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Well Coached with Chris Weinberg
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Well Coached with Chris Weinberg

Author: Chris Weinberg

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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!

70 Episodes
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In this episode of Well Coached, Chris Weinberg sits down with Brittany Schaffer for a conversation about transferable skill sets, reinvention, and leading with vision across very different environments. Brittany shares her career path from entertainment law in Los Angeles, to building and leading teams at Spotify, to her current role as Dean of Belmont University’s Curb College of Entertainment and Music. Together, they unpack what stayed consistent as her titles changed: big picture thinking, relationship building, and the ability to lead through influence rather than authority. Through the People, Sales, Profit, Self lens, Brittany breaks down how her leadership style evolved, what Spotify taught her about difficult conversations and leading up the org chart, and how she’s brought just corporate enough structure into academia without losing creativity. They also dive into how universities communicate their value in a way that aligns with mission, and Brittany shares an initiative she’s passionate about: the Center for Mental Health and Entertainment, designed to help create a healthier, more sustainable industry ecosystem. What You’ll Learn in This Episode: How to build a leadership identity that transfers across industries and titles What Brittany learned at Spotify about feedback, hard conversations, and leading up How to bring structure into creative environments without killing creativity Why mental health is becoming a core leadership and sustainability issue in entertainment Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg sits down with Nikki Boon of Neon Coast for an inside look at what it really takes to build an artist career in today’s creator economy. Nikki shares how she worked her way from Michigan to Nashville, got her start in touring, and grew into artist management - where her job is equal parts vision, strategy, relationship building, and execution. Through the People, Sales, Profit, and Self framework, Nikki breaks down how strong teams keep artists in their highest productivity zone, how fan connection drives real business results, and how creative brand building turns into measurable opportunities. From smart community moves to unexpected brand partnerships and tour problem solving, this conversation is a practical masterclass in leadership, communication, and scaling without losing the human side. What You’ll Learn in This Episode How Nikki builds and supports teams that keep artists focused, productive, and growing Why community and storytelling sell better than constant promotion How artists create revenue through brand partnerships and strategic touring decisions How Nikki stays grounded in a high pressure, high travel industry Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg sits down with Stacy Richter, CEO of Live Lingua, to unpack why communication is quickly becoming one of the most important competitive advantages in a borderless economy. Stacy shares his path from leading major brand accounts in the agency world to building a business focused on business driven, ROI focused language training. Together, they explore how language proficiency and cultural intelligence build trust faster, reduce friction on global teams, and improve outcomes in sales, collaboration, and leadership. They also dig into where AI helps and where it falls short, especially when nuance, relationship, and real human connection are required.  What You’ll Learn in This Episode Why cultural intelligence matters as much as language fluency in global leadership Where leaders underestimate the human side of cross border collaboration How language training can drive measurable ROI through speed, trust, and productivity How to think about AI powered communication tools without outsourcing relationship building Learn more about your ad choices. Visit megaphone.fm/adchoices
Season 7 of Well Coached launches February 24th, and this season is all about leading and scaling without losing your humanity. In this trailer, Chris Weinberg shares what’s ahead: conversations with founders, creatives, legal minds, operators, and leadership experts who are building strong, sustainable businesses rooted in both structure and soul. If you’re done choosing between professionalism and authenticity - and ready to build something deeply human - this season is for you. Follow now so you don’t miss the first episode. Learn more about your ad choices. Visit megaphone.fm/adchoices
