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Making the leap from employment to entrepreneurship can be a scary time. The biggest fear people have is the unknown. Here on the “You Can’t Afford Me Podast” we speak with hustlers and innovators on how to make the most of your journey. If you have questions we have answers.
80 Episodes
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The conversation starts with a simple premise: when access is designed into sports, athletes don’t just participate—they excel. We sit down with Sportable’s Director of Strategic Partnerships to unpack how a small Richmond nonprofit grew from four staff to sixteen, expanded to 18+ adaptive sports, and hosted back‑to‑back National Wheelchair Basketball Association championships, all while keeping independence at the center of every program. The result is a ground‑level view of what it takes to...
What if your meeting room could lower cortisol, sharpen attention, and make hard conversations easier? We sit down with Christian Markow of Lost Office to explore the overlooked science of workspace design—how plants, light, materials, scent, and music quietly rewire how teams think, feel, and collaborate. Christian traces his path from English major to global brand strategist, sharing hard-won lessons from experience design with organizations like Chick-fil-A and major consumer brands. We b...
A $20 palm, a New Jersey sunroom, and a bold move to Virginia—Connie Hom traces how a simple love for plants became Buckingham Greenery, a 40-year interior landscaping brand known for retention, reliability, and real wellness at work. We dig into the early days when a tiny Yellow Pages ad landed hospital and retail clients, then follow the playbook that scaled service across cities: local technicians, centralized operations, and a brand promise that facility managers love—hassle-free, consist...
What if fear—not money—is the real reason most dream renovations never happen? That’s the spark for this conversation with kitchen and bath designer Lea Yeager, who turned a health reset and a pandemic into the launchpad for a thriving, CAD-powered design studio. We get into the exact moves that made it work: building a commission bridge while starting up, pitching design value inside a countertop shop, and pairing her eye for function with her husband Brent’s deep Chief Architect skills to c...
Ever wonder how successful entrepreneurs navigate life's unexpected turns? Will, founder of Creative Project Management, takes us on a captivating journey from college soccer player to rapper to thriving business owner in this raw, unfiltered conversation about finding your path. When illness cost Will his soccer scholarship, music became his refuge—but the skills he developed to promote himself as an artist unexpectedly became his true calling. "I taught myself graphic design because I was ...
Forty years of entrepreneurship creates wisdom that can't be taught in business school. Susan opens up about the remarkable journey that took her from a one-person company to leading Circle S Studio, an experience agency specializing in brand strategy and employee experience design. What begins as a candid conversation about entrepreneurial roots quickly evolves into a masterclass on sustainable business building. Susan reveals how she made the leap from corporate America after her daughter'...
Ever wondered how faith and business can intersect to create something extraordinary? Tony Ponsiglione's story illuminates this powerful connection through his remarkable journey from corporate executive to purpose-driven entrepreneur. Tony's path defies conventional career trajectories. With a geography degree in hand, he unexpectedly landed in human resources at Safeway Stores, launching a corporate adventure that would span Fortune 500 companies, international assignments, and executive l...
The journey to wellness is rarely linear, and no one understands this better than Dr. Leah Johnson. After spending her early twenties in Costa Rica where a surprise yoga teacher training transformed her life, she embarked on a quest to understand why yoga made such a profound difference in her physical and mental wellbeing. Dr. Johnson's path led her to pursue a doctorate in physical therapy, creating a unique healing approach that bridges scientific understanding with ancient practice. "Phy...
Leadership isn't just a position—it's action that transforms organizations and lives. Dr. Keith Hubbard, drawing from 30 years in public education, reveals why so many school leaders struggle despite their best intentions and offers a practical roadmap for meaningful change. As a former teacher, principal, and now Chief Academic Officer of his educational consulting firm, Dr. Hubbard has witnessed firsthand the leadership gap that exists in America's schools. "We are a nation at risk right n...
What happens when you blend childhood friendship, entrepreneurial vision, and a keen eye for market opportunity? Chris Smith's journey with HD Bros Media provides a masterclass in sustainable business growth built on relationship foundations. From convincing his parents to split the cost of camera equipment as a teenager to running a thriving media company covering the East Coast, Chris shares the unfiltered story behind his 13-year entrepreneurial journey. His path began with skateboard vid...
