In this episode, we sit down with Scott Shea, a sell-side advisor, former family business operator, and recovering professional poker player who brings a uniquely grounded perspective to helping owners navigate the sale of their company.

From growing up in an oilfield services family business to sitting across from buyers in private equity, Scott shares how poker taught him more about deals than business school ever could. He breaks down how sellers sabotage their own exits by getting emotional, managing for dollars instead of percentages, and waiting too long to prepare.

Whether you’re years away from selling or getting offers now, this conversation offers a masterclass in readiness, realism, and negotiation psychology.

Topics Covered:

• How to manage deal fatigue and emotional detachment during a sale
• Why timing and identity are critical for business owners looking to exit
• The myth of “I can just sell it myself” and where it goes wrong
• The danger of bad buyer psychology and off-market lowball offers
• Why culture, not just capital, matters in acquisitions
• How to create real buyer competition and why it changes everything

Connect with the Guest:

Scott Shea

Sell-Side Advisor, FA Mergers

Email: [email protected]

Website: https://www.famergers.com

LinkedIn: https://www.linkedin.com/in/escottshea/

Connect with the Hosts & The Deal Podcast:

Joshua Wilson

LinkedIn: https://www.linkedin.com/in/joshuabrucewilson/

YouTube Channel: https://www.youtube.com/@TheDealPodcast

Website: https://www.thedealpodcast.com