The Drive By Entrepreneur Podcast

drivebypodcast
  • 5.0 (5)
  • Entrepreneurship
  • Updated Monthly

The Drive By Entrepreneur Podcast exists to bring current and compelling content to entrepreneurs and influencers of small to mid-sized organizations.

  1. 09/18/2025

    Louie Adamo, United Rent-A-Fence - The Drive By Entrepreneur Podcast S2 E22

    In this episode of Drive by Entrepreneur, host John Frank welcomes longtime friend and United Rent-A-Fence president, Louie Adamo. Louie traces his winding path from a brief stint in corporate America to hands-on experience modernizing Caputo’s markets, trading futures at the Board of Trade, and ultimately helping his father launch United Rent-A-Fence during the 2008 downturn. Starting with a single truck and panels—and “smiling and faxing” for business—they grew through relentless responsiveness, smart pricing, and operational discipline into a regional leader serving construction, major events, and disaster recovery with 10+ daily crews and hundreds of miles of fencing. Louie also shares the deeper roots of his entrepreneurial grit: his parents’ immigration journeys from rural Italy and Argentina, the sacrifices behind building a life in Chicago, and the family’s string of ventures from a bakery to homebuilding and fabrication. He outlines the principles that set United Rent-A-Fence apart—customer, customer, customer; invest in technology and systems; scale thoughtfully; and show up at 2 AM on Christmas if needed. His advice to aspiring founders: keep learning, stay humble, live below your means, reinvest in the business, cultivate thick skin, and focus on service over shortcuts. The episode closes with a fun lightning round on music, favorite holidays, and dream careers.

    1h 3m

  2. 08/27/2025

    Jerry Freund, MidAmerican Printing Systems, Inc - The Drive By Entrepreneur Podcast S2 E21

    In this episode of the Drive By Entrepreneur podcast, host John Frank sits down with Jerry Freund, an experienced entrepreneur with a wealth of stories and insights to share. Jerry walks us through his entrepreneurial journey, from the early days of his career in the printing industry to the founding of Mid-American Printing Systems. He discusses the challenges and triumphs he's faced, including navigating economic downturns like the financial crisis of 2008 and the COVID-19 pandemic. Jerry emphasizes the importance of perseverance, adaptability, and maintaining strong relationships with both customers and bankers to sustain a business through tough times. Throughout the conversation, Jerry and John delve into the lessons learned over decades of entrepreneurship. Jerry shares candid reflections on managing emotions, the importance of continuous learning and adapting business strategies, and the delicate balance between client and team priorities. His anecdotal wisdom offers inspiration and practical advice for aspiring entrepreneurs. The episode also touches on Jerry's personal growth, from overcoming introversion through Second City improv training to maintaining a disciplined lifestyle that supports his business endeavors. Listeners will appreciate Jerry's authentic storytelling and valuable insights that highlight the realities of entrepreneurship. Whether you're starting your entrepreneurial journey or looking to refine your approach, this episode offers a compelling reminder that success often stems from dedication, adaptability, and a commitment to learning and growing through each experience.

    54 min

  3. 07/28/2025

    Ryan Sullivan, North Park Group - The Drive By Entrepreneur Podcast S2 E20

    In this episode of the "Drive By Entrepreneur" podcast, host John Frank explores the world of entrepreneurship with guest Ryan Sullivan, the Managing Director of North Park Group. Ryan shares his unexpected journey from a corporate employee to a seasoned entrepreneur, emphasizing the challenges and triumphs of managing and acquiring small U.S.-based manufacturing companies. With a focus on risk reduction and long-term ownership, Ryan outlines North Park Group's unique investment approach, contrasting it with traditional private equity strategies. His insights reveal the intricacies of managing multiple businesses and the importance of reinvesting in operations to ensure growth and sustainability. Throughout the conversation, Ryan candidly discusses the emotional and practical aspects of buying and selling businesses, highlighting the significance of understanding both the market and the people involved. He shares personal anecdotes about the sacrifices and unexpected turns in his entrepreneurial journey, providing listeners with valuable lessons on resilience and adaptability. Furthermore, Ryan's passion for community impact and giving back is evident in his involvement with the Chicago Children's Advocacy Center, where he addresses the sensitive topic of child abuse and underscores the importance of awareness and prevention. This episode is a treasure trove of insights for aspiring entrepreneurs and seasoned business owners alike, offering a blend of practical advice and heartfelt storytelling. Whether you're interested in the nuances of managing a diversified portfolio or seeking inspiration to take the leap into entrepreneurship, Ryan Sullivan's journey is both enlightening and motivating.

