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Well Coached with Chris Weinberg — Business
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!

Copyright: © That Sounds Fun Network 2024

Latest Episodes:

The $500,000 Decision You're Making Every Week Sep 22, 2026

Show notes

In this solo episode of Well Coached, Chris challenges the way business owners think about big decisions.

Most leaders imagine major financial impact coming from obvious moments: a big hire, a new location, an acquisition, or a major investment. But in many businesses, the most expensive decisions are the ordinary ones repeated week after week; the delayed hire, the unresolved client issue, the un-coached salesperson, the unnecessary meeting, or the pricing exception that slowly becomes normal.

Throughout the episode, Chris shows how leadership choices compound across people, sales, profit, and self. He explains why the cost of inaction is often higher than the cost of action, and why small leaks in accountability, margin, communication, and decision-making can quietly shape the economics of the entire business.

This episode is a clear, practical reminder that the future of a business is not built only in big strategic moments, but in the ordinary decisions leaders make every week.

What You’ll Learn in This Episode

Why small leadership decisions can create major financial consequences
How delayed decisions around people, sales, and profit compound over time
Why leaders need to calculate the cost of inaction, not just the cost of action
How to identify the weekly choices shaping the future of your business

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Cassandra Sotos and Clark Singleton of AmpRx Partner on Product Innovation Sep 15, 2026

Show notes

In this episode of Well Coached, Chris sits down with Cassandra Sotos and Clark Singleton of AmpRX for a conversation about entrepreneurship, partnership, product innovation, and the transferable skills that come from a life in music.

Cassandra and Clark share how their work as full-time musicians shifted in 2020, leading them first into real estate and eventually into acquiring AmpRX and its signature product, the BrownBox - a voltage controller designed to help musicians get more consistency from their gear.

Throughout the conversation, they reflect on what it takes to buy a great product and build the business around it: honoring the original idea, educating customers, navigating manufacturing challenges, managing cash flow, and listening closely to what players and techs actually need.

This episode is a dynamic look at creative problem-solving, measured risk, customer trust, and what it takes to build a business with your partner - without losing sight of who you are.

What You’ll Learn in This Episode

How Cassandra and Clark turned their music backgrounds into entrepreneurial advantage
Why the BrownBox solves a problem many musicians feel before they understand
How AmpRX balances customer education, product innovation, manufacturing, and cash flow
Why trust and alignment matter when building a business with your partner

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The Hidden Cost of Being Too Nice Sep 08, 2026

Show notes

In this solo episode of Well Coached, Chris breaks down a leadership habit that looks generous on the surface but can quietly damage a team: being too nice.

Not kind. Not caring. Not compassionate. Chris is talking about the kind of niceness that avoids tension, softens expectations, delays hard conversations, and keeps a leader focused on being liked instead of being useful. While the intention may be good, the impact is often confusion, resentment, and frustration for the strongest people on the team.

Throughout the episode, Chris explains why clear expectations, timely feedback, and consistent accountability are not the opposite of kindness, they are part of it. He walks through how delayed conversations affect people, sales, profit, and the leader’s own sense of self, showing why avoidance often creates more damage than the hard conversation ever would.

This episode is a practical look at how leaders can stop choosing between care and accountability, and start offering both.

What You’ll Learn in This Episode

How being “too nice” can create confusion instead of safety
Why your strongest employees need clarity, not lowered expectations
How delayed feedback can damage people, sales, and profitability
How to approach hard conversations with both warmth and directness

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Lessons from a Family Business with Miss Kitty's Dog Resort's Cameo Huggins Sep 01, 2026

Show notes

In this episode of Well Coached, Chris sits down with Cameo Huggins, owner of Miss Kitty’s Dog Resort, for a conversation about family business, leadership transition, legacy, and what it means to grow something without losing what made it special.

Cameo shares what it was like to grow up inside the business, first working the front desk as a teenager, then stepping into management, and eventually buying the business from her mother. With a background in accounting and law, Cameo brings a thoughtful, analytical approach to ownership while still honoring the culture, care, and reputation her family built over decades.

