Mastering the Art of Success Hosted by Debbi DiMaggio

Success Mindset with Gary Wilson, Investor, Coach and Speaker

In this episode of Mastering the Art of Success, host Debbi DiMaggio sits down with Gary Wilson, an accomplished entrepreneur, investor, and author, to explore what it truly means to master success — not just in business, but in life.

Together, they dive deep into the mindset, habits, and strategies that fuel consistent growth, purpose, and fulfillment.

Gary shares his personal evolution from corporate professional to multi-million-dollar investor, revealing the powerful mental frameworks that helped him build wealth with integrity and intention.

Debbi and Gary unpack the difference between chasing success and creating a life designed around meaning, contribution, and freedom.

Listeners will walk away with tangible tools for strengthening their mindset, redefining achievement, and activating the courage to pursue their next chapter — whether that’s in real estate, entrepreneurship, or personal growth.

💡 Key Takeaways

Mindset is the Foundation — Success begins with belief and clarity. Learn how to shift from fear-based thinking to confident action.

Purpose Over Profit — Why aligning your business and life goals with your values leads to more sustainable success.

Habits of High Performers — Gary’s daily rituals and focus strategies that keep him grounded and productive.

The Power of Real Estate as a Mindset Tool — How Gary turned real estate into a path for personal growth and freedom.

From Transition to Transformation — Insights on navigating change, staying resilient, and building momentum through uncertainty.

Debbi’s “Mindset in Motion” Approach — Practical ways to apply Debbi’s signature method — Dream, Believe, Share, Activate — to achieve real results.

🌟 Perfect For Entrepreneurs, real estate professionals, and anyone seeking clarity, confidence, and direction in their journey toward success.

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Follow Debbi DiMaggio on

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

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

and visit

CoachWithDebbi.com for coaching, resources, and inspiration.

Your next chapter begins the moment you decide to turn the page. 💫

Interested in buying or selling real estate in the San Francisco Bay Area or LA or anywhere around the globe, reach out DebbiDiMaggio.com Debbi.DiMaggio@corcoranicon.com 510.414.6777 -

Crisis Management Expert Mike Paul – "The Reputation Doctor"

In this powerhouse episode of Mastering the Art of Success, host Debbi DiMaggio sits down with Mike Paul—The Reputation Doctor—a globally recognized crisis and reputation management strategist with 30+ years advising Fortune-level boards, governments, universities, celebrities, and elite athletes. Dubbed the “Master of Disaster” and “Mr. Fix-It,”

Mike breaks down why **truth—not spin—**wins every crisis, how boards should think about governance and cybersecurity, and the mindset leaders need to stay calm when the world is on fire. From catastrophic verdicts to athlete turnarounds, Mike reveals the research-first playbook his firm uses (think intelligence-grade due diligence), why emotional intelligence beats ego, and how diverse, informed leadership reduces risk and grows enterprise value.

Key Takeaways

Truth over spin: Lies create short-term cover and long-term disasters—truth is the only sustainable strategy.

Research is the foundation: Deep, confidential intel drives winning crisis plans.

Board readiness matters: Governance, cybersecurity literacy, and accurate D&O disclosures are non-negotiable.

Diversity = performance: Varied perspectives (including age and gender) improve decisions and reduce risk.

Athlete + celebrity crises: Long-term behavior change programs—not quick statements—restore trust.

Calm is a tactic: Sleep, hydration, and boundaries keep leaders effective under pressure.

Emotional intelligence wins: Assume complexity, challenge ego, and think from many stakeholder lenses.

Career wisdom: Patience compounds—start cultivating it early.

Guest Links Website: ReputationDoctor.com (fully spelled out) www.reputationdoctor.com/mike-paul

Foundation: Reputation Doctor Foundation on GoFundMe

Connect with Debbi 510.414.6777 www.DebbiDiMaggio.com  www.CoachWithDebbi.com 

Podcast: Mastering the Art of Success www.DebbiPodcast.com

Instagram www.instagram.com/debbidimaggio

Thank you for listening, Debbi 

From Burnout to Aligned Ambition: Kelly Parker’s Chicago Playbook

In this episode of Mastering the Art of Success, host Debbi DiMaggio sits down with Kelly Parker—Founder & Team Lead of Home Collective and creator of Aligned Ambition—to talk about building a top 1% Chicago real estate team, navigating burnout, and scaling with intention.

Kelly shares how a four-month sabbatical reset her business, why her Five Buckets framework

Knowledge

Skills

Network

Reputation

Resources

works in any market, and how Human Design helps agents ditch one-size-fits-all tactics for strategies that actually fit who they are.

