Keep Hustling

On this episode of Keep Hustling, host Aaron Gordon welcomes Rob McCarthy to dive deep into breaking free from "the script", societal expectations around success, money, and happiness. Rob McCarthy shares his journey from chasing external benchmarks to redefining achievement in line with personal values, highlighting the pitfalls of debt, comparison, and social media. The conversation explores how...

In this episode of Keep Hustling, host Aaron Gordon welcomes guest Coleman Flentge, who shares his inspirational journey from a small town in Kentucky to building a career and business centered around music. Coleman Flentge discusses the impact of his mother's unwavering hustle and how her sacrifices shaped his own determination and drive. He recalls overcoming early discouragement and finding his...

On this episode of Keep Hustling, host Aaron Gordon welcomes entrepreneur and author Katie Smetherman Holmes for a deep dive into purpose-driven entrepreneurship. Katie shares how her early search for meaningful work led her to a rewarding career in graphic design, despite doubts from others, and how passion and identity fuel lasting professional success. The conversation explores the connection b...

In this episode, Aaron Gordon welcomes Monica McKitterick, nurse practitioner and entrepreneur, to share her journey of pivoting from traditional medicine to pioneering membership-based primary care. Starting with dreams of becoming a pediatric oncologist, Monica McKitterick describes how her upbringing instilled resilience and a drive to excel, traits that guided her through major career transiti...

In this episode, Aaron Gordon welcomes entrepreneur  Jermane Cheathem for a candid discussion about overcoming adversity, building resilience, and simplifying success. Jermane shares his remarkable journey, moving 18 times by age seven, being abandoned twice, and how those challenges shaped his mindset and business approach. Together, they explore why complexity in business and life is often self-...

On this episode of Keep Hustling, host Aaron Gordon sits down with Jevon Gondwe, a three-time NCAA soccer champion and leadership development expert. Jevon discusses how a love for competition and the power of mentorship propelled him to athletic and professional success. He shares lessons on the importance of team culture, personal growth, and how leaders can inspire buy-in and engagement. Jevon...

In this episode of Keep Hustling, host Aaron Gordon sits down with Chelsea Fournier, a former business lawyer turned coach for solo-led founders. Chelsea shares her journey from law to entrepreneurship, emphasizing the importance of redefining your hustle, recognizing personal health needs, and listening to intuition. She breaks down concepts like "nervous system safe strategy" and how to invite i...

In this episode of Keep Hustling, host Aaron Gordon sits down with Jay Sapovits, a driven entrepreneur whose story is all about reinvention, resilience, and the real work behind success. Jay shares how witnessing his father's unhappiness at work inspired him to never settle for a job he hated, fueling his journey through various industries. He reveals the true foundation of entrepreneurship—courag...

In this episode of Keep Hustling, host Aaron Gordon sits down with Zach Griff (aka The Points Guy) to dive into his journey from a South Florida kid obsessed with credit card points to becoming a top travel and loyalty expert. Zach shares how he turned his passion for maximizing miles and loyalty programs into a thriving career, the realities of life on the road (and in the skies), and the hustle...

In this milestone 100th episode of the Keep Hustling Podcast, host Aaron Gordon celebrates the journey of the show and expresses deep gratitude to listeners, guests, and the behind-the-scenes team who make it all possible. The episode features highlights from memorable interviews with a diverse group of hustlers—entrepreneurs, athletes, creatives, and industry leaders—each sharing the unique roots...

On this episode of Keep Hustling, host Aaron Gordon sits down with  Matt Krayton to unpack his unconventional journey from aspiring teacher to seasoned political consultant and leadership coach. Matt discusses how early setbacks in education led him into politics, the importance of authentic leadership, and why Curiosity triumphs over judgment.  Together, they reflect on the complexities of histor...

In this episode of Keep Hustling, host Aaron Gordon sits down with Luke Van Der Veer to explore the journey from a traditional 9-to-5 job to forging a successful path as an entrepreneur. Luke candidly shares how early side hustles and a restless dissatisfaction with corporate life pushed him to search for alternative ways to achieve both time and financial freedom. He details his progression throu...

In this episode of Keep Hustling, host Aaron Gordon welcomes Ariel Meirov, a prominent NFL newsbreaker, to discuss the behind-the-scenes journey of building a successful sports media brand while staying true to his Orthodox Jewish faith. Ariel shares the unique challenges of balancing religious observance—such as navigating the NFL draft schedule around the Sabbath—while remaining fully dedicated...

