Well Coached with Chris Weinberg

In this solo episode of Well Coached, Chris looks at one of the most honest leadership documents in any business: the calendar.

Leaders can say people matter, growth matters, profit matters, and self-care matters, but the calendar tells the truth. It shows what repeatedly receives attention, what keeps getting pushed aside, and whether the leader’s time is aligned with the business they say they are trying to build.

Throughout the episode, Chris walks through how the calendar reveals the real priorities behind people, sales, profit, and self. He challenges leaders to look at whether they are making time for coaching, pipeline review, decision-making, strategic thinking, and personal recovery, or whether the week is being consumed by noise, urgency, and reaction.

This episode is a practical gut-check for any leader who says something is important but cannot find it anywhere on the schedule.

What You’ll Learn in This Episode

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In this solo episode of Well Coached, Chris takes on one of the most common traps for capable leaders: becoming the answer to every problem.

When someone on the team brings an issue forward, many leaders jump straight into solving mode. It feels efficient, supportive, and responsible, but over time, it teaches people to escalate decisions instead of building judgment. The leader becomes the central processing unit for the whole business, while the team becomes more dependent and less capable.

Throughout the episode, Chris explains why great coaching is not about refusing to help. It is about helping in a way that increases the other person’s capacity. He walks through how better questions can strengthen people, improve sales execution, protect profit, and free the leader to focus on the work only they can do.

This episode is a powerful reminder that leadership is not about having every answer, it's about building a team that can think, decide, and grow.

What You’ll Learn in This Episode

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In this episode of Well Coached, Chris sits down with Matt Lauderdale, owner of Frankie’s Bike Shop and Salt Air 30A, for a conversation about building a customer-first business in one of the country’s most desirable vacation markets.

Matt shares what it takes to grow beyond a fun, founder-led operation into a business with stronger systems, clearer leadership, and a team that can deliver the experience without everything depending on him. From bike rentals and retail to inventory, seasonality, staffing, and customer care, Matt reflects on the work behind creating a brand people trust and come back to.

Throughout the conversation, Chris and Matt talk about the power of a high-energy, relationship-driven leader, and why the goal is not to tone that down, but to build the right structure around it. They also explore how great selling can feel less like pressure and more like hospitality, especially when the customer is on vacation and looking for ease, confidence, and a better day.

This episode is a thoughtful look at growth, delegation, customer experience, and what it means to build a business that supports both the owner and the life they are trying to create.

What You’ll Learn in This Episode

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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

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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

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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

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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

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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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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

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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

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