Design Your Legacy - Life Lessons

Steven Wagner is a wealth advisor specializing in guiding business owners and affluent families through exit planning, wealth preservation, and multigenerational legacy strategy. As a Certified Financial Planner™ (CFP®) and Certified Exit Planning Advisor (CEPA®), he helps clients align their financial success with long-term purpose, family continuity, and lasting impact.

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At Legacy Planning©, we work with 'rising gen' entrepreneurs, wealth creators, and family stewards who are ready to turn their success into lasting contribution. Our co-active coaching and advisory services help you clarify what matters—beyond balance sheets and the four corners of a document. We guid...

Many high-achieving leaders are doing everything “right,” yet still feel exhausted by the constant pressure to do more. So how do you design a legacy built not on endless hustle but on sustainable influence that compounds over time? How can clarity, presence as well as boundaries create your legacy plan more than relentless effort?

In this episode, hostess Angelina Carleton speaks with Nell Derick Debevoise Dewey to reveal why the traditional formula for your legacy, or 'being right' based on the past, typically can lead to diminishing returns and personal depletion. She introduces her concept of Systematic Subtraction, an a...

The unemployment rate amongst college graduates is higher than high school graduates in 2026. So what does anyone do if they still want to succeed and reach millionaire status in today's day and age? And what do the latest white papers have to say about this? Is designing a legacy out of reach or how do you get there, starting from where you are at now?

In this episode, hostess Angelina Carleton speaks with Rich Potter about his journey from an employee to owning three businesses with his wife as well as brother. While he may not have thought...

Entrepreneurs often pour everything into building a meaningful business and assets—only to realize too late that without proper protection, their intellectual property ("IP") is vulnerable.  Your legacy plan, too, is a key asset worth your thought leadership as well as protection - so where do you start?

In this episode, hostess Angelina Carleton speaks with Richard Gearhart, Esq. to reveal how legal knowledge can become one hidden infrastructure that determines whether your IP endures or disappears. Drawing from his experience with founders, celebrities, and innovators, he shares his knowledge and life insights to get you started. Tune in...

When leaders feel anxiety around change, they often slip into performance mode instead of asking the deeper questions that matter most: Who am I now, and what does success look like in this next chapter? If we are lucky enough to live to age 80, we have roughly 4,000 weeks, making it essential to design our legacy plan now with intention.

And planning anything can be hard, unless we see the advantages of it right away. In this episode, hostess Angelina Carleton speaks with Mark Vincent, Ph.D. about how succession and wealth transfers are not merely financial events, but...

Many entrepreneurs spend decades building successful companies, yet when it’s finally time to sell, most discover a hard truth: success in business does not automatically translate into a successful exit or a meaningful legacy. 

In this episode, hostess Angelina Carleton speaks with wealth manager Steven Wagner to explain why nearly 80% of businesses that go to market never sell—and why the real issue often has less to do with market conditions and more to do with a lack of intentional planning for the end of the journey. Entrepreneurs are the heroes of their story. They build businesses, create...

If you took 2 months off, what would show up as fragile in your life? What if the lack of preparation destroys your legacy?

If you care about building a Legacy that lasts beyond your lifetime, this episode with Rafael Pinho (originally from Brazil) reveals what affluent individuals and families overlook when planning their Legacy... if one takes the time to plan a Legacy at all. Tune in to learn how to transfer your wisdom and values as a part of your wealth (aka human and relational capital) to ensure success from blind spots so there can be a...

Many family businesses remain dependent on the founder, leaving a ripple effect that challenges power, loyalty as well as motives. And yet "personal identity shifts" are the last to be talked about at meetings, about even if it leads to building a lasting enterprise and stronger family that outlives the founder(s) to serve the 'rising generation'. So do you develop your values so there's an integrated as well as broader purpose for succession, exit planning as well as your legacy?

In this episode, hostess Angelina Carleton speaks with Brandon Moon, COO and strategic partner at TD Pine...

In 2026, blended and step-families are facing unprecedented complexity as multiple households, shifting roles, and unclear expectations strain relationships and derail even the best legacy intentions. So how do you start as well as successfully unpack this complexity in blended families that are often layered with loyalty conflicts, power imbalances, and unspoken emotional histories that most professionals don't know how to resolve?

