A layoff in the Great Recession pushed him out of hospitality and into thousands of renovation projects—now he’s building homes, communities, and entrepreneurs across Tampa Bay. In this episode, discover how he uses construction, strategic networking, and large‑scale events to create lasting impact and opportunity.

In this episode, Leonard and Tommy Whitehead discuss:

● Transition from finance and hospitality into construction and development

● ADUs, affordable housing, and Florida’s evolving regulations

● Disaster renovation, floodplains, and long-term real estate plays

● Leadership, hiring, and building an executive team for growth

● Community impact, networking strategy, and the Building Success Summit

Key Takeaways:

● Career pivots often start in crisis: unemployment during the Great Recession led to thousands of renovation projects and ultimately a thriving construction firm.

● Accessory Dwelling Units are becoming a critical tool for affordability, multi‑generational living, and rental income, but they live and die by local zoning and regulation.

● Reputation is built less by ads and more by visible community contribution, from nonprofit partnerships to hosting high‑value networking events without expecting an immediate return.

● Trying to save money by skipping professionals—accountants, attorneys, permits, inspections—almost always creates bigger, more expensive problems down the road.

● Over‑customizing a property and making emotional renovation decisions can crush resale value; smart owners run the numbers first and design with the next buyer in mind.

“You're your number one fan, and you're your number one obstacle.” - Tommy Whitehead

About Tommy Whitehead: Tommy is the Founder and CEO of TomCo Solutions, a rapidly growing design-build construction firm focused on innovative housing solutions, including custom builds, renovations, and accessory dwelling units (ADUs). A recognized leader in the Tampa Bay business community, Tommy is also the founder of the Building Success Summit and author of the Amazon Best-Selling book Building Success: A Toolbox for Coming Out On Top. With a passion for entrepreneurship, economic empowerment, and community impact, Tommy has built multiple ventures spanning construction, real estate development, and business education. His work blends practical industry expertise with thought leadership, helping others scale their businesses and build lasting success.

Connect with Tommy Whitehead:

Website: https://tommywhitehead.com/

LinkedIn: https://www.linkedin.com/in/tommywhitehead/

Facebook TomCo: https://www.facebook.com/TomCoSolutions

Connect with Leonard Raskin:

Website: https://www.raskinglobal.com/

LinkedIn: https://www.linkedin.com/in/leonardraskin/

Facebook: https://www.facebook.com/RaskinGlobal

Email: lraskin@raskinglobal.com

Show notes by Podcastologist: Francine Poblete

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.