In The Know with Tony Reeves

There are moments in life that don’t seem particularly significant when they’re happening. Then you look back 10, 20, or 30 years later and realize:

That conversation changed everything. During my junior year of college, I was struggling with some of my science courses and seriously considering leaving my biology major. I wasn’t failing to understand the material. I was struggling to produce the grades I expected from myself—and I started interpreting that struggle as evidence that maybe I didn’t belong.

Then I had a conversation with my advisor, Dr. Fred Punzo. He didn’t promise me...

In the fall of 1987, just days into my freshman year at the University of Tampa, I was invited to my first real off-campus college party on Davis Island. I had an idea of what a college party was supposed to look like. Music. Food. Dancing. People having a good time.

What I found was a beach, a couple of kegs, no food, no music, and an environment where I was one of only a few Black students — and I didn’t drink. At the time, I could have easily dismissed the entire experience as a bad party.

For many members of Generation X, success did not come with a roadmap. We entered colleges, professions, leadership positions, and social spaces that were unfamiliar to our families. We learned through experience, experimentation, mistakes, and persistence. Along the way, we became the attorneys, doctors, judges, executives, educators, entrepreneurs, and mentors we may not have personally known when we were younger. That matters because the generations coming behind us are no longer starting where we started. They have access to us. In this companion podcast,

I reflect on the responsibility Gen X has to make our experiences, relationships, and...

A few weeks into my freshman year, I was pulled out of class and told that I owed the university $900. It was 1987.

My student loan had not been processed, my mother could not pay the bill without jeopardizing her own ability to survive, and I was warned that I could be removed from school. I was only 18 years old. 

In this episode of IN THE KNOW with Tony Reeves, I reflect on the emotional weight of that conversation, the painful reality many students face when financial aid falls short, and the moment I realized that I w...

In this companion podcast to my YouTube video, “The Fall of 1988: When I Had to Rebuild My Life Without My Friends,” I reflect on one of the biggest lessons I learned from returning to college after nearly everyone in my support system had disappeared. When I came back to the University of Tampa as a Resident Assistant, I expected to continue building on the friendships I’d made during my freshman year. Instead, I found myself almost completely alone. My closest friends had transferred or chosen not to return, leaving me to rebuild my life from the ground up. In this e...

Returning to the University of Tampa for my sophomore year should have felt familiar—but almost everyone I had depended on was gone.

My best friend and roommate did not return. Other friendships I had begun building disappeared as well. I arrived back on campus after a 24-hour Greyhound bus ride, carrying a military duffel bag on my back and a footlocker on my head, knowing that I would have to figure out this new chapter largely on my own.

At the same time, I was stepping into new responsibilities as a resident assistant, continuing ROTC, be...

We often assume we’re alone when life changes.

That’s exactly how I felt when I returned to college in the fall of 1988.

My closest friends were gone, and I believed I was beginning the year without a support system. What I didn’t know was that others had already stepped into that role.

In this episode, I share how my best friend’s family continued to watch over me, how an unexpected friendship introduced me to an entirely different culture, and why one conversation changed the way I think about being approachable.

There comes a point in almost everyone’s life when the original plan no longer works.

In this episode, I reflect on one of the first major personal resets I experienced during the summer of 1988. What began as a simple return home after my freshman year of college quickly turned into a season of unexpected change. My support system disappeared, my transportation plans fell apart, and I had to decide whether I still believed in the future I had chosen.

More importantly, I explore what that experience taught me about resilience, independence, and making better decisions wh...

What was it really like to become one of the few Black Resident Assistants at a predominantly white university in the late 1980s?

In this episode of IN THE KNOW with Tony Reeves, I share the story behind my unexpected journey from a freshman who never believed he would be hired to becoming a Resident Assistant—and eventually training future RAs on diversity, culture, and leadership.

This isn’t just a story about college housing. It’s about learning to navigate unfamiliar spaces, leading with authenticity, confronting racial realities with honesty, and discovering that your greatest challe...

Sometimes the smallest experiences become the biggest teachers.

As a freshman at the University of Tampa in 1987, all I wanted was a haircut before ROTC. Instead, I encountered racial assumptions, unexpected kindness, and a lesson about perception versus reality that has stayed with me for decades.

