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 to business mindset, this episode offers practical takeaways for anyone looking to build something lasting—from the inside out.

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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 become a better leader, Brendon’s blend of humility, strategy, and real talk offers practical insights you can apply right away.

What You’ll Learn in This Episode:

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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. Packed with wisdom, humor, and hard-won perspective, this episode is a must-listen for anyone navigating growth in a creative or people-focused industry.

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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 lead with greater clarity, integrity, and confidence.

What You’ll Learn in Season 5:

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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 managing celebrity clients and leading through rapid growth, this conversation is full of insight for any founder or creative entrepreneur looking to grow a business with intention.

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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 service, faith, and family—and how intentionality, personal growth, and a commitment to quality have helped him stay grounded while growing something big.

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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 biohacking, this conversation explores what it really means to care for yourself as the CEO of your life—and why taking care of your body and mind is key to scaling sustainably.

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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 innovation. From the power of community to the importance of sleep for leadership and decision-making, this conversation connects the dots between physical health, mindset, and long-term success.

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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 and dream analyzers, this conversation is a treasure trove of creativity, tech, and entrepreneurial grit. If you're curious about the future of innovation and how to harness AI even without a coding background, this episode is your launchpad.

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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 the power of saying “no,” this conversation is a masterclass in leading with purpose and playing the long game in an industry that rarely slows down.

What You’ll Learn in This Episode:

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