WIN

Hosted by Carrie Richardson Fox and Crow Group

Business Entrepreneurship

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Latest episode

Sep 2026

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EN-US

About the show

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/

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60 recent

September 28, 202621 min

WIN x West McDonald: Closing the AI Readiness Gap in the MSP Channel

Send us Fan Mail Fewer than 250 companies out of 110,000 technology service providers in the Fox & Crow Instinct database show up talking about AI workflows, AI policies, or monetizing AI. On this episode of WIN, host Carrie Richardson sits down with West McDonald — founder of GoWest.ai and BizVantage — to unpack why MSPs are so far behind on AI, even though customers are begging for help. West shares why AI hasn't followed the same fast-adoption path as cybersecurity did for MSPs, why "imposter syndrome" is holding channel partners back from owning AI conversations, and why he believes the answer isn't to lead with the technology at all — it's to start with the client's actual pain points. He also walks through GoWest.ai's human-centric philosophy (AI augments people, it doesn't replace them), a real example of an AI inbox-triage agent built for a client, and why agentic search is starting to reshape SEO — including the story behind an $80 million inbound MSP lead that found Fox & Crow Group through an AI answer engine instead of Google. In this episode: Why under 250 of 110,000 MSPs are publicly talking about AI (Fox & Crow Instinct data) The "imposter syndrome" keeping MSPs from claiming AI as part of their stack Why West starts every AI engagement with the client's workflow, not the technology A real-world AI agent example: inbox triage for executives buried in email How agentic search is changing SEO — and how it landed an $80M inbound lead Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

September 17, 202623 min

Matt Tomlinson: MSPs will WIN with AI

Send us Fan Mail Read the accompanying article on the Fox & Crow group blog here. Matt Tomlinson has spent years on both sides of the MSP world, first inside it, now helping MSPs deploy AI at Fixify , and he's watched this exact hesitation play out before with cloud, MDR, EDR, SIEM, and SOC. In this episode, he and Carrie dig into why AI adoption in the MSP channel is following the same slow-then-sudden pattern, and why the real barrier isn't the technology itself. Matt explains the stigma MSPs are up against: the fear that using AI contradicts the personal-touch pitch they've built their businesses on, even though most customers just want their ticket solved quickly. He shares a story about spending twenty minutes on the phone with a hotel chatbot he thought was human, and explains why guardrails, not capability, are what separate a useful AI deployment from a viral horror story. Carrie and Matt also cover sentiment analysis and CSAT, the difference between selling AI and selling automation, why private-equity-backed platforms are positioned to move first on pricing, and what Matt expects to happen when homegrown AI builds start hitting their maintenance ceiling around 2027. They close with concrete advice on what MSPs should actually be publishing if they want to compete for the AI-advisory conversation instead of sitting it out. Matt Tomlinson , Senior Director of MSP Partnerships, Fixify Fixify is an AI solution built to resolve tier-one MSP tickets start to finish. Before joining Fixify, Matt spent years working inside the MSP world himself. Find him at IT Nation this year, or learn more at fixify.com, where an AI assistant named Fiona can answer questions about fit. Chapters 0:00 – Welcome and Introductions 1:10 – Why MSPs Hesitate on AI 2:18 – Stigma and Guardrails 4:25 – Sentiment Analysis and CSAT Insights 6:41 – Adoption Barriers and the Content Gap 8:55 – AI vs. Automation: Two Different Sales Motions 11:18 – The Coming Messaging Shift 14:54 – Future Trends and Homegrown AI Risks 16:44 – Risk Mitigation and Token Costs 18:42 – Content Ideas for MSPs 21:15 – Where to Learn More Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

September 11, 202634 min

Doug Miller at Brightworks Shares on How Sales Coaching Builds WINNING MSP sales teams.