 In this companion episode, I reflect on how one ordinary afternoon helped shape my understanding of race, community, and judging people based on firsthand experience instead of fear or stereotypes.

This is another chapter in my ongoing Black Generation X journey. Call to Action If this episode resonated w...

As a freshman at the University of Tampa, I experienced something that would repeat itself every single year: university police stopping me while I walked across campus at night to ask for my student ID.

Were they simply doing their jobs? Or was I being singled out because I was one of the few Black students on campus? The truth is, I still don’t know.

 In this episode, I explore one of the defining experiences of Black Generation X—living in a world where discrimination wasn’t always obvious, but where many of us constantly questio...

What happens when you enter a space knowing that you earned the opportunity—but still feel that you must prove you deserve it?

In this companion episode of IN THE KNOW with Tony Reeves, I share the personal story behind my micro-book, I Deserve to Be There.

I grew up in Pine Bluff, Arkansas, surrounded by Black educators, professionals, church members and family friends who were committed to nurturing my success. Then I entered the University of Tampa, an overwhelmingly white institution where I suddenly found myself searching for people who understood my experience. My college jo...

During my first semester at the University of Tampa, I was 18 years old, 900 miles away from home, and struggling financially.There were times when I simply did not have enough money to wash my clothes. Instead of asking why, my roommates decided to remove my laundry, strip my bed, and scatter everything throughout the dormitory hallway.What followed was not simply a disagreement about dirty clothes.

It was a moment of humiliation, anger, isolation, and decision.  I had to determine whether I would respond violently, report what happened, leave school, or find another way to protect my dignity a...

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In this companion podcast episode, Tony Reeves reflects on the complicated bridge between HBCU dreams and PWI reality. Drawing from his Black Gen X college experience, he discusses representation, cultural isolation, the importance of Black-centered spaces, and the leadership lessons that came from learning how to survive and thrive in a place that was not built around him.

This episode explores what it means to belong, adapt, build community, and create the college experience you need when the institution does not automatically provide it.

Call to Action If this story connects with your own college experience...

Before GPS, Cash App, cell phones, and streaming music, taking a long road trip required planning, memory, discipline, and a little bit of nerve. In this episode, Tony Reeves reflects on what it meant to drive from Tampa to Pine Bluff in the early 1990s, when every gas stop, radio dead zone, highway turn, and dollar had to be accounted for.

This is not just a story about travel. It is a reminder of how Black Gen X learned resilience, independence, and problem-solving in real time—long before technology made the road feel safer and easier. From $0.99 gas to...

In this companion podcast episode, I reflect on the meaning behind my e-book “Gen X in the Middle: How Black Gen X Bridged Two Worlds” and why Black Generation X deserves to be understood as more than a forgotten or overlooked generation.

Using the end of MTV’s 24-hour music broadcasting stations as a cultural marker, I discuss how Gen X lived through a unique transition point in American history. Black Gen X grew up after major civil rights victories, but we still had to figure out what those victories meant in real life. We were raised by parent...

In this episode of The Anthony Reeves Experience, Tony Reeves reflects on what nightlife and social connection looked like for Black Gen X professionals as they moved beyond the club scene and into more intentional spaces.

From house gatherings among young officers, to cigar bars and jazz lounges, to professional socials in Tampa’s Ybor City, Tony explores how Black professionals created their own spaces for connection before social media, apps, and digital networking became the norm.

This conversation highlights the importance of safe spaces, professional community, cultural identity, and the quiet innovation of a generation th...

In this companion podcast to the main video, Tony Reeves reflects on how Black Generation X learned to navigate college, career, and predominantly white spaces without always having mentors or guides in place.

The episode explores performance, self-sufficiency, safe spaces, organic support, racial identity, and the “show and prove” mindset that shaped many Black Gen X professionals. 

After listening, go watch the full video for the deeper breakdown. Then leave a comment and share your own experience: Who helped guide you when no formal roadmap existed — and what did you have to learn on your own?

In this episode of IN THE KNOW with Tony Reeves, Tony reflects on the danger of romanticizing survival, especially from the perspective of Black Gen X.

Many of us grew up having to figure things out with limited support, limited resources, and few backup plans. We learned how to survive because we had no other choice. But survival should not be confused with something glamorous. Through personal stories about college, financial pressure, unreliable cars, family support, and generational differences,

Tony breaks down why resilience matters — but why struggle should not be celebrated as if it was id...