On this episode of Keep Hustling, host Aaron Gordon sits down with Brad Henderson to dive into the challenges and realities of leadership. Brad shares his personal journey of navigating isolation in leadership roles, learning from mistakes, and the importance of having the right mentors. They explore how true leadership isn't about having all the answers, but about empowering others, building stro...

In the latest episode of *Keep Hustling*, Aaron Gordon chats with Ruben Gomez, a Venezuelan entrepreneur living in Omaha, Nebraska. Ruben opens up about his struggles with anxiety and depression after relocating to the US and adjusting to the harsh Midwest winters. He discusses how the changing seasons shape our routines, overall performance, and mental well-being. Ruben emphasizes the importance...

In this episode of Keep Hustling, host Aaron Gordon sits down with Joel Miller, a financial planner passionate about empowering clients to achieve financial freedom and generational wealth. Joel shares his journey from Chicago to the Twin Cities and dives deep into the myths and mistakes younger clients make—especially the misconception that financial planning is only for the ultra-wealthy or thos...

In this episode of Keep Hustling, host Aaron Gordon sits down with the "Bash Brothers of Hillcrest," Avi Adelman and Dovid Gottlieb, the dynamic duo behind the Hillcrest Salt Bow League (HSL). The trio dive into the power of youth and adult sports, the life lessons learned on the field, and how building leagues can foster community, confidence, and lifelong memories. They share stories about manag...

In this episode of Keep Hustling, Aaron Gordon welcomes entrepreneur and podcast host Jordan Edwards to dive into what it truly means to hustle. Jordan shares his unique approach, built around five life pillars: mental health, physical health, community service, philanthropy, spirituality, and relationships, which he uses to shape his goals and measure success beyond just money or career wins. The...

In this inspiring episode of Keep Hustling, host Aaron Gordon sits down with Dave Levinger, a rising videographer whose story is a testament to embracing creativity and relentless self-belief. Dave shares how, as recently as 2022, he began his journey with little experience, filming his brother's magic tricks for $20 before teaching himself the ins and outs of the craft using only a basic camera a...

In this episode of Keep Hustling, host Aaron Gordon sits down with Ryan Englin, founder of Core Matters , to dig into the challenges and opportunities of hiring and retaining talent in blue-collar industries. Ryan shares his personal journey from a blue-collar upbringing to entrepreneurship and discusses the image problem faced by the trades, emphasizing the essential and undervalued role of skill...

In this episode of Keep Hustling, host Aaron Gordon talks with Tom Kubiniec, a self-taught business leader who never attended college or worked for another company. Tom shares his unconventional journey from aspiring musician to becoming the global leader in military weapon storage solutions. He discusses the importance of perseverance, learning from setbacks, and fostering "creative conflict" to...

In this powerful episode of Keep Hustling, Aaron Gordon sits down with Dr. Rob Kelly to uncover his extraordinary journey from homelessness and addiction in Manchester, England, to becoming a leading expert in addiction recovery and mindset coaching in the US. Dr. Kelly shares the pivotal moment of his spiritual awakening, the impact of childhood trauma on addictive personalities, and how he trans...

In this episode, Aaron Gordon sits down with Tina Larson, a Swedish-born expert in New York City's condo and co-op market. Tina shares her journey from a farm in Sweden to thriving in NYC real estate, discussing how she pivoted from a career on Wall Street to founding a business that helps building boards operate smarter and save money. She dives into the challenges of building management, the imp...

On this episode of Keep Hustling, host Aaron Gordon sits down with veteran and entrepreneur Karl Jacobi to explore the transformative power of discipline, resilience, and brotherhood. Karl shares his journey from troubled youth to military service, revealing how seeking structure and an escape led to lifelong lessons in grit, teamwork, and leadership. He discusses overcoming betrayal and setbacks...

In this inspiring episode of Keep Hustling, host Aaron Gordon sits down with Kelly Meyer, whose journey from a near-high school dropout to a professor, author, and coach is anything but ordinary. Kelly shares powerful stories from his rebellious teenage years, the pivotal moments and people that challenged his trajectory, and how defying expectations ultimately led him to pursue higher education a...