Legacy Leaders

Latest Episodes:

Tina Fishman: Decoding the Alphabet Soup of Medicare Jun 12, 2025

Show notes

In this episode of Legacy Leaders, Chris Baldino sits down with Tina Fishman, an expert Medicare broker and licensed insurance agent in Florida. Together, they explore the complexities of Medicare education and plan selection, sharing valuable insights and practical tips for listeners.

Tina draws from her extensive experience to discuss how to navigate the overwhelming choices in Medicare, offering actionable advice for retirees and those approaching 65. This episode is a must-listen for anyone seeking clarity and confidence in their Medicare journey, providing both knowledge and tools to navigate this critical decision.
Key Takeaways:
● 💡 Trustworthy Guidance: Tina emphasizes the importance of working with someone who genuinely cares about finding the best plan for each individual, rather than focusing on commissions.
● 📋 Customized Solutions: She explains how she tailors solutions to each client’s specific needs, working with 14 carriers and over 120 plans to find the perfect fit.
● 🩺 The Human Element: Tina shares her belief that while AI and technology can streamline some processes, the human touch is essential when dealing with healthcare decisions.
● 🚑 Navigating Challenges: She recounts a powerful story about helping a client navigate a sudden health crisis and how her expertise ensured they had the coverage they needed.
● 🧠 Education First: Tina loves educating clients on the "ABCs of Medicare," ensuring they fully understand their options before making decisions.
Quotes from Tina Fishman:
● "I think I care. I really don’t pay attention to commissions when I’m talking with people. I try to figure out the best path for them."
● "It’s intimidating to navigate Medicare alone – you’re learning a whole new language!"
● "I’m here to help."
🔗 Conclusion: Tina’s dedication to her clients and deep knowledge of the industry make her a trusted guide through the Medicare maze.
Connect with Tina:
Website: www.CustomCareIns.com
Facebook: https://www.facebook.com/share/1LAXXhwRoq/?mibextid=wwXIfr Instagram: https://www.instagram.com/customcareinsurancesolutions?igsh=Z2VpcmZpMG02MjBi&utm_source=qr

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Josh Meyer: The Power of Values and Meaningful Actions Jun 11, 2025

Show notes

Have you ever wondered how to turn personal challenges into a powerful legacy for your family? This episode dives deep into that journey and how it can reshape your life.

In this episode of Legacy Leaders, Stan and Katie Beth sit down with Josh Meyer, a financial strategist and legacy planning advocate. Together, they explore how to build a meaningful legacy that goes beyond money, sharing valuable insights and practical tips for listeners. Josh draws from his personal experiences—overcoming adversity, surviving a nine-story fall, and facing a life-threatening diagnosis—to discuss how intentional decisions can shape the legacy you leave. This episode is a must-listen for anyone striving to create a legacy of impact, values, and meaning for their family, providing both knowledge and tools to navigate this important subject.

Key Takeaways:
● 🏆 The Power of Agency: No matter your upbringing, you have the power to shape and redefine the legacy you leave behind.
● 🌟 Legacy Beyond Wealth: True legacy is built on values and impact, not just financial assets.
● ⚖️ The Importance of Values Clarity: Clarifying your values is a crucial first step to crafting an intentional legacy for your family.
● 🔨 Legacy as a Daily Construction Project: It’s not just about the end goal—small daily actions build the foundation of your legacy.
● 💪 Becoming a Transitional Character: Anyone can be the one to stop negative patterns in their family and start a new, positive legacy.

Quotes from Josh Meyer:
● "Legacy is not this big unveiling at the end of your life—it's something you build brick by brick every single day."
● "Whether you had a great childhood or a challenging one, you have the power to decide what your family’s legacy will be."
● "The person who says 'this stops with me' is having one of the most profound impacts on the future of their family."

🔗 Conclusion:
Legacy planning isn’t just for the wealthy—it’s for everyone. Josh’s story and wisdom show how you can start today, no matter where you come from.

