WIN
Business is a battle, and we came here to WIN! Carrie and Ian Richardson are partners and serial entrepreneurs who specialize in strategic growth and exit planning for SMBs. Every week, we ask business owners and leaders two important questions: "What's Important Now?" "How are you winning?" Created by entrepreneurs who love strategy, sales and strategic selling, we interview business owners and sales leaders at all stages of growth across multiple industries. Learn from experts sharing their strategies and the tactics they use to identify and pursue opportunities. Take away actionable ideas that you can use to help you scale and/or sell your business. Learn more about Fox and Crow Group at https://foxcrowgroup.com
Episodes
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, Pater...
In this episode of the WIN Podcast, host Carrie Richardson sits down with Jennifer Roy to unpack how vendors can successfully connect with enterprise-grade managed service providers. Roy shares insights from her leadership at Nucleus Networks, a multi-location MSP within the Lyra Technology Group family, and breaks down how her team prepares for events like Pax8 Beyond.
Roy discusses what catches her attention at ven...
If you're heading to Pax8 Beyond—or any major MSP channel event—this episode is your tactical prep guide.
Channel legend Len DiCostanzo joins host Carrie Richardson to share strategic insights from his 40+ years in the IT channel, including leadership roles at Autotask, Kaseya, and Datto. Now leading the coaching and consulting practice at MSP Toolkit, Len helps vendors and MSPs alike improve their partner progr...
Rex Frank on the Process-Powered MSP: Why Heroics Aren’t a Strategy
In this episode, Carrie Richardson sits down with Rex Frank, VP of PAX8 Academy, to unpack the real reasons most MSPs stall out.
From the dangers of hero culture to the strategic misuse of vCIOs, Rex shares decades of insight on what separates mature MSPs from the rest. He doesn’t pull punches—and he doesn’t believe talent alone is enough. ...
Join channel veteran Nick Wolf as he shares MSP event engagement strategies with Carrie Richardson from Fox & Crow Group.
Learn how Nick's career progressed from sales intern at Datto (Nick was employee 17 at Datto...) through to his current role with Cork.
Nick shares his pre-event process, his on-site tips and his follow-up expertise.
At 32, Nick is already a channel veteran, having spent ten years with Da...
Winning Through Strategic Partnerships with Eric Roach of Dropsuite
In this episode of the WIN Podcast, host Carrie Richardson sits down with Eric Roach, SVP of Global Sales and Marketing at Dropsuite, to explore how strategic partnerships can supercharge growth.
With PAX8 Beyond on the horizon, Eric shares how Dropsuite leverages major events not just for exposure—but for creating deep, scalable engagement ...
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, Pater...
Winning MSP Event Planning with Alec Stanners
In this episode, we dive deep into what it really takes to plan MSP events that create community, drive real ROI, and elevate vendor relationships beyond the trade show table.
Featuring Alec Stanners, VP of Business Development at Bvoip and a core leader behind the MSP Initiative and MSP Block Party, we explore how grassroots strategy, thoughtful sponsor integration, and...
From Booths to Buy-In: Aaron Peterik’s Playbook for Winning Pax8 Beyond
Episode Description:
What separates a vendor with a busy booth from one that builds a sales pipeline? Aaron Peterik, Director of Channel at Zero Networks and former Pax8 insider, joins us to share real-world strategies for dominating Pax8 Beyond. From microsegmentation to sales team alignment, Peterik unpacks what actually works for MSP vendors t...
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, Pater...
In this episode of The WIN Podcast, host Carrie Richardson interviews Craig Fulton, M&A Advisor at Evergreen Services Group, about how to maximize your experience at industry events like PAX8 Beyond.
Craig offers thoughtful advice on preparing for large conferences, engaging meaningfully with other attendees, and creating experiences that leave lasting impressions. Drawing on his own journey from technician to M&...
In this episode of WIN, host Carrie Richardson chats with Allan Jocson, CEO of Agilitec and member of the PAX8 Partner Advisory Council. Allan shares his playbook for getting the most out of major MSP industry events like PAX8 Beyond—from strategic pre-event planning to making meaningful connections that drive long-term growth.
You'll hear why collaboration beats competition in the MSP world, how to make vendor ...
Trade shows are back in a big way, and Pax 8 Beyond 2025 is one of the most important events on the MSP calendar. In this episode of the WIN Podcast, host Carrie Richardson talks with Andrew Mora from Cork about what it really takes to turn a sponsorship into a sales strategy.
Mora pulls back the curtain on Cork’s full event playbook—from how they pivoted messaging to lead with their platform (not their warranty prod...
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 aft...
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 transi...
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 o...
"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 f...
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 engag...
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 r...
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 ho...
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