MSP Mastery: Ctrl-Alt-Deliver

Jeni Clift, Nick Clift
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Welcome to Ctrl-Alt-Deliver: MSP Mastery — the podcast for IT leaders, MSP owners, and service delivery professionals who want to elevate performance, improve processes, and stay ahead in the fast-changing managed services landscape.

  1. 2D AGO

    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 👉 Learn more about Morphability: morphability.au 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog 📸 Follow on Instagram: instagram.com/mspmastery ▶️ Subscribe on YouTube: youtube.com/@mspmastery

    58 min

  2. APR 26

    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 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog 📸 Follow on Instagram: instagram.com/mspmastery ▶️ Subscribe on YouTube: youtube.com/@mspmastery

    53 min

  3. APR 19

    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 🌐 Learn more about Remap AI: Remap AI 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    45 min

  4. APR 12

    The Insurance Trap: Is Your MSP Unknowingly Underwriting Your Clients? with Tim Stephinson

    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 how we manage risk, professional liability, and the critical boundaries between our business and our clients’ data. In this episode, we sit down with Tim Stephinson, COO at Sherpa Tech and an Australian insurance specialist with over 20 years of commercial experience. Tim helps us cut through the complexity and confusion surrounding cyber insurance and professional indemnity to ensure MSP owners are properly protected without the usual friction. Here’s what we covered together:  ✅ Why the phrase "we don't need insurance because our MSP has it" is a massive red flag  ✅ The "survival vs. inconvenience" rule: how to prioritise the risks that could actually kill your business  ✅ Why you must have the insurance conversation before onboarding a high-risk client  ✅ The vital difference between a "process failure" and an "absence of process" (and which one is insurable)  ✅ How to stop being the silent insurer for your clients and start saying "your data, your problem" 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 questioning your current coverage, struggling to explain cyber responsibility to your clients, or worried about being "on the hook" for a third-party breach, this episode with Tim offers a grounded and timely perspective on what leaders need to do now to build a business that is both profitable and fulfilling. 👉 Connect with Tim on LinkedIn: Tim Stephinson 🌐 Learn more about Sherpa Tech: sherpatech.com.au  🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    47 min

  5. APR 6

    Fish in a Sandpit: Finding the Right People and Processes for Scalable Growth with Melissa Hockenberry

    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 how we lead our people and the intentional decisions we make around operational discipline. In this episode, we sit down with Melissa Hockenberry, an MSP industry veteran with over 20 years of experience, to unpack what it really takes to transition from a reactive "firefighting" culture to a proactive, system-driven business. Melissa shares her unique perspective on client retention and why understanding the "friction" in your team is the only true path to a scalable MSP. Here’s what we covered together:  ✅ Why "knee-jerk" reactions to problems are masking deeper systemic issues  ✅ The "Fish in a Sandpit" analogy and why letting the wrong fit go is a gift  ✅ Why standardisation is more important than ever in an era of rapid AI and M&A shifts  ✅ How to identify if you have a "people problem" or actually a "process problem"  ✅ Simple steps to experience your own business from the client’s perspective to find hidden friction 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 struggling with team performance, looking to improve client retention, or questioning why your current processes aren't scaling, this episode with Melissa offers a grounded and timely perspective on what leaders need to do now to build a business that is both profitable and fulfilling. 👉 Connect with Melissa on LinkedIn: Melissa Hockenberry 🌐 Learn more about From the Front to the AC: ftftac.com 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    50 min

  6. MAR 29

    Building an MSP that Runs without You with Allan Michelmore

    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 way we structure our teams and leverage modern tools like AI. In this episode, we sit down with Allan Michelmore, Managing Director of Control Networks, to unpack what it really takes to build a business that is an entity in itself. Allan shares his deep experience with offshore resourcing and why systems and documentation are the only true path to freedom for an MSP owner. Here’s what we covered together:  ✅ Why the 80 20 rule is the secret to overcoming documentation overwhelm  ✅ How to put essential guardrails around AI to protect your business and your clients  ✅ The biggest myths about offshoring and why it fails for most MSPs  ✅ Why treating your offshore team as true colleagues is non negotiable for success  ✅ How to transition from being the bottleneck to having a business that runs with or without you 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’re already using offshore resources, starting to think about AI governance, or questioning how to finally step out of the day to day operations, this episode with Allan offers a grounded and timely perspective on what leaders need to do now to stay ahead. 👉 Connect with Allan on LinkedIn: Allan Michelmore 🌐 Learn more about Control Networks: Control Networks 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    47 min

