WIN
I'm Carrie Richardson, and this is WIN: a podcast for MSP owners and IT channel sales leaders who are done guessing at sales and marketing and ready to get good at it on purpose.
My co-host Ian Richardson and I have both sat on both sides of the table. Ian built and exited an MSP and I've spent 15 years building pipeline for MSPs and channel vendors.
Between us, we've made the calls, missed the quotas, and closed the deals that actually moved revenue.
Every episode we sit down with an MSP owner, a sales leader, or a vendor exec and ask:
How are you winning?
No theory.
No recycled advice you've already read on LinkedIn.
Just the actual plays IT channel leaders are running right now to land new logos, protect MRR, and build something worth selling one day.
New episodes weekly. Learn more about Fox & Crow Group at https://foxcrowgroup.com/
Episodes
93 episodes
Matt Koenig shares winning MSP event strategies for new IT channel vendors
Matt Koenig Shares Winning MSP Event Strategies for New IT Channel VendorsTrade shows eat a huge chunk of a new vendor's marketing budget, and most of them get it wrong in the same handful of ways. This episode kicks off WIN's Fal...
How Do I WIN the Attention of Larger MSPs? Jennifer Roy, CEO of Nucleus Networks, Gives You The Cheat Codes
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
Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In!
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 strategi...
Rex Frank - Winning MSPs Follow A Process
Rex Frank on the Process-Powered MSP: Why Heroics Aren’t a StrategyIn this episode, Carrie Richardson sits down with Rex Frank, VP of PAX8 Academy, to unpack the real reasons most MSPs stall out.&nb...
Nick Wolf Shares MSP Event Engagement Strategies
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 ...
Eric Roach and Dropsuite - Winning Through Strategic Partnerships
Winning Through Strategic Partnerships with Eric Roach of DropsuiteIn 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 str...
MSP Event Planning - How the MSP Initiative Creates Winning MSP Events
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.&nbs...
Aaron Peterik Shares Winning Advice for first-time Sponsors of Pax8 Beyond
From Booths to Buy-In: Aaron Peterik’s Playbook for Winning Pax8 BeyondEpisode Description: What separates a vendor with a busy booth from one that builds a sales pipeline? Aaron Peterik, Director of Channel at<...
Craig Fulton from Evergreen - WIN by Making Lasting Memories
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.Crai...
MSPs WIN When They Collaborate at MSP Industry Events
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—f...
Andrew Mora Shares How Cork Wins at MSP Events
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 wit...
Winning at Reinvention: Mark Chamberlin on Building Legacy and Active Retirement
From “Who’s Who” to “Who’s He?” – Reinventing Yourself After Leaving Your BusinessAfter 40 years in high-tech leadership, Mark Chamberlin found himself at an unexp...
Winning Customer Transition Strategies for MSPs with Matt Yesbeck
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...
WIN at Scaling Your MSP with Matthew Pincus and Helpt
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...
Winning at Social Media Marketing with Heather Margolis
"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 ...
Winning Podcast Strategies from Command Your Brand
WIN More PR Opportunities with Advice from Josh SilvestroIn this episode, host Carrie Richardson is joined by
Andrew Moore WINS by Operationalizing Trust
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) industr...
Mike Ita WINS by supporting one niche specialization.
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 j...
How Waident WINS the best technical talent
Winning Strategies for Recruiting and Retaining Top Talent in the MSP SpaceIn this episode of WIN (What's Important Now), host Carrie Richardson talks with repeat guest Jo...
Technique - Daryl D'Souza
Daryl D'Souza, Co-Founder of TechniqueIn this episode of the WIN podcast, host Carrie Richardson sits down with Daryl D’Souza, managing partner at
Justin Breen WINS by Connecting Visionaries to Serve Humanity
In this compelling episode, Carrie Richardson interviews Justin Breen, a master connector who spends his days linking some of the world's most brilliant and misunderstood vis...
Kirk Halpern: Restaurants, Redemption Stories, and WINNING
In this episode of "What's Important Now," host Carrie Richardson sits down with Kirk Halpern, the visionary behind Farmers and Fishermen Purveyors. Kirk shares his remarkable journey from practicing law to becoming a major player in the meat a...
