In this episode of Sellside Shorts, Michael Stanley breaks down key estate tax considerations business owners should think about before selling their company. He explains the current estate tax exemption thresholds, why a successful sale can quickly create taxable estate issues, and how early planning can make a major difference in preserving wealth for your family.

Using a recent real-world example, Michael walks through how a business owner couple used Spousal Lifetime Access Trusts (SLATs) and early valuation planning to transfer equity before a sale, helping reduce future estate tax exposure. This episode is a practical overview of why exit planning should include more than just the transaction itself and why involving an estate attorney early can lead to meaningful tax savings and smoother family outcomes.

https://www.linkedin.com/in/michael-k-stanley-jr-mba-cexp™-30916131/

In this episode of The Sell Side Podcast, Builder Brock shares the story behind Waypoint — from producing fishing TV shows to building a leading outdoor streaming platform in the FAST space.

He walks through the pivotal Samsung breakthrough, the evolution from app-first thinking to distribution-first strategy, and what it was like to receive — and ultimately turn down — multiple acquisition offers. Builder breaks down what buyers actually value, how the team shifted focus from vanity metrics to profitability, and why Waypoint chose to stay bootstrapped and in control.

https://waypointtv.com

https://www.linkedin.com/in/builderbrock/

https://www.linkedin.com/in/michael-k-stanley-jr-mba-cexp™-30916131/

In this episode, Michael Stanley breaks down one of the most important documents in any business sale: the purchase agreement.

Michael walks through how the purchase agreement serves as the final, definitive contract that officially transfers ownership once the deal closes and funds are wired. He explains how this document is developed alongside the due diligence process, beginning after the Letter of Intent and evolving as buyers verify financials, operations, and risk.

The conversation covers what actually goes into a purchase agreement, including net working capital true-ups, seller representations and warranties, and how different deal structures like seller notes, earnouts, and rollovers are documented. Michael also explains how legal teams negotiate the agreement throughout due diligence and how everything comes together at closing.

Whether you’re a founder preparing for an exit or just trying to better understand how deals actually get done, this episode offers a practical, real-world look at what happens between LOI and close.

https://www.linkedin.com/in/michael-k-stanley-jr-mba-cexp™-30916131/

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/

https://www.linkedin.com/in/michael-k-stanley-jr-mba-cexp™-30916131/overlay/photo/

In this episode of Sell Side Shorts, Michael Stanley breaks down one of the most critical documents in the M&A process: the Letter of Intent, or LOI. He explains what an LOI is, when it shows up in a transaction, and why it represents a major turning point for business owners considering a sale.

Michael walks through what an LOI typically includes, such as purchase price, deal structure, timing, exclusivity, and key contingencies. He also explains how an LOI differs from an indication of interest, why leverage often shifts once exclusivity is signed, and what happens during the pre-sale due diligence phase that follows.

If you’re a founder or business owner thinking about selling your company, this short episode provides a clear, practical look at why the LOI is the first real commitment in a transaction and why it deserves careful consideration before signing.

In this episode of the Sell Side Podcast, Michael Stanley sits down with Wilbur Ellis to break down platform acquisitions, add-on strategies, and what they mean for founders navigating today’s M&A landscape. They unpack how private equity groups execute buy-and-build strategies, what makes certain markets attractive, and why many business owners are surprised by the value and flexibility these deals can offer. The conversation also dives into unsolicited offers, common pitfalls, and how running a professional, competitive process can significantly impact valuation. Whether you’re building toward a platform transaction or considering an add-on exit, this episode offers practical insight into preparation, timing, and maximizing outcomes for founders.

https://www.linkedin.com/in/michael-k-stanley-jr-mba-cexp™-30916131/

In this episode of Sell Side Stories, we break down one of the most fundamental concepts in business valuation: how EBITDA and multiples work together to determine a company’s true enterprise value. We explore why EBITDA—earnings before interest, taxes, depreciation, and amortization—is used to normalize profitability and reveal a business’s real free cash flow.

From there, we dive into valuation multiples, unpacking how risk, industry dynamics, market trends, and strategic fit all influence where multiples land. We also discuss common EBITDA adjustments, including pro forma add-backs and one-time expenses, that can shape the final valuation picture.

Whether you're preparing to sell, exploring acquisition opportunities, or simply wanting to understand how buyers assess value, this episode offers a clear, practical breakdown of the mechanics behind business valuation.

In this Sell Side Shorts episode, we break down the real mechanics behind how small-to-mid-sized businesses are bought and sold beyond the simple “cash at close” model everyone thinks of.

Michael walks through common deal structures, including:

• 💵 Cash at Close — the straightforward “check at closing” approach

• 🧾 Seller Notes — when sellers effectively finance part of the deal to bridge valuation or risk

• 📈 Earn-Outs — tying a seller’s payout to the future performance of the business

You'll hear why these structures exist, how they allocate risk between buyer and seller, and the tax implications sellers should understand when evaluating their sale options.

Whether you're considering selling your company or just want to understand how deals actually get done in the real world, this episode gives a clear, concise look at modern transaction strategies.