Most MSPs invest in security tools — firewalls, endpoint protection, SIEM — but few have a reliable way to know whether those tools are actually configured correctly. Misconfigurations in the very products designed to protect your clients are one of the leading attack vectors in cybersecurity today. Adam Bennett has spent 25+ years on the front lines and built a company to solve exactly this problem.

Adam Bennett is the Co-Founder & CEO of SureStack and CEO of Crosshair Cyber. In this conversation, we explore why security stack misconfigurations create silent compounding risk, how cyber insurance gives many SMBs a false sense of protection, and why the MSP that takes ownership of security posture earns the trust — and contracts — of serious clients.

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🎙 What We Cover in This Episode

• Why the tools meant to protect you may be your biggest vulnerability
• Real-world incidents caused by two unchecked configuration boxes
• The growing role of regulation and compliance in driving security adoption
• How SureStack automates continuous security stack validation using AI
• Why MSPs should enforce minimum security stacks for every client
• Using security posture assessments as a pre-sales differentiator
• Adam's journey from government cybersecurity to building a product company
• Cyber insurance gaps: what happens when the application doesn't match reality

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👤 Guest Links

Guest LinkedIn: https://www.linkedin.com/in/adam-bennett-0290881bb/ Company Website: https://surestack.ai

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📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #92 — Your Security Stack Is Lying to You | From the Trenches (Adam Bennett)

Most MSP owners who struggle with sales performance aren't dealing with a bad salesperson - they're dealing with no system. In this roundtable, Josh Peterson and Gary Boyle respond to a real listener email from an MSP owner who has tolerated five years of inconsistent results from a salesperson he's afraid to hold accountable. The diagnosis: this isn't a sales problem. It's a leadership problem wearing a personnel costume.

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🎙 What We Cover in This Episode

• Why no quota means no sales role - not a flexible arrangement
• How the owner's vision must precede the salesperson's target
• The two-quota framework: activity quota and results quota
• What base pay is actually purchasing - and why most MSP owners have it backwards
• How to interview a salesperson to reveal whether they're metrics-driven before you hire them
• What to do when the horse is already out of the barn
• Why accountability is clarity, not punishment - and how to introduce structure without blowing up the relationship

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👤 Your Hosts

Josh Peterson - CEO, Bering McKinley

Gary Boyle - Partner for Strategy & Business Development, Bering McKinley

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🚀 Subscribe & Follow BMK Vision

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🔎 SEO Keywords

• MSP sales management
• MSP salesperson performance
• MSP sales system
• Managed service provider sales quota
• MSP accountability
• BMK Vision Podcast

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📝 Credits

Host: Josh Peterson

Co-Host: Gary Boyle

Producer: Bering McKinley

Episode: #91 - No Quota, No Sales Role: The MSP Sales System Reset

Most MSPs have invested heavily in perimeter security. But there is a financial risk hiding in plain sight: the unstructured data organizations create every day — spreadsheets, Word docs, old deal rooms, payroll files — that has never been inventoried, valued, or protected at the file level. That gap is what Return on Mitigation was built to close.

James Oliverio is the Founder & CEO of ideaBOX and a Senior Advisor at Actifile. With 30+ years spanning Wall Street CIO roles, MSP ownership, and a Harvard certification in cybersecurity risk management, James developed the ROM framework to help C-suites quantify data exposure in dollars and connect that number to the controls that actually reduce it.

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🎙 What We Cover in This Episode

- What Return on Mitigation (ROM) is and how the financial calculation works - Why traditional DLP tools detect risk but stop short of real remediation - How AI tools like ChatGPT are creating a new hidden liability for organizations - Why 44% of 2024 cyber insurance claims were denied — and how to protect clients from that trap - How to run a data risk assessment on your own MSP before offering it to clients - The FAIR Institute methodology and financial modeling for breach exposure - File-level encryption as the true remediation strategy — not just detection - How to position the ROM conversation at the C-suite level

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👤 Guest Links

Guest LinkedIn: https://www.linkedin.com/in/james-oliverio-7659ab/ Company Website: https://ideabox.com

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🔎 SEO Keywords

- MSP cybersecurity - Return on Mitigation - Data risk management - Cybersecurity insurance - Unstructured data security - DSPM - AI data exposure - MSP security strategy - Data breach liability - ideaBOX

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📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #90 — Data Risk Is the MSP's Invisible Liability

Most MSP owners say they're great at sales — but when you examine what's actually happening, many are confusing orders with selling. In this BMK Vision Roundtable, Josh Peterson and Gary Boyle unpack why sending quotes too early kills deals, why the order of selling matters more than any closing technique, and how a simple three-pillar framework can transform close rates for MSPs at any size.

Co-Host Introduction Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. A former MSP owner and entrepreneur, Gary brings firsthand sales experience to a conversation about what it really takes to earn the right to deliver a proposal.

