Tommy's Toolbox

What does it take to become “the first” when the path was never built for you?

Dr. Sandra Braham’s story begins with challenges most people never see.

Raised by a mother with schizophrenia.
Moved through the foster care system.
Forced to understand resilience long before she had the language for it.

Today, she is the President and CEO of Gulf Coast Jewish Family and Community Services, a $60 million nonprofit serving nearly 30,000 people a year across Tampa Bay and beyond.

In this episode of Tommy’s Toolbox: Leadership Edition, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Dr. Sandra Braham for a powerful conversation about mental health, leadership, forgiveness, access, representation, and what it means to become the first Black woman to chair the St. Petersburg Area Chamber of Commerce in its 150-year history.

This conversation goes far beyond a title.

Dr. Braham shares how her childhood shaped her work, why writing her memoir An Angel for Detroit became part of her healing process, and how forgiveness, including forgiving yourself, can become a leadership tool.

She also breaks down the work happening at Gulf Coast JFCS, including more than 45 programs across 40 counties, a team of 550+ employees, and the CALL program, which sends social workers instead of police officers to certain 911 calls.

The result: 20,000 diverted calls, zero incidents, and a model

that is helping reshape how communities respond to people in crisis.

In this episode, you’ll hear:

• How Dr. Braham’s childhood shaped her leadership and commitment to service

• Why Gulf Coast JFCS is nonsectarian and what that means for the people it serves

• How writing An Angel for Detroit helped her process her own story

• Why forgiveness is essential, especially when it includes yourself

• How she helped grow a 52-year-old nonprofit into a $60 million organization

• What the CALL program teaches us about mental health, public safety, and crisis response

• What to say to someone who may be silently struggling

• What it means to be the first Black woman to chair the St. Pete Chamber

• Why access, not just opportunity, is often the real barrier

• How golf, mentorship, and representation all connect to leadership

This episode is about more than personal achievement.

It is about turning pain into purpose.
It is about building systems that meet people where they are.
And it is about understanding that leadership is not just what you accomplish, but who gets to see themselves in your story.

If you care about mental health, nonprofit leadership, community impact, representation, or building organizations that serve people with dignity, this is a conversation worth hearing.

Learn more about Gulf Coast Jewish Family and Community Services: GCJFCS.org
Connect with Dr. Sandra Braham on LinkedIn.

If you or someone you know is struggling, the 988 Suicide & Crisis Lifeline is available 24/7 by call or text at 988.

About the Show:
Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox: Leadership Edition features real conversations with the leaders, founders, executives, and changemakers shaping Tampa Bay. Each episode goes beyond surface-level success to explore the decisions, challenges, pivots, and leadership lessons that actually matter.

Tommy’s Toolbox is brought to you by TomCo Solutions.

Tampa City Council member Bill Carlson says the arts aren't a nice-to-have for a city — they're economic infrastructure. He sits down with Tommy Whitehead to talk city culture, the $300 million museum Tampa almost lost to St. Pete, and what he learned building consultancies across Asia.

Bill Carlson represents District 4 on Tampa City Council. He's CEO of Tucker Hall, co-founder of Café Con Tampa and the Tampa Arts Alliance, and a former international business consultant who worked with clients like Citibank Asia and Singapore Airlines.

Tommy's Toolbox features conversations with the entrepreneurs, innovators, and community builders shaping Tampa Bay. New episodes weekly.

Learn more about host Tommy Whitehead at tommywhitehead.com and TomCo Solutions at tomcosolutions.com.

Habitat for Humanity does not give houses away.

That is the biggest myth Mike Sutton has spent the last 12 years correcting.

In this episode of Tommy’s Toolbox: Leadership Edition, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Mike Sutton, President of Habitat for Humanity Tampa Bay, for a conversation about housing, leadership, nonprofit culture, and what it really takes to help families become homeowners.

Under Mike’s leadership, Habitat for Humanity Tampa Bay has grown from 280 homes to more than 1,050, helping hundreds of families purchase their first home through sweat equity, homebuyer education, and a 0% interest mortgage model.

No down payment.
No PMI.
But plenty of work.