In this solo episode, Chris Weinberg takes you backstage into the world of music empires to reveal how artists, managers, and labels scale careers, and what small business owners can learn from their playbook. Whether you’re building a brand, a business, or a legacy, the same success principles apply. Looking through the lens of People, Sales, Profit, and Self, Chris shares real-life takeaways from the artist world that translate directly to entrepreneurship. From building the right team to protecting your energy, this episode will inspire you to scale with purpose—and maybe even think like a mogul. What You’ll Learn in This Episode: How artists build strategic teams—and why your business should too The power of nurturing your warm leads instead of chasing cold ones How to create layered revenue streams that feed your primary business Why protecting your energy is one of the highest forms of leadership Learn more about your ad choices. Visit megaphone.fm/adchoices
Behind every hit song is a crew of unsung heroes, and the same is true for every thriving business. In this solo episode, Chris Weinberg pulls back the curtain on the "hidden team" that powers success, drawing parallels between music industry tour teams and the behind-the-scenes talent in your business. Through the typical lens of People, Sales, Profit, and Self, Chris shares what it really takes to build loyalty, delegate with trust, and lead in a way that drives long-term performance. Whether you're managing two people or twenty, this episode is your reminder that investing in your team is one of the smartest business decisions you can make. What You Will Learn in This Episode How to identify and elevate the hidden team roles in your business Why leadership language matters The high cost of turnover and how to avoid it Why letting go of control is actually a power move for growth Learn more about your ad choices. Visit megaphone.fm/adchoices
In this AMA-style solo episode, Chris answers listener-submitted questions about work-life rhythm, team dynamics, and his own journey with burnout and business ownership. Candid, unfiltered, and full of takeaways, this episode is a window into the real conversations founders and leaders are having but don’t always say out loud. What You'll Learn in This Episode: How Chris manages personal boundaries in a high-demand business The balance between being present and being ambitious How to handle feeling overcommitted (and what to do about it) Advice for those questioning if the entrepreneurial path is still right for them Please donate today at ⁠⁠MercyShips.org/podcast⁠⁠⁠⁠2:40⁠⁠ Visit ⁠⁠OmahaSteaks.com⁠⁠ for 50% off sitewide during their Sizzle All the Way Sale. And for an extra $35 off, use promo code FUN at checkout! Learn more about your ad choices. Visit megaphone.fm/adchoices
My 2025 Reflections

My 2025 Reflections

2025-12-3009:03

Chris looks back at his own personal and professional growth in 2025; sharing the unexpected lessons, hard-won insights, and the quiet realizations that changed everything. It’s a vulnerable, honest snapshot of life behind the scenes of Well Coached, and a call to slow down and notice what’s shaping us. What You'll Learn in This Episode: How emotional awareness makes you a better entrepreneur The tension between building and being present Why 2025 felt like a threshold year, and what that means The case for slowing down to move forward Please donate today at ⁠MercyShips.org/podcast⁠⁠2:40⁠ Visit ⁠OmahaSteaks.com⁠ for 50% off sitewide during their Sizzle All the Way Sale. And for an extra $35 off, use promo code FUN at checkout! Learn more about your ad choices. Visit megaphone.fm/adchoices
In this reflective and personal episode, Chris invites listeners to consider what 2025 revealed about their habits, beliefs, and patterns. Leadership starts with self-awareness, and this conversation explores the emotional, mental, and behavioral lessons that shaped how we lead ourselves this year. What You'll Learn in This Episode: How identity and leadership intersect Why rest and margin are performance tools, not luxuries The cost of staying busy to avoid discomfort What it means to show up for yourself in 2026 Please donate today at ⁠MercyShips.org/podcast⁠⁠2:40⁠ Visit ⁠OmahaSteaks.com⁠ for 50% off sitewide during their Sizzle All the Way Sale. And for an extra $35 off, use promo code FUN at checkout! Learn more about your ad choices. Visit megaphone.fm/adchoices
Profit isn’t just about revenue, it’s about how well your business can run without you. In this solo episode, Chris walks through the most powerful shifts business owners made in 2025 to increase value, reduce chaos, and build a business that’s actually worth something. If you’ve been stuck in survival mode, this one’s for you. What You'll Learn in This Episode: What makes a business "valuable" beyond profit margins Why profit follows structure, not just hustle How to design for healthy delegation and scalability Simple metrics that helped business owners sleep better in 2025 Learn more about your ad choices. Visit megaphone.fm/adchoices
