On this episode of Sell Side, host Michael Stanley sits down with Shelby Ashley, founder of Optimized Financial Solutions, to unpack what small business owners often misunderstand about their finances—and how that confusion can limit growth, cash flow, and exit opportunities.

Shelby shares her journey from corporate financial analyst to fractional CFO and explains why most businesses outgrow basic bookkeeping long before they’re ready for a full-time CFO. The conversation dives into cash vs. accrual accounting, why profit on paper doesn’t always mean money in the bank, and how forward-looking financial strategy helps owners regain clarity and confidence.

Michael and Shelby also explore the M&A side of small business finance, including preparing a company for sale, internal succession planning, common valuation mistakes, and how buyers should evaluate cash flow, debt, and operational risk before acquiring a business. Along the way, Shelby offers practical advice on hiring, forecasting, and removing the owner from day-to-day operations so the business can truly scale—or sell.

Whether you’re overwhelmed by your numbers, thinking about an eventual exit, or considering acquiring another business, this episode delivers grounded, real-world insight into what healthy financial leadership actually looks like.

https://optimizedfinancialsolutions.com

https://www.linkedin.com/in/shelby-ashley-mba-a72903b9/

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