Leaders + Legends Podcast

Michael Calamaras

A podcast where killers of comfort zones come to talk shop. From CEOs and resilient entrepreneurs to athletes and outliers, we get into the real stories behind the wins - no fluff, no filters just real stories, real strategy, and real grit. It's raw insight on leadership, personal & business growth, mindset, and what it actually takes to dominate your field and your life. If you want the uncut playbook form people who are truly crushing it, if you're chasing success, building something big, or leveling up your life - join the hustle, join the community.

  1. May 1

    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 businessTransitioning from operator to business ownerChallenges in scaling a service-based businessBuilding a reputation in a local marketPersonal brand and content creationLaunching the Sarasota Speax podcastBusiness 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

    49 min

  2. Apr 10

    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/ Leaders + Legends: https://linktr.ee/leaderslegends #buildingbusinesses #makingmillions #miamihurricanes #businessownership #sellmybusiness #sellabusiness #buyabusiness

    47 min

  3. Feb 27

    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

    56 min

  4. Jan 2

    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 marketHow adversity can change your relationship with work and successLessons learned from sales, systems, and customer experienceThe difference between chasing growth and building something sustainableThis 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 ownershipHome services entrepreneurshipSarasota small business landscapeOvercoming adversity as a business ownerSales systems and local reputationLeadership 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

    1h 1m

  5. 09/03/2025

    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

    46 min

  6. 07/10/2025

    BEYOND TRADITION | Shelbi Loftin & Therese Johnson w/ Michael Calamaras

    In this episode of Leaders + Legends, we sit down with Shelbi Loftin and Therese Johnson, the powerhouse duo behind the Beyond Tradition Podcast. These two women are redefining what it means to grow a business—and a life—that breaks the mold. We dive into their entrepreneurial journeys, the real stories behind building bold brands, and how they balance ambition with authenticity. From the boardroom to personal breakthroughs, this conversation is filled with raw wisdom, plenty of laughs, and the kind of inspiration that’ll get you thinking bigger. Whether you’re a founder, creative, or someone tired of following “the rules,” this one’s for you.  Connect with Shelbi & Therese:  https://beyondtraditionpodcast.com  Topics Covered: Why “traditional” paths aren’t for everyonePersonal growth through business challengesFemale leadership in today’s landscapeHow to stay real while scaling bigAdvice for entrepreneurs embracing their own voice  #BeyondTradition #WomenInBusiness #Entrepreneurship #AuthenticLeadership #PersonalGrowth #BusinessPodcast #FemaleFounders #ShelbiLoftin #Therese #LeadersAndLegendsPodcast

    48 min

  7. 06/25/2025

    BEST FOOD CATERPRENEUR | Phil Mancini w/ Michael Calamaras

    On the menu for this episode, join Phil Mancini, thelegendary co-founder of Michael’s On East and one of the most beloved figures in Florida’s catering world, alongside Michael Calamaras, a Forbes-ranked financial planner andentrepreneur with a passion for people, planning, and purpose. This episode dives into the stories behind building aworld-class catering business — from the early days of washing dishes to serving presidents, celebrities, and generations of Sarasota families. Along the way, you’ll hear timeless lessons on business growth, client relationships,family dynamics, community service, and what it really takes to create a brand people love for life. This isn’t just about food. It’s about building somethingthat lasts.    About Phil Mancini: Phil is the co-founder of Michael’s On East and ahospitality icon in Southwest Florida. With over four decades in the industry, he’s known for creating unforgettable events and a catering empire rooted in excellence, integrity, and heart. He’s served everyone from everyday locals to U.S. presidents — and treats them all like family. www.bestfood.com   About Michael Calamaras: Michael is a financial planner, podcast host, and founder ofCalamaras Wealth Strategies, a boutique firm recognized by Forbes for three straight years. He’s also a proud father of three, a community connector, and a passionate interviewer who brings out the best in the people he sits down with. https://linktr.ee/leaderslegends   Catering podcast, hospitality business, food entrepreneur,Sarasota business, Phil Mancini, Michael’s On East, Best Food, event planning, small business podcast, building a business, family business, leadership podcast, restaurant podcast, Florida entrepreneurs, community leaders, cateringsuccess stories, Michael Calamaras podcast

    53 min

  8. 06/13/2025

    UNLOCKING ATHLETIC POTENTIAL | Dr. Michael Sclafani & Michael Calamaras

    In this powerful episode, we sit down with Michael Sclafani, founder of Tide Line Sports Performance, to go beyond just sports rehab and talk about the mindset, business strategy, and life lessons that come with building a performance-driven brand. Michael shares how he grew his sports performance and rehab facility from the ground up, the challenges of entrepreneurship in the fitness space, and what it really takes to build trust with elite athletes, youth clients, and everyday movers. We dive into:  How Michael built a performance brand rooted in results and relationships The overlap between athletic training and business growth The psychology of rehab and return-to-play Lessons in leadership, burnout, and balance Real stories from athletes, business owners, and weekend warriors Why mindset matters more than just mobility Whether you’re an athlete, entrepreneur, coach, or just someone looking to optimize your life, this episode is full of raw insights and real talk about what high performance really means—in sports, in business, and in life.  Topics Covered: Sports performance trainingInjury rehab and recoveryEntrepreneurship in fitnessBuilding a small business brandAthletic mindset and mental toughnessSarasota fitness and health community  Connect with Michael Sclafani: Website: tidelinesportsperformance.com Instagram: @tidelinesportsperformance YouTube / Spotify / Rumble: Search Tide Line Sports Performance #Businesspodcast #sportsperformance #sportsrehabilitation #mindset #businessgrowth #fitness #life #buildingthedream

    53 min
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Ratings & Reviews

5
out of 5
5 Ratings

About

A podcast where killers of comfort zones come to talk shop. From CEOs and resilient entrepreneurs to athletes and outliers, we get into the real stories behind the wins - no fluff, no filters just real stories, real strategy, and real grit. It's raw insight on leadership, personal & business growth, mindset, and what it actually takes to dominate your field and your life. If you want the uncut playbook form people who are truly crushing it, if you're chasing success, building something big, or leveling up your life - join the hustle, join the community.

Information

  • Creator
    Michael Calamaras
  • Years Active
    2024 - 2026
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © Michael Calamaras
  • Show Website
    Leaders + Legends Podcast