Episodes

  • From Break-Fix to Boardroom: Chris Day's Blueprint for MSPs

    From Break-Fix to Boardroom: Chris Day's Blueprint for MSPs
    Aug 21 2025

    In this compelling episode, MSP legend Chris Day shares his transformative journey from an IT services entrepreneur to a software visionary who helped solve the industry's biggest documentation problem.

    Join us as we discuss:

    • Why a plumber role is a dangerous posture for an MSP and how to pivot to a strategic advisor.

    • The birth of IT Glue: How solving a core business problem led to a multi-million-dollar software company.

    • The importance of relentless perseverance and why the moment you're ready to quit is often when a miracle happens.

    • How to go from a reactive "break-fix" mindset to building a strategic "growth loop."

    • Navigating the AI revolution and becoming an "AI shepherd" for your clients.

    This is more than a conversation; it's a blueprint for building a high-impact, high-value business. Watch now and discover the keys to unlocking your next step altitude!

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    36 mins
  • Building Community, Automating Impact: The ImmyBot Way with Tara Rummer

    Building Community, Automating Impact: The ImmyBot Way with Tara Rummer
    Jul 24 2025
    What if automation wasn’t about replacing people—but freeing them up to do what matters most? In this episode, Tara Rummer of ImmyBot shares how her team is helping MSPs scale smarter, eliminate revenue leaks, and reclaim valuable time—without losing their human touch. We uncover: The real origin of ImmyBot (from a 20-year-old MSP!) Why automation ≠ AI, and why that distinction matters Fixing revenue leakage through smart PSA integrations How freeing up engineers leads to higher-margin work Community-first growth without a sales team Why trust, culture, and people still matter most Whether you’re scaling an MSP or streamlining your stack, this is a must-listen conversation with someone who’s been in your shoes. Visit ImmyBot: https://immy.bot #MSPCommunity #MSPAutomation #ImmyBot #BuildITLive #PeopleFirstLeadership #TimeFreedom #OperationalExcellence
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    20 mins
  • Ryan Bowman Unfiltered: Cybersecurity, AI & the MSP Advantage

    Ryan Bowman Unfiltered: Cybersecurity, AI & the MSP Advantage
    Jul 17 2025
    In this episode, Ryan Bowman of ThreatLocker joins Sunny Kaila for an insightful conversation on what it takes to defend today’s MSPs from modern cyber threats. From his time in the trenches as an MSP operator to his current work helping partners at ThreatLocker, Ryan shares powerful insights on: Why “Zero Trust” isn’t a buzzword: it’s a necessity How attackers are using AI to rewrite and bypass defenses Why familiar tools, when misused, are the most dangerous What vendors get wrong about AI—and how to stay human-first Plus: How to grow techs into transformational leaders This isn’t a hype session: it’s a wake-up call. Want to stay ahead of the threats and lead with clarity? Don’t miss Ryan live at Build IT LIVE 2025: http://itbd.net/live Subscribe for more unfiltered leadership conversations: Click Here #MSPCybersecurity #ZeroTrust #AIThreats #BuildITLIVE2025 #MSPLeadership #RyanBowman #ThreatLocker #HumanFirstSecurity #MSPStrong
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    23 mins
  • Baxter Lanius: Why Cash Confidence Is the Hidden Growth Lever for MSPs

    Baxter Lanius: Why Cash Confidence Is the Hidden Growth Lever for MSPs
    Jul 10 2025
    What’s stopping your MSP from scaling? Hint: it’s not sales, it’s cash flow. In this episode of Sunny’s Silver Linings, I sit down with Baxter Lanius, CEO of Alternative Payments, to unpack why cash confidence is the true growth engine for modern MSPs. From Wall Street investing to launching a fintech built for the channel, Baxter shares how automation, clarity, and a shift in mindset can transform your operations — and your EBITDA. Key Takeaways: Why most MSPs unknowingly bleed value from slow AR processes How to reduce DSO from 35 to 10 days with automation The mindset shift from technologist to strategic operator How PE thinking helps you prioritize the right growth bets “Revenue is vanity, profit is sanity, cash flow is reality” — explained Whether you’re bootstrapped or PE-backed, this is a must-watch for any MSP leader serious about scaling smarter.
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    20 mins
  • Kendra Lee: Boost MSP Sales ROI & Build Authentic AI-Powered Growth

    Kendra Lee: Boost MSP Sales ROI & Build Authentic AI-Powered Growth
    Jul 3 2025

    Struggling to get real ROI from your MSP sales efforts? In this episode of Sunny Silver Linings, Kendra Lee: sales strategist, HubSpot Gold Partner, and AI-for-sales expert: shares how MSP leaders can use AI to drive smarter prospecting, tighter follow-ups, and repeatable revenue growth.