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🎙 What We Cover in This Episode

- Why most MSP "sales" are really just order-taking - The order of selling: yourself first, company second, services last - What happens when you send a quote before earning the right - How to establish budget without asking "what's your budget?" - The three-pillar sales framework: FTA → Discovery → Close - Why the proposal should memorialize what's already been agreed - The trial close and solution delivery meeting - Close ratio and its dangerous relationship to pricing - Hidden revenue opportunities inside your existing client base

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👤 Host & Co-Host Links

Josh Peterson: https://www.linkedin.com/in/joshdpeterson/ Gary Boyle: https://www.linkedin.com/in/garyboyle/

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Learn More About the Vision Platform: https://beringmckinley.com/vision

Apply to Be a Guest: https://beringmckinley.com/blog#speaker-form

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🎙️ Co-Host Bio — Gary Boyle Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. With a background spanning network engineering, entrepreneurship, and strategic consulting, Gary brings real-world operator experience to helping MSP owners build stronger, more profitable businesses.

🎙️ Host Bio — Josh Peterson Josh Peterson is the CEO of Bering McKinley and host of The BMK Vision Podcast. Since 2004, Josh has worked with hundreds of MSP owners to build operationally sound, profitable businesses through consulting, peer teams, and direct coaching.

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📝 Credits

Host: Josh Peterson Co-Host: Gary Boyle Producer: Bering McKinley Episode: #89 — Stop Sending Quotes: The MSP Sales Process That Actually Closes

Most MSP owners will tell you they want to improve profitability. But when the solution involves cutting recurring revenue, the conversation gets uncomfortable fast. This roundtable tackles the hard truth: not all revenue is healthy revenue, and the clients you're afraid to lose may be the ones destroying your margins.

Josh Peterson, Gary Boyle, and Ryan Alter dig into a real client scenario where 15% of agreements were operating below sustainable margins — and explore why MSP owners tolerate it, what it costs them, and how to break the cycle.

🎙 What We Cover in This Episode

• Why revenue growth masks profitability problems in MSPs • The real cost of low-margin agreements on service capacity and team morale • How Gary and Ryan both repriced 100% of their clients — and lost none • The ego trap: why owners protect revenue that's hurting them • Standardizing pricing as the first step toward financial clarity • Why buyers purchase EBITDA, not top-line revenue • The vicious cycle of underpricing to zero

👤 Guest & Co-Host Bios

Ryan Alter is the founder and former CEO of Alter Enterprise, a managed IT services provider he built over 17 years in Missoula, Montana. Ryan successfully exited in 2023 when Alter Enterprise was acquired by Fisher's Technology. He now runs Silver Stream AV. LinkedIn: https://www.linkedin.com/in/ryan-alter-896a5b11/

Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. With a background spanning network engineering, entrepreneurship, and strategic consulting, Gary brings real-world operator experience to helping MSP owners build stronger, more profitable businesses. LinkedIn: https://www.linkedin.com/in/garyboyle/

Josh Peterson is the CEO of Bering McKinley and host of The BMK Vision Podcast. Since 2004, Josh has worked with hundreds of MSP owners to build operationally sound, profitable businesses through consulting, peer teams, and direct coaching. LinkedIn: https://www.linkedin.com/in/joshdpeterson/

🚀 Subscribe & Follow BMK Vision

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Learn More About the Vision Platform: https://beringmckinley.com/vision

Apply to Be a Guest: https://beringmckinley.com/blog#speaker-form

📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #88 — Revenue Is Vanity: Why MSPs Must Fire Unprofitable Clients | BMK Vision Roundtable

Not every MSP story ends with a big exit or a moonshot growth curve. Some of the most important transitions in this industry happen when an owner realizes that ownership itself was never the right fit — and does something about it. David Norelid spent nearly a decade running his own MSP before making the decision to close it down and take a role at another MSP, a move he now calls the best decision of his career.

David Norelid is the Technical Alignment Manager at 5 Factor Technology, and in this conversation, we explore the hidden costs of solo MSP ownership, the mindset shift from "get to" to "don't have to," and what the future of managed services demands from technologists who want to stay relevant.

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🎙 What We Cover in This Episode

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👤 Guest Links

Guest LinkedIn: https://www.linkedin.com/in/davidnorelid/ Company Website: https://www.5factortech.com/

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Learn More About the Vision Platform: https://beringmckinley.com/vision

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📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #87 — MSP Owner to Employee: Why He Walked Away | From the Trenches

In this episode of the BMK Vision Podcast, Josh Peterson sits down with Gary Boyle, Partner for Strategy & Business Development at Bering McKinley. They dig into why MSP partnerships break down, how undefined roles create a slow-burning disaster, and what owners can do right now to get ahead of it — drawing from real client situations happening right now.

This conversation explores how the most common partnership problems — misaligned expectations, weak operating agreements, and murky equity structures — quietly erode MSP businesses for years before anyone faces them head-on. Practical and honest takeaways for any MSP owner in a partnership or thinking about starting one.

🔗 Learn more about the BMK Vision Operating System: https://beringmckinley.com/vision

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About Gary Boyle

Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. With a background spanning network engineering, entrepreneurship, and strategic consulting, Gary brings real-world operator experience to helping MSP owners build stronger, more profitable businesses.

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast, helping MSPs grow through operational maturity, financial clarity, and leadership development. Learn more: https://beringmckinley.com/vision

🎤 Apply to be a guest: https://beringmckinley.com/blog#speaker-form