In this episode, Tony Reeves reflects on one of the most emotionally powerful moments of his young adult life: the day after college graduation.

Graduation itself was a celebration—family, achievement, recognition, commissioning, and the completion of a long journey. But the next day brought something different: silence. As the campus emptied, students checked out, and the familiar rhythm of college life disappeared, Tony found himself confronting the reality of transition. The question was no longer whether he would graduate. He had done that.

The question became: What now?

This episode explores the emotional co...

In this episode of IN THE KNOW with Tony Reeves, Tony reflects on what it truly means to be “the first” — not as a slogan, but as a lived experience.

When Tony left Pine Bluff, Arkansas, to attend the University of Tampa, he entered a world no one in his immediate circle had experienced. There was no social media, no campus visit, no one close by who could explain the culture, the distance, or the emotional weight of being 900 miles from home at a predominantly white private institution.

This conversation explores the difference between going somewhere new an...

In this episode of In the Know with Tony Reeves, Tony reflects on a season when he felt professionally stuck after completing graduate school.

On paper, he had done everything right: earned the degree, kept working full-time, and positioned himself for growth. But once graduation passed, nothing changed — because he had not created a plan for what came next. Through this personal story, Tony breaks down a hard but necessary lesson: sometimes we are waiting for doors to open when we have not even started looking for them. He shares how he moved from frustration and stagnation to cl...

In this episode, Tony Reeves reflects on a defining high school experience with his biology teacher, Miss Jewel Watley, at Pine Bluff High School. What began as intimidation — being placed in the school’s first AP Biology class alongside some of the top students in his class — later became one of the most important turning points in his educational and professional journey.

This episode explores the role of Black educators, the “it takes a village” philosophy, and the responsibility older generations often felt to identify, challenge, and cultivate young Black talent. Tony connects that classroom experience to his later path...

In this episode, Tony Reeves reflects on the major professional pivot points that shaped his career — from state employment to military service, law school, private practice, entrepreneurship, and the judiciary.

This conversation is not about chasing titles or making reckless moves. It is about understanding that every career decision happens inside a specific season of life. The facts, pressures, risks, and opportunities change as you evolve. Tony breaks down why career crossroads are rarely simple, why money and status are only part of the equation, and why learning to trust your analysis is essential when the outcome is un...

In this episode, Tony Reeves answers a question he has been asked many times:
Why did you go to law school?

The answer is not as polished or predictable as some might expect. Tony reflects on growing up as part of Generation X, watching his mother’s educational journey, and being shaped by the belief that education was the gateway to security, survival, and opportunity. He shares how law school became both a personal milestone and a professional contingency plan—even though he had no clear idea where the degree would take him.

Along the way...

In this episode of The Anthony Reeves Experience, Tony Reeves reflects on what it means to be part of Black Generation X — a generation raised by parents, grandparents, and elders who lived through Jim Crow, segregation, discrimination, and daily racial hostility.

Many of those elders did not share the full weight of what they experienced. They protected their children from the burden of the trauma, while still passing down the lessons they learned from surviving it.

Tony discusses family history, his grandfather’s military service, his mother’s experiences, the silence surrounding racial trauma, and why unders...

In this deeply personal reflection, Tony Reeves shares the emotional experience of selling his mother’s house after her passing.

For decades, that house was more than property—it was an anchor, a family gathering place, and a physical reminder of his mother’s presence. But as Tony walks through the process of clearing out the home, signing the paperwork, and saying goodbye to one of the last tangible connections to his mother, he reflects on a truth many people eventually face: letting go of a thing is not the same as letting go of the person.

T...

During his time as a young Black naval officer at Camp Lejeune, Tony Reeves discovered the profound importance of safe spaces and informal support networks.

What began as casual social gatherings hosted by a fellow officer turned out to be something much deeper: a deliberate effort to build a community where young Black professionals could connect, support one another, and stay aware of unseen risks. 

In this episode, Tony reflects on how those relationships became an invisible infrastructure of protection and guidance — and why having people who watch your back can make all the difference.

After my mother passed away in 2025, I found myself facing one of the hardest decisions an only child can make: selling the house that had become the center of her life and the anchor point for mine.

