In the world of finance, strategic foresight can make or break a business. On this episode of The Roadmap, host Lee Heisman sits down with Tabitha Regan, owner, founder, and managing partner of LittleOwl CPA, to discuss how business owners can better navigate their financial journeys—from everyday decision-making to long-term exit strategies. With 20 years of experience in the CPA space, Tabitha shares insights on financial planning, common pitfalls, and the power of creative accounting to drive business success.
First, Regan emphasizes how she has spent the past two decades helping business owners make smarter financial decisions. She outlines her transition from working at a small accounting firm for 13 years—seven of which she spent as a partner—to launching her own practice. Inspired by her grandfather’s entrepreneurial spirit, she always envisioned owning a firm and took strategic steps to get there.
In addition, Regan explains the philosophy behind LittleOwl CPA, noting that she wanted a name that represented her role as an advisor rather than simply listing her surname. After spending a great deal of time considering what to name her company, she notes that the name actually stems from the owl associated with the Greek goddess Athena, symbolizing wisdom and guidance—qualities she aims to provide her clients.
Moreover, her firm specializes in advising high-net-worth and ultra-high-net-worth individuals, including entrepreneurs navigating mergers and acquisitions (M&A). Heisman highlights Regan’s ability to hold her own against top legal teams in high-stakes transactions and credits her with providing insightful, practical advice. Regan emphasizes that accounting is not just about numbers but requires creativity—connecting financial data with business strategy to ensure clients achieve their goals.
Regna also addresses common financial mistakes, pointing out that wealth does not guarantee financial stability. Some millionaires, she notes, still live paycheck to paycheck due to poor planning. Regan urges business owners to establish long-term financial roadmaps, align tax strategies with investment goals, and prepare for major financial events—especially exits. Good accounting systems, accurate data, and foresight in due diligence are essential for maximizing a company’s value before a sale.
Throughout the conversation, Regan underscores the importance of proactive planning, whether it’s paying taxes on time, setting a retirement goal, or structuring a business for future success. By taking a strategic approach, business owners can make informed decisions that will lead to financial security and long-term prosperity.
"My goal is to help clients create a solid financial foundation so they can build wealth with confidence and clarity."– Tabitha Regan
