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From “Who’s Who” to “Who’s He?” – Reinventing Yourself After Leaving Your Business

After 40 years in high-tech leadership, Mark Chamberlin found himself at an unexpected crossroads—let go at 61.5 and faced with a big question: What’s next? Instead of chasing another corporate role, he reinvented himself with impact, influence, and freedom.

In this episode, Mark shares:

• The biggest mistakes business leaders make after exiting
• Why your old title won’t open new doors—and what will
• How to leverage your network without looking for a job
• The surprising way sharing knowledge creates new opportunities
• How he redefined success beyond just money

Mark spends his time volunteering for groups that support start up founders, new entrepreneurs and "rising stars" - young adults beginning their searches for their first job. You may see him in the halls at Chapman University, teaching founders at Octane, or conducting mock interviews for the Boys and Girls Club YES Youth Employment Services.

Listen in for Mark’s insights and actionable strategies to help bridge the transition from "Who's who" to "who's he?"

How Does Fox and Crow Group Help with Building Legacy?

Stepping away from a business—whether through sale, retirement, or transition—can feel like an identity crisis. If you’re struggling with what comes next, Paterson LifePlan can provide clarity and a structured roadmap for your next chapter.

Ian Richardson is certified to walk with transitioning leaders and entrepreneurs through life planning - a strategic plan for your life and legacy.

Learn more about Paterson LifePlan at Fox & Crow Group. Get Started Here ➝

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with Carrie here!

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.

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Are you leaving money on the table when offboarding MSP clients?

Matt Yesbeck and his son Gage saw a massive gap in the MSP industry—no structured way to transition low-value or misfit clients without losing revenue or damaging reputation. Instead of accepting the status quo, they built MSPX, the first-ever MSP contract exchange platform, helping IT service providers monetize client offboarding, ensure smooth transitions, and protect brand reputation.

In this episode of WIN Podcast, Carrie Richardson digs deep into:
✅ The story behind MSPX and how it’s transforming the MSP industry
✅ How Matt and Gage launched an MSP AFTER creating a tech startup
✅ The real challenge of pruning clients—and how to make it profitable
✅ The father-son dynamic of running two businesses together

If you’re an MSP owner, IT leader, or entrepreneur, this episode is a must-listen. Learn how to WIN in the MSP space by making strategic moves that fuel growth.

💡 Subscribe now and don’t miss out on game-changing conversations that help you scale, sell, and WIN!

In this episode we refer to The Pumpkin Plan for MSPs, a book by Dave Cava, who was a previous guest on WIN - Check out his episode here!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with Carrie here!

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.

Send us a text

Why is Winning at Scale So Difficult?

Scaling a business comes with big challenges—hiring, retention, marketing, and making smart decisions that drive growth.

In this episode of WIN, host Carrie Richardson sits down with Matthew Pincus, Founder & CEO of HELPT, to discuss the lessons learned from scaling a company, navigating the trade show circuit, and balancing speed with strategy.

They dive into the realities of outsourcing, the importance of building trust, and why the right approach to hiring can make or break a business.

What You’ll Learn in This Episode:

✔️ The biggest challenges businesses face when scaling
✔️ How to hire and retain top talent without burnout
✔️ Outsourcing vs. in-house: When to delegate for growth
✔️ Trade show strategies—getting ROI without breaking the bank
✔️ The role of AI in customer support and business operations
✔️ Why brand reputation and community engagement matter

About Our Guest:

Matthew Pincus is the Founder & CEO of HELPT, an outsourced tech support company that helps businesses streamline customer service while maintaining quality and efficiency. With a background in operations, marketing, and sales, Matthew shares his insights on smart business growth and how to navigate the challenges of scaling.

Resources & Links:
🔗 Connect with Matthew Pincus & HELPT – GETHELPT.com
🔗 Follow Carrie Richardson & Fox and Crow – FoxCrowGroup.com

🎧 Enjoying the show? Subscribe, rate, and leave a review! Your support helps us keep bringing you expert insights.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with Carrie here!

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.