In this episode, Aaron Gordon welcomes Jay Conner, a private money expert, who shares how the 2009 banking crisis forced him to seek alternative funding for his real estate deals. Jay explains his pivot from traditional bank loans to private money and how educating ordinary people about lending enabled him to raise over $2 million in just 90 days. The conversation covers common misconceptions about bank dependence, the critical role of trust and deal management, and why private money isn’t the r...

In this lively episode of Keep Hustling, host Aaron Gordon chats with Amy Hager, founder of the Joyful Business Revolution. Amy Hager shares her unique journey from childhood go-kart racer in Iowa to radio DJ and now entrepreneur, highlighting the hustler’s spirit that shaped her career. The conversation dives deep into redefining “hustle”, focusing on finding joy, building community, and personal alignment in life and business. Both Aaron Gordon and Amy Hager offer practical tips for overcoming...

In this episode of Keep Hustling, host Aaron Gordon sits down with Eric Hawkins, who left behind a 3,000-square-foot home for a tiny living lifestyle and never looked back. They unpack the pivotal moments behind Eric’s decision, the transformative impact it had on his finances, relationships, and sense of freedom, and how simplicity can actually fuel a stronger hustle. Eric shares insights from his journey, including the importance of focusing on a single motivating image and staying flexible wh...

In this episode of Keep Hustling, host Aaron Gordon sits down with , a multi-patented inventor, entrepreneur, and creativity coach. Dr. Walton shares how his upbringing fueled his creative drive, leading to innovations used by icons like Elton John...

In this episode of Keep Hustling, Aaron Gordon welcomes a narrative coach and author, to explore how personal stories shape our lives and career paths. Carrie West shares her journey from humble beginnings to discovering the power of rewriting her...

In this episode of Keep Hustling, Aaron Gordon sits down with Kyle Bailey, an Austin-based entrepreneur whose journey spans from lumberjack and tradesman to digital marketing agency owner. Kyle Bailey shares how his hands-on beginnings in the trades prepared him for a pivotal career shift into online marketing after the 2009 housing crash. The conversation dives deep into the impact of AI on the trades and digital marketing, the importance of adaptability, and why embracing change is vital for l...

In this episode of Keep Hustling, Aaron Gordon sits down with Kyle Bailey, an Austin-based entrepreneur whose journey spans from lumberjack and tradesman to digital marketing agency owner. Kyle Bailey shares how his hands-on beginnings in the trades prepared him for a pivotal career shift into online marketing after the 2009 housing crash. The conversation dives deep into the impact of AI on the trades and digital marketing, the importance of adaptability, and why embracing change is vital for l...

In this episode of Keep Hustling, host Aaron Gordon sits down with podcast coach Erik Johnson to explore the art of pursuing your passion and sharing your story through podcasting. Erik Johnson discusses his journey from hustling as a young magician to building a business helping others leverage podcasts for personal and professional growth. The conversation dives into mastering trust, building authentic relationships, and why embracing curiosity and courage are key traits of successful podcaste...

On this episode of Keep Hustling, Aaron Gordon welcomes Joseph Binelli, a Brooklyn-based entrepreneur with roots in Georgian culture and the custom kitchen cabinet industry. Joseph Binelli shares how his passion for food and family shaped his unique path from an aspiring chef to an expert in kitchen design, emphasizing the importance of kitchens as communal spaces that bring people together. The conversation explores how growing up surrounded by the values of first-generation immigrants instille...

In this episode of Keep Hustling, host Aaron Gordon sits down with photographer Tyler Caisse for an inspiring look at what it means to build a career behind the lens. Tyler shares how his journey started in high school, finding passion and purpose in photography as an escape and later a vocation, especially during the challenges of Covid and personal struggles. He opens up about the unique mindset required to thrive in a role that’s often invisible, the pride and humility he feels when his work ...

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 traditional nine-to-five to pursue his passion for property investment and entrepreneurship. Throughou...

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 taking action are key for entrepreneurs. She emphasizes that success comes from following curiosity and...

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 buyers and sellers, expands on the importance of preparing and staging a home, and stresses that the...

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 into finding balance between professional commitments and family, the value of learning from failure, a...

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 relationships, why real value is created beyond mere transactions, and how hustling is really about striving f...

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 preparation, mindset, and focusing on activities that truly move the needle. The conversation also touche...

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, independent financial advice accessible to everyone. The conversation dives into defining financial freed...

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 small, consistent wins and authentic self-reflection are the true building blocks for personal grow...

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 passion for music, eventually moving to Florida to pursue his dreams and earning a master's degree ...

On this episode of Keep Hustling, host Aaron Gordon welcomes entrepreneur and author 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...

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 transitions. Realizing the burnout of conventional healthcare, she launched her own direct primary care prac...

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-imposed, and how focusing on leverage, efficiency, and eliminating busywork leads to more freedom and...

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 also unpacks his "Culture of Champions" framework, explaining why developing personal growth habits ...

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 intuition into the business world without sacrificing structure. Chelsea also offers practical advice...