    We cover everything from sales consistency and CRM discipline to the right way to use AI without losing your authenticity. This is your playbook for building a sales machine that works without sounding like a robot.

    Don’t miss out! Subscribe for more leadership and growth strategies!

    #SunnySilverLinings #MSPSales #AIforSales #RevenueGrowth #SalesStrategy #MSPGrowth #LeadershipInTech
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    30 mins
  • Jamison West: The MSP Owner's Blueprint to Time Freedom & Scaling Impact

    Jamison West: The MSP Owner's Blueprint to Time Freedom & Scaling Impact
    Jun 12 2025

    Are you an MSP owner feeling indispensable? In this episode, Jamison West, a serial entrepreneur and MSP veteran, unveils his transformative "Five Ps" framework for building a business that thrives independently. Learn how to overcome the founder's fear, delegate effectively, and unlock unparalleled freedom.

    Key Highlights:

    • The profound shift: from indispensable owner to replaceable leader.

    • Jamison's "Five Ps" for building a scalable, high-value business.

    • How to find and empower your ideal "number two.”

    • Aligning incentives for mutual growth and shared success.

    • Overcoming common owner pitfalls and the power of Highest and Best Use (HABU).

    This episode is packed with actionable insights for MSP leaders ready to create enterprise value, gain time freedom, and truly enjoy their entrepreneurial journey. Don't miss out—subscribe for more leadership and growth strategies!
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    35 mins
  • The HR Edge: How to Attract, Grow & Lead Top Talent in the MSP World

    The HR Edge: How to Attract, Grow & Lead Top Talent in the MSP World
    May 30 2025

    Struggling to scale your MSP with the right people? You're not alone. In this powerful episode, IT By Design CEO Sunny Kaila talks with Ainsley Lump of Entech about the real HR strategies that drive growth, loyalty, and culture in today’s MSP landscape.

    From recruiting smarter to building magnetic culture and performance systems your team actually wants—this is the leadership masterclass you didn’t know you needed.

    Here’s a synopsis of what Ainsley shares:

    • Why scalable processes are the #1 thing MSPs overlook

    • What top talent looks for before they even apply

    • How to create a culture that retains, inspires, and grows people

    • The truth about performance reviews (hint: your team wants them!)

    • And much more!

    If you want to lead with heart and strategy, hit play now!

    #MSPLeadership #PeopleStrategy #CultureDrivesGrowth #HRForMSPs #ScalableGrowth #Entech #ITByDesign

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    11 mins
  • From IT Fixers to Strategic Advisors: Reinventing the MSP Game

    From IT Fixers to Strategic Advisors: Reinventing the MSP Game
    May 15 2025

    What’s the secret to building an unstoppable MSP in today’s fast-moving tech world? In this episode, Peter Melby, CEO of New Charter Technologies, breaks down how top MSPs are shifting from reactive IT support to proactive business problem-solvers.

    Discover why the future belongs to those who ask better questions, embrace AI with purpose, and treat their MSP like an innovation lab—not just a service desk.

    Key Highlights:

    • Why solving business problems is the new MSP superpower
    • The hidden cost of not asking the right client questions
    • How AI can drive client value—not just internal efficiency
    • Why MSPs must own their innovation strategy
    • Balancing vendor support with internal agility
    • The people-first mindset that builds lasting trust

    This is a must-watch for MSP leaders ready to evolve, innovate, and lead their clients through real business transformation. Subscribe for more growth-focused conversations!

    #MSPStrategy #BusinessTransformation #AIforMSPs #TechLeadership #ManagedServices #DigitalInnovation

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    38 mins