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Doug Davidoff: Unveiling the Revenue Acceleration Framework Jun 04, 2025

Show notes

🎧 What if asking better questions was the secret to accelerating your business growth?
In this episode of Legacy Leaders, Stan and Katie Beth sit down with Doug Davidoff, Founder and CEO of Lift Enablement and author of the #1 best-selling book Revenue Acceleration Framework. Together, they explore the core components of sustainable business growth, sharing valuable insights and practical tips for listeners. Doug draws from decades of experience to discuss how strategy, structure, and systems determine business success, offering actionable advice for business owners and entrepreneurs ready to scale smart. This episode is a must-listen for founders, CEOs, and leaders of mid-sized companies looking to break past growth plateaus and increase profitability with precision.
🔑 Key Takeaways:
● 📣 Focus Cuts Through the Noise: In a world flooded with messaging, the businesses that win are those that deeply understand who they want to be a hero to—their ideal customer.
● 📊 Strategy is About Decision-Making: Strategy isn’t just planning—it’s the framework for deciding what actions your business takes and how you evaluate results.
● 🧠 Systems Drive Performance: Every system is perfectly designed to get the results it’s currently producing. Change the system, change the outcome.
● 🚚 Structure Influences Behavior: Invisible structures silently guide your team's decisions and actions. Making them visible helps teams work smarter and more profitably.
● 🔁 Anticipate. Act. Learn.: Growth isn’t just from taking action—it comes from learning through iteration and making informed adjustments along the way.
🗣️ Quotes from Doug Davidoff:
● "The more you can narrow the focus, the more you expand your yield."
● "Every system is perfectly designed to get you the results that you're getting right now."
● "There’s nothing worse than losing while playing someone else’s game."
🔗 Conclusion: Doug Davidoff reminds us that sustainable business growth isn't about doing more—it's about doing the right things better. This episode equips you with the mindset and tools to think differently, act strategically, and grow intentionally.
Ready to rethink your revenue? 🎯 Listen now!

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Steve Whitteberry: Navigating Business Ownership Transitions: Strategies for Success and Legacy Building May 29, 2025

Show notes

🧠 What’s Your Business Really Worth — and Are You Ready to Let Go?
Most business owners think they’ll know when it’s time to transition — but are they prepared for what it really takes to exit without regret?
In this episode of Legacy Leaders, guest host James Moore sits down with Steve Whitteberry, M&A advisor and founder of Invictus MA, who specializes in helping privately held businesses navigate ownership transitions. Together, they explore the often-overlooked realities of exit planning, sharing valuable insights and practical tips for business owners nearing retirement or preparing for succession. Steve draws from decades of experience in finance, M&A, and corporate leadership to discuss valuation gaps, emotional readiness, and why exit planning isn’t just about a number — it’s about legacy. This episode is a must-listen for entrepreneurs, business owners, and advisors looking to lead their company into its next chapter with purpose and clarity.

🔑 Key Takeaways:

💵 Valuation Reality Check: Most owners overestimate their business’s worth based on personal financial goals — not market realities.

🧰 Opinion of Value vs. Full Appraisal: Steve explains a cost-effective way to understand what your business could actually sell for in the next 18 months.
🧠 Transition is Emotional: Owners struggle with identity and letting go — and many don’t think beyond “golfing” into their next purpose.
🏗 The Stronger the Team, the Smoother the Exit: If your business can’t run without you, it’s not ready to sell.
📊 Start Sooner Than You Think: Planning now — even if you’re years from retiring — means a better, more profitable outcome later.

"Most business owners determine value based on what they need to retire — not what the business is actually worth."
"If you can leave your business for six months and it runs without you, that’s a business ready for transition."
"Planning a transition isn’t an expense — it’s an investment that can return 10x or more."

💬 Quotes from Steve Whitteberry:
🔗 Conclusion:
Exit planning doesn’t start when you're ready to leave — it starts when you’re ready to think differently about your business. To connect with Steve, visit invictusma.com or email him directly at steve@invictusma.com.
🎁 BONUS: Mention this podcast to receive a complimentary copy of How to Transition from Your Business Without Regret or the Beating the Boomer Bust report!

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Jeff Oak: Embracing Failure, Empowering Leaders May 28, 2025

Show notes

Want to know the real secret weapon CEOs use to grow, lead with purpose, and overcome blind spots? You’ll find the answer in this empowering episode.
In this episode of Legacy Leaders, Stan and Katie Beth sit down with Jeff Oak, Vistage Chair, executive coach, and host of the Taking Care of Your Business podcast. Together, they explore the power of peer advisory groups, the vital role of trust, accountability, and vulnerability in leadership, and how leaders can confront their blind spots to unlock their full potential. Jeff draws from decades of experience stewarding culture at billion-dollar organizations and coaching CEOs to dive deep into the inner challenges leaders face, offering practical guidance to help them succeed with both excellence and humility. This episode is a must-listen for executives, entrepreneurs, and leadership teamsseeking to lead more authentically, grow with intention, and leave a lasting legacy.

