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

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Disclaimer: Founder's Fortune is intended for informational and educational purposes only. The opinions expressed by the hosts and guests are their own and do not necessarily reflect those of Clear Harbor Wealth Management.
 

Nothing discussed on this podcast should be considered investment, legal, tax, or financial advice. All investing involves risk, and listeners should consult their own professional advisors before making financial decisions.