Episode 205 - Why Timing Matters More Than Investments in Family Wealth with Gary Preisser

Gary Preisser is the Co-Founder of Stonebriar Wealth Advisors and the creator of the Cash Flow Clock framework, a financial planning approach that prioritizes purpose, timing, and liquidity over traditional asset allocation models. He works with family business owners and high-net-worth individuals to align investments with real-life cash flow needs, helping families navigate succession, taxes, and multi-generational wealth transfer more intentionally. Gary is known for challenging conventional wealth management by focusing on how and when money is used rather than just how it is invested.

SHOW SUMMARY

In this episode, Jonathan Goldhill is joined by Gary Preisser, Co-Founder of Stonebriar Wealth Advisors and creator of the Cash Flow Clock framework, to explore how liquidity, taxes, succession planning, and family expectations can impact long-term wealth far more than portfolio performance.

Gary challenges traditional wealth management approaches that focus on risk tolerance and asset allocation while ignoring the timing of future cash needs. He explains why purpose should come before portfolio design, how families can avoid liquidity traps during business transitions, and why volatility is not the same as risk.

The conversation also dives into family business succession, tax planning, multi-generational wealth transfer, and the critical mistakes business owners make before selling a company or transitioning leadership.

Whether you're a founder, successor, family business owner, or wealth creator, this episode offers practical insights into protecting wealth across generations.

KEY TAKEAWAYS

• Gary argues that traditional wealth management often starts in the wrong place. Instead of focusing on investment products and risk questionnaires, families should first identify the purpose of their assets and when those assets will be needed.
• His Cash Flow Clock framework separates assets into different time horizons, helping families maintain liquidity, reduce forced selling during market downturns, and make more intentional tax decisions.
• For family businesses, successful succession planning requires more than leadership development. It requires aligning ownership, liquidity, taxes, income needs, and family expectations long before a transition occurs.

QUOTES

• "Assets are not trophies. They're tools."
• "Volatility is not risk. Volatility becomes risk when a cash flow need collides with a market decline."
• "When we pay tax determines how much tax we pay."
• "The purpose of wealth is not to be admired. The purpose of wealth is to be utilized."

Connect and learn more about Gary Preisser.
https://www.linkedin.com/in/garypreisser/

If you enjoyed today’s episode, please subscribe, review, and share with a friend who would benefit from the message. If you’re interested in picking up a copy of Jonathan Goldhill’s book, Disruptive Successor, go to the website at www.DisruptiveSuccessor.com

What is Disruptive Successor Podcast?

The Disruptive Successor Show is a podcast for next-generation leaders in family businesses and entrepreneurs who want to disrupt the status quo to grow their business and take it to the next level.

We all know that what got us here isn’t going to get us there.

If you are taking control over your family’s business or trying to get your business to the next level, you will need inspiration, advice and resources to help you create a massive impact.

Listeners of my show include not only the millennial or Gen Z but also the Baby Boomer and Gen Y. My listeners tend to be involved in these industries: business services, construction, design-build-maintain landscape contracting, food manufacturing, property management, real estate, and technology.

And are interested in issues like business coaching, branding, communication, difficult conversations, disruption, employee ownership, exit planning, financial management, leadership, innovation, intergenerational transfer, marketing, multi-generational family businesses, business operations, process documentation, security, selling, storytelling, succession, visioning, wealth management,

My guests are entrepreneurs, family business advisors, multi-generational and Gen 2 family business leaders, heads of university family business programs, consultants, coaches and firms that serve those who are growth businesses.

Clients of my show typically are running businesses with 10 to 200 employees and $1M to $20M in revenues.

Their concerns include: scaling up, exit planning, succession, leadership development, disruption, business planning, finances, growth planning, transferring generational wealth, transferring control, ownership issues, and more.

The benefits listeners receive are introductions to experts and advisors around the issues of growing and exiting a business, whether it’s a family business or entrepreneurial venture. They get a feel for the challenges other business owners and leaders face and how they overcame them. They will hear stories from people and how they came to do their work and why.

My shows feature handpicked guests who engage with me in casual conversations lasting between 30 to 40 minutes. You can expect to be entertained, engaged and may even get takeaways like business tools or ideas for implementation in your business.

I’ve led entrepreneurial adventures in art, clothing, a holistic health lifestyle magazine and trade show, shoe manufacturing. I’ve also led several non-profit organizations. I earned an MBA from the University of Southern California in Entrepreneurship.

I’ve been advising, coaching and consulting family-owned, family-run and entrepreneur-led businesses since 1989. My love for entrepreneurship follows the closure of my family’s sizeable multi-generational clothing manufacturing company after eight decades of operation because there were no successors.

After uncovering the code to scale up a family-run business - a playbook and a disruptive successor - I wrote a book called Disruptive Successor: A Guide To Driving Growth in Your Family Business.

My podcast is my effort to bring interested people into the conversation to benefit disruptive successors.