Well Coached with Chris Weinberg

Well Coached with Chris Weinberg

Welcome to Well Coached — the podcast that guides entrepreneurs to scale their businesses while preserving their freedom and authenticity. I'm Chris Weinberg, your host and fellow entrepreneur, here to share inspiring stories and practical strategies across four key pillars: People, Sales, Profits, and Self. Whether you're a seasoned entrepreneur or just starting out, this podcast offers actionable advice to help you thrive without sacrificing your entrepreneurial spirit. Together, we'll unlock the potential within you to build a business that's both profitable and purpose-driven. Join me as we explore the journeys of entrepreneurs who've struck the perfect balance between structure and creativity, growth and authenticity. From navigating challenges to seizing opportunities, we uncover the insights that fuel success in business and life. So, tune in to 'Well Coached' and let's embark on this journey together. Because in the world of entrepreneurship, finding the sweet spot between structure and freedom is the key to unlocking your true potential. Looking for a business coach? I would love to be yours! Connect with me here!

Episodes

September 23, 2025 65 mins
In this episode of Well Coached, Chris sits down with Stephen Richards, Jr., founder of Richards Bespoke, a custom suit company built on timeless design, intentional leadership, and a commitment to quality. Stephen shares the story behind launching his brand, the values that drive him, and how a focus on discipline, customer relationships, and long-term thinking has helped him grow in a competitive industry. From personal rituals t...
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In this episode of Well Coached, Chris Weinberg sits down with Brendon Donelson, a seasoned mortgage executive and coach, to unpack what it takes to lead in a high-stakes, high-pressure industry. Brendon shares how he scaled a successful mortgage company, the importance of emotional intelligence in leadership, and why coaching is the secret weapon in both sales and life. Whether you're in the mortgage world or simply striving to be...
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In this episode of Well Coached, Chris Weinberg sits down with Jennie Smythe, Founder and CEO of Girlilla Marketing, to explore the mindset and leadership strategies that have allowed her to build a dynamic career at the intersection of marketing, music, and media. Jennie speaks candidly about how values like boundaries, curiosity, and trust have shaped her personal leadership style—and why your career can evolve as often as you do...
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Business coach and host Chris Weinberg returns for Season 5 of Well Coached, launching September 9th. This season dives deeper into the four foundational pillars of a well-run business: People, Sales, Profit, and Self, through real-world conversations with entrepreneurs who’ve put these principles into action. From marketing and real estate to addiction recovery and journalism, each episode will challenge, equip, and inspire you to...
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In this episode of Well Coached, Chris sits down with Lisa Field Armstrong, co-founder of BRND House, to explore how she and her business partner built a boutique creative agency in Nashville—and sold it in a multi-million dollar deal just four years later. Lisa shares candid lessons about partnership, leadership, and staying rooted in your values while scaling quickly. From the early days of working with scrappy startups to managi...
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In this inspiring episode of Well Coached, Chris Weinberg sits down with Justin Kershaw—a former athlete, father of five, and co-founder of So Strong Foods, a mission-driven snack brand he built alongside his wife, Shakira. Justin shares how they went from making snacks in their basement kitchen to getting on shelves across the country. He opens up about the challenges, wins, and lessons learned while building a brand grounded in s...
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In this empowering episode of Well Coached, Chris welcomes Dr. Alec Dragelin, a concierge physician who works with high-performing entrepreneurs to redefine self-care and optimize well-being. Drawing from his unique medical practice that blends personal coaching with proactive health management, Dr. Dragelin shares how the most successful leaders he works with prioritize sleep, recovery, mental health, and purpose. From burnout to ...
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In this energizing episode of Well Coached, Chris sits down with Todd Anderson, former NFL athlete turned entrepreneur and founder of Dream Recovery, to talk about the intersection of wellness, performance, and business. Todd shares his journey from walk-on college athlete to NFL player to health entrepreneur, revealing how his passion for recovery, sleep, and optimization led to building a brand rooted in science, trust, and innov...
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In this energetic and forward-thinking episode, Chris sits down with creative strategist Allister Hercus, co-founder of Lab31—a month-long experiment where he built a new AI-powered tool every day for 31 days. Allister shares the origin of the project, the lessons learned from rapid prototyping, and why he believes AI isn’t something to fear—it’s something to play with. From teacher report card generators to real estate video tools...