Key Takeaways:

🔑 Trust as a Foundation: Jeff explains how trust, rooted in vulnerability, is essential for real leadership growth and team performance.

👥 The Power of Peers: Peer advisory groups create safe, honest environments where CEOs can confront blind spots and gain unfiltered feedback.
🧠 Accountability Without Fear: Accountability should be about promise-keeping, not punishment—and works best when paired with psychological safety.
🛑 Avoiding Leadership Pitfalls: Leaders must be conscious of how power dynamics and imposter syndrome can both sabotage trust and performance.
🔍 Blind Spot Awareness: Continuous feedback from trusted peers is the most reliable way to uncover and work through the things leaders can't see themselves.

“Without trust, there is no growth. Trust is built on vulnerability.”
“The truth will set you free, but usually it’ll make you miserable first.”
“I hope my legacy is empowering people to reach their highest potential—in their values, their purpose, and their leadership.”

Quotes from Jeff Oak:
🔗 Conclusion: Leadership is not about having all the answers—it's about creating the conditions for growth, truth, and transformation. Jeff Oak shows us how.
Connect With Jeff:
Website: www.vistage.com/legacy (this will be a dedicated Welcome Page for your listeners)
LinkedIn: https://www.linkedin.com/in/jeffoak/
Facebook: https://www.facebook.com/profile.php?id=100082981682259
YouTube: https://www.youtube.com/channel/UCVrMnz4DiVi2NfnCLy3smDw

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Brad Hamblen: Building Generational Wealth Through Real Estate May 21, 2025

Show notes

Is real estate still the smartest path to building lasting wealth and legacy — even in a high-rate, low-inventory market? Find out why now might be the most critical time to act.

In this episode of Legacy Leaders, guest host Josh Meyer sits down with Brad Hamblen, Branch Manager at Citywide Mortgage and Real Estate Investor. Together, they explore how homeownership and real estate investing build financial security and generational wealth, sharing valuable insights and practical tips for listeners. Brad draws from his extensive experience to discuss navigating high interest rates, low housing inventory, and creative financing solutions, offering actionable advice for first-time homebuyers, investors, and anyone serious about building their legacy. This episode is a must-listen for young professionals, families, and aspiring real estate investors, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 🏠 Start Early with Real Estate: Buying your first home or investment property early dramatically impacts your long-term wealth and security.

● 💡 Affordability vs. Pre-Approval: Understand the critical difference — just because you qualify for a certain amount doesn't mean it's financially wise to spend it all.

● 📈 Creative Strategies for High Rates: Solutions like temporary rate buy-downs can help buyers manage payments and enter the market confidently.

● 🎖️ VA Loan Opportunities: Veterans have access to incredible benefits that many aren't fully utilizing — Brad explains how to maximize them.

● 🛠️ House Hacking and Legacy Planning: Real estate strategies like house hacking can lay the groundwork for a strong, enduring financial legacy for future generations.

Quotes from Brad Hamblen:

● "Pre-approval is not the same thing as affordability — you have to know what you’re really comfortable with paying every month."

● "They're not building any more $200,000 starter homes. If you can buy one, do it now."

● "Building generational wealth means creating options and freedom — and real estate is one of the best vehicles to do that."

🔗 Conclusion: Whether you're a first-time homebuyer, a veteran, or a future real estate investor, this conversation with Brad Hamblen gives you practical advice and inspiration to take action today and build a legacy that lasts.

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Gary Heldt: Mastering Your Finances: The Key to Long-Term Success May 21, 2025

Show notes

💼 Are you building your business without a forward-looking tax strategy? You might be leaving thousands on the table. This episode is your wake-up call.

In this episode of Legacy Leaders, Stan and Katie Beth sit down with Gary Helt, CPA, Certified Tax Coach, and owner of Small Business Advisors. Together, they explore the powerful difference between tax preparation and tax planning, sharing valuable insights and practical strategies to help small business owners lower their tax burden and build smarter, more sustainable financial futures. Gary draws from his extensive experience to discuss the risks of reactive tax filing, the rise of misleading online financial advice, and proven techniques for legally reducing taxes. This episode is a must-listen for business owners, entrepreneurs, and high-income professionals, providing both the mindset and tools to take control of your financial story.