Mike breaks down how Habitat’s model actually works, why it is built around ownership instead of handouts, and why the organization’s mission matters more now than ever in a region facing a serious workforce housing challenge.

Because when nurses, teachers, firefighters, service workers, and working families cannot afford to live in the communities they serve, the impact reaches far beyond housing.

It becomes an economic issue.
A workforce issue.
A community stability issue.

And a leadership issue.

In this episode, you’ll hear:

• Why “Habitat gives houses away” is the biggest misconception about the organization
• How sweat equity, 38 homebuyer classes, and 0% interest mortgages create a path to ownership
• How Habitat Tampa Bay grew from 280 homes to more than 1,050
• Why Mike says they are a “501c3 by tax status, not business model”
• How Habitat built a Best Places to Work culture four years in a row
• Why paying for talent matters, even in nonprofit leadership
• How the organization kept every employee through COVID
• Why workforce housing may be one of Tampa Bay’s most urgent challenges
• How AI, 3D printing, and new building methods could shape what comes next

This conversation is about more than affordable housing.

It is about building systems that create dignity, stability, and long-term opportunity. It is about leading a nonprofit with business discipline without losing the mission. And it is about what happens when an organization gets everyone rowing in the same direction.

Whether you are a business leader, nonprofit executive, builder, policymaker, employer, or Tampa Bay resident trying to understand the housing pressures facing this region, Mike’s perspective will challenge how you think about homeownership, leadership, and community impact.

Learn more about Habitat for Humanity Tampa Bay: HabitatTampaBay.org

Tommy’s Toolbox is brought to you by TomCo Solutions.

About the Show:
Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox: Leadership Edition features real conversations with the leaders, builders, founders, executives, and changemakers shaping Tampa Bay. Each episode goes beyond surface-level success to uncover the decisions, challenges, pivots, and leadership lessons that actually matter.

Florida's oldest restaurant shouldn't still be here — andthat's exactly why it is.

Casey Gonzmart is the 5th generation to lead ColumbiaRestaurant in Ybor City — a 120-year Tampa institution that started as the Columbia Saloon in 1903. Most family businesses die by generation three. The Columbias survived the Depression, Prohibition, two World Wars, urban renewal, and COVID. What's the real secret sauce?

In this Leadership Edition of Tommy's Toolbox, Casey revealswhy they call themselves a "community restaurant, not a familyrestaurant," what he learned leaving the family business to work for LevyRestaurants, how they keep scratch-made quality at Tampa International Airport,and what "heavy is the head that wears the crown" actually feels likewhen you're steering a 121-year legacy.

Brought to you by TomCo Solutions.

🎧 Guest: Casey Gonzmart | Columbia Restaurant (YborCity & Tampa International Airport)
📍 Filmed in Tampa Bay | Leadership Edition Playlist

TIMESTAMPS
00:00 — The 121-year legacy no one planned for
01:49 — 1903 vs 1905: The salad that tells the history
03:20 — Why 5 generations is "exceptionally rare air"
06:18 — "We're a community restaurant, not a family restaurant"
09:40 — The secret sauce beyond the 1905 dressing
10:30 — "You have to live and breathe it"
13:30 — From Ybor to TPA: The last taste of Tampa
17:02 — Heavy is the head that wears the crown
22:00 — Tommy's Toolbox: Parenting in the age of social media

🔗 Learn more about Columbia Restaurant:columbiarestaurant.com
👉 Subscribe for weekly Leadership Edition conversations with the people shaping Tampa Bay.

What happens to a city when the people telling its stories disappear?

In this episode of Tommy’s Toolbox: Leadership Edition, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Ray Roa, part-owner of Creative Loafing Tampa Bay, for a conversation about local journalism, Tampa’s identity, and why human storytelling still matters in an AI-driven world.

Ray’s path into media was anything but traditional.

He failed out of college.
Bartended for eight years.
Learned how to listen to people before he ever interviewed them professionally.
Then eventually became part-owner of one of Tampa Bay’s most recognized locally owned alt-weekly newspapers.

But this conversation is about more than one career path.