Sales in 2025 wasn’t just about closing deals, it was about consistency, simplicity, and the long game. In this episode, Chris breaks down what actually worked in sales this year and what fell flat. Whether you’re a founder, seller, or operator, this is a candid debrief on systems, strategies, and selling with integrity. What You'll Learn in This Episode: Why the sales cycle is really a trust cycle What to do when marketing lags behind the product The difference between selling to survive vs. selling to scale How to stop overcomplicating your sales process Please donate today at MercyShips.org/podcast2:40 Visit OmahaSteaks.com for 50% off sitewide during their Sizzle All the Way Sale. And for an extra $35 off, use promo code FUN at checkout! Learn more about your ad choices. Visit megaphone.fm/adchoices
In this reflection episode, Chris Weinberg explores what made 2025 a defining year for leadership development. From rethinking team structure to learning how to truly listen, he unpacks the most meaningful lessons around building high-trust teams and leading through clarity. If you want to elevate how you show up for others, this episode is your starting point. What You'll Learn in This Episode: How letting go of people-pleasing creates stronger leadership Why listening is your most underrated leadership skill What made great teams work (and not work) in 2025 The difference between being likable and being trusted Please donate today at ⁠MercyShips.org/podcast⁠⁠2:40⁠ Visit ⁠OmahaSteaks.com⁠ for 50% off sitewide during their Sizzle All the Way Sale. And for an extra $35 off, use promo code FUN at checkout! Learn more about your ad choices. Visit megaphone.fm/adchoices
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: The role of coaching in driving sales and team development How emotional intelligence builds better leaders and stronger culture Strategies for scaling a business without losing your people Why your mindset matters more than the market Interested in advertising on this show? Learn more here! Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg is joined by John Chisum, a seasoned veteran in the Christian music space. With a career spanning over 40 years, John has worked with iconic names such as Bill and Gloria Gaither and served as the VP of publishing at Integrity Music. He’s now the founder of Nashville Christian Songwriters, a platform that equips and uplifts Christian songwriters. John shares his journey from early struggles in the music industry to building a successful business focused on songwriting, artist development, and coaching. This episode explores themes of resilience, overcoming challenges, and the balance between ministry and business success, all while fostering the creative development of others. What you will learn in this episode: How John helps songwriters turn passion into excellence and overcome creative blocks The evolution of the Christian music industry and how digital platforms have changed the game John’s approach to balancing ministry with profitability in a faith-based business The role of a supportive partner and self-care in maintaining a successful career and personal health Learn more about your ad choices. Visit megaphone.fm/adchoices
Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg interviews Wendy Whittemore, a pioneering figure in aerial and ground photography since 2003. Wendy shares her entrepreneurial journey, detailing how her high D personality on the DISC profile and a resilient spirit have helped her scale Aerial Innovation Southeast across multiple cities. She provides valuable insights into building a cohesive photography team, maintaining strong company culture, and leveraging drone technology to stand out in a competitive market. What You Will Learn in This Episode: Wendy Whittemore's journey as a trailblazer in the aerial and ground photography industry. The role of her entrepreneurial spirit and high D DISC profile in scaling her business. Strategies for building a cohesive photography team while maintaining a strong company culture across locations. The importance of the DISC profile in hiring and fostering shared values within teams. Insights into the dynamic photography and drone industry and differentiating services in a competitive market. Techniques for maintaining long-term client relationships and a strong market presence. Wendy's approaches to work-life balance, motivation, and mentoring the next generation of photographers. Strategies for profitability amidst technological evolution and market demands, including sustainable pricing and diversified revenue streams. Encouragement for aspiring photographers to embrace opportunities in the industry despite competition. Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, host Chris Weinberg dives into the critical topic of mastering cost controls within your business. Whether you're a startup or an established entrepreneur, understanding how to effectively manage cost of goods sold (COGS) can dramatically improve your profitability. Chris provides actionable takeaways that you can implement immediately to help your business thrive. By focusing on five essential controls—ordering, receiving, storing, making to specification, and getting paid—you can streamline operations and ensure your margins are working for you. What You Will Learn in This Episode: The importance of balancing revenue with cost control for business success How cost of goods sold (COGS) impacts your profit and loss statement Why managing your purchasing power and procurement process is key Best practices for ordering, including negotiation and quality control How to effectively receive and inspect goods to ensure accuracy The value of proper storage to prevent theft, waste, and loss How adhering to specifications in production prevents margin erosion Tips for creating an easy and efficient process to get paid for your products The five essential cost controls that can improve your bottom line immediately Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg dives into the importance of sharing financial information with your team to build trust, accountability, and alignment within your business. He discusses the fear many entrepreneurs face when it comes to revealing numbers, how to overcome that fear, and why transparency is key to fostering a productive and engaged workforce. By sharing financial insights, entrepreneurs can help their teams understand how their actions impact the bottom line, creating a culture of ownership and empowerment that drives better results. Chris offers practical advice on how to start sharing financials with your team and how it can lead to a more successful and profitable business. What you will learn in this episode: Why many entrepreneurs hesitate to share financial information with their teams and how to overcome that fear. The damaging impact of keeping financials private and the assumptions it creates. How sharing financials can foster trust and accountability within your team. Practical ways to start sharing financial information with your team without overwhelming them. The benefits of aligning your team with the company’s financial goals to drive better results. How to delegate financial tasks effectively to reduce overwhelm and increase productivity. Why transparency in financials is crucial for a motivated and informed team. Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Well Coached, Chris Weinberg engages in an enlightening conversation with Leigh Holt, a trailblazer in entertainment, sports, and music management. Leigh shares her remarkable journey from Warner Music Nashville to founding Madjett and co-creating Hsquared Management, highlighting her innovative strategies and partnerships with industry icons like Oprah and Lauren Daigle. The discussion explores her insights on building successful teams, adapting to changing dynamics in the wake of the pandemic, and navigating the intricate world of artist management and strategic partnerships. What You Will Learn in This Episode: The journey and bold strategies of Leigh Holt in the entertainment and music industries. Insights on building and leading successful teams based on Leigh's personal experiences in sports. How the pandemic reshaped team dynamics and the importance of shared workspaces. The balance between nurturing personal relationships and achieving commercial success in artist management. Strategies for transitioning artists from intimate venues to larger arenas while maintaining their identity. The complexities of securing strategic partnerships and aligning brand values with artist identities. Valuable lessons on entrepreneurship, risk-taking, and the significance of strong professional relationships. Inspiration from Leigh's commitment to innovation and holistic personal and professional growth. Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of "Well Coached," host Chris Weinberg explores how to boost your sales game by focusing on your ideal clients and engaging them through a consultative approach. Instead of casting a wide net, Chris emphasizes the importance of truly understanding your client’s needs, leveraging natural strengths, and adapting your sales tactics to build long-term success. Drawing from personal experiences and the DISC profile, Chris discusses how different personality types can adjust their approach to maximize effectiveness in sales. What You Will Learn in This Episode: How to identify and engage your ideal clients for greater sales success. The power of a consultative sales approach that focuses on understanding your client’s true needs. Insights on leveraging your natural strengths to improve your sales tactics. How different DISC personality types navigate the sales landscape and how to adapt your approach based on your natural tendencies. How High D and I types can thrive in fast-paced environments by focusing on listening. Strategies for High S and C types to improve assertiveness and patience in closing deals. How to align your sales strategies with your business objectives for sustainable growth. Tips for ensuring increased shareholder value by selling smartly and effectively. Learn more about your ad choices. Visit megaphone.fm/adchoices
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