10 Sept 2026
Selling on Your Terms: How ESOPs Can Preserve Legacy and Reward Employees
Welcome back to The Entrepreneur’s Journey. In this episode, Jason Gabrieli is joined by Vince Capone, Senior Vice President with SES ESOP Strategies, and Sean Matthew, shareholder at Stevens & Lee, to discuss employee stock ownership plans, or ESOPs, as an alternative exit strategy for business owners. They explain how ESOP transactions work, how they are financed, and why they can help owners receive fair market value while preserving company culture and creating wealth-building opportunities for employees. The conversation also covers tax advantages, seller financing, valuation, employee engagement, and how ESOPs compare with private equity and strategic buyers.
Tune into this episode to also learn:
● How an ESOP allows business owners to sell some or all of their company while maintaining greater control over the transition.
● How ESOP transactions are financed through third-party debt and seller financing.
● Why employee ownership can create stronger alignment, retention, and long-term wealth-building opportunities for employees.
● How ESOP valuations and tax advantages can compare with other exit options such as private equity or strategic acquisitions.
What we discussed
● [00:02:11] Vince explains how SES ESOP Strategies helps middle-market companies plan, structure, finance, and implement ESOP transactions.
● [00:03:13] Sean describes the legal process behind an ESOP transaction and the regulatory requirements that come with employee stock ownership plans.
● [00:04:51] Vince explains the different roles an ESOP can play as a business succession tool, corporate finance tool, and wealth creation tool for employees.
● [00:06:40] Sean walks through the basic ESOP transaction process, from determining fair market value and owner liquidity needs to selecting a trustee and negotiating the transaction.
● [00:10:47] Vince explains how employees receive shares over time and how an independently appraised stock price can help employees think more like business owners.
● [00:12:08] Sean discusses how communication, financial transparency, and an ownership culture can help companies make the most of employee ownership.
● [00:13:44] Vince explains how an ESOP transaction analysis models proceeds to the seller, company cash flow, debt sustainability, and potential employee benefits.
● [00:15:00] Vince breaks down how ESOP transactions are commonly financed through bank debt and seller financing, including the potential role of warrants.
● [00:19:24] Vince explains that an ESOP cannot pay more than fair market value but can pay fair market value, and compares that with strategic and financial buyers.
● [00:20:30] Vince discusses potential capital gains tax deferral when qualifying C-Corporation stock is sold to an ESOP and proceeds are placed into qualified replacement property.
● [00:22:09] Vince addresses the misconception that selling to an ESOP necessarily means accepting a discounted valuation.
● [00:23:10] Sean explains that ESOPs can be viable for a broader range of companies than many owners assume, including some businesses with approximately $1 million of EBITDA and around 20 employees.
● [00:26:21] Jason compares the structure of an ESOP sale with private equity transactions, noting that many traditional deals also involve holdbacks, earnouts, or continued owner involvement.
● [00:28:41] Sean discusses the evolving employee ownership market and how new capital sources can create additional options for owners with shorter exit timelines.
● [00:29:24] Vince emphasizes the importance of considering every available exit option before making what may be the largest financial transaction of a business owner’s life.
3 Things To Remember
An ESOP can provide business owners with a flexible succession option that allows them to sell some or all of their company while helping preserve the company’s identity, culture, and operations.
Employees generally do not purchase the company stock out of pocket; shares are allocated to them over time as part of the ESOP benefit, creating an opportunity for long-term wealth creation.
Business owners evaluating an exit should compare the total economics of each option, including valuation, taxes, financing, continued involvement, and control over the transition—not simply the headline sale price.
Useful Links
Like what you’ve heard…
Learn more about HFM HERE:
https://hfmadvisors.com/working-with-hfm (https://hfmadvisors.com/working-with-hfm)
Schedule time to speak with us HERE:
https://calendly.com/builtwealth-hfmadvisors/60min (https://calendly.com/builtwealth-hfmadvisors/60min)
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com (https://thepodcastconsultant.com/))
