Cover image of show WIN

WIN

Podcast by Carrie Richardson Fox and Crow Group

English

Business

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About 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

All episodes

92 episodes

episode Why SASE is a WINNING part of the Modern MSP Security Stack artwork

Why SASE is a WINNING part of the Modern MSP Security Stack

Send us Fan Mail [https://www.buzzsprout.com/1986903/fan_mail/new] Carrie [https://linkedin.com/in/carrielynnrichardson]Richardson and Ian [https://linkedin.com/in/ianalexanderrichardson] 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 [https://www.foxcrowgroup.com] Book time with Carrie here! [https://randr.membrain.com/Meet/carrie@croocial.com] Be a guest on WIN!  [https://randr.membrain.com/Beacon/Form/4de426f6-c941-4583-9127-62dba3d00fc9]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.

8 Jun 2025 - 19 min
episode How Do I WIN the Attention of Larger MSPs? Jennifer Roy, CEO of Nucleus Networks, Gives You The Cheat Codes artwork

How Do I WIN the Attention of Larger MSPs? Jennifer Roy, CEO of Nucleus Networks, Gives You The Cheat Codes

Send us Fan Mail [https://www.buzzsprout.com/1986903/fan_mail/new] 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 [https://yournucleus.ca], a multi-location MSP within the Lyra Technology Group [https://lyratechgroup.com] family, and breaks down how her team prepares for events like Pax8 Beyond. [https://pax8beyond.com] 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. [https://foxcrowgroup.com/insights/how-to-sell-to-large-MSPs] Carrie [https://linkedin.com/in/carrielynnrichardson]Richardson and Ian [https://linkedin.com/in/ianalexanderrichardson] 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 [https://www.foxcrowgroup.com] Book time with Carrie here! [https://randr.membrain.com/Meet/carrie@croocial.com] Be a guest on WIN!  [https://randr.membrain.com/Beacon/Form/4de426f6-c941-4583-9127-62dba3d00fc9]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.

30 May 2025 - 16 min
episode Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In! artwork

Len DiCostanzo Has Been Building Winning MSP Event Strategies for Over 40 Years. Tune In!

Send us Fan Mail [https://www.buzzsprout.com/1986903/fan_mail/new] If you're heading to Pax8 Beyond [https://pax8beyond.com]—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 [https://msptoolkit.com], 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 shows * What to do instead of hiding behind your booth table * How to evaluate your event ROI—and what metrics actually matter * Why relationships, not branding, drive long-term value * Tips for making every handshake, hallway chat, and happy hour count Whether 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 [https://foxcrowgroup.com] at booth 929 at Pax 8 [https://pax8.com] Beyond.   Read the blog post inspired by the interview here. [https://www.foxcrowgroup.com/insights/msp-event-marketing-strategies-for-new-it-channel-vendors] Carrie [https://linkedin.com/in/carrielynnrichardson]Richardson and Ian [https://linkedin.com/in/ianalexanderrichardson] 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 [https://www.foxcrowgroup.com] Book time with Carrie here! [https://randr.membrain.com/Meet/carrie@croocial.com] Be a guest on WIN!  [https://randr.membrain.com/Beacon/Form/4de426f6-c941-4583-9127-62dba3d00fc9]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.

28 May 2025 - 22 min
episode Rex Frank - Winning MSPs Follow A Process artwork

Rex Frank - Winning MSPs Follow A Process

Send us Fan Mail [https://www.buzzsprout.com/1986903/fan_mail/new] 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 [https://pax8.com] 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 back * How to reposition the vCIO role for long-term client impact * The one thing your org chart says about your growth ceiling * Why PAX8 Academy is reengineering the MSP maturity model Find Rex Frank onsite at Pax8 Beyond [https://pax8beyond.com]!  Read the article [https://www.foxcrowgroup.com/insights/growing-an-msp-that-doesnt-break-at-scale] inspired by this interview on the Fox and Crow Group blog [https://foxcrowgroup.com/insights]. Carrie [https://linkedin.com/in/carrielynnrichardson]Richardson and Ian [https://linkedin.com/in/ianalexanderrichardson] 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 [https://www.foxcrowgroup.com] Book time with Carrie here! [https://randr.membrain.com/Meet/carrie@croocial.com] Be a guest on WIN!  [https://randr.membrain.com/Beacon/Form/4de426f6-c941-4583-9127-62dba3d00fc9]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.

20 May 2025 - 10 min
episode Nick Wolf Shares MSP Event Engagement Strategies artwork

Nick Wolf Shares MSP Event Engagement Strategies

Send us Fan Mail [https://www.buzzsprout.com/1986903/fan_mail/new] 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 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 [https://linkedin.com/in/carrielynnrichardson]Richardson and Ian [https://linkedin.com/in/ianalexanderrichardson] 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 [https://www.foxcrowgroup.com] Book time with Carrie here! [https://randr.membrain.com/Meet/carrie@croocial.com] Be a guest on WIN!  [https://randr.membrain.com/Beacon/Form/4de426f6-c941-4583-9127-62dba3d00fc9]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.

14 May 2025 - 15 min
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