🎯 Key Takeaways:

● 📊 Tax Planning ≠ Tax Preparation: Most CPAs are historians, not strategists. True value comes from forward-thinking planning—not just form filing.

● 🏠 Use the Augusta Rule: Rent your home to your business for up to 14 days and receive tax-free income—a simple strategy often overlooked.

● 💰 Stack Your Strategies: Layering multiple tax strategies (like defined benefit plans) can drastically reduce your tax bracket—sometimes from 37% to 24%.

● 📉 IRS Audit Trends: Schedule C and E filers are facing more scrutiny, especially as the IRS relies on newer, less experienced agents.

● 🚫 Beware of TikTok Tax Advice: Misleading or outright illegal financial advice is everywhere online. Know who you’re listening to—and verify everything.

🗣️ Quotes from Gary Helt:

● "There’s a big difference between tax preparation and tax planning—preparation looks backward, planning looks forward."

● "The IRS has more money, more time, and more power than you do—you have to play smart, not just aggressive."

● "Just because you got it for free on social media doesn’t mean it won’t cost you everything in the end."

🔗 Conclusion: Don’t wait until year-end to think about taxes. Strategic planning now could save you more than you realize. Listen in and start planning forward—not backward.

Want more from Gary? Find him on LinkedIn or visit SBAdvisors.cc. Also, check out his podcast: Grow Your Business and Grow Your Wealth for more expert insights.

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Dave Goetz and Melissa Parks: Preserving Family Legacies Through Stories: The Power of Connection and Healing May 14, 2025

Show notes

Have you ever wondered how families can preserve their legacy, values, and business success across generations? This episode will inspire you to think about the stories that shape who we are — and why it's critical to capture them now.

In this episode of Legacy Leaders, Stan and Katie Beth sit down with Dave Goetz and Melissa Parks, co-founders of Journey 66 and experts in creative consulting for families and businesses. Together, they explore the power of storytelling in preserving family legacies and strengthening multi-generational businesses, sharing valuable insights and practical tips for listeners. Dave and Melissa draw from their extensive experience to discuss how capturing and interpreting family stories can build connection, preserve values, and even strengthen business continuity, offering actionable advice for business owners, family leaders, and legacy planners. This episode is a must-listen for anyone who cares about preserving their family's history, values, and impact for future generations, providing both knowledge and tools to navigate this important subject.

Key Takeaways: ● 📝 The Power of Storytelling: Capturing family stories isn't just sentimental — it's strategic for preserving values and business continuity. ● 🎥 Flexible Legacy Projects: From books to documentaries to digital anthologies, there are creative ways to capture and share a family's story based on their unique needs and resources. ● 🛠️ Customizable Processes: Journey 66 offers flexible options, from full-service projects to coaching families on DIY storytelling efforts. ● 🧠 Discovery Before Delivery: A thorough discovery phase ensures that families identify their key messages and choose the right storytelling medium. ● 💬 Stories Heal and Connect: Honest, even vulnerable storytelling can open up communication, heal old wounds, and forge strong connections across generations.

Quotes from Dave Goetz and Melissa Parks: ● "Stories have the power to connect family members that have been disconnected." ● "Every family has multiple stories they could tell — the key is to choose the right narrative arc for the moment." ● "The values families want to pass on are often born out of real-life struggles and pivotal moments — and without capturing those stories, those values can be lost."

🔗 Conclusion: Family stories aren’t just history — they’re the foundation for future generations. Capturing them thoughtfully can keep families strong, values alive, and businesses thriving for decades to come.

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Dr. Alise Cortez: Empowering Purpose: Unveiling Soulful Leadership May 07, 2025

Show notes

Are you building a workplace that people are drawn to — one where passion and purpose fuel success? Discover how purpose-driven leadership can transform your business and your team culture in this powerful episode.

In this episode of Legacy Leaders, Stan and Katie Beth sit down with Dr. Alise Cortez, Chief Ignition Officer at Gusto Now and expert in human capital, meaning, and purpose-driven leadership. Together, they explore how activating purpose within organizations can dramatically increase engagement, retention, and profitability, sharing valuable insights and practical tips for listeners. Dr. Cortez draws from her extensive experience to discuss how to uncover organizational purpose, align employees' personal purpose with company values, and build "destination workplaces", offering actionable advice for business owners, financial advisors, attorneys, and leaders who want to create thriving, people-centered organizations. This episode is a must-listen for anyone seeking to deepen team loyalty, increase business performance, and leave a lasting legacy through leadership.

