Top Tax Matters to Consider for Business Owners and Individuals episode artwork

EPISODE · Jun 2, 2026 · 31 MIN

Top Tax Matters to Consider for Business Owners and Individuals

from Journeys to the Summit · host Ilya Zlotnik

Most business owners focus on revenue, growth, and brand when thinking about enterprise value—but overlook one critical factor: taxes.In this episode of Journeys to the Summit, Dean Pearson, Principal at PBG Financial and head of their State & Local Tax group, breaks down how tax decisions made today can directly impact your business valuation tomorrow. From missed filings to multi-state tax exposure, Dean explains how small oversights can lead to major reductions in purchase price during a sale.We also dive into one of the hottest trends right now: relocating to low-tax states like Florida. Dean unpacks the biggest misconceptions around residency changes, why simply moving doesn’t eliminate your tax obligations, and how business owners often get caught off guard.Key topics include:-How tax compliance impacts enterprise value during a sale-Why unfiled taxes can reduce your purchase price-The real cost of waiting to clean up tax issues-Multi-state tax obligations (even without physical presence)-The truth about moving to Florida and avoiding taxes-Residency audits and what states actually look for-Why most business sales still trigger state taxes—even after relocatingIf you’re a business owner thinking about scaling, selling, or relocating, this conversation could save you significant money and headaches.

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