Jason Caras on Leadership, Failure, & the Fight to Rebuild

Blake Poole on Planning for Life After the Deal

Most M&A conversations focus on getting to closing. This episode begins after the deal is done and explores three layers of the emotional reality of transition, the practical mechanics of wealth planning, and the preparation that should happen before a founder ever goes to market. Dara sits down with Blake Poole, Managing Director, accompanied by Christopher Steele, Director for Trust and Estate Planning from Bernstein Private Wealth, to discuss what happens when a founder sells their business, receives the wire, and suddenly has to navigate a new financial and personal reality. From “sudden wealth syndrome” to identity, loneliness, estate planning, tax strategy, and the shift from operating income to invested wealth, this conversation explores why the M&A and wealth management processes are two halves of the same event. What You’ll Learn in This Episode * What “sudden wealth syndrome” looks like for founders after a transaction * How business owners transition from concentrated business ownership to invested wealth * The difference between traditional wealth management and private wealth advisory * Why identity, purpose, and loneliness often become major challenges after a sale * How core versus surplus wealth planning can help founders define lifestyle and legacy goals

Jason Caras on Leadership, Failure, & the Fight to Rebuild

On this episode of Closing Remarks, host Dara Shareef sits down with Jason Caras, co-founder of IT Authorities and founder of Caras Institute, to discuss leadership, culture, failure, resilience, and rebuilding after losing everything. Jason shares the story behind scaling IT Authorities to $34 million in revenue, stepping away from day-to-day leadership, and the business began to unravel after bringing in an outside CEO. He opens up about the emotional and financial toll that followed, what it took to recover the company, and the lessons founders cannot afford to ignore. Today, Jason works with founders through the Caras Institute and speaks at juvenile detention centers, helping young people and entrepreneurs build discipline and self-belief through adversity. What You’ll Learn * Why scaling a business requires more than revenue growth * The leadership mistake that nearly cost Jason everything * The warning signs that leadership transitions are failing * What rebuilding after failure actually looks like * How culture impacts long-term business success * The mindset shifts that changed his life and career

Derrick Brooks on Life Beyond the Game

On this episode of Closing Remarks, host Dara Shareef sits down with Pro Football Hall of Famer Derrick Brooks for a conversation that goes far beyond his legendary career with the Tampa Bay Buccaneers. Known for a Super Bowl championship, eleven Pro Bowls, and a defining Hall of Fame career, Derrick reflects on the mindset behind the success one he built on humility, discipline, and a relentless standard that never stopped at football. The conversation traces the foundation of that mindset, from growing up in Pensacola and the influence of his mother, to playing under Bobby Bowden at Florida State, and becoming a cornerstone of championship culture in Tampa Bay. Rooks also opens up about his leadership inside elite football environments, including the discipline demanded by coaches like Tony Dungy and the expectations that shaped how he led on and off the field. But this episode is just as much about what came after football as it is about the game itself. Derrick shares how he transitioned into business, education, and community leadership, including his work with Vinik Sports Group as Executive Vice President of Corporate and Community Development, and Chief Operating Officer of USF Athletics.   What You’ll Learn in This Episode * How humility and excellence mindsets carried Derrick Brooks from the NFL to business, investing, and community leadership * How championship cultures are built from Tony Dungy’s Buccaneers team to Jeff Vinik’s vision for Tampa Bay * Why one $35,000 investment in a t-shirt company became a lesson that ultimately saved millions down the road and allowed him to develop discipline * How to navigate identity, purpose, and reinvention after the career or role change that once defined you

Introducing Closing Remarks with Dara Shareef

There’s often a moment in the life of a business owner when everything shifts. A conversation begins, the language changes, and unfamiliar terms start to surface. EDITDA, multiples, earnouts, letters of intent, indemnification. The stakes are high, the pace is fast, and many choose to keep nodding rather than slow things down. This podcast exists for that moment. In this episode, Dara Shareef introduces Closing Remarks, a podcast built to help business owners and spouses understand the realities of selling a business and what it takes to navigate the process with clarity and confidence. What You’ll Learn in This Episode * Why the M&A process often feels unfamiliar, even to experienced operators * How industry language creates an information gap for business owners * What buyers, advisors, and investors are really thinking during a deal * Why preparation before going to market leads to stronger outcomes * The emotional realities of selling a business and how to navigate them

Coming Soon!

Coming Soon! First Episode Launches May 6th