Although I didn’t grow up in this house, it became the place I always returned to. It was where family gathered, where friends stayed, and where my mother built the life she had worked so hard to create.

When the time came to clean it out and sell it, I realized I wasn’t just dealing with real esta...

What does it really mean to be Black Generation X? We are the generation that came after the Civil Rights Movement…

Raised to believe progress had already happened…
But lived through experiences that told us something very different. In this video, I break down:
The reality of growing up as part of the transitional generationThe difference between progress and the illusion of progressHow history, culture, and lived experience shaped our perspectiveAnd most importantly… what Black Gen X must do moving forwardThis isn’t just about the past.

This is about our responsibility right now. If you’v...

What does progress really look like—and who gets to define it?

In this episode of IN THE KNOW with Tony Reeves, Tony takes a deeply personal and thought-provoking look at what it means to be part of Black Generation X—the generation caught between the overt racism of the past and the subtle, coded language of the present.

From phrases like “I don’t see color” to accusations of “playing the race card,” Tony breaks down how seemingly harmless language can carry deeper meaning—and why it often leaves Black Gen X navigating a complicated reality: acknowl...

This isn’t just a story about where we sat. It’s a story about why we had to sit there—and what we built because of it. Growing up as part of Black Generation X, we entered spaces that were technically “integrated”…
but not always inclusive.

From:
✔️ Boot camp
✔️ College campuses
✔️ Law school
✔️ Early professional environments We found ourselves in rooms where we were often the only ones.

So what did we do? We found each other. Not to isolate.

Not to exclude. But to survive, understand, and move strategically. What loo...

At some point in your career, you’ll face a decision that forces you to choose between what you know and what you don’t. In this episode of In The Know with Tony Reeves, I break down one of the biggest obstacles professionals face at career crossroads: the psychological weight of the unknown. Drawing from my own journey—from running my law firm to becoming a judge—I share how fear, comfort, and bias toward the “known” almost kept me from preparing for a life-changing opportunity.   You’ll learn:Why we naturally favor the “known” (even when it limits us)How failing to p...

We’ve all heard it: “Live your best life.” But what does that actually mean across generations? This episode explores:The structured path of older generationsThe urgency of younger generationsAnd the Gen X mindset that blends bothIf you’re building something—or rebuilding—this conversation matters

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What happens when everything you’ve relied on… suddenly changes? In this episode of In the Know with Tony Reeves, I take you back to a pivotal moment in my life—leaving a steady paycheck to start my own law practice. What seemed like a bold and exciting move quickly became something much deeper: a confrontation with uncertainty, fear, and responsibility. From losing the predictability of a direct deposit…
To realizing no one else was responsible for generating income…
To the moment it truly hit: “When am I getting paid again?” This episode isn’t just about entrepreneurship—it’s about identit...

There comes a point in life where you have to make a decision most people aren’t prepared for…
 
Do you hold on to the comfort you worked so hard to achieve—or do you take a risk on yourself?

In this episode, I walk through one of the most defining moments of my life. After years of struggling just to survive—stretching groceries, living paycheck to paycheck, and dealing with instability—I finally reached a level of comfort through my military career. 

Stable income. Housing covered. Food covered. A lifestyle I never imagined. 

An...

What really drives you?

In this episode, Tony Reeves breaks down a powerful truth most people overlook—motivation isn’t a straight line. It shifts, evolves, and sometimes starts from places we don’t fully understand.

Drawing from his own journey—from leaving Pine Bluff to attending the University of Tampa—Tony shares how his initial motivation wasn’t about purpose or planning… it was about proving someone wrong. But once he got there, a deeper question emerged:

“Now what?” 

What follows is a raw and honest reflection on: 
How motivation can be both positive...

Even after decades of achievement, imposter syndrome can still show up.

In this episode, I reflect on a reunion with law school classmates that forced me to confront how I see myself versus how others see me—and why that gap matters.

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This episode is personal.
I take you back to a defining moment in my career—when I thought I was on track to become a partner after years of dedication… only to be told it wasn’t enough.
What followed were two conversations that changed everything:
One that helped me understand the value of my timeAnd another that forced me to make a decision

A close friend told me something I’ll never forget:
If we’re still having this conversation months from now… it’s a hobby.
And my wife gave me the clarity I...