The Clear Cut

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. 

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. 

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. 

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. 

In this episode of The Clear Cut with Claire Hollander, we sit down with Matthew del Junco, Director of Financial Planning and Senior Wealth Advisor II at Liberty Wealth Management. LLC., to explore the mindset and meaning behind true financial wellness. Matthew shares how his athletic background as an NCAA gymnastics champion shaped his approach to teamwork and resilience, and how he brings that same focus to guiding clients through some of life’s most important financial decisions. 

We discuss what makes a financial plan comprehensive, how procrastination can quietly erode your financial future, and why building trust goes far beyond investment returns. From legacy conversations to handling volatility with grace, Matthew reveals the value of reflection, intention, and listening—both in life and in leadership. 

In this episode of The Clear Cut with Claire Hollander, we sit down with Chris Olofson, founder of DIVEE Financial, to explore how she’s helping clients take control of their financial futures during one of life’s most difficult transitions: divorce. With a background in accounting, banking, and real estate, Chris shares how her personal experiences and professional expertise inspired her to build a practice focused on empowering individuals—especially women—through financial education and planning. 

We discuss the often-overlooked financial aspects of divorce, from the hidden costs of keeping the family home to the complexities of dividing tech compensation and pensions. Tune in for insights on resilience, informed decision-making, and redefining the path forward after divorce. 

In this episode of The Clear Cut with Claire Hollander, we dive into the inspiring career journey of Tracy Tamura, Director of Sales at Liberty Wealth Management. From her entrepreneurial roots to a career in the insurance industry, Tracy shares her passion for life insurance as a financial cornerstone and her innovative approach to integrating behavioral finance into her work. We explore her diverse background, from nonprofit work to earning financial designations, and learn how psychology and finance intersect to create meaningful client relationships. Tune in for insights on perseverance, leadership, and transforming financial planning through deeper understanding. 

In this episode of The Clear Cut, Claire Hollander is joined by Steve Jackman, partner at VLP Law Group and business law instructor at De Anza College. Steve shares his career journey, from leading legal teams to mentoring the next generation. Learn his top tips for authentic networking, balancing business risks, and helping young professionals thrive in today’s competitive environment. Tune in for actionable advice on building meaningful connections and navigating career transitions. 

Learn more about Steve here: https://www.vlplawgroup.com/attorneys/steven-h-jackman/