MSP After Hours

Hosted by Craig Willard

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Oct 2025

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Whether you're a seasoned MSP veteran or just stepping into the captivating world of managed services, "MSP After Hours" is your source for compelling stories, expert advice, and unfiltered conversations. Join us as we challenge the status quo, embracing the unexpected, and forging new paths when others choose to follow the crowd. Delve into the fusion of technical prowess and human psychology that drives success in managed services. From decoding operations to navigating the human psyche, we're your compass in a landscape where innovation meets introspection.

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20 recent

October 21, 20257 min

EP9 The Identity Crisis of Most MSPs (and what to do about it)

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpySummaryIn this conversation, Craig Willard discusses the critical importance of identity for Managed Service Providers (MSPs). He emphasizes that many MSPs lack a clear identity, which leads to confusion in pricing, service offerings, and client relationships. Willard provides tactical steps for MSPs to define their identity, including understanding what they want to be known for, what they refuse to compromise, and who they are not for. He highlights the alignment of identity with operations as a key to achieving business clarity and growth. The conversation concludes with a challenge for MSP leaders to articulate their identity and the standards they uphold.TakeawaysMost MSPs struggle with their identity.A strong identity leads to better alignment and clarity.Pricing issues often stem from a lack of identity.Defining what you refuse to compromise is crucial.Understanding who you are not for helps in client selection.Identity should guide every business decision.Alignment between identity and operations simplifies processes.Leaders must have conviction in their identity.Your team reflects your clarity and confidence.Identity is the competitive advantage in the MSP market.Chapters00:00 Intro00:31 The Internal Layer: Leadership Identity01:06 The Root Problem: “The Chameleon MSP”01:58 The Power of Identity02:42 Why Identity Comes Before Pricing03:32 How to Define Your Identity (Expanded)05:42 Alignment: The Multiplier Effect06:54 Closing — Challenge & Takeaway

October 21, 2025Episode 87 min

EP8 The Myth of the Loyal Client (And What To Do About It)

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpySummaryIn this conversation, Craig Willard discusses the misconceptions surrounding client loyalty in Managed Service Providers (MSPs). He emphasizes that true loyalty is not derived from long-term contracts but from genuine relationships built on trust, communication, and responsiveness. Willard critiques the traditional approach of quarterly business reviews, advocating for more frequent and proactive communication to foster real connections with clients. He concludes with strategies for earning loyalty through consistent engagement and treating clients with respect, even when they choose to leave.TakeawaysIf the only reason your client stays is because of a contract, that's not loyalty, that's captivity.Real business value doesn't come from locking people in.You can't measure trust by term length; you measure by freedom of choice.We don't do long-term contracts; we just ask for a 90-day intent to cancel.Real loyalty comes from responsiveness, not routine.Happy clients don't feel forced to stay; they stay because they want to.Real loyalty isn't about contracts; it's about connections.Communication should be constant, not quarterly.Loyalty lives in how your clients feel about you, not what your ticket metrics say.The way you handle a departure says more about your culture than your self-pitch.Chapters00:00 Intro00:29 The False Sense of Security02:01 The Pulse Philosophy03:19 THE QBR Myth04:20 The Vendor Mirror04:54 Don't Be That MSP05:40 The Reality of Loyalty06:07 Practical Takeaways06:38 Closing

