MSP Mastery: Ctrl-Alt-Deliver

Why MSP Growth Starts With Community with Jake Webber-Cadby

Welcome to MSP Mastery: Ctrl Alt Deliver Podcast, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. In this episode, we sit down with Jake Webber-Cadby from Inforcer, one of those people in the MSP channel who brings both big vendor experience and a genuinely practical view of what MSPs need to succeed. With a background that includes Datto, ConnectWise, and now Inforcer, Jake has spent years working closely with MSPs and understanding the realities of the industry from both the commercial and operational side. Jake shares his journey into the MSP space, from a sports focused upbringing and dreams of professional golf through to building a career in the channel. We explore what makes the MSP industry so unique, why community matters more than ever, and how relationships, events, and peer networks can create real momentum for business growth. We also unpack the challenges MSPs face when adopting new tools, navigating Microsoft’s moving partner landscape, and making sure technology investments actually deliver value. Here is what we covered together: ✅ How Jake’s career began through family connections and an introduction to Datto ✅ What makes the MSP community so unique and why peer support matters ✅ Why MSP owners need to go where their clients gather instead of waiting for growth to happen ✅ How events, communities, and real conversations help build stronger business relationships ✅ Why so many MSPs underuse the tools they buy and what successful adoption looks like ✅ The importance of clear onboarding, ownership, and accountability when bringing in new technology ✅ Why MSPs need to be intentional about the tools they choose and the clients they serve ✅ How to stay on top of Microsoft changes and make better use of partner relationships We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP, practical insights from people who understand the challenges, pressures, and opportunities in this industry. 👉 Connect with Jake Webber-Cadby on LinkedIn: Jake Webber Cadby [https://www.linkedin.com/in/jake-webber-cadby-92477a111/] 👉 Learn more about Inforcer: Inforcer [https://www.inforcer.com/] 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog [https://mspmastery.blog] 🎧 Listen through YouTube Podcast here: YouTube Podcast [https://www.youtube.com/playlist?list=PLiaUnypUyICxq4_-PnoZhnMd-LlqL22-E] 📸 Follow on Instagram: instagram.com/mspmastery [https://instagram.com/mspmastery] ▶️ Subscribe on YouTube: youtube.com/@MSPMastery [https://www.youtube.com/@MSPMastery]

The Traineeship Strategy: Building a Team That Stays and Grows with Nathan Gemmill

Welcome to MSP Mastery: Ctrl-Alt-Deliver Podcast, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. In this episode, we sit down with Nathan Gemmill, someone we have known since he joined us straight out of high school as a trainee. Over the years, we watched Nathan grow from a junior team member into a confident and capable IT professional, making this a deeply personal and insightful conversation about career development in the MSP industry. Nathan shares his journey from school leaver to experienced technician, reflecting on the value of learning on the job, the importance of having the right support around you, and why curiosity can be one of the greatest assets in a technology career. We also explore the realities of bringing trainees into an MSP, how to help them succeed, and why creating a culture where people can make mistakes and learn from them is essential for long term success. Here is what we covered together: ✅ How Nathan’s IT career began with one unexpected conversation at a service station ✅ Why traineeships can be a powerful long term strategy for MSPs ✅ The importance of buddy mentors, structure, and support in the early days ✅ Why curiosity, hands on learning, and real world experience matter so much in IT ✅ How to build a workplace culture where mistakes are owned, communicated, and resolved ✅ The differences between MSP life and internal IT roles ✅ Why training the trainer can help build stronger teams and future leaders We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP, practical insights from people who understand the challenges, pressures, and opportunities in this industry. 👉 Connect with Nathan Gemmill on LinkedIn: Nathan Gemmill [https://www.linkedin.com/in/nathan-gemmill/] 👉 Learn more about GMHBA: GMHBA [https://www.gmhba.com.au/] 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog [https://mspmastery.blog] 📸 Follow on Instagram: instagram.com/mspmastery [https://www.instagram.com/mspmastery/] ▶️ Subscribe on YouTube: youtube.com/@MSPMastery [https://www.youtube.com/@MSPMastery]