It is about what local journalism does for a community that national media, algorithms, and AI tools cannot replace.

Ray breaks down why Creative Loafing still matters, how print continues to survive when done differently, and what Tampa risks losing as the region grows faster than its culture can sometimes keep up.

Because growth is not just about new buildings, new businesses, and new residents.

It is also about memory.
Accountability.
Culture.
And who is paying attention when no one else is.

In this episode, you’ll hear:

• How Ray went from HCC dropout to co-owner of Creative Loafing Tampa Bay

• What bartending taught him about interviewing, listening, and understanding people

• Why Ray embraces the word “rag” when describing alt-weekly journalism

• How Creative Loafing returned to local ownership

• Why print is not dead when the product still has a point of view

• What Tampa may be losing as it grows and changes

• The interviews and media moments that shaped Ray’s career

• Why AI can assist journalism, but can never replace a reporter who knows the community

• What local media reveals about a city’s soul

This episode is built for anyone who cares about Tampa Bay, media, culture, small business, leadership, or the future of storytelling.

Because AI can summarize a city.

But it cannot walk its streets, know its people, earn their trust, or understand what a story means to the community living inside it.

Follow Ray Roa’s work at CreativeLoafing.com.

About the Show:

Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox: Leadership Edition features real conversations with entrepreneurs, innovators, public figures, and community builders shaping Tampa Bay. Each episode goes beyond surface-level success to explore the decisions, failures, pivots, and lessons that actually matter.

Tommy’s Toolbox is brought to you by TomCo Solutions.

What if the biggest mistake in selling your business happens before you ever meet a buyer?

Most business owners spend years building value.
But when it comes time to sell, many try to navigate the process alone, without realizing how much strategy, timing, positioning, and deal structure can shape the outcome.

In this episode of Tommy’s Toolbox: Leadership Edition, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Dara Shareef of Benchmark International, a sell-side M&A firm with deal teams involved in more than 250 company sales.

Dara has seen business transactions from nearly every angle: buyer, seller, board member, operator, venture capital professional, and now M&A advisor.

That perspective matters.

Because selling a business is not just about finding someone willing to buy it. It is about understanding what buyers actually value, how deals get structured, what makes a company attractive, and why the language of mergers and acquisitions can feel intentionally confusing to people outside the industry.

In this conversation, Dara breaks down what business owners need to understand long before they are ready to exit.

You’ll hear:

• Why trying to sell your business alone can create costly blind spots
• What buyers really look for when evaluating a company
• Why a “perfectly clean” business is not always what buyers expect
• How the right exit strategy can help a deal reach the finish line
• Why timing matters when deciding whether to sell
• The meaning behind Dara’s line: “The time to sell your business is when your money is less valuable than your time”
• Why Benchmark International’s name appears on a major Tampa Bay arena, despite being one of the smaller firms in the space
• How Dara’s path from venture capital to operator to M&A advisor shaped the way he works with business owners
• What moving to Tampa taught him about building relationships and doing business in this market

This episode is built for founders, owners, executives, and leaders who may not be ready to sell today, but want to make smarter decisions before that moment arrives.

Because the best exits are rarely accidental.

They are planned, positioned, and prepared for long before the deal starts.

Tommy’s Toolbox is brought to you by TomCo Solutions.

About the Show:
Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox: Leadership Edition features real conversations with business leaders, founders, executives, and changemakers shaping Tampa Bay and beyond. Each episode goes beyond surface-level success to uncover the decisions, risks, pivots, and leadership lessons that actually matter.

It looks like resilience.
It looks like visibility.
It looks like business owners, advocates, nonprofit leaders, and community pioneers building something that lasts.

In this special supercut episode of Tommy’s Toolbox, in collaboration with Building Success Productions, you’ll hear directly from the people shaping Tampa Bay’s LGBTQ business community.

Recorded live at the Tampa Bay LGBT Chamber’s 45th Anniversary Membership Luncheon, Shirley Jump of Building Success Productions sat down with leaders across business, media, advocacy, nonprofit work, banking, hospitality, health care, and community development to capture the stories behind a network that has been growing for more than four decades.

