Becoming Self Made

Small businesses don't just support local economies, they create the communities we want to live in. For entrepreneur Caroline Weaver, that belief became the foundation of an unexpected journey. After building one of the world's only pencil stores, closing that chapter of her career, and walking every neighborhood in New York City to document more than 14,000 independent businesses, she came to a simple realization: thriving local businesses create thriving communities. In this episode of Becoming Self Made, Mike Michalowicz sits down with Caroline, founder of The Locavore Guide and The Locavore Variety Store, to explore why supporting small businesses is about far more than where we shop. It's about strengthening local economies, preserving neighborhood character, and creating communities where entrepreneurs (and the people around them) can succeed together. Caroline shares how a fascination with everyday objects evolved into a mission to champion independent retailers, why she believes every purchase is an investment in your community, and what entrepreneurs can learn from the thousands of small business owners she has met along the way.

When David Stark graduated from art school, he wasn't following a blueprint for entrepreneurship. He was arranging flowers in his apartment, taking on small creative projects, and searching for a way to turn his artistic vision into a career. What followed was something he never could have predicted: the creation of one of the world's leading experiential design firms, and the pioneering of ideas like the modern pop-up shop that would reshape how brands connect with people. In this episode of Becoming Self Made, Mike Michalowicz sits down with David Stark, founder and Chief Creative Officer of David Stark Design, to explore how an artist became an entrepreneur by building an entirely new category of business. David shares how he transformed creativity into a competitive advantage, why innovation often comes from saying "yes" before you know exactly how you'll get there, and what it takes to build a company around imagination. Together, they discuss entrepreneurship, creative leadership, brand storytelling, and the challenge of scaling a business whose product is ideas. David also reflects on trusting his instincts, embracing unconventional opportunities, and why some of the best businesses are created by people who don't realize they're inventing something new.

The greatest competitive advantage in business isn't always your product. Sometimes, it's the community that believes in it. When Dr. Brent Ridge and Josh Kilmer-Purcell first arrived in Sharon Springs, New York, they weren't looking to build a skincare brand like Beekman 1802. They simply fell in love with a historic farm and the quiet charm of a small community they hoped would become their weekend escape. But when the 2008 recession upended their plans, their neighbors helped them discover an entirely new future. In this episode of Becoming Self Made, Mike Michalowicz sits down with the founders of Beekman 1802 to explore how kindness, collaboration, and a shared commitment to their community became the foundation for one of the most beloved lifestyle brands in America. Brent and Josh share how Sharon Springs shaped their entrepreneurial journey, why they chose to invest in the people around them, and how that same spirit helped transform not only their company, but an entire town. Together, they discuss what it means to build a business that creates opportunity beyond its own walls, why supporting fellow entrepreneurs can strengthen an entire local economy, and how growing "neighbor by neighbor" became more than a philosophy, it became a blueprint for sustainable success.

What does it take to lead a family business into its next generation? For Jamie Deering, becoming CEO of Deering Banjo Company wasn't simply about carrying on a family legacy, it was about earning the opportunity to lead it. Growing up around the factory that her parents, Greg and Janet Deering, built from the ground up, Jamie learned every corner of the business long before stepping into the CEO role. Today, she's guiding one of America's most respected instrument manufacturers while helping shape its future. In this episode of Becoming Self Made, host Mike Michalowicz speaks with Jamie alongside her parents, Greg and Janet Deering, for a multi generational conversation about entrepreneurship, succession, craftsmanship, and what it takes to grow a family business without losing sight of its values. Together, they discuss building trust as a leader, balancing innovation with tradition, empowering employees, and why passing down a company is about far more than handing over a title; it's about preparing the next generation to take the business further than the founders ever imagined.

What do you do when there’s no blueprint for the career you want? For Tim Milgram, the answer was to create one. After leaving a promising path in software engineering, Tim pursued a career in dance and filmmaking, eventually building TMilly Studio into a globally recognized creative brand. Today, Tim is the founder of TMilly TV, a filmmaker, choreographer, and creative entrepreneur whose groundbreaking dance videos have helped redefine how movement is captured and shared online. In this episode of Becoming Self Made, Tim shares what it takes to build a sustainable business around art, why reinvention is a requirement for creative entrepreneurs, and how persistence, innovation, and passion helped turn an unconventional dream into a thriving career.

What does it take to build a small business that lasts for more than 15 years in one of the most competitive industries in the world? For Andrew Ahn, founder of Boo's Philly Cheesesteaks in Los Angeles, the answer starts with family, hard work, and a willingness to do whatever it takes. Born to Korean immigrant parents, Andrew grew up watching entrepreneurship firsthand before eventually building Boo's into one of Los Angeles' most beloved cheesesteak destinations. But staying successful has required more than great food. As customer habits, technology, and marketing continue to evolve, Andrew has embraced new ways to reach customers while staying true to what made Boo's successful in the first place. In this episode of Becoming Self Made, Andrew shares lessons on entrepreneurship, small business marketing, community building, and how to grow a small business without losing its identity. He and Mike discuss family, resilience, social media, going viral, adapting to change, and why long-term success comes from serving your local community long after the buzz fades.