In this episode, hostess Angelina Carleton speaks with Emily Bouchard about practical remedies to help affluent blended families, couples, and next-generation members create clarity, strengthen trust, and prepare all branches of the family for better relationships. Tune...

In today’s private aviation landscape, many high-net-worth and UHNW families enter ownership seeking freedom and convenience—only to encounter hidden complexity, staffing challenges, financial inefficiencies, and governance gaps. Without the built-in infrastructure that corporations rely on, family office aviation can expose individuals as well as families to operational risk, cultural misalignment, and unnecessary capital drain. 

In this episode, hostess Angelina Carleton speaks with David Clark of Integris Aviation Consultancy about clarifying the differences between corporate aviation, fractional ownership, and family aviation—so families can honor the Founder's legacy vision. David outlines a path forward: intentional staffing aligned with fa...

Successful individuals and families don’t always fail financially—they can also fracture relationally, in "expectations", and due to outside influences, and no amount of wealth can fix what design was meant to prevent. Many high-achievers build assets "without realizing there can also be emotional costs" re: the climb re: their success, leaving their relationships and next generation rich in capital but poor in connection, trust, and kept promises. Without "front loading discomfort", about one's values when under pressure, the drive to succeed in business can become all consuming instead of a single element to a more meaningful 'legacy vision', crea...

Most families focus on protecting assets, but the real breakdown happens in the relationship systems when individuals haven’t done their inner work or built healthy communication patterns. Without safe spaces in family council meetings or a family's culture for honesty, financial infidelity can replace trust—creating silence, secrecy, and fractured relationship dynamics. For many, this begins in childhood, when prior generations never learned how to process emotions, conflict, or uncertainty. When role models and caretakers fail to evolve beyond their authority role, values aren’t truly transferred—only control, confusion, and expectations.

In this podcast episode, hostess Angelina...

Do you pick your legacy vision and plan or does it pick you?

In this episode, hostess Angelina Carleton speaks with Lyubim Kogan—a New York University graduate who worked as an RIA (registered investment advisor) on Wall Street, a Winter Olympian and now, a humanitarian—about what remains when worldly success metrics, systems, and certainty disappear. After rebuilding a company in war-torn Ukraine only to lose everything to targeted infrastructure attacks, Lyubim chose not to return to 'business as usual', but to answer a deeper calling to serve. Out of those ashes, "Wings4Heroes" was born, restoring dign...

You’ve built momentum—but without financial clarity, every decision still feels heavier than it should.

In this episode, hostess Angelina Carleton speaks with Austin McMillan reveals why most entrepreneurs unknowingly operate blind, and how that hidden chaos quietly limits growth, freedom, and peace of mind. He shares how shifting from revenue-obsession to profit-first thinking creates confidence, sustainability, and optionality for founders ready to scale with intention. You’ll learn the few financial rhythms and metrics that act as your business dashboard—so you can finally lead with clarity instead of anxiety. Austin explains how strategic CFO guidance transfor...

What if the real risk to your legacy isn’t market volatility or taxes—but the way your business thinks about risk in the first place? Most founders and business owners, with over $2M in profit, sense that something in their risk strategy is incomplete—but they can’t quite name it.

In this episode, hostess Angelina Carleton sits down with Van Carlson, Founder of Strategic Risk Advisors, to clarify what 831(b) captives truly are, separating legitimate risk architecture from the rumors that create hesitation. Together, they reveal why institutions treat risk as infrastructure—not an afterthought—and how discipli...

Building significant wealth in one country often creates an invisible risk: total exposure to a single political, legal, and regulatory system. As policies, taxes, and enforcement priorities shift, even successful individuals and families can find their wealth vulnerable to changes beyond their control. Many hesitate to diversify internationally due to regulatory complexity, misinformation, or fear of 'the unknown' in an increasingly transparent global system. Others delay action until uncertainty feels urgent, at which point options narrow and decisions become reactive rather than strategic.

In this episode, hostess Angelina Carleton speaks with Anne Liebgott about finding trusted guidance, as...