    1h 17m

  4. 06/25/2025

    Aaron Moore, PPD Painting - The Drive By Entrepreneur Podcast S2 E19

    In this engaging episode of "Drive By Entrepreneur," host John Frank sits down with Aaron Moore, a dynamic entrepreneur with a fascinating journey in the painting industry. Aaron shares his story of evolving from a small-time residential painter to the founder and president of Precision Painting and Decorating (PPD), and a co-founder of the Commercial Painting Industry Association. With a degree in finance and an entrepreneurial spirit, Aaron's career took an unexpected turn into the painting world, where he swiftly moved from painting residential homes to managing large commercial projects. His journey is a testament to the power of grit, adaptability, and the willingness to seize opportunities as they arise. Throughout the conversation, Aaron emphasizes the importance of continuous innovation and authenticity in entrepreneurship. He discusses how his company has embraced technology and innovative practices, such as using drones for painting and power washing, to stay ahead in a competitive market. Aaron also shares his experiences in expanding his business through strategic acquisitions and partnerships, highlighting the importance of building strong relationships and leveraging collective expertise. His insights into navigating the challenges of labor shortages and seasonal work in the painting industry offer valuable lessons for entrepreneurs facing similar hurdles. Listeners will find inspiration in Aaron's story of perseverance and his commitment to giving back through initiatives like the Commercial Painting Industry Association. His journey underscores the importance of staying true to one's vision, constantly seeking improvement, and being open to learning from both successes and failures. This episode is a must-listen for entrepreneurs looking to gain insights from a seasoned professional who has successfully navigated the ups and downs of building a thriving business from the ground up.

    58 min

  5. 06/03/2025

    Desiree Vargas Wrigley, Velocity Catalyst - The Drive By Entrepreneur Podcast S2 E18

    In this episode of the Drive By Entrepreneur podcast, host John Frank welcomes Desiree Vargas Wrigley, a dynamic leader and founding GP of the Velocity Catalyst Fund. They discuss the unique challenges and opportunities of entrepreneurship, particularly in the context of small to mid-size organizations. Desiree shares her journey, starting with her role as Chief Innovation Officer at P33 Chicago, her experience founding companies like Parachute and GiveForward, and her transition into a pivotal role in the venture capital ecosystem. She emphasizes the importance of resilience and adaptability in entrepreneurship, recounting her own experiences with GiveForward, the world's first crowdfunding platform, and Parachute, both of which encountered significant hurdles but also considerable successes. Desiree also elaborates on her vision for Chicago as a burgeoning hub for innovation, particularly in venture capital. She discusses her work with Techrise and the Velocity Catalyst Fund, aimed at bolstering investment in early-stage ventures within the city. By leveraging Chicago's diverse economy and rich talent pool, she hopes to establish the city as a leader in various innovative industries, from healthcare to quantum computing. Desiree underscores the need for local capital investment to retain talent and foster a thriving entrepreneurial ecosystem, countering the traditional outflow of resources to coastal regions. The conversation concludes with Desiree's insights into personal resilience and balance in the high-pressure world of entrepreneurship. She shares her strategies for managing stress and maintaining focus, emphasizing the importance of presence and adaptability. The episode wraps up with a light-hearted discussion about music, favorite holidays, and potential alternative career paths, revealing more about Desiree's personality and interests.