Throughout the conversation, Cameo reflects on the shift from managing employees to leading managers, the challenge of building authority with people she has known for years, and the importance of creating systems without flattening the heart of the business. She also shares how Miss Kitty’s continues to stand out in a crowded market by selling peace of mind, building real relationships with clients, and refusing to compromise on dog care.

This episode is a thoughtful look at what it takes to lead a second-generation business with both discipline and heart; protecting the legacy while building the next version of the company.

What You’ll Learn in This Episode

How Cameo transitioned from growing up in the business to becoming its owner
Why leading managers requires a different skill set than managing employees directly
How Miss Kitty’s balances high-touch dog care, customer trust, and business profitability
Why systems, culture, and human connection matter when carrying a family business forward

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Season 9 Trailer Aug 25, 2026

Show notes

Welcome to Season 9 of Well Coached.

This season, Chris Weinberg continues exploring what it takes to build a business that actually works - where people, sales, profit, and self all have a seat at the table.

Across Season 9, Chris sits down with entrepreneurs, business owners, leaders, and builders for honest conversations about growth, leadership, decision-making, customer experience, financial discipline, team development, and the personal work required to lead well.

From creative founders and service-based businesses to product companies, hospitality, wellness, music, and more, this season looks at the real work behind building something sustainable - not just from the outside, but from the inside.

Whether you’re leading a team, growing a company, navigating change, or trying to build a business that supports the life you actually want, Season 9 is full of practical insight, honest stories, and coaching conversations to help you stay well coached.

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Hiring Smarter: How DISC Helps Small Businesses Build Better Teams Jul 28, 2026

Show notes

In this solo episode of Well Coached, Chris explores how small business owners can use DISC to make smarter hiring decisions and build stronger, more balanced teams.

Hiring is not just about finding someone with the right experience. It is also about understanding how a person communicates, solves problems, handles pressure, and fits into the role and team around them. Chris explains how DISC can give leaders a clearer view of a candidate’s natural behavioral style and help them determine whether that style supports the actual needs of the position.

Throughout the episode, Chris unpacks how each DISC style can bring value to a business, from fast-moving results-driven leaders to relationship-builders, steady team players, and detail-focused operators. He also shows why no style is “better” than another - the key is knowing what the role requires and hiring with more clarity, intention, and alignment.

This episode is a practical guide for small business owners who want to move beyond gut-feel hiring and start building teams that communicate better, work smarter, and support the business long-term.

What You’ll Learn in This Episode

How DISC can help small business owners better understand candidates and team dynamics
Why hiring for behavioral fit matters as much as hiring for skill or experience
How different DISC styles can support different roles inside a growing business
How to use DISC as a tool for clarity, alignment, and better long-term hiring decisions

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Be the CEO of Your Own Health with Scott Crosbie of Next Health Jul 21, 2026

Show notes

In this episode of Well Coached, Chris sits down with Scott Crosbie of Next|Health for a conversation about entrepreneurship, reinvention, health optimization, and what it means to take ownership of both your business and your well-being.

Scott shares his journey from corporate life to buying and building multiple businesses, leading teams, creating successful exits, and eventually realizing that retirement was not the finish line he thought it would be. After stepping away from business, Scott found himself looking for a new challenge; one that connected his entrepreneurial experience with his growing passion for prevention, longevity, and health data.

Throughout the conversation, Scott reflects on the lessons he has learned from building teams, making hard hiring decisions, working with advisors, and learning how to move from operator to strategic leader. He also shares how his mother’s dementia diagnosis shaped his personal health journey and ultimately led him into the wellness and longevity space with Next Health.

This episode is a thoughtful look at what it means to keep evolving, build with intention, and treat your health the same way you would treat a business - with a team, a plan, and metrics that help you know where you stand.

