s...
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Overcoming Poverty to Longevity & Success with Barry Bandera, Agency Owner

January 26, 2026 • 45 mins
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 be...
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Bringing Out the Best with John David Mitchell, Agency Owner

May 26, 2025 • 56 mins
Today, Mike sits down with Agency Owner John David Mitchell. JD’s journey began in a small Alabama town where he grew up inspired by his father’s career. After finding early success in elevator sales, he walked away from a six-figure salary job to return home and take a chance following his dad’s footsteps. Through humility, hard lessons, and a relentless commitment to growth, John David carved his own path to leadership, proving t...
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Letting Go to Lead with Matt Carder, Agency Owner

May 5, 2025 • 54 mins
Today, Mike sits down with Agency Owner Matt Carder. Matt's journey into leadership began with his humble upbringing in a small Arkansas town where he developed his work ethic mowing lawns at age 13. He later faced obstacles when building his agency in Phoenix after leaving everything familiar behind. But through his positive mindset and willingness to let go to lead his team, Matt broke through the challenges that life put in his ...
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Five to Nine Gave Me Freedom with Brian Cannington, Agency Owner

April 14, 2025 • 60 mins
Today, Mike sits down with Agency Owner Brian Cannington. After struggling in college and bouncing between hourly jobs, Brian found his calling as an agent. When his performance slumped, a pivotal decision to "hire himself" and commit to a serious work ethic transformed his career. Through his “5 to 9” philosophy, Brian built a thriving agency spanning six locations across Georgia and Florida. His story demonstrates how persistenc...
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Setting, Spiking, & Scoring with Amanda Violand, Agency Owner

February 17, 2025 • 72 mins
Today, Mike sits down with Agency Owner Amanda Violand. Amanda’s journey into leadership began as she cultivated a work ethic of steel as a farmhand in rural Ohio. She later faced obstacles when exploring opportunities in New York City. But by her driven nature and sticking to the decisions she made, Amanda broke through all the blocks that life put in her way to achieve the success and lifestyle she always wanted. This is the Le...
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One Step Away with Alfredo Gonzalez, Regional Director

February 3, 2025 • 75 mins
Today, Mike sits down with Regional Director, Alfredo Gonzalez. We get to hear the story of Alfredo’s family’s harrowing journey out of war-torn El Salvador. The hardships his family endured to bring him to a better life paved the way for a lifestyle of immense gratitude and rock solid work ethic. Because of the sacrifice of his family, Alfredo has been able to face every setback and victory with the attitude of achieving the next ...
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Beating Hurricanes & Building Home with Jayson Stirrup, Executive Director of Casa Hogar

November 25, 2024 • 73 mins
Today, Mike sits down with Jayson Stirrup, Executive Director of Casa Hogar in Cabo San Lucas. Jayson takes us through his unexpected journey from Toronto, Canada, to leading a children's home in Mexico, where he dedicates his life to helping kids overcome the trauma of their pasts. He shares powerful stories of resilience, the challenges of running a nonprofit in a foreign country, and the unique strategies Casa Hogar employs to f...
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From Small Town to the Big Leagues with Luke Gilliam, Senior Vice President

November 11, 2024 • 77 mins
Today, Mike sits down with Luke Gilliam, Senior Vice President at Liberty National. Luke shares his journey from a small-town upbringing in Texas to overcoming the challenges of a declining journalism industry. He dives into his transition from traditional journalism to leading a digital media startup, reflecting on the hard lessons learned along the way. Luke’s insights on innovation, leadership, and adapting to change offer valua...
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Pitching Strikes & Hitting Curveballs with Brandon Jones, Agency Owner

October 28, 2024 • 66 mins
Today, Mike sits down with agency owner Brandon Jones. Brandon takes us through his journey from a small town in Lower Alabama to becoming a successful agency owner. He shares his early love for sports,  the derailment of a surgery in college, and the struggles of moving far away from home to take on his toughest challenge. Brandon’s story is a testament to perseverance, making tough decisions, and never letting adversity define yo...
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Earning Back the Shotgun with Clint McLain, Agency Owner

October 14, 2024 • 62 mins
Today, Mike sits down with Clint McLain, agency owner in Birmingham, Alabama. Clint shares his journey from living on his own out of high school on a movie theater salary to his rewarding but challenging climb to a steady career. Following his family legacy, he had to make a painful decision with one of his most prized possessions to escape rock bottom. Clint’s story highlights perseverance, adaptability, and the enduring impact of...
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From Family Legacy to Lasting Leadership with Drew Aderholt, Agency Owner

September 30, 2024 • 63 mins
Today, Mike sits down with Drew Aderholt, agency owner in Alpharetta, Georgia. Drew takes us through his journey from growing up in the insurance industry to carving out his own path within the company. He shares his experience as the son of a successful agency owner, the challenges of transitioning from the worksite to the individual market, and the unexpected hurdles he faced in his first years as an agency owner. Drew's story is...
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