The Playbook

In today’s episode, I sit down with Captain Glenn Shephard, television personality and longtime superyacht captain best known for Below Deck Sailing Yacht . Glenn shares how an unexpected opportunity brought him to reality television, what it feels like to be recognized, and why the show’s most memorable moments are rooted in real events. We discuss leadership, managing ego, making calculated deci...

In today’s episode, I sit down with Jack Canfield, co-creator of the Chicken Soup for the Soul series and author of The Success Principles , to discuss intention, persistence, and lifelong impact. Jack shares how teaching struggling students introduced him to goal-setting, visualization, affirmations, action, and feedback. We talk about overcoming 143 publishing rejections, creating demand before...

In today’s episode, I share six lessons for turning problems into possibilities by creating clarity, removing interference, and focusing on what actually moves the needle. I explain how questioning assumptions, staying curious, learning from others, and testing and adjusting your approach can help you find what works. Most importantly, I share why letting go of the need to be right or in control a...

In today’s episode, I sit down with Genetic Lifespan founder and CEO Adam Vincent Gilmer and Tony Drexel Smith, managing director of Micro Venture Capital Fund and managing member of The Stirling Club. We discuss why character, integrity, loyalty, faith, and keeping your word remain essential as technology accelerates business. Tony explains why simplicity, patience, and knowing when to pivot help...

In today’s episode, I sit down with world champion skimboarder and Marshwater founder Austin Keen to discuss the consistency, patience, and intuition behind his success. Austin shares how his blue collar upbringing shaped his work ethic, why mastering any craft requires a willingness to endure setbacks, and how he turned a connection to the Southern marshlands into a growing business. We also talk...

In today’s episode, I sit down with Barry Oberholzer, an entrepreneur, former intelligence operative, licensed helicopter pilot, and host of The Flying Felon . Barry shares how his experience in prison inspired him to build a platform centered on redemption, accountability, and the lessons found in failure. We discuss how interviewing celebrities in a helicopter encourages vulnerability, helping g...

In today’s episode, I sit down with Brian Rose, an American-British podcaster, political candidate, former banker, and founder of London Real. Brian shares why he walked away from a lucrative banking career to build a media company before podcasting and personal brands became mainstream. We discuss overcoming the fear of other people’s opinions, improving through consistent action, and creating la...

In today’s episode, I sit down with Dave Portnoy, the American businessman behind Barstool Sports, to talk about building a media company from the ground up. Dave shares how he left a stable sales career, launched Barstool as a free newspaper, and handled nearly every part of the business himself. We discuss hard work, timing, audience loyalty, brand voice, scaling without losing identity, and why...

In today’s episode, I sit down with Joe Hart, President and CEO of Dale Carnegie and coauthor of Take Command , to discuss intentionality, relationships, resilience, and transformational leadership. Joe explains why taking command begins with creating space to consider what we want, what is working, and what needs to change. We talk about strengthening relationships by accepting responsibility for...

In today’s episode, I share six lessons to help you accelerate your potential by choosing action over indecision, abundance over scarcity, and purpose over pain. I explain how to turn the fear of other people’s opinions into joy, control the meaning you give to your experiences, and move through fear, doubt, and uncertainty. Most importantly, I share how consistent, non-negotiable behaviors aligne...

In today’s episode, I sit down with Blake Mycoskie, founder of TOMS and ENOUGH, host of No Magic Pill, and co-founder of Morning Water and Moovlab. Blake shares how TOMS grew from a simple idea into a global giving movement, then opens up about the depression and isolation he experienced after selling the company. We discuss the achievement myth, separating self-worth from external success, and th...

In today’s episode, I sit down with Kishore Lulla, founder and chairman of Eros Innovation, to discuss how culture, ethics, and human experience can shape the next era of artificial intelligence. Kishore explains why AI should be viewed as an assistant that expands human potential, rather than a replacement for human judgment. We explore sovereign AI, culturally trained models, and the responsibil...