For Tiffany Aliche, better known as The Budgetnista, entrepreneurship began with a simple mission: teach everyday people how to take control of their finances. But after losing her job in 2008 and facing financial hardship herself, Tiffany discovered that financial education alone wasn't enough. People needed support, accountability, and a community they could trust. In the Season 2 premiere  of Becoming Self Made, Tiffany shares how she transformed personal setbacks into a thriving business, built one of the most trusted brands in personal finance, and grew a community that has helped thousands of people improve their financial lives. She and host Mike Michalowicz discuss entrepreneurship, small business growth, building trust, creating loyal communities, and why education became her most powerful marketing strategy. Tiffany shares her perspective on abundance, mindset, making money, and why she believes that when you change your beliefs, you change the opportunities you're able to see. From side hustles and speaking engagements to building scalable programs and a recognizable brand, Tiffany's story offers practical lessons for entrepreneurs, educators, and anyone looking to grow a business by creating genuine value for others.

Becoming Self Made is a video podcast presented by Relay and hosted by entrepreneur and bestselling author, Mike Michalowicz. In Season 2, host Mike Michalowicz sits down with entrepreneurs, founders, creatives, and business leaders, including Tiffany Aliche (The Budgetnista), Tim Milgram (TMilly Studio), Jamie Deering (Deering Banjos), and Dr. Brent Ridge and Josh Kilmer-Purcell (Beekman 1802), and more to uncover the moments that changed everything. What is Becoming Self Made about? Every episode uncovers the raw, personal transformation behind the business—the raw moments, the mindset shifts, and the pivotal decisions that shaped who these founders became, not just what they built. Because success isn't just about what you build, it's who you become. Who hosts Becoming Self Made? Mike Michalowicz is one of today's most prolific small business authors. He's founded four multi-million dollar companies and written the frameworks—Profit First, Clockwork, The Pumpkin Plan—that have helped thousands of entrepreneurs get financially fit and operationally sound. What is Relay? Relay is digital banking built to give small business owners the tools and know-how to be great with money. By connecting accounts, cards, bills, invoices, capital, and more together in one place, Relay replaces financial guesswork with real visibility, helping owners turn cash flow from a constant source of stress into a clear signal they can use to run stronger, more resilient businesses.  Learn more at https://relayfi.com/ New episodes every Tuesday. Subscribe so you never miss an episode. Find every episode at: https://relayfi.com/becoming-self-made Learn more about Mike Michalowicz: https://mikemichalowicz.com/ Becoming Self Made Season 2 Q&A with Mike: https://relayfi.com/blog/becoming-sel... Follow us for more stories, tips, and resources to help grow your business: Blog: https://relayfi.com/blog LinkedIn:   / relayfinancial   Instagram:   / bankwithrelay   Facebook:   / relayfinancial   Twitter: https://x.com/relayfinancial Relay is a financial technology company, not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC. Certain conditions must be satisfied for pass-through deposit insurance coverage to apply. #BecomingSelfMade #MikeMichalowicz #ProfitFirst #SmallBusiness #Entrepreneurship #BusinessPodcast #Relay #FounderStories

Lauren Makler, co-founder and CEO of Cofertility, joins Mike Michalowicz to share how a life-altering medical diagnosis became the catalyst for building a more human, accessible fertility system with Cofertility. Lauren explains how falling in love with the problem, not just the solution, led her to reimagine egg freezing and donation in a way that removes financial barriers for individuals and couples while preserving dignity and choice.  Along the way, Lauren opens up about trusting gut instinct as accumulated wisdom, navigating leadership through deeply emotional work, and building a mission-driven company that balances empathy, optimism, and scale.

Yoseph West, CEO and Co-founder of Relay, joins host Mike Michalowicz to share his journey of transformation, moving from an entrepreneur with a chip on his shoulder to a leader focused on learning, growth, and maximum impact. The conversation explores the lessons learned while scaling Relay, emphasizing the critical insight that the ability for the business to grow is a function of how much you grow. Mike and Yoseph get into the power of constantly questioning everything, a mindset Yoseph attributes to his early upbringing that encouraged independent thinking. The episode also details what great partnerships truly require, underscoring the importance of a long-term orientation and human empathy to ensure both sides win.  Finally, Yoseph discusses the continuous personal reinvention necessary for leading a fast-scaling company, sharing how his coaching, including unconventional methods, helps him find the leverage needed for exponential growth.