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In this reflective episode of Well Coached, Chris sits down with veteran artist manager Anthony Piedmonte, whose decades-long career has included managing global icons like Chris Tomlin and working with Bon Jovi. Anthony shares how trust, loyalty, and personal alignment drive his leadership style—and how building long-term careers starts with protecting the artist’s creative spirit. From the challenges of burnout and fatherhood to ...
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In this high-energy episode of Well Coached, Chris sits down with Coach Michael Burt, the former championship basketball coach turned business strategist behind The Greatness Factory. Coach Burt breaks down his signature concept of "prey drive"—the instinct to pursue what you want with intensity—and how to activate it in yourself and your team. He shares lessons from coaching elite athletes, working with high-performing entrepreneu...
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In this episode of Well Coached, Chris sits down with Charly Salvatore, founder of Underscore Works, to talk about the long game of artist development. From spotting talent in small-town bars to breaking artists, Charly shares his philosophy on building trust, leading with empathy, and cultivating work ethic. You’ll hear how his DISC profile as a High S leader helps shape his steady, people-first approach in a fast-paced industry. ...
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In this incredibly inspiring episode of Well Coached, bestselling author and speaker Mary Marantz joins Chris to talk about her journey from a single-wide trailer in rural West Virginia to Yale Law School and beyond. Mary unpacks how her new book Underestimated calls women to stop shrinking themselves to fit a story they’ve outgrown. With grace, grit, and wisdom, she shares what it means to own your story—especially the hard parts—...
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In this episode of Well Coached, Chris sits down with music industry powerhouse Kelli Haywood—founder of KCH Entertainment and co-founder of the That Sounds Fun Network and H Squared Management. From building major artist brands to steering emerging voices, Kelli shares the mindset, clarity, and conviction required to succeed in today’s saturated market. You’ll hear stories of pivoting, partnering, and pushing through challenges—al...
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Season 4 of Well Coached is here—and this time, it’s all about inspiring, creative entrepreneurs who are building brands, leading teams, and redefining success. Join Chris Weinberg as he dives into powerful conversations rooted in the four pillars that drive everything: people, sales, profit, and self. Expect honest stories, actionable strategy, and leadership tools like DISC, emotional intelligence, and situational leadership. Thi...
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In this episode of Well Coached, Chris Weinberg unpacks how to build a feedback-rich culture using emotional intelligence (EQ). From navigating tough conversations to celebrating small wins, feedback—when delivered well—becomes a catalyst for growth, trust, and performance. Chris breaks down how to give feedback that’s specific, timely, and constructive, and how to receive it without defensiveness. With practical tools like the SBI...
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In this episode of Well Coached, Chris Weinberg breaks down the overlooked superpower in any high-stakes conversation: emotional intelligence. Whether you're negotiating a deal, structuring a compensation package, or just trying to get buy-in, it's not just what you say—it’s how you make the other person feel. Chris unpacks the four components of emotional intelligence and how to use them to read the room, manage your own emotions,...
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In this episode of Well Coached, Chris Weinberg dives deep into how mastering the DISC personality profile can unlock your team’s full potential. Great teams aren’t just about skills—they’re about communication, collaboration, and understanding how people tick. Chris breaks down each DISC type and shows you how to use this powerful tool to build a team where everyone thrives. From role alignment to conflict resolution, you'll learn...
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Episode Summary: In this episode of Well Coached, Chris Weinberg breaks down how great leaders navigate crises using the power of situational leadership. From unexpected challenges like COVID to everyday organizational curveballs, Chris explores how adaptive leadership, clear communication, and emotional regulation can help you lead your team through turbulent times. With real-world examples and tactical advice, this episode is a m...
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In this episode of Well Coached, Chris Weinberg sits down with legendary Nashville developer Tony Giarratana, whose name is synonymous with vision, grit, and transformation. With nearly four decades of urban development experience, Tony shares the philosophy, patience, and long-game thinking it takes to reshape a city—building iconic skyscrapers, preserving beloved historical spaces, and navigating the complexities of public-privat...
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