October 21, 2025Episode 78 min

EP7 Stop Including Microsoft 365 in your stack

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpySummaryIn this conversation, Craig Willard discusses the challenges and implications of bundling Microsoft 365 with managed services. He argues that while bundling may seem convenient, it can lead to complications with pricing, renewals, and profit margins. Willard advocates for separating licensing from service rates to maintain financial health and transparency with clients. He outlines a structured approach for MSPs to manage Microsoft 365 licenses effectively while ensuring clear communication and stable pricing for clients.TakeawaysBundling Microsoft 365 can create pricing and renewal issues.Separating licensing from service rates improves financial clarity.Maintaining a standard Microsoft configuration is crucial for control.Charging a management fee for Microsoft services is essential.Clients appreciate transparency in billing and services.Separation leads to smoother onboarding and contract management.Your margins should ideally be around 70% or better.Bundling can inflate service rates and complicate contracts.Clear communication with clients about pricing changes is vital.Separating software costs helps maintain profitability.Chapters00:00 Intro00:46 Why Bulding Feels Easy .... Until It Isn't02:32 How We Do It - Standards, Separation, and Control02:39 Implementing a Standard Microsoft Configuration03:06 What Happens When You Separate It03:35 What Happens When you Separate M365 From Your Services04:23 Transitioning Current Clients04:40 How To Explain This To Your Clients05:17 Handling Pushback06:08 Transitioning Current Clients06:50 Real World Wins06:59 Conclusion: The Path to Profitability07:21 Closing

October 21, 2025Episode 66 min

EP6 Mastering MSP Proposals: Avoiding the Weeds, The Art of Framing Services for Clients

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpyIn this conversation, I emphasize the importance of avoiding technical jargon in MSP proposals and instead focusing on client experience and outcomes. I discuss how getting into the weeds can undermine trust and lead to clients viewing MSPs as mere vendors rather than strategic partners. By framing services in a way that highlights the benefits to clients, MSPs can create more effective proposals that close deals more efficiently.TakeawaysYour proposals should not look like technical manuals.Separate sales calls from proposals; they serve different purposes.Proposals should confirm what has already been discussed.Frame your services through the lens of client experience.Avoid listing tools and technical details in proposals.Clients care about outcomes, not technical specifications.Use storytelling to convey the value of your services.Stop training clients to nickel and dime you.Build trust by focusing on outcomes rather than tools.Keep proposals clean, high-level, and outcome-driven.Chapters00:00 Intro00:49 Sales vs. Proposal – Making the Distinction01:43 How to Talk About Tools03:41 Why Getting in the Weeds Hurts You04:04 Focusing on Outcomes Over Technicalities04:34 CPA Analogy04:50 Doctor Analogy

October 21, 2025Episode 55 min

EP5 The Cost of Saying YES in Your MSP!

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpySummaryIn this conversation, Craig Willard discusses the detrimental effects of saying yes too often in the Managed Service Provider (MSP) industry. He emphasizes that while saying yes may seem like good customer service, it often leads to hidden costs that affect margins, team morale, and overall business health. Craig advocates for a strategic approach to decision-making, encouraging MSP owners to set clear boundaries and understand when to say no to protect their business and serve their clients better.Takeaways-Every time you say yes to something outside of your standards, you're also saying no.-Saying yes feels like great customer service but can lead to hidden costs.-Customizing stacks for clients can crush MSP margins.-Scope creep can lead to significant financial losses.-Saying yes out of fear means losing control of your business.-Clients respect you more when you confidently say no.-Strategic yeses can open doors for growth.-Your job is to be the most reliable and secure partner.-Mastering the art of saying no leads to better opportunities.-You deserve to protect your team's sanity and your profitability.Chapters00:00 Intro00:41 The Illusion of Great Customer Service01:22 Where MSPs Bleed Margin01:27 Customizing Stacks01:45 Discounting02:03 Scope Creep02:57 Understanding the Fear Behind Yes03:21 When to Say YES vs. When to Say NO03:51 How to Say NO Without Losing Respect04:32 Closing👉 If you got value from this episode, don’t forget to like, follow, and share with another MSP owner who needs to hear it.For coaching and resources, visit https://craigwillard.com

October 21, 2025Episode 47 min

EP4 The 7 Laws of Building MSP Services

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpyMost MSPs build their services the wrong way...chasing tools, customizing packages for every client, and believing vendor hype. The result? Chaos, weak margins, and constant firefighting.In this episode of MSP After Hours, I break down the 7 Laws of Building MSP Services:Identity shapes everythingStrategy, not tailoringNon-negotiables protect you and themStop guessing—build on certaintiesStay engaged, stay aheadStandards are non-negotiableVendors don’t define your successThis is the roadmap to building services that scale, protect your clients, and keep your MSP profitable.👉 If you got value from this episode, don’t forget to like, follow, and share with another MSP owner who needs to hear it.For coaching and resources, visit https://craigwillard.com

