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The night two critical PHP flaws leaked before their patches, Josh Peterson asked Gary Boyle what was really happening. Gary's answer: AI has made attackers faster than any MSP can patch, the open-weight models they run have no guardrails, and the frontier models defenders use refuse the targeted vulnerability work attackers do freely.
Then Gary turns the question on MSP owners. Most MSPs became brokers of security, handing backup, cloud and antivirus to someone else, and a thousand unpatched endpoints mean something different when the bots never sleep. He argues against freezing AI development and for learning the tools, because AI security expertise is the differentiator MSPs have chased for twenty years.
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What We Cover in This Episode
- Unpack the PHP flaws that leaked before their patches
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SEO Keywords
- AI cyberattacks
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Credits
Host: Josh Peterson
Josh Peterson gave Claude a ConnectWise API user with write access to his time entries and did not lose a minute of sleep over it. Then he asks Gary Boyle the question every MSP owner is now facing: where is the actual security risk, and how much of it should you accept?
Gary's answer starts with where API keys really leak and ends with a cheat code. An MSP that already trusts ConnectWise and QuickBooks with everything cannot single out the LLM as the bigger risk, you cannot stop data leaving a small business anyway, and the owners who stay AI-first while their competitors lock everything down are the ones pulling ahead. Together they work out what a sane risk assessment looks like, and where an MSP should be on the levels from one to four.
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What We Cover in This Episode
- Decide what a Claude integration with ConnectWise actually exposes
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YouTube (Video Podcast):
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SEO Keywords
- MSP AI security
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Credits
Host: Josh Peterson
An MSP owner finds a buyer, signs a letter of intent and starts thinking about the number. Hartland Ross has watched hundreds of those deals from the middle, and he argues the number is only half of what a seller agrees to. The terms decide what you are actually paid, and how long you stay.
Hartland is Founder and Managing Partner of The Host Broker, a brokerage for MSPs and IT services businesses based in Vancouver, British Columbia. In this conversation with Josh Peterson he walks through LOI break fees and exclusivity, how to choose a buyer on fit, how long sellers really stay after the close, and why earnouts exist. Josh brings two deals he saw up close: a $200,000 break fee paid when a buyer walked away, and a seller who realized days before closing that the buyer would inherit his $100,000 hardware investment.
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What We Cover in This Episode
- Unpack a $200K LOI break fee, and why most never survive
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Guest Links
Guest LinkedIn: https://www.linkedin.com/in/hartlandross/
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SEO Keywords
- selling an MSP
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Credits
Host: Josh Peterson
Josh Peterson built a working app in Claude in a day without writing a line of code, and he already has clients who could use it. So he asks Gary Boyle the question every MSP owner is starting to ask: why not build tools like this for clients and charge for them?
Gary's answer starts with a map of the AI journey and the stage he calls the danger zone, where a build is exciting, easy to make and hard to support. Together they work out what an MSP has to settle before it sells software nobody on the team fully understands, and the decision every MSP now faces.
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What We Cover in This Episode
- Build a working app in Claude without writing code, and see why that changes the MSP's role
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YouTube (Video Podcast):
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SEO Keywords
- MSP AI strategy
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Credits
Host: Josh Peterson
Who decides whether an MSP is qualified to hold the keys to a client's business? Right now, mostly nobody, and Josh Peterson suspects insurance companies are quietly taking the job, the same way an insurer, not the FAA, decided which plane he was allowed to fly.
MJ Shoer is Chief Community Officer at GTIA, the IT channel association formerly known as CompTIA, and ran his own MSP for close to nineteen years. In this conversation he argues the industry has to regulate itself before regulators do it instead, and explains the self-regulatory organization GTIA is building with Texas A&M to accredit the whole MSP business.
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What We Cover in This Episode
- Compare how an insurer and the FAA decide who flies, and what it means for MSPs
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Guest Links
Guest LinkedIn: https://www.linkedin.com/in/mshoer/
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YouTube (Video Podcast):
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SEO Keywords
- MSP accreditation
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Credits
Host: Josh Peterson
Josh Peterson opens with a claim most MSP owners will recognize: the owner who says he can't sell and the owner who says he's great at it often end up with the same pipeline. The difference, Josh argues, is not talent. It is the steps both of them skip in the first meeting.
He walks Gary Boyle through the order of selling and the four things every first appointment has to produce before you leave the room: a budget, a time frame, the next meeting date, and a referral request. Then he shows how to stop chasing prospects by making the proposal a formality rather than a surprise.
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What We Cover in This Episode
- Sell yourself first, the company second, and goods and services last
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SEO Keywords
- MSP owner sales
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Credits
Host: Josh Peterson
Josh Peterson has pushed MSP owners to enter all forty hours for more than twenty years, and lately he has noticed something new: they have mostly stopped arguing. Gary Boyle thinks the reason is money. Labor costs keep rising while contracts priced years ago never moved, and owners who want to know where the margin went end up at the timesheet.
The two work through the one number Josh says explains nearly every weak service P&L: the effective hourly rate on your agreements, measured against the rate you would charge for a project hour. For most MSPs it comes out at roughly half.
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What We Cover in This Episode
- Explain why MSP owners have stopped fighting time entry
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YouTube (Video Podcast):
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SEO Keywords
- MSP effective hourly rate
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Credits
Host: Josh Peterson
Josh brought a live client problem to this one. He had given a single leader about thirty action items for one initiative goal, and that leader told him it felt like being treated like a child. The feedback was fair. The instinct behind the thirty items was not wrong either, and that tension is the whole episode.
Josh Peterson and Gary Boyle work through where action items actually belong in a strategic plan, when a step deserves to be its own task, and how you tell whether a plan is working or the quarter simply went your way.
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What We Cover in This Episode
- Locate action items correctly: yearly plan, quarterly initiatives, monthly goals, weekly actions
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YouTube (Video Podcast):
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SEO Keywords
- MSP strategic planning
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Credits
Host: Josh Peterson
A million dollars in revenue, a hundred and eighty thousand to the owner, three percent left at the bottom. The owner is not careless. They are comfortable, and comfort is what stopped the examination.
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An MSP owner asked Josh Peterson a question with an obvious answer, right up until you look at it closely. He pays fifty to sixty thousand a year for a capable appointment setter. An AI outreach service quoted him thirty-six thousand to do more of the same work, across far more of the market. He goes on the sales call either way.
Gary Boyle settles the technology question quickly, then moves to the part that decides whether the money works. A vendor controls nothing after the email lands, so a click reported as a lead marks the boundary of their control rather than a lie. The buyer's job is to name the outcome first and make the vendor answer against it. The back half is about fixing your message before you buy any channel.
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What We Cover in This Episode
- Whether cold calling still works for MSPs in 2026, and what actually changed
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Hosts
Josh Peterson: https://www.linkedin.com/in/joshdpeterson/
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YouTube (Video Podcast):
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Apply to Be a Guest:
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SEO Keywords
- AI outreach for MSPs
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Credits
Hosts: Josh Peterson and Gary Boyle
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