Whether you’re a new agent or a seasoned pro, you’ll learn how to grow a referral-driven business, lead with heart, and create sustainable success—without burning out.

Key Takeaways

Burnout to Breakthrough:  How stepping away (strategically) can create clarity—and unlock 4x growth.

The Five Buckets Framework:  Fill Knowledge and Skills first; Network, Reputation, and Resources follow.

Aligned over Hustle:  Build systems and boundaries that support your life—and your clients—long-term.

Human Design in Business: Choose lead gen and marketing that match your energy (open houses vs. socials, small groups vs. cold outreach).

Mentorship Matters: Find expanders who model what’s possible—and shorten your learning curve.

Chicago Micro-Markets: Why hyperlocal expertise wins in a city of 200+ micro-neighborhoods.

Referral Flywheel: Serve with excellence, communicate consistently, and let your clients become your marketers.

Connect Guest: Kelly Parker — Home Collective & Aligned Ambition

Host: Debbi DiMaggio — The DiMaggio Betta Group, Corcoran Icon

🎙 Learn More About Our Podcast: If you enjoyed this episode, don’t forget to Like, Comment, and Subscribe for more conversations on real estate, design, art, and success mindset.

📌 Learn more about Debbi DiMaggio: DebbiDiMaggio.com | CoachWithDebbi.com

🎧 Listen now and discover how giving more can lead to getting more than you ever imagined.

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💬 Leave me a comment — I’d love to hear your thoughts!

Thank you for watching.

📩 Connect with Us Want to be a guest or collaborate?

Email: ✉️ Chase.Betta@corcoranicon.com

✉️ Debbi.DiMaggio@corcoranicon.com

📞 Real Estate Inquiries Buying or selling in the San Francisco East Bay or Los Angeles?

📱 Call/Text Debbi directly at 510.414.6777

Superyacht Captain Carsten Franik on Purpose & Leadership Insights

Mastering the Art of Success with Debbi DiMaggio and Guest: Carsten Franik, Superyacht Captain & Transformation Mentor.

In this inspiring full-length conversation, host Debbi DiMaggio sits down with Carsten Franik, a seasoned superyacht captain with over 20 years of experience navigating the world’s oceans, managing elite crews, and serving high-profile clients.

Beyond his maritime career, Carsten has emerged as a transformation mentor, guiding high achievers who feel “successful but stuck” toward deeper purpose, resilience, and authentic fulfillment. From his early beginnings as a six-year-old sailor in Germany to commanding multimillion-dollar vessels across Monaco, Thailand, and Mallorca, Carsten shares how discipline, curiosity, and presence shaped his leadership style. He opens up about extreme challenges at sea—including near-disasters, long stretches away from land, and the mental and physical toll of relentless schedules—while also reflecting on the profound personal growth that came through facing adversity head-on.

This episode is more than just a story about yachting. It’s about leadership, mindset, and transformation—how to stay grounded in the face of uncertainty, lead with clarity and compassion, and redefine success as more than titles or achievements.

Topics We Cover

Carsten’s unconventional journey from sailor to superyacht captain

Lessons in leadership: delegating, team-building, and trust at sea

The balance between structure, discipline, and compassion in high-pressure environments

Near-sinking stories, resilience, and learning through crisis

Transforming adversity into opportunity: Carsten’s kite-surfing expeditions in Namibia

Why true success comes from alignment, presence, and inner freedom His transition into coaching and mentoring high performers

About the Guest — Carsten Franik Carsten embodies a rare combination: a captain of the seas and a seeker of inner truth. His coaching helps individuals rediscover purpose, unlock resilience, and embrace a life led by authenticity and awareness.

About the Host — Debbi DiMaggio Debbi DiMaggio is a top-producing real estate leader, coach, and host of Mastering the Art of Success. She shares real stories and strategies from world-class guests to help you design your next chapter with purpose, passion, and impact.

New Episodes Each Week

Real Estate Leader, Community Builder and Founder of Cigars and Conversation

Welcome to Mastering the Art of Success with host Debbi DiMaggio. Today’s guest joins us from Las Vegas, Nevada—Rich Robledo. By the end of this interview, you may find yourself thinking Rich should be nominated as Mayor, or even Senator. His generosity, leadership, and heart for service shine through every story he shares.

In this episode, you’ll discover where Rich came from, the pivotal moments that shaped his journey, and how one life-changing realization—while jumping on a trampoline with friends—set him on a path that transformed his future. It’s a conversation filled with insight, resilience, and inspiration you won’t want to miss. Rich Robledo is a multifaceted entrepreneur, real estate broker, and community leader.

Founder of Cigars & Conversation, he’s built a powerful hub connecting innovators and entrepreneurs. As the founder of The Robledo Group, Rich has earned a reputation in Las Vegas real estate for trust, integrity, and unmatched client care, with 22+ years of experience.