Send us Fan Mail Doug Miller of Brightworks spent 15 years trying to fix his MSP's sales problem. Cold email blasts, LinkedIn programs, hired reps who couldn't prospect - everything, really. Then he found a process that actually worked. In this episode, host Carrie Richardson talks with Doug about why a business built entirely on referrals can't be sold, why cold calling still works in the IT channel, and how stepping back from sales completely helped Brightworks post its best year ever, with an internal sale to his son and COO already in motion. Topics covered: Why an MSP built on referrals can't actually be sold Why owners can't just teach their own sales playbook to a rep Why cold calling isn't dead for MSPs How Brightworks built and supported a top-performing sales rep Red flags for disqualifying the wrong-fit client Doug's exit plan, and what he's doing to prepare for it Watch the video here. Read the blog post here. Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

September 4, 202620 min

David Reid's "Getting to Exit" is a book on building winning MSP exit strategies

Send us Fan Mail How David Reid Sold His MSP for 8X (and Got a Decade of His Life Back) David Reid sold his business before he turned 50. That wasn't luck. It was the plan. He built Epic Information Solutions in Winnipeg back in 1995, rode the shift from break-fix to recurring revenue, and decided at 40, sitting at his cabin, that he wanted out by 50. Eight years later he sold to the local telco he'd been quietly courting the whole time, for just over 8X. David wrote the book Getting to Exit and built a nine-step framework for planning an MSP exit that's actually sellable, not just profitable. Carrie sits down with him to talk about what most MSP owners get wrong about exit planning, and what he'd tell his 40-year-old self. Read more about David's approach to exit planning on the Fox & Crow blog here. In this episode: Why David picked his buyer eight years before he sold to them The nine-step framework for an MSP exit, starting with "figuring out your why" Why a legacy exit (selling to family or employees) usually means a lower valuation and a longer wait to get your money The classic MSP hiring mistake David made: promoting his best salesperson to sales manager. He calls it a cardinal sin. Why five-plus years is the real minimum runway for exit planning, not two or three Guest: David Reid, author of Getting to Exit. Find the book and his exit-planning resources at gettingtoexit.com. If you're an MSP owner thinking about your own exit, or you just want to hear a "Holy moly, that's a big gap I gotta fill" moment turn into an actual plan, subscribe. Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

August 31, 202627 min

Matt Koenig shares winning MSP event strategies for new IT channel vendors

Send us Fan Mail Matt Koenig Shares Winning MSP Event Strategies for New IT Channel Vendors Trade 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 Fall 2026 relaunch with Matt Koenig, the channel sales veteran who built a 45-person team at RapidFire Tools, spent years as VP of Sales at Nodeware, and just launched his own practice, White Tiger Consulting . Matt and Carrie get into what a brand-new IT channel vendor actually needs before committing sponsorship dollars: which shows are for branding versus lead generation, what belongs on a banner nobody's going to read anyway, how to build a $50,000 first-year event budget, why swag is either worth doing well or not worth doing, and how to avoid showing up with your booth stuck in customs. Read more on the Fox & Crow Group website here. In this episode: CHAPTERS 00:00:00 Welcome Back to WIN 00:00:43 Catching Up Before ChannelCon 00:00:59 Launching White Tiger Consulting 00:03:01 What Vendors Can Expect From White Tiger 00:05:15 Where New Vendors Should Start 00:06:32 Event Logistics and Shipping Timelines 00:10:00 Getting Ready to Commit Sponsorship Dollars 00:12:32 Bare-Bones Budget: Booth Basics and Banners 00:14:26 Crafting Your Talk Track and Slides 00:15:21 Stage Presence and Public Speaking Lessons 00:17:02 Building a Marketing Budget and Picking Shows 00:18:20 Working the Show Floor Between Booth Time 00:20:23 Off-Site Dinners and Vendor Politics 00:20:55 Swag Strategy That Actually Works 00:23:50 Attracting Booth Traffic Without Swag 00:24:43 Wrapping Up and Where to Find White Tiger Matt is offering a free 30-minute consultation to vendors and MSPs, no strings attached. Learn more at White Tiger Consulting. Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

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? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms 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 Mail 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 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? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms 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 Mail 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 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 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? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms 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 Mail 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. 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 ! 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? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms 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 Mail 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 Richardson and Ian Richardson host the WIN Podcast - What's Important Now? They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses. Learn more at: Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses Book time with Carrie here! Be a guest on WIN! We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.