Design Your Legacy - Life Lessons

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,...

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...

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 fea...

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 mo...

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 j...

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 transf...

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...

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—a...

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 cr...

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 w...

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...

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 Isr...

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...

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...

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 throu...

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?   I...

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...

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...

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 h...

How do you shift from focusing on loss to being able to move past grief to see the joy and beauty each day? We know processing emotions is difficult but what’s worse is sweeping it under the rug when the rug is only so big. So how do you move the energy trapped within you, caused by stress, grief or loss, so as to be grateful and present compared to checking out? There are many forms of escape as...

What if men asked women more often to join boards, in trusting they can handle it, and women trusted themselves more in their experiences and skills ... to show up and become board members in the design of their legacies? And how is unconscious bias getting in the way when we look at examples of the Finnish Prime Minister vs. the Australian PM? Why do so many women all over the world get left out...

Parents traveling with young children often face the stressful reality of rideshares and taxis without car seats. In 2016, Nelson Nigel saw this firsthand as an Uber driver and recognized the risk families were forced to take... even before app's were well known as they are in 2025. Instead of waiting for another to lead, he chose to act as a pioneer, creating apps such as Kidmoto (under "Moto Nat...

Many women stepping into philanthropy face common but rarely discussed challenges: uncertainty about how to give effectively, lack of confidence in navigating male-dominated financial structures, and difficulty finding trusted advisors who truly honor their values and vision. Add to this the pressure of balancing family expectations with their desire to lead boldly, and the path to creating a mean...

For too long, venture capital has been a game reserved for the elite—where only accredited investors with deep pockets get access to the most promising startups. But what happens when you challenge that system and design a future where everyone can participate? In this episode of Design Your Legacy, host Angelina Carleton sits down with Gerry Hays, JD, founder of Doriot, to discuss how he’s tearin...

Few agents, lenders, or brokers can communicate in sign language, forcing reliance on interpreters who may not always be provided. On top of that, closing documents are full of legal jargon. Without clear, accessible communication, deaf/HoH clients risk signing documents they don’t fully understand. In some scenarios, interpreters aren’t offered at all, or those provided aren’t trained in legal te...