Tommy's Toolbox

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Aug 2026

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Get the latest on the construction industry … and have some fun doing it with the podcast version of the popular newsletter. Tommy’s Toolbox offers high-level information that can be understood and enjoyed by anyone seeking a foundational understanding of construction-related topics. The host, Tommy Whitehead, is the CEO of TomCo Solutions. TomCo is a full-service building, renovation and storm restoration contractor based in Tampa, Florida. Learn more about TomCo's construction services at www.tomcosolutions.com and get to know Tommy Whitehead at www.tommywhitehead.com.

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38 recent

September 10, 2026Episode 1823 min

This 120-Year-Old Restaurant Survived Everything — Here's His Secret Feat. Casey Gonzmart Jr.

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.

August 21, 202633 min

What happens to a city when the people telling its stories disappear feat. Ray Roa (Creative Loafing)

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.

August 13, 2026Episode 1627 min

Dara Shareef: What Business Owners Get Wrong When Selling Their Company

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.

July 9, 2026Episode 1538 min

45 Years of LGBTQ Business in Tampa Bay: The Stories Behind the Movement

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.

June 25, 2026Episode 1420 min

Amanda Payne: If You’re Not Evolving, You’re Dying

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.

June 18, 2026Episode 1324 min

From Blueberry Farm to Florida Agritourism Empire with Clay Keel of Keel Farms

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.

June 12, 2026Episode 1231 min

What does it actually take to lead a city after the cameras are off and the problems are still there? feat Bob Buckhorn

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.

June 11, 2026Episode 1125 min

What does it really take to lead a city through growth, pressure, failure, and constant criticism? feat. Bob Buckhorn

Before Bob Buckhorn became the mayor of Tampa, he arrived in the city at 22 years old with $300, a 15-year-old Dodge Dart with no air conditioning, and no clear path forward. Decades later, he was leading a $2 billion city. In this episode of Tommy’s Toolbox , Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , sits down with former Tampa Mayor Bob Buckhorn for a raw conversation about leadership, resilience, public service, and the failures that shaped his life. Buckhorn’s story doesn’t start with success. It starts with setbacks. A Navy discharge that crushed his original dream. Campaign losses that could have ended his political career. Moments where the only option was to get back up and keep going. But according to Buckhorn, those failures did not make him a victim. They made him a leader. In Part 1 of this conversation, Tommy and Bob unpack the lessons behind Buckhorn’s rise, from his childhood exposure to politics at Bobby Kennedy’s headquarters to his time playing Division I lacrosse at Penn State, where he developed the underdog work ethic that followed him into public life. This episode also gets into the practical realities of running a city, including what it takes to manage 4,500 employees, oversee a $2 billion budget, and make decisions that affect an entire community. You’ll hear: Why Buckhorn says he is a product of his failures, not a victim of them How early political exposure shaped his view of leadership and service The Navy misdiagnosis that changed the direction of his life What losing taught him before he ever won What it is actually like to run a major city government How he overhauled Tampa’s permitting process in 2011 Why he believes Tampa may need that kind of urgency again His perspective on Tampa’s housing affordability crisis and who should help solve it This conversation is about more than politics. It is about what leadership looks like when the stakes are real, when the pressure is public, and when failure becomes the training ground for everything that comes next. Whether you are a business owner navigating local government, a leader building your career, a contractor working in Tampa Bay, or someone who wants to better understand where the city has been and where it may be headed, this episode gives you a rare look inside the mindset of someone who helped shape modern Tampa. And this is only Part 1. Follow Tommy’s Toolbox for Part 2 and more conversations with leaders, builders, business owners, and changemakers who are shaping the future of Tampa Bay and beyond. About the Show: Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , Tommy’s Toolbox features real conversations on construction, business, leadership, and community impact. Each episode is designed to give you practical insight, challenge your perspective, and help you build smarter in work and in life.

May 28, 2026Episode 1024 min

Stop Using AI for Contracts Until You Hear This (A Lawyer’s Warning)

What if the contract you’re relying on is the very thing that puts you at risk? Most business owners are trying to move fast. Some are moving too fast… and skipping the steps that actually protect them. In this episode of Tommy’s Toolbox , Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , sits down with attorney Matt DePasquale of Porter Wright to break down the legal mistakes that quietly cost business owners time, money, and control. This conversation starts with real stories. A client sends a threatening email before a case even begins. Another skips the contract phase entirely and spends 18 months dealing with the fallout. And then there’s the growing trend… Business owners relying on AI tools and templated platforms to generate contracts without understanding what’s missing. Matt’s message is direct: The best time to call your lawyer is long before anything goes wrong. In this episode, you’ll start to understand: Why AI-generated contracts often miss critical protections The foundational legal documents every business should have in place How everyday communication, including emails, can be used against you Why proactive legal strategy is almost always less expensive than litigation The difference between a breach of contract and a criminal issue and why that distinction matters This isn’t about fear. It’s about awareness. Because most legal problems don’t start in a courtroom. They start in the decisions you make before anything ever happens. Matt also shares his unconventional path from a VH1 appearance as an aspiring actor to becoming a leading construction and litigation attorney, and how that experience shaped the way he communicates and advocates today. If you’re a business owner, contractor, or entrepreneur making decisions without legal guidance, this episode will challenge how you think about risk. About the Show: Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , Tommy’s Toolbox features real conversations on business, leadership, and real-world decision making. Each episode is designed to give you practical insights you can apply immediately.

May 21, 2026Episode 917 min

Why Qualified Candidates Still Don’t Get Hired (And What Recruiters Really Look For) feat. Tamara Galla

Why do strong candidates still get passed over… even when they look perfect on paper? Most job seekers think they know what matters in the hiring process. Most are wrong. In this episode of Tommy’s Toolbox , Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , sits down with Tamara Galla of PDI Connection, a top recruiter known for her no-nonsense approach to hiring, to break down what actually drives decisions behind the scenes. This conversation pulls back the curtain on how recruiters really evaluate candidates and why resumes, experience, and even strong interviews don’t always translate into offers. Tamara shares insights that most professionals never hear: Why strong resumes still fail to get attention The subtle mistakes candidates make in interviews that cost them opportunities What recruiters are actually looking for beyond qualifications How hiring decisions are made when multiple “qualified” candidates are on the table The disconnect between how candidates present themselves and how they’re perceived This isn’t just about job seekers. If you’re hiring, leading a team, or trying to build a stronger organization, this conversation will challenge how you think about talent, communication, and fit. Because the truth is… Getting hired isn’t just about being qualified. It’s about being understood. If you want to stand out in today’s job market or make better hiring decisions, this episode gives you a perspective most people never get access to. About the Show: Hosted by Tommy Whitehead, CEO of TomCo Solutions and Building Success Productions , Tommy’s Toolbox features real conversations on business, leadership, and career growth. Each episode is designed to give you practical insights you can apply immediately. #TommysToolbox #Hiring #Leadership #CareerGrowth #Recruiting