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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.

Send us a text

"Winning at Social Media Marketing with Heather Margolis"

In this episode of the WIN Podcast, host Carrie Richardson interviews Heather Margolis, founder of Channel Maven, to uncover her strategies for leveraging social media as a powerful tool in B2B marketing. Heather shares invaluable advice on using platforms like Instagram and TikTok to drive engagement, create impactful campaigns, and generate leads for businesses of all sizes.

Key Takeaways:

• Why Instagram is becoming a B2B powerhouse: “If they're searching on their phone for channel marketing, and then they go to Instagram, I want them to find me,” Heather explains, emphasizing the importance of visibility across platforms.
• The power of affordable social media advertising: “My Instagram budget is about $2,000 a month, including the agency to manage it. If I did that on LinkedIn, it would be $6,000 a month,” she reveals, offering a compelling case for diversifying ad spend.
• Creating high-impact, targeted content: Heather advises, “Your video needs captions that call to your audience. If I’m selling to CMOs, the video and words will say, ‘Are you a CMO in the tech industry?’ It grabs their attention instantly.”
• Tailoring strategies to your audience’s environment: “I scroll Instagram for videos at home, but in a business meeting, I use Threads because I can’t play a video. It’s about knowing your audience and how they consume content,” Heather notes.

Heather also offers actionable insights for managed service providers (MSPs) and other B2B organizations on how to make social media ads work for them:

• Target decision-makers with specific industry-related keywords.
• Utilize simple funnels to convert viewers into leads.
• Balance creativity and analytics for campaign success.

This episode is a must-listen for businesses seeking to enhance their digital marketing strategies while keeping costs in check.

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.