Living Your Legacy

Lindsay Mingee enters commercial real estate as a single mother with no guaranteed paycheck, powerful network, or safety net. Fifteen years later, she has facilitated more than $844 million in transactions, but the path there demands far more than learning how to close deals. In this episode of Living Your Legacy, she explores how courage, discipline, and reinvention shape a career built around both wealth and family. She unpacks why family-business owners may already be sitting on their greatest real estate asset, how commercial properties can become tools for generational wealth, and why the best advisors look beyond the transaction. She also reveals how endurance sports sharpen her entrepreneurial mindset and why building a meaningful legacy starts with giving yourself permission to design life around what matters most.
Key Takeaways
• Success does not require a perfect starting point. Courage, discipline, adaptability, and persistence can turn uncertainty into opportunity.
• Family-business owners may already be in the real estate business without realizing how valuable their property has become.
• Commercial real estate can create both wealth and flexibility, allowing entrepreneurs to design their lives around family and personal priorities.
• Great advisors look beyond the surface-level problem and help clients make decisions that protect their capital, family, and legacy.
• Endurance training reinforces an entrepreneurial mindset by repeatedly proving that difficult things can be endured and completed.
Notable Quotes
• “There’s opportunity at every point in the real estate cycle depending on who you are and what you need.”
• “You can’t have a commercial real estate conversation without having a people conversation.”
• “You’re constantly proving to yourself every day that you can do something hard.”
• “Commercial real estate is a great way to make a lot of money and have that type of flexibility.”
• “It’s been such a gift to me as a single mom all these years.”

After 15 years in the military and a string of corporate jobs that never fit, Curtis Kinsey finds himself moving toward a future he never planned. The veteran entrepreneur starts with a mower and a willingness to work, then discovers what happens when rejection becomes fuel for building something of his own. In this episode of Living Your Legacy, Curtis explores the transition from military service to entrepreneurship, the growing pains behind scaling a landscaping business, and why grit alone can only take a founder so far. He reveals how leadership, systems, company culture, AI in business, and calculated expansion shape GI-Mow as the stakes rise. His unconventional path challenges the traditional mold of entrepreneurship and asks a bigger question: what if the failures that seem to hold someone back are actually the raw material for building something meaningful? Pasted text Inside Success Onboarding Form …
Key Takeaways
• Rejection and career setbacks can become fuel for entrepreneurship.
• Military discipline can translate into leadership and accountability in business.
• Scaling from one mower requires hiring, equipment, systems, and learning to navigate growing pains.
• Founders eventually have to move beyond doing everything themselves and build a team they can trust.
• AI and emerging technology can help traditional blue-collar businesses improve operations, design, and growth. Pasted text Pasted text
Notable Quotes
• “I don’t like being told what to do, and I damn sure don’t like being micromanaged.” Pasted text
• “You never think that I could actually own a business. I was never taught that way.” Pasted text
• “You just lower your head and you keep going.” Pasted text
• “Growing pains is a thing. It’s hard to keep up.” Pasted text
• “If you haven’t implemented AI into your business at this stage of this AI bubble, you’re going to get left behind.”

Michele A. Leahy knows firsthand how complicated life with a disability can be. Born with spina bifida, navigating benefits herself, and later losing her leg, she turns lived experience into a mission to help others build greater independence. After returning to disability benefits and spending a year and a half out of work, a simple question pushes her toward entrepreneurship. What begins as an experiment becomes Leahy Life Plan, serving families across 16 states. In this episode, Michele challenges the idea that government benefits are a handout, exposes why leaving someone money does not automatically create a meaningful life, and explains how disability life planning, SSI/SSDI, employment support, and community services can help families create more secure futures.
Key Takeaways
• Why disability benefits can be a “hand up” toward independence rather than a barrier to working
• How Michele turns her own experience navigating disability and government benefits into a business
• Why money alone cannot guarantee a fulfilling, independent life for an adult with disabilities
• How SSI/SSDI, job coaching, healthcare, and community services can work together to support independence
• Why families need to plan beyond finances when preparing for an adult child’s long-term future
Notable Quotes
• “They think it’s a hand out and it’s really a hand up.”
• “It’s providing a house, but it’s not providing a life.”
• “Why don’t you start your own business?”
• “Well, there’s something here.”
• “I’m just excited to just serve more people.”

Relationship coach and author Vesta Gauntlett believes couples can spend years avoiding the one conversation that could redefine their future. After working with couples who struggled with communication, intimacy, and connection, she searched for a practical tool to help them decide what they truly wanted. When she could not find one, she created Are You In or Out?, an interactive book designed to confront the questions partners often avoid. Vesta explores why relationships slip into roommate mode, how unspoken expectations create resentment, and why couples must continually recalibrate their shared vision. She also reveals how intentional choices, honest communication, and a willingness to face uncomfortable truths can help partners discover what they want their next chapter to become.
Key Takeaways
• Couples can remain stuck for years because they lack the tools and shared vocabulary to discuss what they truly want.
• Long-term relationships require partners to regularly revisit their goals instead of assuming the future they once planned still fits.
• Communication, intimacy, and connection mean different things to different people and need to be defined within the relationship.
• Small unresolved frustrations can compound into resentment when couples attach stories and assumptions to each other’s behavior.
• Honest conversations can give couples clarity about whether they want to rebuild their future together or respectfully choose separate paths.
Notable Quotes
• “You have to choose love every day. You have to choose joy every day.”
• “The tiny places are where we die.”
• “You decide what is important to you.”
• “Reading this book will change your relationship.”
• “You have to be much more intentional in your relationship.”

Dan Mastropolo drops out of high school, learns business through sales, and eventually turns an unexpected firing into the start of his entrepreneurial journey. But building companies is only part of the story. After surviving repeated brushes with bankruptcy, the staffing entrepreneur discovers how work, technology, and trust can become tools for something bigger than revenue. In this episode of Living Your Legacy, Dan reveals why he believes work ethic can outproduce talent, how a different staffing model survived when others doubted it, and why staying connected to people at ground level shapes every venture he builds. From workforce development to the Eliza Park Homeless Initiative, his path raises a bigger question: what happens when an entrepreneur uses the platform he built to give unheard people a voice and create lasting change? Pasted text Pasted text
Key Takeaways
• Why relentless work ethic can become an advantage when talent and formal education are not enough
• How an unexpected firing can become the catalyst for entrepreneurship
• Why trust architecture and consistency matter when creating meaningful social impact
• How technology can become a growth engine in the staffing industry without removing human oversight
• How entrepreneurs can use their business platforms to create opportunity, dignity, and a voice for underserved communities Pasted text Pasted text
Notable Quotes
• “The grind and that work ethic can outproduce talent or knowledge any day of the week.” Pasted text
• “I’ve never been the smartest person in the room.” Pasted text
• “Your network equals your net worth.” Pasted text
• “It really honestly just starts with saying yes and making a commitment.” Pasted text
• “It is a different story for every face that’s behind those things.”