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
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June 8, 202519 min
Why SASE is a WINNING part of the Modern MSP Security Stack
Send us Fan Mail 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.
May 30, 202516 min
How Do I WIN the Attention of Larger MSPs? Jennifer Roy, CEO of Nucleus Networks, Gives You The Cheat Codes
Send us Fan MailIn 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 vendor booths, how her team prioritizes discovery calls, and why follow-up matters more than flash. She emphasizes the importance of being informed, respectful of time zones, and strategically aligned with an MSP’s operational goals. Vendors who come prepared—and stay professional—are the ones who make it onto her calendar.If you're an IT channel vendor trying to land a meaningful partnership with a large MSP, or a new MSP owner wondering how operationally mature MSP owners prioritize their time at industry conferences, this episode is packed with unfiltered guidance from someone who receives hundreds of outreach attempts per quarter—and still takes the time to coach the channel on how to do it better.Read the article inspired by the podcast on the Fox & Crow Group blog 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.
May 28, 202522 min
Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In!
Send us Fan MailIf 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 programs and sales performance—and in this conversation, he breaks down what it really takes to make an event worth the investment.You’ll learn:The top mistakes vendors make when exhibiting at trade showsWhat to do instead of hiding behind your booth tableHow to evaluate your event ROI—and what metrics actually matterWhy relationships, not branding, drive long-term valueTips for making every handshake, hallway chat, and happy hour countWhether you're a first-time sponsor or a seasoned exhibitor, this episode delivers real-world advice to help you turn event spend into sales results.Find Fox & Crow Group at booth 929 at Pax 8 Beyond. Read the blog post inspired by the interview 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.
May 20, 202510 min
Rex Frank - Winning MSPs Follow A Process
Send us Fan MailRex 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. 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. If you're tired of duct-taping your business together with hustle, this conversation is your roadmap to building a resilient, scalable MSP.Topics Covered:Why “doing it all yourself” is holding your MSP backHow to reposition the vCIO role for long-term client impactThe one thing your org chart says about your growth ceilingWhy PAX8 Academy is reengineering the MSP maturity modelFind Rex Frank onsite at Pax8 Beyond! Read the article inspired by this interview on the Fox and Crow Group blog. 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.
May 14, 202515 min
Nick Wolf Shares MSP Event Engagement Strategies
Send us Fan MailJoin 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 Datto, then another 2 years with Scout Security prior to their exit. Now Nick is bringing his expertise to a whole new category of MSP solutions: cyber-warranty.Don't miss this one! 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.
May 14, 202521 min
Eric Roach and Dropsuite - Winning Through Strategic Partnerships
Send us Fan MailWinning 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 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 with MSP partners.You’ll learn how Dropsuite transforms post-event reflections into proactive planning, how they equip their teams for meaningful conversations on the show floor, and why true alignment with vendor partners starts long before the booth setup.Whether you’re prepping for your next event or evaluating your vendor ecosystem, this conversation will help you make your next move intentionally—and strategically.Learn more about strategic vendor partnerships in this Fox & Crow Group article. 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.
May 10, 202518 min
Will Ominky and Nerdio's Winning Approach to MSP Events Like Pax 8 Beyond
Send us Fan Mail 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.
May 10, 202515 min
MSP Event Planning - How the MSP Initiative Creates Winning MSP Events
Send us Fan MailWinning 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 movement-based design can turn a basic gathering into a channel-defining experience. With a discussion around Pax8 Beyond’s intentional structure to the anatomy of a successful block party, this conversation is packed with tactical insight for event organizers, vendors, and anyone serious about building meaningful moments in the managed services space. Read more about this interview on the Fox & Crow blog here: foxcrowgroup.com/insights/how-to-plan-msp-events-that-actually-work 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.
May 8, 202518 min
Aaron Peterik Shares Winning Advice for first-time Sponsors of Pax8 Beyond
Send us Fan MailFrom 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 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 trying to stand out, connect authentically, and convert leads into long-term revenue. If you’re planning to exhibit—or just want to sharpen your MSP sales game—don’t miss this one.Topics covered:Microsegmentation and Zero Trust: What MSPs need nowBooth KPIs that drive revenue—not just scansHow to prep your team two weeks before the eventWhy MSPs ignore your pitch (and how to fix it)The surprising value of hotel-lobby conversations🎧 Listen now. Show up better. Sell smarter. 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.
May 6, 202517 min
Mark Sokol from CyberFox shares Winning MSP Event Strategies
Send us Fan Mail 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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