Founder's Fortune

Clear Harbor Wealth Management
  • 0.0 (0)
  • Entrepreneurship

You built the business, but who’s helping you build what comes next? Founder’s Fortune is a podcast for entrepreneurs whose greatest asset isn’t just their investment portfolio–it’s the company they’ve spent years creating. Every week, host and small business expert Nick Carman sits down with founder Dustin Terry and Director of Research Mike Zaccardi to explore how founders transform business success into enduring wealth, purposeful retirement, and lasting impact. You’ll also hear clear, research-driven perspective on markets and the broader economy, designed to cut through noise and provide grounded insight you can actually use in both your business and investment decisions. From uncovering hidden exit opportunities to navigating stock market uncertainty and aligning investment strategy with long-term goals, we bring clarity to those seeking comprehensive financial advice and true wealth management. Tune in every other Wednesday and discover how intentional planning can turn today’s success into tomorrow’s freedom.

Episodes

  1. Aug 12

    EP 4: Tax Planning Starts Before Tax Season

    Saving money on taxes isn’t just about finding the right deduction. For business owners, the best tax strategy depends on where the business is going, what the owner is trying to accomplish, and what comes next. In this episode, host Nick Carman sits down with Clear Harbor founder Dustin Terry, Director of Research Mike Zaccardi, and Luke Smith, CPA and founder of Blue Point Financial, to discuss why proactive tax planning requires more than an annual meeting with your accountant. They explore commonly overlooked opportunities, the growing role of AI in tax planning, cost segregation and depreciation, and why a tax strategy that looks great today could work against a business owner preparing for an exit. What You’ll Learn: Why meeting with your CPA once a year isn’t enough for proactive planning.The questions every business owner should be asking their CPA.Why tax strategies should be built around your long-term business and exit plans.How business owners can miss deductions as tax laws change.How depreciation and cost segregation can create meaningful tax-planning opportunities.Why a large tax deduction isn’t automatically a good financial decision.How AI can help business owners ask better questions without replacing professional advice.Why your CPA, wealth advisor, attorney, and other professionals should be working from the same plan.Ideas Worth Sharing: “If we don’t know where we are and we don’t know what the goals are, then we’re kind of just wandering around in the dark.” — Luke Smith“This tax strategy you heard of doesn’t work because you plan on selling your business in two years.” — Dustin Terry“Get your CPA or tax advisor involved in the planning conversation. Don’t just talk to them once a year.” — Dustin Terry

  2. Jul 29

    EP 3: Why Your Exit Target Is Probably Wrong

    Hitting your exit number is only half the battle. Between hidden lifestyle inflation, complex estate planning, and the psychological shift of leaving a business behind, defining true financial freedom requires a far deeper look than conventional advice provides. In this episode, host Nick Carman sits down with Clear Harbor's founder, Dustin Terry, and Director of Research, Mike Zaccardi, to discuss what it really takes to determine your "freedom number." They unpack the nuances of lifestyle inflation, how to manage multi-generational wealth, and why finding an advisor who understands the unique complexities of business ownership makes all the difference when preparing for an exit.

  3. Jul 17

    EP 2: Retiring From vs. Retiring To: Why Purpose Matters More Than Money

    For entrepreneurs, retirement isn't just a financial milestone. Often, it can be an identity crisis waiting to happen. After decades of building a business that defines who you are, what happens when the alarm clock, the purpose, and the daily grind disappear overnight? And how do you transition into a retirement that actually feels fulfilling? In this episode, host Nick Carman is joined by Dustin Terry and Mike Zaccardi, along with a special guest, Clear Harbor's Senior Wealth Advisor and resident CFP Jerry Skalsky, to dig into what it really means to retire well as an entrepreneur. Listen in as they cover the psychological side of stepping away, how to define your “freedom number,” and why a conservative portfolio can quietly put an early retirement at risk.

  4. Jun 23

    EP 1: Transforming Business Success Into Enduring Wealth

    How can entrepreneurs bridge the gap between running a highly successful business and building a personal wealth strategy that lasts beyond a lifetime? For many founders, their business is their single largest asset and greatest wealth creator, yet traditional financial advice often leaves them underserved. Welcome to Founder's Fortune, the podcast that explores how founders can transform business success into enduring wealth, purposeful retirement, and lasting impact. In this inaugural episode, host Nick Carman sits down with Dustin Terry and Mike Zaccardi to introduce the core philosophy behind the Founder’s Fortune framework. Listen in as they unpack the dangers of fragmented advice from well-meaning but disconnected professionals, as well as why a business owner cannot simply rely on cookie-cutter, W2-oriented financial planning. Together, they share how entrepreneurs can accurately assess their enterprise value, balance concentration in their business with strategic diversification, and prepare for the massive wave of business transitions on the horizon.

  • 4 Episodes

About

You built the business, but who’s helping you build what comes next? Founder’s Fortune is a podcast for entrepreneurs whose greatest asset isn’t just their investment portfolio–it’s the company they’ve spent years creating. Every week, host and small business expert Nick Carman sits down with founder Dustin Terry and Director of Research Mike Zaccardi to explore how founders transform business success into enduring wealth, purposeful retirement, and lasting impact. You’ll also hear clear, research-driven perspective on markets and the broader economy, designed to cut through noise and provide grounded insight you can actually use in both your business and investment decisions. From uncovering hidden exit opportunities to navigating stock market uncertainty and aligning investment strategy with long-term goals, we bring clarity to those seeking comprehensive financial advice and true wealth management. Tune in every other Wednesday and discover how intentional planning can turn today’s success into tomorrow’s freedom.

Information

  • Creator
    Clear Harbor Wealth Management
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2026 Clear Harbor Wealth Management
  • Show Website
    Founder's Fortune