    1h 19m

  6. 03/07/2025

    Robert Duncan, Duncan Law Group - The Drive By Entrepreneur Podcast S2 E17

    In this engaging episode of the Drive By Entrepreneur podcast, we dive deep into the life and career of Robert Duncan, founder of the Duncan Law Group. Host John Frank leads an insightful conversation that not only explores Robert's professional journey but also sheds light on the personal values and experiences that shape his approach to law and community service. The episode begins with a warm introduction, setting the stage for a candid discussion about entrepreneurship, perseverance, and the importance of integrity in one's career. Robert shares his unique path to becoming a successful attorney, including the influences of his father, a judge and military veteran, and his unexpected journey from studying political science to starting his own law firm. Join us for an exploration of Robert's commitment to making a difference, both in the lives of his clients and within his community. He discusses the values instilled in him by his family, the joy and challenge of running a law firm, and the critical importance of doing things the right way. The conversation also delves into the future of the legal profession, touching on the impact of artificial intelligence and the evolving landscape of legal practice. With anecdotes of personal growth, professional insights, and the occasional foray into his love for cooking, this episode offers a rich tapestry of lessons for aspiring entrepreneurs and seasoned professionals alike. Join John Frank and Robert Duncan as they explore the intersections of law, leadership, and life.

    1h 3m

  7. 02/20/2025

    Lily Barcelona, Via Barcelona Learning - The Drive By Entrepreneur Podcast S2 E16

    Welcome to another exciting episode of the Drive By Entrepreneur podcast, hosted by John Frank, owner of Third Road Management. In this episode, we dive deep into the entrepreneurial journey of Lily Barcelona, founder of Viva Barcelona Learning. Join us as we explore how Lily transitioned from academia to entrepreneurship, driven by her passion for the Spanish language and culture. Lily shares her inspiring story, starting from her days at the University of Illinois to becoming a successful business owner focused on helping individuals and professionals revive their Spanish skills. Discover how she leveraged her background in education to create a thriving online learning community and expanded her reach to the corporate world, providing essential Spanish language training for healthcare professionals. In this engaging conversation, Lily discusses the challenges and triumphs of being an entrepreneur, the importance of passion and perseverance, and her vision for scaling her business to new heights. Whether you're an aspiring entrepreneur, a language enthusiast, or someone interested in personal growth, this episode offers valuable insights and inspiration. Tune in to learn about: - The art and science of entrepreneurship - The evolution of Viva Barcelona Learning - The significance of community and mentorship in business - Strategies for scaling and diversifying a niche business Don't miss out on Lily's unique perspective on entrepreneurship and her commitment to empowering others through language. Subscribe to the Drive By Entrepreneur podcast for more compelling content and entrepreneurial insights. Connect with Lily Barcelona: - Website: VivaBarcelonaLearning.com - LinkedIn: Lily Barcelona - Instagram: @senyora.barcelona Sponsors: - Third Road Management - Two Hound Red Brewery - NWC Media Join us in this episode and be inspired to embark on or enhance your entrepreneurial journey!

    59 min

  8. 02/07/2025

    Nate Ernst, Envoi Partners - The Drive By Entrepreneur Podcast S2 E15

    Welcome to another inspiring episode of the Drive-By Entrepreneur podcast, where we bring you captivating stories and insights from entrepreneurs and influencers driving change in small to mid-size organizations. In this episode, host John Frank, owner of Third Road Management, sits down with Nate Ernst, the dynamic founder of Envoi Partners, a real estate development firm known for transforming underutilized properties into neighborhood gems. Join John and Nate as they explore the entrepreneurial journey of Nate, tracing his beginnings in Southern Illinois to the establishment of Envoi Partners. Delve into how Nate's fervor for real estate and unwavering quest for opportunities have influenced his strategy in value investing across Chicago's dynamic neighborhoods. This episode is enriched with compelling anecdotes, pivotal life experiences, and candid reflections on the challenges and successes inherent in entrepreneurship. It promises to be a source of wisdom and inspiration for those aspiring to make their mark in the business arena. Tune in to learn about the importance of relationships, the power of persistence, and the art of spotting hidden potential in real estate. Whether you're an aspiring entrepreneur or a seasoned business owner, this conversation will motivate you to chase your dreams and embrace the entrepreneurship journey. Don't miss it!

    1h 17m
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The Drive By Entrepreneur Podcast exists to bring current and compelling content to entrepreneurs and influencers of small to mid-sized organizations.

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