Keep Hustling

In this episode of Keep Hustling, host Aaron Gordon welcomes real estate entrepreneur Ernest Smith for an insightful dive into the realities of building success through grit, relentless learning, and integrity. Ernest Smith shares how he began house hacking at just 22, funded by his parents, and mastered the fundamentals of real estate by moving 12 times in six years. He reflects on leaving the tr...

In this episode Keep Hustling, host Aaron Gordon welcomes Toronto-based entrepreneur Jennifer Yeh, aka The Fempreneur Babe, to discuss her journey from a corporate career to helping women embrace relentless, unapologetic passion in business. Jennifer Yeh shares her insights on overcoming self-imposed limitations, the power of manifestation at "hyper-speed," and why adaptability, gratitude, and tak...

On this episode of Keep Hustling, host Aaron Gordon sits down with experienced real estate advisor Will Helfricht to unpack the human side of real estate. Will Helfricht shares insights from his 15+ years in the industry, discussing how people skills, psychology, and a clear-eyed approach help clients navigate emotional home buying and selling decisions. He offers actionable advice for first-time...

In this episode of Keep Hustling, Aaron Gordon sits down with Aubie Knight, CEO of Big I North Carolina, for an in-depth conversation about the power of relationships, innovation, and leadership in the insurance industry. Aubie Knight shares insights on the importance of showing up, building real connections, and how investing in people drives both culture and performance. The discussion dives int...

On this episode of Keep Hustling, host Aaron Gordon is joined by marketing veteran Ira Gleser, whose career includes leadership roles at Coca-Cola, Microsoft, and AT&T. Ira Gleser shares insights on the dual nature of marketing, combining creativity and analytics, and the importance of hands-on experience for building successful brands. The conversation delves into the power of customer relationsh...

In this episode of Keep Hustling, host Aaron Gordon sits down with Matt Sapaula, renowned financial coach, entrepreneur and Marine Corps veteran, to dive deep into the roots of hustle, resilience, and discipline. Matt shares stories from his upbringing, the impact of his parents' work ethic, his time in the Marine Corps, and overcoming adversity at rock bottom. He discusses the importance of prepa...

In this episode of Keep Hustling, host Aaron Gordon sits down with guest Michael Scarpati, an independent fiduciary financial planner and founder of Retire Us. Michael Scarpati shares his personal journey growing up with two contrasting financial influences, a frugal, banking-minded mother and an entrepreneurial, free-spirited father. This perspective led him to a mission of making advanced, indep...

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...