What You’ll Learn in This Episode

How Scott moved from corporate life into entrepreneurship and multiple successful business exits
Why building the right team is one of the hardest and most important decisions an entrepreneur can make
How retirement led Scott to rethink purpose, passion, and what he wanted to build next
Why health optimization starts with data, prevention, and taking ownership as the CEO of your own health

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Why Your Team Isn’t Listening: Using DISC to Communicate Jul 14, 2026

Show notes

In this solo episode of Well Coached, Chris breaks down one of the most practical tools he uses with business owners and teams: the DISC profile.

If you’ve ever wondered why an employee does not seem to follow direction, why a client needs so many details, or why a manager feels overwhelmed by change, the issue may not be bad intentions, it may be a communication mismatch. Chris explains how DISC helps leaders understand the different ways people communicate, process information, and respond to their environment.

Throughout the episode, Chris walks through the four DISC styles: Dominance, Influence, Steadiness, and Conscientiousness, and explains how each style hears the same message differently. He also shares practical ways to adjust your leadership communication so your team receives direction with more clarity, less conflict, and better follow-through.

This episode is a practical look at how leaders can stop treating everyone the same and start communicating in a way that actually connects.

What You’ll Learn in This Episode

How DISC helps leaders understand different communication and behavioral styles
Why workplace conflict is often caused by communication mismatches, not bad intentions
How to lead D, I, S, & C styles with more clarity and effectiveness
Why adapting your communication style can help your team listen, respond, and perform better

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Building Something Sweet with Carolyn Nugent and Alen Ramos of Poulette Bakeshop Jul 07, 2026

Show notes

In this episode of Well Coached, Chris sits down with Carolyn Nugent and Alen Ramos, owners and pastry chefs of Poulette Bakeshop, for a conversation about entrepreneurship, partnership, resilience, and what it takes to turn world-class craft into a business that actually works.

Carolyn and Alen share their journey from elite fine dining and Michelin-level kitchens to building their own nationally recognized bakery in Parker, Colorado. After years of training under some of the best chefs in the world, they took the leap into entrepreneurship — bringing their artistry, discipline, and relentless work ethic into a business of their own.

Throughout the conversation, Carolyn and Alen reflect on what it means to work together as spouses, lead a team with both excellence and empathy, and stay committed through challenging seasons. They talk about the realities of cash flow, customer education, leadership, health challenges, and the daily grind behind creating something beautiful.

This episode is a powerful look at partnership, perseverance, and the kind of disciplined creativity it takes to climb the mountain; one rep, one decision, and one pastry at a time.

What You’ll Learn in This Episode

How Carolyn and Alen turned elite culinary training into their own entrepreneurial path
Why trust, shared vision, and communication matter when spouses work together
How disciplined leadership and empathy can shape a strong team culture
What it takes to balance artistry, customer experience, financial realities, and personal resilience

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Selling with Grit with Andrea Anderson of Andrews Cadillac Jun 30, 2026

Show notes

In this episode of Well Coached, Chris sits down with Andrea Anderson of Andrews Cadillac Sales for a conversation about grit, resilience, personal branding, and what it takes to create trust in an industry many people walk into with their guard up.

Andrea shares how she went from working as a registered dietitian and personal trainer to becoming one of the top Cadillac sales producers in the country. What started as a bet with her dad turned into a career that tapped into her competitive drive, athletic discipline, and willingness to prove herself in a male-dominated industry.

Throughout the conversation, Andrea reflects on the importance of customer experience, listening well, and creating momentum instead of waiting for opportunity to show up. She also shares how building an online presence helped her educate customers, grow trust before people ever step into the dealership, and turn authenticity into real business growth.

This episode is a powerful look at resilience, reinvention, and the habits that help high performers keep moving forward, even after life knocks them down.

What You’ll Learn in This Episode

How Andrea turned transferable skills, competition, and discipline into a successful sales career
Why listening and efficiency are essential to creating a better customer experience
How personal branding and social media can build trust before the first conversation
What resilience looks like when career, motherhood, health challenges, and ambition all intersect

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