Family, Finances & Health: Planning Ahead Before Crisis Hits

Divorce and Dollars: Reclaiming Financial Independence After 50

In this episode of The Clear Cut, Claire Hollander unpacks Chapter 4 of her book A Clear Path Forward, tackling the rising trend of Gray Divorce and its financial impact. From dividing assets with after-tax value in mind to navigating Social Security, pensions, and the family home, Claire shares strategies for protecting your future. Through reflective Q&A, she offers guidance on building the right advisory team, avoiding common pitfalls, and taking steps to move forward with clarity and confidence.

Family, Finances & Health: Planning Ahead Before Crisis Hits

In this episode of The Clear Cut, Claire Hollander dives into Chapter 3 of her book A Clear Path Forward, exploring the powerful link between physical health and financial health. From the emotional challenges of starting hard family conversations to the practical need for organizing vital documents, Claire unpacks why waiting until a crisis strikes can create unnecessary chaos. Through real client stories and reflective Q&A, she shares strategies for preparing loved ones for the realities of aging, long-term care, and estate planning. Tune in to learn how proactive planning can ease burdens, protect relationships, and truly become the ultimate gift to your family.

From Courtroom to Celebrations: Tiffany Klein on Designing Unforgettable Events

What does it take to transition from a career in civil litigation to building a thriving luxury event planning business? In this episode of The Clear Cut, Claire Hollander sits down with Tiffany Klein, owner of Rosecrest Special Events, to explore her remarkable journey. Tiffany shares how her background as a litigator shaped her approach to timelines, contracts, and problem-solving—and how those skills now fuel her creativity in crafting extraordinary events. From intimate milestone celebrations to show-stopping productions featuring world-class talent like Chris Stapleton, Tiffany reveals what goes into designing experiences that guests will never forget. Tune in for insights on entrepreneurship, creativity, and the art of gathering with intention.

Rethinking Debt and Investing: A Clearer Path to Financial Confidence

This episode of The Clear Cut continues the journey through Claire Hollander’s book, A Clear Path Forward, focusing on tackling debt and exploring intentional investing. Claire offers insights into managing common forms of debt, adjusting spending habits, and approaching investment decisions with clarity. She also discusses how generational perspectives on money are evolving and introduces ideas like diversification and values-based investing. This conversation is designed to help you reflect on your current approach and explore what might align better with your goals.

The Confidence Gap: Why Women Undervalue Their Financial Strength

In Claire Hollander’s first solo episode inspired by her new book A Clear Path Forward, she explores a powerful paradox: despite being natural planners and strong long-term investors, many women still lack confidence when it comes to money. From the impact of the pay gap to social narratives around finance, Claire breaks down why this happens, and how to change it.  You’ll learn how to identify your own money superpowers, take simple steps to boost financial confidence, and start meaningful conversations with your partner about shared goals and future planning. This episode also features self-reflection prompts to help you move from financial uncertainty to clarity, one small step at a time.