When life strips everything away—health, security, and certainty—most people retreat, but Scott Curry chose to rebuild with intention.

In this episode, hostess Angelina Carleton speaks with Scott as he shares how faith, clarity, and disciplined action helped him create financial freedom before he ever had money. You’ll hear how he transformed profound loss, illness, and betrayal into a business model that restored stability, purpose, and personal sovereignty. Scott reveals the mindset shifts and principles that allowed Faith Roar to grow rapidly while anchoring his life in meaning rather than survival. This conversation offers a realistic yet po...

At just 20 years old, Drew Carmichael has built seven-figure e-commerce brands—but success raises a deeper question: what is he really building long term for his legacy?


In this episode of Design Your Legacy, Drew shares how working alongside people twice his age shaped his thinking beyond growth into durability, values, and responsibility. We explore how being self-made early can accelerate not just income, but identity, meaning, and perspective. Drew reflects on the unseen pressures young high-performers carry and why thinking long-term now prevents regret later. This conversation reveals why legacy isn’t something you leave at the...

Many successful leaders build financial capital—but unintentionally give away ownership of the very stories and creativity that define them. How can authorship and intellectual property become foundational legacy assets, not vanity projects? How can a well-designed and planned out book, with strategic brand design, become a platform for authority, governance, and intergenerational knowledge transfer?

In this episode, hostess Angelina Carleton speaks with bestselling author and founder of Same Page Publishing, Aurora Winter, about her journey from television executive to publisher in her understanding of IP control, continuity, and long-term influence.  Tune in to hear how claiming your leg...

Success in law and business doesn’t automatically create a lasting legacy—and many high achievers struggle with what comes next.  In this episode of Design Your Legacy, host Angelina Carleton sits down with Rob Levine, Esq., to explore how purpose, service, and leadership transform success into enduring impact. Rob shares how building a powerful brand rooted in advocacy requires more than wins—it demands values, resilience, and responsibility.

Together, they unpack the tension between strength and empathy in leadership and why giving back is not optional for those who want their influence to last. Listeners will gain clarity...

Most individuals feel a sense of the world's weariness on their shoulders known as "weltschmerz"—quietly aware that time is slipping away faster than they’d like to admit. Why do we drift into disconnection, burn out, and unconscious living, and how can simple, intentional shifts realign you back towards awe as well as your highest and best legacy? It's time to stop living the same day on repeat—and start designing a legacy that compounds meaning—yet where do you begin?

In this episode, hostess Angelina Carleton speaks with Alex Dripchak as he explains how the power of awe-i...

Outwardly successful, inwardly stressed? Why is knowledge alone not a remedy to fix financial stress when couples lack alignment, communication or emotional clarity around money ... which designs your legacy? How are even high-achievers trapped by generational cycles of confusion, conflict as well as overwhelm? What are the real problems keeping couples and families stuck and how do you move to create that path forward built on unity, peace and shared values?

In this episode, I speak with Dr. Nicholas Michels to expose the hidden financial wounds many successful individuals carry from childhood—fear, instability, and patterns of scarcity th...

Misaligned spaces can create stagnation, overwhelm, and even self-doubt, especially during life transitions like succession, divorce, or the receiving of an inheritance. Most people have no idea that their homes are silently shaping their confidence, clarity, and ability to create their ideal legacy—and Kim Costa has spent three decades decoding that connection. How can aligning your environment with your core values become a foundational step in designing your legacy with intention, purpose, and long-term clarity?

In this episode, hostess Angelina Carleton speaks with Kim to reveal why so many high-achieving individuals feel “off” in spaces that look beauti...

What are the unique pressures facing today’s affluent families, where complexity—not lack of resources—is the true adversary?  Rising wealth fragmentation, global mobility, and multi-jurisdictional assets have made succession planning more overwhelming than ever. Affluent individuals often find themselves isolated, unsure whom they can trust, and hesitant to discuss money, purpose, or legacy—even within their own families.

In this episode, hostess Angelina Carleton speaks with guests Ben Ulrich, Dan Kertesz and Maxim Jardai to bring clarity to these challenges by bridging wealth, psychology, and human connection in a way that helps families design legacies—not just portfo...