And the history is bigger than most people realize.

From a small meeting in a gay bar in 1996 to a chamber with more than 300 members today.
From a laundromat in 1992 to a thriving community health organization celebrating 35 years.
From St. Pete Pride’s $67 million economic impact to Winter Pride growing from 57,000 to 85,000 attendees in just two years.

This episode is not just about looking back.

It is about understanding how community becomes infrastructure.
How visibility becomes opportunity.
And how business leadership can become a force for belonging, advocacy, and economic impact.

In this episode, you’ll hear from voices including:

• Asa Harris, Marketing Director for Hotel Flor
• Nicole Waters, Founder of Amplify Women Tampa Bay and Executive Director of the Edge District St. Pete
• Don Kiciena Jr., Tampa Bay Business Guild veteran in media and advertising
• John Harris Maurer, General Counsel at Equality Florida
• Maureen Cacioppo, natural sea salt business owner
• Ryan Williams-Jent, Editor-in-Chief of Watermark OUT News
• Sarah Peacock, candidate for Hillsborough County Judge

You’ll also hear from representatives connected to CAN Community Health, Enterprise Mobility, Bay First Bank, Winter Pride St. Pete, and more.

This special episode highlights what happens when business, advocacy, and community move together with purpose.

Whether you are an entrepreneur, ally, community leader, chamber member, or someone who wants to better understand the LGBTQ business landscape in Tampa Bay, this conversation offers a powerful look at the people and partnerships behind the progress.

Learn more about the Tampa Bay LGBT Chamber: TampaBayLGBTChamber.org
Follow Building Success Productions: BuildingSuccessProductions.com

This episode is a collaboration between Tommy’s Toolbox and Building Success Productions.

About the Show:
Tommy’s Toolbox, led by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, features real conversations with the entrepreneurs, builders, leaders, and changemakers shaping Tampa Bay. Each episode explores the stories, strategies, pivots, and lessons that define business, leadership, and community impact.

What do you do when the old way of leading no longer works?

For Amanda Payne, the answer was simple: rebuild.

In this episode of Tommy’s Toolbox: Leadership Edition, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Amanda Payne, CEO of Amplify Clearwater and founder of Premier Anesthesia Care, for a conversation about leadership, reinvention, and what it takes to build something stronger when the world forces you to start over.

Amanda did not just step into leadership.
She stepped into complexity.

She helped merge two competing chambers into one unified organization, led through the uncertainty of COVID, built a team culture around trust and accountability, ran for office, and continued leading her own business along the way.

But the part most people miss is this:

COVID did not just disrupt her organization.
It gave her a whiteboard.

Amanda shares how that season became an opportunity to question everything, rebuild systems, rethink member value, and create what became Amplify Clearwater.

Her leadership philosophy is direct:
“If we’re not evolving, we’re dying.”

In this episode, you’ll hear:

• How Amanda helped merge two competing organizations into Amplify Clearwater
• Why COVID became a reset point instead of just a setback
• What real leadership looks like when no one is watching
• How she built a loyal team of working moms
• Why the old idea of “you only get out what you put in” may no longer be enough
• How her “seasons” approach changed the way she thinks about work-life balance
• What Clearwater’s recovery looks like and what may be coming next

This conversation is not just about chambers of commerce.

It is about adapting before you are forced to.
It is about leading through uncertainty.
And it is about building organizations that actually serve the people inside them and around them.

Whether you are a CEO, entrepreneur, community leader, business owner, or someone trying to navigate your next season of growth, Amanda’s story will challenge how you think about leadership, change, and resilience.

Learn more about Amplify Clearwater: AmplifyClearwater.com

Tommy’s Toolbox is brought to you by TomCo Solutions.

About the Show:
Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox: Leadership Edition features real conversations with business leaders, founders, public figures, and changemakers shaping Tampa Bay. Each episode goes beyond surface-level success to uncover the decisions, failures, pivots, and leadership lessons that actually matter.

What do you do when your business looks like it might be over… and then one phone call changes everything?

Clay Keel of Keel Farms in Plant City, Florida knows what that moment feels like.