In today’s episode, I sit down with Leonardo Leao, CEO of Leao Group, to discuss global mobility, self-image, and the freedom created by expanding beyond familiar borders. Leonardo shares how leaving a stable career in Brazil reshaped his understanding of opportunity and inspired his work helping others build lives across multiple countries. We talk about aligning immigration, taxes, education, ca...

In today’s episode, I sit down with tax strategist, author, and entrepreneur Courtney Epps, founder of OTB Tax and Tax Rebels, to talk about building lasting wealth through smart tax planning, business ownership, and real estate investing. We discuss practical strategies like hiring your children, using short term rental tax benefits, and creating generational wealth by working within the tax code...

In today’s episode, I sit down with former NBA players Tarik Black and CJ Miles to discuss storytelling, authenticity, mentorship, and the transition from professional basketball into new pursuits. CJ explains why the best storytellers must live the story first and how years on the court shaped his creative work as a writer and photographer. Tarik shares lessons from Kobe Bryant, including how pur...

In today’s episode, I sit down with entrepreneur, bestselling author, and real estate industry leader Ryan Serhant to talk about building a career by pursuing success instead of clinging to a single path. Ryan shares how adapting to new opportunities helped him grow from aspiring actor to leading one of the most recognizable real estate brands in the world. We also discuss why social media has bec...

In today’s episode, I break down the difference between being nice and being kind, and why choosing truth over approval can transform the way we lead and communicate. I share how to serve others through honest conversations, set boundaries with confidence, and use empathy, accountability, and courage to create better outcomes for everyone. To join my next free Friday Training sessions, email me at...

In today’s episode, I sit down with Pro Football Hall of Famer Ray Lewis to discuss the principles that guide his life beyond the field. Ray shares how faith, kindness, and service shaped him from childhood and continue to define his approach to leadership. We talk about beginning each morning with prayer, refusing to let critics dictate your identity, and surrounding yourself with people who elev...

In today’s episode, I join Rebecca Whitman, magnetic abundance mentor, keynote speaker, and host of the globally ranked Balanced, Beautiful & Abundant podcast, for a conversation about building success without sacrificing your values. We discuss why long-term relationships matter more than short-term wins, how to recognize toxic business partnerships, and why kindness remains a competitive adv...

In today’s episode, I sit down with Canadian author and personal development pioneer Bob Proctor to talk about the mindset shifts that transformed his life. Bob shares how a single mentor, a copy of Think and Grow Rich , and a commitment to repetition helped him go from struggling financially to building a multimillion dollar business. We discuss the power of belief, why paradigms shape our behavi...

In today’s episode, I sit down with Blaine Bartlett to discuss the danger of measuring the wrong things in business and leadership. We break down why revenue, quarterly performance, and dashboards only tell part of the story, while trust, engagement, loyalty, culture, and communication shape long-term success. Blaine explains the difference between leading and lagging indicators, the value of meas...

In today’s episode, I sit down with FUBU founder, Shark Tank investor, and business executive Daymond John to discuss the value of building a personal brand rooted in wisdom, service, and humility. Daymond explains why adding value to others creates lasting opportunities and how leaders can use their unique perspective to stand out in a world where information is readily available. We also discuss...

In today’s episode, I sit down with Pro Football Hall of Famer Nick Lowery, one of the most accomplished kickers in NFL history, to talk about the mindset that helped him overcome rejection, pressure, and adversity at the highest level. Nick shares why getting cut by 11 teams became the foundation for his success, how persistence creates confidence, and why mistakes are opportunities instead of se...

In today’s episode, I break down the five expenditures that determine your business's success and why emotional expenditure is the one most leaders overlook. I share how mastering your emotions, making intentional decisions, and using my Cancel, Clear, Connect framework can help you eliminate hidden costs, create greater value, and build a business aligned with your purpose. To join my next free F...

In today’s episode, I sit down with Ryan Serhant, founder and CEO of SERHANT, to talk about the mindset behind building a successful career, brand, and business. We discuss how manual labor shaped his work ethic, why empathy creates stronger client relationships, and how rejection can become one of your greatest competitive advantages. Ryan shares his approach to handling difficult negotiations, m...