In a world where wealth is growing faster than wisdom, affluent individuals as well as families face an invisible crisis: How do you turn prosperity into purpose — and build a legacy that transcends geography, politics as well as generations?

In this podcast episode, hostess Angelina Carleton speaks with Naava Mashiah, a global connector and CEO of ME LINKS, known for mobilizing capital across Israel, the Middle East, Africa, and Asia. With a background in diplomacy and a lifelong commitment to cross-cultural dialogue, Naava helps family offices and 'rising generation' family members move from preserving wealth to activating it. Tu...

Most individuals and families want to pass on more than money, but legacy is slow food for the soul — it requires intention, preparation, and steady nourishment. Like sex education class, talking about your legacy can be awkward — but avoiding the discomfort only guarantees confusion later.

In this episode, hostess Angelina Carleton speaks with Simon Holzapfel of CrowBox Partners to reveal why you can’t build on chaos, and why individuals and families must first create emotional order before they can create generational continuity. He explains how legacy isn’t a single event but how it happens one conversation at a tim...

Most affluent individuals excel at building wealth but struggle to build emotional continuity, because unprocessed trauma quietly drives control, perfectionism, and isolation.

In this episode, hostess Angelina Carleton speaks with licensed therapist and TEDx speaker Marcy Pusey about how unresolved pain becomes an unintentional legacy that gets passed down through silence, avoidance, and emotional distance. She explains why success cannot protect anyone from the “freeze patterns” of PTSD—and how those patterns sabotage succession planning, family unity, and true fulfillment. You’ll learn practical tools to break generational cycles, shift from survival mode into intentional design, and build emotiona...

In multi-generational families of wealth, dyslexia can quietly challenge the very ideals of achievement, confidence, and continuity. A child who struggles to read may internalize shame or feel they’ve disappointed the family. Parents, driven by high expectations, often oscillate between guilt and overcorrection—seeking to fix rather than understand. Grandparents may misinterpret the struggle through outdated notions of discipline, unaware of the opportunity for growth it presents.  

In this episode, hostess Angelina Carleton speaks with Russell Van Brocklen about his personal struggles as well as his latest research project. When a family can reframe dyslexia as difference inste...

Many affluent parents struggle with teaching their children the true value of wealth beyond material possessions. Without guidance, kids can grow up thinking money alone defines success, missing out on lessons in generosity, gratitude, and emotional richness. So where do you start … so your legacy can be passed on as well as your values, alongside their personal development beyond consumerism?  

In this episode, hostess Angelina Carleton speaks with Suzy Riedman who shares actionable strategies for helping children understand money, happiness, and privilege. You’ll learn how to guide your children to make thoughtful choices with money—whether to spend...

Many business owners waste money on marketing that looks good but doesn’t actually bring in qualified leads — Wes Towers knows why. For over two decades, he’s helped builders and trades cut through the noise, turning their websites and SEO into tools that earn market share and generate steady work. In a world drowning in digital fluff, Wes shows founders how to stand out authentically and connect with real people.

In this episode of Design Your Legacy, Wes shares his field-tested strategies for building trust at scale, simplifying what really moves the needle, and keeping your brand human...

Many affluent individuals want to leave a meaningful legacy, but they often feel overwhelmed by the complexity of wealth, taxes, and family dynamics. So what are the hidden challenges wealthy individuals and families face, from the “No Talk Rule” around money (as the #1 reason around financial failure) to fears of not having enough, and fears around ‘doing the wrong thing’. What are a few steps to move from being completely paralyzed to aligning your wealth with your actions, turning your answers to key questions as the framework for your legacy plan?

In this episode, hostess Angelina Carleton speaks with Pet...

Many individuals families want to secure their retirement and also pass on a meaningful legacy, but the fear of outliving money or leaving loved ones unprepared can feel overwhelming. For older generations, echoes of the Great Depression and Dust Bowl have shaped how we view money—through the lens of scarcity and survival.

In this episode, hostess Angelina Carleton speaks with Laura Phillips on how reverse mortgages can free trapped equity and transform fears into confidence. By preserving investments, easing financial pressure, and opening new streams of stability, individuals and families can plan not just for themselves but ...