Beyond business, Rich is deeply committed to leadership and service—through the Caldera Club, the Salvation Army, and as a mentor with the Boys & Girls Club and YMCA. His vision, expertise, and heart for community continue to make a lasting impact.

Moving to Portugal or Spain? Visas, Financing & Where to Buy — with Ricardo Sousa

On this episode of Mastering the Art of Success, host Debbi DiMaggio sits down with Ricardo Sousa, CEO of Century 21 Portugal & Spain (Iberia) and a driving force behind the launch of Corcoran in Portugal. With 6,000+ agents and 300+ offices across Iberia, Ricardo shares how mentorship, culture, and technology helped him scale from a single brokerage at age 25 to leading one of Europe’s most innovative real estate networks.

We dig into the real differences between Portugal and Spain’s real estate systems—from licensing and regulation to exclusive vs. open listings, cooperation without a traditional MLS, and why education is the #1 unlock for a young agent population. Ricardo also introduces Finance21, a fintech mortgage platform that connects to Portuguese banks via API for instant pre-approvals, transparent offers, and a smoother client journey.

Thinking about relocating to Portugal or Spain? Ricardo explains current visa pathways (post–Golden Visa changes), who’s moving, and the most in-demand regions: Lisbon, Porto, Comporta, Algarve, Madeira, Azores, Barcelona, Valencia, Marbella, Ibiza, Mallorca—plus why Portugal’s market skews boutique and sustainable while Spain spans broader price points.

You’ll also hear pandemic-era leadership lessons, how to get agents back into the office with purpose, and why relationships + culture still beat any tool.

Connect with Ricardo: Instagram & LinkedIn
Connect with Debbi: DebbiDiMaggio | Instagram | YouTube | Podcast

Topics: Portugal & Spain property markets • Licensing & regulation • Exclusives vs. open listings • MLS alternatives • Mortgage financing & APIs • Visas & relocation • Market hotspots • Culture, mentorship & tech adoption

Living in the Cayman Islands | Real Estate, Lifestyle & Moving Insights with Paul Young

In this episode, Debbi DiMaggio sits down with Paul Young, a top real estate professional in the Cayman Islands with over 40 years of sales expertise. From launching his first business at 17 to becoming a leader in luxury Caribbean real estate, Paul shares his incredible journey, his passion for island living, and why the Cayman Islands is one of the world’s most sought-after destinations for real estate, lifestyle, and investment.

 

🌟 Discover:

 

🏝️ What makes the Cayman Islands unique (low crime, tax-free living, world-class dining & more)

 

💼 Paul’s career journey from Canada and California to Bermuda and Cayman

 

🏡 Insights into buying property in the Caribbean, from second homes to luxury estates

 

🌊 Lifestyle, culture, and activities that make Cayman a true paradise

 

📈 Why investors and families are choosing Cayman for long-term living and wealth building

 

Whether you’re curious about Caribbean real estate, dream of island living, or just love inspiring success stories, this conversation will open your eyes to what life in Cayman is really like.

 

Connect with Paul: www.instagram.com/paulyoungcorcorancayman

 

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🔗 Stay Connected: Website: www.dimaggiobettagroup.co

 

Coaching: www.CoachWithDebbi.com

 

 

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Global Storytelling, Branding & Photography with Krystal Chryssomallis

Welcome to Mastering the Art of Success with host Debbi DiMaggio. In this inspiring interview, Krystal Chryssomallis—global storyteller, brand strategist, and photographer—shares her journey from working alongside her father, world-renowned musician Yanni, to building brand legacies with Disney, NASA, and UNICEF.

 

🌍 With over 20 years of experience across 60+ countries, Krystal has helped mission-driven organizations uncover their most powerful stories, build trust, and create lasting impact.

 

She opens up about:

✨ Lessons from touring the world with her father, Yanni

✨ Defining brand storytelling in the age of social media

✨ Collaborating with NASA, Disney, and UNICEF

✨ Her photography journey—from hobby to legacy work

✨ The life-changing story behind her lion encounter in Kenya

✨ How joy, culture, and community shape lasting brands

 

Whether you’re an entrepreneur, creative, or mission-driven leader, this conversation is packed with takeaways to help you master storytelling, branding, and success in your own journey.

 

🔗 Connect with Krystal: instagram.com/krystalann 

🔗 Connect with Debbi: instagram.com/debbidimaggio

 

👉 Don’t forget to like, comment, and subscribe for more inspiring interviews on lifestyle, success, and purpose-driven leadership.

 

‪@DebbiDiMaggio‬

 

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