Key Takeaways:

🔥 Discovering Organizational Purpose: Learn why identifying and articulating your organization's purpose is the critical first step to igniting employee engagement.
🌟 Aligning Personal and Company Purpose: Find out how encouraging employees to connect their personal values to the company’s mission transforms commitment and passion.
🏆 Purpose-Driven Performance: See how companies with authentic purpose outperform competitors — sometimes by a factor of 15 to 1!
📈 Building a Destination Workplace: Explore proven strategies for creating a workplace that attracts, retains, and inspires top talent.
✨ Real-World Success Stories: Hear examples of businesses that used purpose activation to achieve massive growth, resilience, and even successful acquisition.

Quotes from Dr. Alise Cortez:

"Every organization has a purpose, but you have to articulate it — and you have to enroll your people in it."
"It takes two and a quarter satisfied employees to equal the productivity of one inspired employee."
"Purpose is not just a feel-good idea — it's a powerful business strategy that drives profitability, loyalty, and growth."

🔗 Conclusion:

Embedding purpose into your organization isn’t just good for culture — it’s a strategic move that fuels performance, retention, and long-term success. Don't miss this inspiring conversation with Dr. Alise Cortez!

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Greg Schenk: Mastering Tenant Representation: A Legacy of Resilience and Success May 01, 2025

Show notes

Gregory P. Schenk is President of The Schenk Company, Inc., Central Ohio’s premier tenant advisory firm. With 38 years of experience, Greg specializes in site selection, investment property, and win-win negotiation strategies. A sought-after national speaker, he has educated professionals across industries—realtors, attorneys, CPAs, and financial advisors—for over 25 years.

Greg is a published author (Tenant Rep A to Z), a seasoned property investor, and a recognized industry leader. His accolades include the Commercial Real Estate Hall of Fame, Micro Entrepreneur of the Year, CB University’s Presentation Excellence Award, and Business First’s “40 Under 40.”

Listen to this informative Legacy Leaders episode with Greg Schenk about the value of tenant representation in commercial real estate, the importance of early lease negotiations, key lease clauses that can impact tenants, misconceptions in leasing and purchasing processes, and the impact of COVID-19 on real estate markets.

Here is what to expect on this week’s show:

● Greg emphasizes the importance of surrounding yourself with a mastermind group or think tank for mutual growth and support.

● Through his Lease Review Service, Greg helps clients navigate disadvantageous lease clauses, particularly focusing on clauses like notification periods and holdover clauses that can heavily favor landlords.

● Greg's success and growth, both personally and professionally, have been driven by his willingness to face challenges and step out of his comfort zone. Encouraging others to do the same, he teaches about risk tolerance, strategy development, and the importance of having an exit strategy in real estate investments.

Connect with Greg:

Website: https://schenkcompany.com

Training: https://schenkcompany.com/schenktraining/

LinkedIn: https://www.linkedin.com/in/gregschenk/

LinkedIn: https://www.linkedin.com/company/theschenkcompany/

Instagram: https://www.instagram.com/theschenkcompany/

YouTube: https://www.youtube.com/@schenkseminars

X: https://x.com/tenantrep1

With your Guest Host: Josh Meyer

Josh is a dedicated father, husband, and entrepreneur with 16 years of experience in financial services. He is passionate about helping individuals and families envision, design, and move towards their true legacy. Through his work with business and family leaders, Josh focuses on creating balance and alignment, empowering clients to be effective both at home and in their business by living out their legacy vision.

Josh's dedication to legacy planning was shaped by life-changing experiences, including a near-fatal accident and a prolonged battle with cancer, which gave him a profound appreciation for the value of time and purpose. A qualifying member of the Million Dollar Round Table, "The Premier Association of Financial Professionals," Josh brings expertise and credibility to his mission.

Connect with Josh:

Website: www.yourpeaklegacy.com

LinkedIn: www.linkedin.com/in/JoshSmeyer

IG: @peaklegacypartners

FB: https://wwwhttps://www.facebook.com/profile.php?id=61556805146972facebook.com/profile.php?id=61556805146972

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