The Growth Trap with Brendan Rose: Why Hiring and Hoping is Costing Your MSP

Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. In this episode, we sit down with Brendan Rose, a true veteran of the Adelaide MSP scene and business consultant at Morphability. Brendan brings over 20 years of experience across sales, operations, and executive leadership, offering a unique perspective on what it actually takes to scale a team without burning through cash. Brendan shares the hard truths about the growth paradox, why simply hiring a BDM to sell more often fails, and why building the map before you hire the person is the only way to set them up to succeed. We also dive into the idea of breaking up marriages, and why your next high value client is likely sitting in your competitor’s portfolio right now. Here is what we covered together: ✅ Why hiring a salesperson without a plan is the fastest way to waste money ✅ The breaking up marriages model and how to disrupt the bond between your competitor and your future client ✅ Why your next customer is not sitting at MSP industry events and where you should be showing up instead ✅ The lead generation trap and why you need to fix your internal sales engine before chasing volume ✅ The first sales hire and why the owner must stay close for longer than they think ✅ Sales versus operations and how to align delivery capacity so growth does not break your business We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP, practical insights from people who understand the challenges, pressures, and opportunities in this industry. 👉 Connect with Brendan on LinkedIn: Brendan Rose [https://www.linkedin.com/in/brrose/] 👉 Learn more about Morphability: morphability.au [https://www.morphability.au/] 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog [https://mspmastery.blog] 📸 Follow on Instagram: instagram.com/mspmastery [https://instagram.com/mspmastery] ▶️ Subscribe on YouTube: youtube.com/@mspmastery [https://youtube.com/@mspmastery]

The Second Deal Trap and the Six Month Slump with Ryan Fuzzy Spillane

Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. In this episode, we sit down with Ryan Fuzzy Spillane, CEO of 360 Consulting and a long time MSP operator turned trusted adviser. Ryan has been on both sides of the table, completing multiple acquisitions and then living through the integration journey after a major exit. Ryan shares the hard truths MSP owners need to hear about acquisitions, valuation, and what really happens after the deal is signed, including the moment many owners do not expect: the six month mark can be the lowest point when you still carry responsibility but no longer have control. Here’s what we covered together: ✅ Why your second acquisition is often your most dangerous ✅ Why product revenue adds little to business value, and why recurring revenue changes the valuation conversation ✅ Why you cannot acquire when your leadership team is already at full capacity ✅ What sellers need to tighten up before an exit, including agreements, financial clarity, and documentation ✅ The post sale reality and how to prepare for what comes next We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP, practical insights from people who understand the challenges, pressures, and opportunities in this industry. 👉 Connect with Ryan on LinkedIn: Ryan Fuzzy Spillane [https://www.linkedin.com/in/fuzzyaus/] 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog [https://mspmastery.blog] 📸 Follow on Instagram: instagram.com/mspmastery [https://www.instagram.com/mspmastery] ▶️ Subscribe on YouTube: youtube.com/@mspmastery [https://www.youtube.com/@mspmastery]

The "Enthusiastic Intern" and the Impact Effort Matrix for AI Adoption with Andrew Herbert

Welcome to MSP Mastery, the podcast for MSP owners and leaders who want to build a better MSP; one that actually works for them. I’m Jeni Clift, joined by my husband and long-time business partner, Nick Clift. Together, we’ve spent decades building, scaling, and eventually exiting our own MSP business. Over the years, we’ve seen firsthand that the MSPs who thrive are the ones willing to evolve. And right now, few shifts are more important than the rise of AI and automation. In this episode, we sit down with Andrew Herbert, founder of Remap AI, to pull back the curtain on how MSPs can actually implement AI without getting lost in the noise. Andrew shares his "operator first" approach, explaining why treating AI as an "enthusiastic intern" is the best way to maintain quality while scaling output. Here’s what we covered together: ✅ Why thinking of AI as an enthusiastic intern helps you manage its knowledge and its limitations ✅ How to use the Impact Effort Matrix to identify the high value friction points in your business ✅ The "Annualised Sunk Cost of Time" and how it creates a financial business case for automation ✅ Why MSPs must avoid free AI accounts and the critical security risks of "leaving the keys on the table" ✅ How to transition from being a tech focused MSP to an "AI ready" business partner for your clients We created this podcast to share the real conversations and lessons we wish we’d had more of while running our own MSP — practical insights from people who understand the challenges, pressures, and opportunities in this industry. Whether you are looking for quick wins in your operations or a long term strategy to lead your clients through the AI revolution, this episode with Andrew offers a grounded and practical roadmap for what is possible today. 👉 Connect with Andrew on LinkedIn: Andrew Herbert [https://www.linkedin.com/in/herbertandrew/] 🌐 Learn more about Remap AI: Remap AI [https://remap.ai/] 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog [https://mspmastery.blog]