Success without service is hollow—something Joe Dunn embodies as one of Virginia's top mortgage brokers. His remarkable story unfolds as he shares how losing everything in the 2008 financial crisis forced him to reimagine his approach to business and life. "The only way I can ever get out of this financially is to get back into the mortgage business," Dunn recalls thinking after a catastrophic loan to professional athletes went bad, coinciding with the housing market crash. What makes his jo...
Ever wished for a fairy godmother to tackle your endless to-do list? That's exactly what Kristin Richardson created with Sherah, her revolutionary personal assistant platform connecting moms to other moms for both virtual and in-person support. In this captivating conversation, Kristen shares her journey from C-suite corporate executive to passionate entrepreneur, detailing the moment during COVID that pushed her to leave a 26-year career and build something new. When schools closed and her ...
Ever wonder how a 12-year-old with a push mower transformed into a successful business owner? Justin Rubel's entrepreneurial story begins with a spring break disappointment and $1,500 earned in a single afternoon - money that would be worth $3-4K today. His determination to break his family's financial cycle started early and never wavered. Now running Homeview Builders, a thriving exterior remodeling company, Justin shares the principles that guided his journey from lawn care to home improv...
What happens when a society neglects to teach men how to be fathers? The Fatherhood Foundation of Virginia steps into this void with practical solutions that transform broken men into present, engaged dads. Executive Director Chris Beach joins us to reveal startling statistics that demand attention: 64% of Richmond children go home to fatherless houses, while one-third of Virginia children grow up without a father's presence. But rather than dwelling on problems, Beach shares how his organiz...
Bill's journey through the electrical trade reveals a road less traveled but infinitely more practical than the traditional college path many believe is mandatory for success. Starting as a $8.25/hour apprentice at age 20, he combined daytime work with evening classes costing just a few hundred dollars annually. Within five years, he earned his master electrician license and launched his own successful business – all without accumulating crushing student debt. What makes Bill's story particu...
Discovering the transformative power of authentic connection in young men's lives takes center stage as Warren, Executive Director of Boyz To Men nonprofit, reveals how their organization is creating safe spaces where boys can truly be themselves. Warren shares the remarkable journey of an organization that started 26 years ago with a simple mission: to provide young men with environments where they could discuss their emotions and challenges without judgment. Now serving over 650 youth acro...
Letting someone go from your company ranks among the toughest responsibilities of leadership - and contrary to what many believe, it doesn't get easier with experience. After a decade as an entrepreneur, I've learned the hard truth: no matter how fair, flexible, or generous you are as a leader, you'll still be viewed as the villain when terminating someone's employment. This raw, honest exploration of firing employees tackles the emotional and practical realities business owners face. If you...
From virtual assistance to corporate travel planning, and from a steady paycheck to real estate entrepreneurship, Justin and ShaCoria's journey exemplifies what it means to bet on yourself while building a rock-solid partnership. When Justin walked away from his management position at the Richmond Association of Realtors to pursue real estate full-time, he didn't just have a dream—he had years of preparation behind him. Their story reveals how calculated risk-taking, diversified income strea...
Medical Home Plus stands as a beacon of hope for families navigating the often complex and overwhelming world of special needs education. This episode dives deep into how this vital nonprofit empowers parents of children with special healthcare needs across Virginia. Executive Director Emily J shares her 18-year journey with the organization, revealing how MHP has expanded to serve families in over 60 counties throughout the Commonwealth. The shift to virtual meetings during COVID actually a...
Have you ever hired someone who seemed perfect on paper but turned out to be completely wrong for the role? Meet Aaliyah, the 24-year-old founder and CEO of Otterwise who's tackling this universal problem with a refreshingly practical solution. Fresh out of college and frustrated by her own career mismatch, Aaliyah built a platform that lets employers and candidates "test drive" working relationships before committing. Her company creates comprehensive, real-world assessments that reveal wha...
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