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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.

Send us a text

WIN More PR Opportunities with Advice from Josh Silvestro

In this episode, host Carrie Richardson is joined by Josh Silvestro, brand ambassador at Command Your Brand, a podcasting agency specializing in helping businesses amplify their voice and connect with the right audiences. Together, they explore the challenges and opportunities of podcasting, tips for effective public relations, and the secret to creating engaging content that converts.

Key Takeaways:

1. Why Storytelling Matters in Podcasting
   • Build genuine connections with your audience by sharing your authentic journey.
   • Avoid polarizing topics; focus on relatable and inspiring content.
2. Overcoming Podcasting Fears
   • Learn to embrace mistakes and use them as stepping stones for growth.
   • Practice and preparation are key to becoming a confident speaker.
3. The ROI of Podcasting
   • Understand how guest appearances on niche podcasts can lead to unexpected opportunities.
   • Repurpose podcast content into blog posts, social media clips, and more to maximize value.
4. Creating a Personal Brand Through Public Relations
   • People buy from people, not businesses. Focus on showcasing your unique expertise.
   • Start small but strategic by targeting niche audiences and growing from there.

Quotes from the Episode:

• "People buy from people, not businesses." – Josh Silvestro
• "Podcasting is not just about being heard; it's about building trust and visibility." – Carrie Richardson

Actionable Tips:

1. Start by clarifying your niche and target audience.
2. Use platforms like YouTube or podcast networks to explore similar content for inspiration.
3. Don’t underestimate the power of repurposing podcast content across channels.

Technology Tip:
Leverage AI tools to analyze transcripts, generate content, and identify key insights to streamline your podcast marketing efforts.

Links & Resources Mentioned:

• Visit Command Your Brand to learn more about their services.
• Book a call with Josh or the Command Your Brand team at CommandYourBrand.com/bookacall

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

In this episode of What's Important Now, host Carrie Richardson sits down with Andrew Moore, founder of Ridgeview Advisors, to dive deep into the concept of "Operationalizing Trust" in the managed services provider (MSP) industry.

Andrew shares insights on how scaling trust is critical for MSPs and how it directly impacts profitability, client satisfaction, and business scalability. Andrew recounts his journey from his early days in IT to becoming a COO and now running his own consultancy.

From practical sales strategies, cost of client acquisition, to the art of expectation management, this episode is packed with actionable advice for business owners looking to optimize their operations and build long-lasting client relationships. Whether you're an MSP owner, entrepreneur, or simply interested in operational efficiency, this episode is a must-listen.

Key Takeaways:

1. Operationalizing Trust: Scaling trust beyond the owner and embedding it into sales, operations, and client management.
2. Cost of Acquisition: The importance of knowing your numbers to improve profitability.
3. Expectation Management: How clear contracts and upfront communication can save relationships and margins.
4. Scaling MSPs: From hiring the right salespeople to implementing scalable processes, Andrew shares what worked (and didn’t) during his time scaling an MSP from 8 to 65 employees.
5. The Power of Letting Go: Why business owners need to trust their teams to grow effectively.

Quotes from Andrew Moore:

• "If you operationalize trust, you’re not just selling a service — you're creating a system that scales trust across your entire business."
• "Understanding your cost of client acquisition is crucial. Most MSPs don't have a handle on these numbers, and it’s a game-changer."
• "Expectation management isn't just a service strategy; it's a business survival skill."

Connect with Andrew Moore:

• Website: Ridgeview Advisors
• LinkedIn: Andrew Moore

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

Host Carrie Richardson sits down with Mike Ita, founder and CEO of IT Corps, a managed service provider based in Ohio. Mike shares his inspiring journey from a general IT consultant to a highly successful niche business specializing in IT services for veterinary practices. He talks about the challenges and triumphs of carving out a unique space in the market, his strategies for building lasting relationships, and how IT Corps adapted to industry changes driven by private equity and cloud-based technologies. This is a must-listen episode for entrepreneurs, IT professionals, and anyone looking to specialize their business in a competitive industry.

Episode Highlights:

• [00:00:29] Mike's start in IT Corps after a business partnership fallout.
• [00:01:44] How a sick cat led Mike to discover his veterinary niche.
• [00:03:41] Early challenges in acquiring veterinary clients and the breakthrough at the Midwest Veterinary Conference.
• [00:05:52] Mike's transition from attending events to speaking at them and gaining more clients.
• [00:07:45] The explosive growth of IT Corps' veterinary client base after a successful conference.
• [00:10:17] How private equity acquisitions of veterinary practices impact his business.
• [00:14:33] Telemedicine opportunities in veterinary practices and Mike’s attempt to break into the market.
• [00:18:12] Carrie and Mike discuss niche specialization and pricing strategies in IT services.
• [00:26:47] The importance of maintaining personal relationships with clients and Mike’s approach to customer retention.

Notable Guest Quotes:

• "I realized I loved working with veterinary clinics—they’re appreciative, and the relationships are just better." – Mike Ita
• "People love their pets, and they’re willing to pay for the best care, including making sure their systems work efficiently." – Mike Ita
• "Specialists can charge whatever they want. If you’re a specialist in veterinary IT support, you set the price." – Carrie Richardson

Guest Information: Mike Ita is the founder and CEO of IT Corps, a managed service provider that focuses exclusively on veterinary practices. With years of experience in various industries, Mike pivoted to specialize in veterinary IT services, helping clinics manage their IT infrastructure more efficiently. He’s a frequent speaker at industry events and has been featured

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 Strategies for Recruiting and Retaining Top Talent in the MSP Space

In this episode of WIN (What's Important Now), host Carrie Richardson talks with repeat guest John Ahlberg, the CEO of Waident Technology Solutions.

They explore Waident's successful strategies for recruiting and retaining talent, especially in the Managed Service Provider (MSP) industry.

John explains the importance of a people-first culture, work-life balance, and a unique hiring process that emphasizes culture fit, talent, and experience over traditional qualifications. He also shares insights on maintaining flexibility, providing opportunities for employee development, and avoiding the pitfalls of settling for less-than-ideal candidates.

00:00 Introduction and Welcome

00:45 Recruiting and Retaining Talent

01:48 Flexible Work Culture

03:44 Onboarding and Training

04:08 Encouraging Innovation and Change

06:36 Hiring for Culture and Weirdness

10:09 Transparent Job Postings and Interview Process

16:59 Advice for MSPs on Hiring

19:17 Conclusion and Farewell

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

Daryl D'Souza, Co-Founder of Technique

In this episode of the WIN podcast, host Carrie Richardson sits down with Daryl D’Souza, managing partner at Technique, a managed IT services provider based in Toronto, Canada.

Daryl shares his unique approach to signing two to three new clients monthly while working only two to three hours a day.

He discusses the importance of providing free value, building trust, and leveraging LinkedIn automation tools and Loom videos to connect with prospects.

Daryl also delves into the challenges and rewards of focusing on business outcomes rather than just tech stacks, his plans for expanding Technique, and maintaining a work-life balance.

He provides actionable insights on the importance of defining company values, recruitment strategies, and ensuring a seamless client onboarding process.

Tune in to WIN and try Daryl's process in your own business!

00:00 Introduction and Guest Welcome

00:21 Daryl's Unique Client Acquisition Strategy

01:42 The Importance of Providing Value

02:35 Leveraging Tools for Efficiency

03:48 Building Trust and Relationships

06:00 Challenges and Adaptations

10:27 Future Plans and Business Growth

20:21 Recruitment and Company Culture

23:28 Conclusion and Final Thoughts

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.