In this episode of Tommy’s Toolbox, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, sits down with Clay to unpack how a 45-year-old blueberry farm became one of Florida’s most unique agritourism destinations.

But this story is not just about farming.

It is about reinvention, timing, resilience, and learning how to turn a difficult moment into a new direction.

Clay shares the story behind Keel Farms, from his military background to stepping into the world of agriculture, hospitality, craft wine, hard cider, festivals, and family-friendly experiences. What started as a farm has grown into a destination where people come not just to buy a product, but to experience where food, community, and entrepreneurship come together.

Then came COVID.

Employees were laid off.
Doors were closed.
The future was uncertain.

And then a 30-pallet Publix order helped change the trajectory of the business.

In this conversation, you’ll hear:

• How Clay went from military service to leading a farm, winery, and agritourism brand
• The behind-the-scenes story of Keel Farms’ COVID pivot
• Why agritourism is becoming one of Florida’s most exciting business opportunities
• How Keel Farms uses festivals, events, and family experiences to bring people onto the farm
• The story behind the Cinnamon Toast Crunch cider collaboration supporting Feeding Tampa Bay
• What sustainability looks like on a working Florida farm
• How solar power, private wells, and operational independence play into the future of agriculture
• Why AI and technology are becoming part of modern farming
• What happens when kids growing up in Florida see a live chicken for the first time

This episode is a look at what happens when a business refuses to stay in one category.

Keel Farms is agriculture.
It is hospitality.
It is manufacturing.
It is tourism.
It is community.

And that combination is exactly why the story matters.

Whether you are a business owner, entrepreneur, farmer, leader, or someone interested in how Tampa Bay businesses are evolving, this conversation will challenge how you think about growth, adaptation, and building something people actually want to be part of.

Learn more about Keel Farms: KeelFarms.com

About the Show:Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox features real conversations with the entrepreneurs, builders, leaders, and changemakers shaping Tampa Bay. Each episode explores the wins, failures, pivots, and practical lessons behind building something that lasts.

In Part 2 of this conversation on Tommy’s Toolbox, Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, continues his sit-down with former Tampa Mayor Bob Buckhorn for a deeper look at the issues shaping Tampa’s future.

This episode moves beyond the personal origin story from Part 1 and gets into the real work of city leadership: infrastructure, transportation, permitting, housing affordability, culture, and the kind of public service that does not fit neatly into party politics.

Buckhorn explains why he “loved every single day” of being mayor, but also why leading a city means taking responsibility for problems most people do not see until they affect daily life.

Transportation is not just a commute issue.
Permitting is not just a paperwork issue.
Housing affordability is not just a market issue.

Together, they reveal whether a city is truly prepared for growth.

In this episode, you’ll hear:

• Why Buckhorn says being mayor was the best job he ever had
• What it means to lead from the front at a citywide level
• How a mayor sets culture across 4,500 employees
• Why Tampa’s transportation challenges are an economic issue, not just a traffic complaint

• How permitting delays can quietly add major costs to housing and development

• Why Tampa cannot afford to become another Atlanta
• The leadership philosophy behind “you just build a city”
• The quirky habit that helped Buckhorn understand Tampa better than most leaders

This conversation is about more than politics.

It is about whether Tampa can keep growing without losing what makes it work. It is about the decisions that shape neighborhoods, businesses, builders, commuters, and families. And it is about why leadership at the city level requires urgency, accountability, and a willingness to make hard calls before problems become impossible to ignore.

Whether you are a business owner, builder, voter, Tampa Bay resident, or someone who cares about the future of your city, this episode gives you a clear look at what leadership really looks like when the stakes are local and the impact is immediate.

If you missed Part 1, start there first for Buckhorn’s full backstory, including how failure, resilience, and early setbacks shaped the leader he became.

Follow Tommy’s Toolbox for more conversations with the leaders, builders, entrepreneurs, and changemakers shaping Tampa Bay.

About the Show:
Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions, Tommy’s Toolbox features real conversations on business, leadership, construction, community, and the future of Tampa Bay. Each episode is designed to give you practical insight, challenge your perspective, and help you understand the people and ideas shaping the region.