Leaders + Legends Podcast

Roofing, Reputation & Reach | Trey Martell & Michael Calamaras

What does it really take to grow a roofing business, build a brand, and create a life you actually want? In this episode of Leaders + Legends, host Michael Calamaras sits down with Trey Martell — owner of Strong Roofing and co-host of the Sarasota Speax podcast — to talk about the real, unfiltered journey behind building a service-based business. This conversation goes beyond roofing. Trey shares what it looks like to transition from working in the business to building a business — including the mindset shifts, challenges, and lessons that come with growth. From navigating early-stage hurdles to developing a reputation and standing out in a competitive market, this episode offers a grounded look at what it takes to move forward. Michael and Trey also discuss the launch of Sarasota Speax and why content, communication, and personal brand are becoming increasingly important for business owners. The conversation highlights how building a presence outside of your core service can create new opportunities and expand your network. Whether you’re in the trades, running a service business, or exploring your next move professionally, this episode focuses on practical insights around growth, consistency, and long-term thinking.  Topics Covered: * Growing a roofing business * Transitioning from operator to business owner * Challenges in scaling a service-based business * Building a reputation in a local market * Personal brand and content creation * Launching the Sarasota Speax podcast * Business growth and life balance roofing business, how to grow a roofing company, service business growth, contractor business tips, small business podcast, entrepreneurship podcast, personal brand building, local business marketing, trades business growth

MID-MARKET DEAL MAKING | David McCombie III & Michael Calamaras

In this episode Michael talks with David McCombie. David is an entrepreneur and dealmaker. He is founder and CEO of McCombie Group, an investment banking and M&A advisory firm guiding mid-market businesses to build, fund, and sell. To date, he has successfully closed billions in transactions. Unique amongst advisors, he has successfully led various private equity investments himself. David is author of “Selling Your Business with Confidence” published by Wiley. An ongoing contributor to Forbes regarding middle-market M&A and private equity, he also has been a featured speaker at various private equity conferences and has been profiled in the Wall Street Journal and Bloomberg. David is also an owner and board member of Atlantic Tractor, a John Deere dealership with 18 locations across Maryland, Delaware, and southern Pennsylvania. He is an active member of Young Presidents Organization (YPO) and serves as Membership Chair of the Miami chapter. Prior to founding McCombie Group in 2010, David was a management consultant at McKinsey & Company and an investment banker at Citigroup Global Banking in New York. David graduated from Harvard Law School where he focused on corporate law and negotiation strategy, and also did extensive coursework in corporate finance at the Harvard Business School. His thesis, ‘Hispanic Private Equity- A Cultural Approach to Achieving Superior Investment Returns’ was published in the Harvard Latino Law Review. He graduated Phi Beta Kappa from the University of Miami with a degree in economics and finance, where he was a Cuban American National Foundation Mas Scholar. A proud Cane, he taught FIN499, a private equity course, as an adjunct professor at the University of Miami and now serves as a Finance department advisory board member and an executive committee member of the Citizens Board. David is also a licensed Florida attorney and real estate broker. David's Website: https://www.mccombiegroup.com/ [https://www.mccombiegroup.com/] Leaders + Legends: https://linktr.ee/leaderslegends [https://linktr.ee/leaderslegends?utm_source=linktree_profile_share<sid=85fd1423-f2cd-4b7c-adca-64a0af183267] #buildingbusinesses #makingmillions #miamihurricanes #businessownership #sellmybusiness #sellabusiness #buyabusiness

XWERKS & Ecommerce | Mike Kolb & Michael Calamaras

In this episode Michael talks with Mike Kolb the founder of XWERKS. Michael and Mike share similar passions of CrossFit, Car Racing, and enjoying life! Mike founded XWERKS, a sports nutrition company launched in 2014. Based in Lakewood Ranch, he leads his brand focused on performance driven supplements for athletes and fitness enthusiasts, with an emphasis on quality and transparency. XWERKS: https://xwerks.com/ Find Leaders + Legends on Social Media: https://linktr.ee/leaderslegends #podcast #sportsnutrition #ecommercebrands #buildinganecommerce

CONQUERING ADVERSITY | Joey Coco & Michael Calamaras

In this episode of Leaders + Legends, host Michael Calamaras sits down with Joey Coco, a Sarasota-based business owner and Budget Blinds franchise owner, for a powerful conversation about entrepreneurship, resilience, and perspective. Joey shares his journey into franchise ownership in the home-services industry, along with how personal adversity reshaped the way he approaches business, leadership, and life. Joey opens up about surviving a serious car accident that changed his life - how it tested him physically, mentally, and emotionally. Rather than defining him, the experience became a catalyst—sharpening his focus, gratitude, and commitment to building something meaningful. This episode explores: * What it’s really like running a service-based business in a local market * How adversity can change your relationship with work and success * Lessons learned from sales, systems, and customer experience * The difference between chasing growth and building something sustainable This conversation is equal parts business strategy and human story—valuable for anyone building a company, facing setbacks, or recalibrating what success truly means.  Topics Covered * Budget Blinds franchise ownership * Home services entrepreneurship * Sarasota small business landscape * Overcoming adversity as a business owner * Sales systems and local reputation * Leadership through hardship  About Leaders + Legends Leaders + Legends is a podcast featuring candid conversations with business owners, executives, and entrepreneurs navigating growth, risk, and real-world challenges. Hosted by Michael Calamaras, the show highlights the stories behind the success. Joey Coco Sarasota Budget Blinds Sarasota Budget Blinds franchise owner Home services business owner Entrepreneur resilience story Small business podcast Franchise ownership podcast Leaders and Legends podcast

WIFE, MOTHER, MENTOR | Krystal Roberts w/ Michael Calamaras

In this episode of Leaders + Legends, we sit down with Krystal Roberts, a wife, mother, mentor, and trusted health advisor with USHEALTH Advisors. Krystal’s story is one of balancing business success with family values. As a wife and proud mom, she understands firsthand the importance of protecting what matters most. That perspective has fueled her career in insurance—helping families, individuals, and small business owners find affordable and reliable coverage that truly fits their lives. But Krystal’s influence doesn’t stop with her clients. As a mentor and team leader, she has dedicated herself to guiding new agents, sharing the lessons she’s learned, and building a culture of encouragement and growth within her team. Her leadership style blends compassion with accountability, showing that success in business can go hand-in-hand with kindness and integrity. In this conversation, we explore how Krystal integrates family, mentorship, and entrepreneurship into a life that inspires others to lead with purpose—both at home and in business. Krystal's Links: https://www.linkedin.com/in/krystal-roberts https://www.ushagent.com/krystalroberts https://www.instagram.com/mrsk.roberts Michael's Links: https://linktr.ee/leaderslegends #business #mentorship #entrepreneur #family #mother #wife #worklifebalance #growthmindset