  7. MAR 22

    Tas Gray: Why AI and Automation Will Make or Break the Modern 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. 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 Tas Gray, Managing Director of Axiom IT, to unpack what AI and automation really mean for MSPs — not as hype, but as a practical business reality. Tas shares why increasing efficiency, reducing manual effort, and driving costs down are no longer optional for businesses that want to stay competitive and profitable. Here’s what we covered together:  ✅ Why AI and automation can dramatically improve efficiency and reduce operating costs  ✅ How manual processes can leave MSPs vulnerable to shrinking margins and rising costs  ✅ Why clients are already looking for meaningful ways to use AI to improve productivity  ✅ The risks MSPs face if they delay automation for too long  ✅ How AI is reshaping expectations across software, service delivery, and business operations 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’re already experimenting with AI, starting to think more seriously about automation, or questioning how these changes will affect your MSP in the years ahead, this episode with Tas offers a grounded and timely perspective on what leaders need to do now to stay ahead. 👉 Connect with Tas on LinkedIn: Tas Gray 🌐 Learn more about Axiom IT: Axiom IT 🎧 Listen to other MSP Mastery Podcast episodes here: mspmastery.blog

    54 min

  8. MAR 15

    Why Most MSP Marketing Leaks with Niall Mackay

    Welcome to MSP Mastery Podcast. I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business. Along the way, we learned something fundamental. Operational maturity isn't just about your tech stack—it’s about how you present your authority to the market. In this episode, we’re joined by Niall Mackay, the "Podcast Guy" and founder of Seven Million Bikes Podcasts. Niall lives and breathes audio and video production, helping founders move past the "shiny tool" phase to create content that actually sticks. As the editor behind the scenes of Control Alt Deliver for the last six months, Niall has developed a unique outsider-in perspective on the MSP industry. He’s seen firsthand how the principles of delegation, automation, and niche authority apply just as much to a podcast as they do to a managed service provider. What becomes clear in this conversation is that most MSP marketing doesn’t explode. It leaks. We explore: The Exit Strategy Reality Check: Why building a business around yourself is just selling a client list, not a saleable asset.The DIY Trap: Why spending 8 hours editing a podcast is a "false economy" when your time is worth hundreds per hour.Removing the Founder: How Niall used Notion and AI to automate his production and take himself out of the day-to-day grind.The ROI of Authority: Why your podcast should be a lead magnet that sends people back to your business, not your guests'.Consistency vs. Frequency: Why a weekly cadence is the non-negotiable standard for building trust.The "Cost" of Waiting: Why every business will eventually have a podcast and why the window to stand out is closing.Video & 4K Standards: The minimum viable tech you need to stop looking "grainy" and start looking professional.We also discuss the psychological hurdle of "hating your own voice" and Niall’s pointed reminder: “Don't give free advertising to your guests. They're there to help prop you up. You need to be the expert.” This episode is not about shiny microphones. It’s about operational discipline. Brand authority. Founder freedom. If you are an MSP owner who has been "thinking about" starting a podcast but is worried about the time drain, this conversation provides the roadmap to doing it right. Connect with Niall Mackay on LinkedIn: https://www.linkedin.com/in/niallmackay/ Learn more about Seven Million Bikes Podcasts: https://www.sevenmillionbikes.com/ Listen to this episode and explore more MSP Mastery conversations at: https://www.mspmastery.blog/episodes Join our Facebook community for MSP owners and leaders: https://www.facebook.com/groups/192546407744556 Subscribe to our YouTube channel: https://www.youtube.com/@MSPMastery Follow MSP Mastery on Instagram: https://instagram.com/mspmastery

    49 min
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About

Welcome to Ctrl-Alt-Deliver: MSP Mastery — the podcast for IT leaders, MSP owners, and service delivery professionals who want to elevate performance, improve processes, and stay ahead in the fast-changing managed services landscape.

Information

  • Creator
    Jeni Clift, Nick Clift
  • Years Active
    2025 - 2026
  • Episodes
    38
  • Rating
    Explicit
  • Copyright
    © 2026 MSP Mastery: Ctrl-Alt-Deliver
  • Show Website
    MSP Mastery: Ctrl-Alt-Deliver