Most business owners don’t wake up one day and decide to sell their company. The decision is usually years in the making.

In this episode of Closing Remarks, host Dara Shareef talks to Ben Wagner, Senior Director at Benchmark International, for a special Q&A focused on the questions business owners ask most often before going to market.

Ben brings forward topics that frequently shape exit decisions:

• Should I sell now, or wait?
• What if my EBITDA improves in two or three years?
• How do I know if private equity is the right fit?
• What will happen to employees after the deal?
• And how can I prepare before I am ready to sell?

Drawing from his conversations with business owners every day, Ben shares practical insights on market preparation, buyer interest, private equity, business durability, unsolicited offers, and the factors that can influence a successful outcome.

Whether you’re considering a sale in the near future or simply want to build a stronger, more valuable business, this episode provides actionable guidance to help you prepare for whatever comes next.

What You’ll Learn

• Why waiting to sell isn’t always the safest or most profitable strategy
• The key factors buyers evaluate when assessing a business
• How to determine whether your company is ready for the market
• What private equity firms are looking for in today’s environment
• How market conditions can impact timing, valuation, and buyer interest
• Ways to increase business value
• The role of management teams, recurring revenue, and customer diversification in buyer demand
• Why unsolicited offers do not represent the full value of your business
• How preparation can protect your team, legacy, and future options
• How to prepare emotionally and strategically for an exit
• Why building a durable business creates more options, whether you sell or not

What does it take to build a business that can withstand uncertainty, adapt to changing markets, and continue to grow?

In this episode of Closing Remarks, host Dara Shareef speaks to Andrew Wright, the CEO & Founder of Franklin Street, Chief Executive Officer and Founder of Ally Capital Group, and Co-Founder of Next Level Brands. Drawing from his experience of building businesses, investing in companies, and leading teams, Andrew shares practical lessons on navigating market uncertainty, evaluating risk, and creating long-term value.

Discover how diversification helped Franklin Street navigate the 2008 financial crisis, why the strongest leaders put people first, and what separates businesses that thrive through change from those that struggle to adapt.

Andrew also discusses his approach to evaluating investment opportunities, building high-performing cultures, identifying emerging talent, and adapting to technologies such as artificial intelligence (AI). Throughout the conversation, he offers candid insights on leadership, community, entrepreneurship, and the importance of staying focused on what you can control.

Whether you’re growing a business, leading a team, evaluating opportunities, or preparing for your next stage of growth, this episode delivers valuable lessons on communication, resilience, and long-term planning.

What You’ll Learn:

• How to build resilience into your business during changing market conditions
• Why diversification can create opportunity during periods of uncertainty
• The traits successful leaders and investors look for in people
• How to transition from operator to leader
• What business owners should know about AI and the future of work
• Why authentic relationships remain a competitive advantage
• How purpose can drive stronger long-term results than success alone

In this episode of Closing Remarks, Dara Shareef answers common questions business owners ask about valuation, buyers, and the M&A process as unfamiliar terms start to surface.

Joining him is Kayla Sullivan, Benchmark International’s Operations Director, who brings more than a decade of M&A experience and insights gained from hundreds of transactions. Acting as the voice of the audience, she asks the questions business owners want answered, while Dara Shareef breaks down what EBITDA is, how businesses are valued in the M&A market, and what factors impact business value.

Whether you’re actively preparing for a sale, considering a sale, or simply looking to better understand what drives business value, this conversation delivers practical insight into how buyers evaluate opportunities and what business owners should know as they plan for the future.

What You’ll Learn

• What EBITDA is and why buyers use it
• How businesses are valued in the M&A market
• The difference between enterprise value and equity value
• Common misconceptions about private equity
• What buyers look for when evaluating a business
• Factors that can impact business value and buyer interest
• Why timing and market conditions matter in the sale process

Many know Thaddeus Bullard as WWE Global Ambassador and WWE Hall of Fame Warrior Award recipient Titus O’Neil. Throughout Tampa Bay, however, he has become equally recognized for creating opportunities for underserved families, supporting students, and investing in the next generation of leaders.

In this episode of Closing Remarks, Dara Shareef sits down with Thaddeus for a conversation about leadership, purpose, mentorship, business, and the responsibility that comes with influence. From overcoming poverty and food insecurity to building a global platform through WWE, Thaddeus shares how one mentor changed the trajectory of his life and why purpose, not passion, is what sustains people through challenges.

The conversation explores identity beyond titles, the power of storytelling in business, and the importance of investing in communities. As President and Chair of the Bullard Family Foundation, Thaddeus has led mentorship, scholarship, and family support programs that have impacted thousands across the Tampa Bay area. His work with the Thaddeus M. Bullard Academy at Sligh Middle Magnet School has helped transform the campus into a hub centered on opportunity, mentorship, wellness, and long-term community support.

Content Warning:

This episode contains sensitive discussion involving sexual assault, rape, and personal trauma. Listener discretion is advised.

What You’ll Learn

• Why is purpose bigger than passion
• How mentorship changed the trajectory of Thaddeus’ life
• How Leaders can influence and create opportunities for others
• Why identity should never be tied to a title
• How the Bullard Family Foundation is helping strengthen Tampa Bay Families
• What it means to move from success to significance

What happens when the thing that defines your identity disappears overnight? In this episode of Closing Remarks, host Dara Shareef interviews Jerry Bell, the former Tampa Bay Buccaneers tight end and CEO of Bell & Associates Business Consultants, to discuss reinvention, resilience, and preparation for life after the point when everything changes.

Jerry Bell was drafted by the Buccaneers in 1982 and established himself as one of the most loyal tight ends in the history of the franchise until the unfortunate event that resulted in the termination of his NFL career. However, this was far from the end of the road for him; this incident only served as a prologue to the rest of his life.

Having been influenced by the discipline and high expectations of his parents, he received a bachelor’s degree in computer information systems from Arizona State University, obtained his MBA while playing for the Buccaneers, and started working at IBM to be better prepared for life after the sport.

In this episode, Jerry discusses the challenges of transitioning from professional sports to business, the attitude needed to reinvent yourself, and the lessons that can be learned by business owners regarding purpose, discipline, and post success life.

What You’ll Learn

• How Jerry prepared for life after the NFL before his career ended

• What business owners can learn from identity loss after an exit

• The mindset required to reinvent yourself after an exit

• Why self-worth cannot be tied to one title or career

• How Jerry built a second career in technology and consulting

• Why success means more than money or recognition post-success

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

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

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