October 21, 2025Episode 35 min

EP3 Why Your MSP Keeps Getting Bad Clients (Hard Truth Inside)

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpyBad clients aren’t just a headache—they’re a business killer. In this episode of MSP After Hours, I break down why so many MSPs end up with clients who nickel-and-dime, blow up the helpdesk, and drain profit… and how to stop it.Most MSPs think bad clients are just part of the business. But here’s the truth: they don’t just show up—you attract them. And the biggest reasons are underpricing and failing to filter prospects through your sales and proposal process.Inside this episode you’ll learn:✅ Why the “cheap” pricing trap fills your roster with the wrong clients✅ How to use your sales and proposal process as a filter, not just a pitch✅ Why line-item pricing destroys your margins (and what to do instead)✅ The real cost of bad clients—on money, morale, and culture✅ A simple framework to filter out bad fits and protect your businessBad clients don’t just happen—they’re chosen. And the good news? You can choose differently.👉 If this episode hits home, make sure to like, subscribe, share it with another MSP owner, and drop a comment below. I’d love to hear your take: How do you filter out bad clients?🎯 Looking for 1:1 guidance? I coach MSP owners on pricing, packaging, sales, and leadership. Learn more at www.craigwillard.com.00:00 Intro00:18 Identifying bad clients01:15 The Truth01:35 Segment 1: The Pricing Trap02:16 Segment 2: The Sales & Proposal Process Problem03:47 Segment 3: The Cost of Bad Clients04:27 Segment 4: How to Filter Clients05:07 Closing

October 21, 2025Episode 25 min

EP2 The High Performance MSP: Why Your Business Growth Starts With Your Mindset

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpyMost MSP owners think their biggest problem is tech. It’s not your stack, your tools, or even your technicians.The real bottleneck? It’s you — the owner.In this episode of MSP After Hours, Craig Willard shares lessons from his new book The High Performance MSP and reveals how upgrading your mindset is the key to building a thriving, profitable, and sustainable MSP.Inside, you’ll learn:✅ Why most MSPs stall (and how to break the cycle)✅ The simple mindset shift that lets you charge what you’re worth✅ How to reframe “failure” so you never actually fail✅ Practical tools (ABCDE method, affirmations, focus exercises) to reset your thinking✅ Why obstacles are opportunities — and how to use them to grow your MSP👉 Don’t forget to subscribe to MSP After Hours for more deep dives into mindset, pricing, packaging, and scaling strategies for MSPs.

October 14, 20254 min

EP1 Why Your MSP Pricing Sucks (and What To Do About It)

Get my book THE HIGH PERFORMANCE MSP https://a.co/d/iy2Pb3QGet by book PROFIT BY TIME https://a.co/d/ihftXpyMost MSPs think their biggest problem is sales, tools, or talent shortages. But the truth? Your pricing is holding you back.In this episode of MSP After Hours, I break down why most MSP pricing models fail — and what you can do about it.💡 Here’s what you’ll learn:The #1 mistake MSPs make when it comes to pricing.Why delivery costs (not overhead) should drive your strategy.The real reason your pricing sucks — and how to fix it.How we went from $39.99/workstation pricing to building a profitable, scalable model.A simple 3-step framework to design profit into your MSP.If every dollar you spend to deliver services isn’t coming back with buddies… you’re not building a business. You’re running on a hamster wheel.👉 Watch this video to learn how to break the cycle and design pricing that actually scales.🔗 Connect with me🌐 Website: craigwillard.com📘 LinkedIn: https://www.linkedin.com/in/craig-willard-mba-phd-abd-b3034819/🎙️ Podcast: MSP After Hours (Spotify/Apple/YouTube)

March 28, 202436 min

MSP Education: Cyber Insurance vs. Cyber Warranty with Nick Wolf

As an MSP owner, I've started to hear more about cyber warranties. Honestly, at first thought, I went straight for "Gimmick" and blew it off. After having this conversation, I now understand how and where cyber warranties fit in.. Listen in as Nick and I discuss!