The BMK Vision Podcast

#92 - Your Security Stack Is Lying to You | From the Trenches

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)

#91 - No Quota, No Sales Role | BMK Vision Roundtable

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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🔎 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

#90 - Data Risk Is the MSP's Invisible Liability | From the Trenches

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 PetersonProducer: Bering McKinleyEpisode: #90 — Data Risk Is the MSP's Invisible Liability

#89 — Stop Sending Quotes: The MSP Sales Process That Actually Closes | BMK Vision Roundtable

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 IntroductionGary 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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🎙️ Co-Host Bio — Gary BoyleGary 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 PetersonJosh 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 PetersonCo-Host: Gary BoyleProducer: Bering McKinleyEpisode: #89 — Stop Sending Quotes: The MSP Sales Process That Actually Closes

#88 - Revenue Is Vanity: Why MSPs Must Fire Unprofitable Clients | BMK Vision Roundtable

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/
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📝 Credits
Host: Josh PetersonProducer: Bering McKinleyEpisode: #88 — Revenue Is Vanity: Why MSPs Must Fire Unprofitable Clients | BMK Vision Roundtable

#87 - MSP Owner to Employee: Why He Walked Away | From the Trenches

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
- The 25-year journey from Craigslist trunk slammer to MSP owner to MSP employee
- Why the transition from break-fix to managed services was both exciting and financially dangerous
- Losing a whale client and the cascading impact on tools, staff, and morale
- The liberating power of asking "What if that's okay?"
- Why MSPs get stuck at $500K–$1M and what actually holds them back
- The Technical Alignment Manager role: half sales, half technology
- Microsoft's long game and the licensing squeeze on MSPs
- Where AI adoption really stands in MSP client environments
- Why the most important skill in IT is learning how to learn
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👤 Guest Links
Guest LinkedIn: https://www.linkedin.com/in/davidnorelid/ Company Website: https://www.5factortech.com/
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📝 Credits
Host: Josh Peterson Producer: Bering McKinley Episode: #87 — MSP Owner to Employee: Why He Walked Away | From the Trenches

#86 – Stop Hiring People — Start Designing Roles | BMK Vision Roundtable

Most MSP owners don't plan their hires — they react to them. A great person shows up, excitement takes over, and suddenly you're building a role around a person instead of filling a seat you've already designed. In this BMK Vision Roundtable, Josh Peterson and Gary Boyle break down why that pattern keeps repeating and what it's actually costing you.
Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley, and in this conversation, we explore the hidden cost of reactive hiring, the clarity gap behind most role failures, and why designing the seat before finding the person is a leadership discipline — not an HR task.
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🎙 What We Cover in This Episode
Why "I found a great person" is the start of most hiring mistakes
The real reason your best tech shouldn't become your service manager
How undefined roles turn great employees into failed hires
The one number that defines the service manager job: 55% gross profit
Why evangelizing your vision is a three-time exercise — not forever
The planning gap that forces reactive hiring at the 1–3M mark
How a $600,000 lesson inside Bering McKinley changed everything
Signs you're already falling into the trap and don't realize it
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👤 Host Links
Josh Peterson LinkedIn: https://www.linkedin.com/in/joshdpeterson
Gary Boyle LinkedIn: https://www.linkedin.com/in/garyboyle/
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🔎 SEO Keywords
MSP hiring mistakes
MSP role design
MSP service manager
MSP leadership
MSP business planning
Managed service providers
MSP staffing
MSP org design
Small business hiring
BMK Vision Podcast
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📝 Credits
Host: Josh Peterson Co-Host: Gary Boyle Producer: Bering McKinley Episode: #86 — Stop Hiring People — Start Designing Roles

#85 — Why MSP Partnerships Fail (And How to Save Them) | BMK Vision Roundtable

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

#84 – “We Don’t Track Time” – Why MSPs Stall at $2M | BMK Vision Roundtable

You don’t need time tracking to survive at $1M — but you absolutely need it to scale past $2M.
 
In this episode, we break down one of the most common growth ceilings in the MSP industry: the belief that “we don’t track time” is a culture win. Josh Peterson and Gary Boyle unpack why that mindset often leads to stalled margins, mispriced agreements, technician burnout, and emotional decision-making instead of operational clarity.
Guest Introduction
 
Gary Boyle is a Partner at Bering McKinley, and in this conversation, we explore service profitability, agreement gross profit, technician capacity, and the real economics behind scaling a managed services business. This episode challenges the idea that time tracking equals micromanagement and reframes it as leadership discipline.
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🎙 What We Cover in This Episode
 
• Why MSPs stall between $1M–$3M in revenue
• The “noisy vs quiet client” profitability problem
• Agreement gross profit and why it matters
• The illusion of flat-rate pricing
• Service salary to service revenue ratio
• Capacity modeling for technicians
• Why “we’re profitable” isn’t enough
• Leadership discipline vs micromanagement
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👤 Guest Links
 
Guest LinkedIn: https://www.linkedin.com/in/garyboyle/
Company Website: https://beringmckinley.com
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https://beringmckinley.com/vision
 
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https://beringmckinley.com/blog#speaker-form

#83 – Getting Lost on the Way to Relevance | From the Trenches (Ray Stasieczko)

In this From the Trenches episode of the BMK Vision Podcast, Josh Peterson sits down with Ray Stasieczko for an unfiltered conversation about the copier-dealer-to-MSP transition—and why so many businesses lose their way chasing relevance instead of building real value.
 
Ray shares hard-earned lessons from decades in the print and IT services space, challenging vendor-driven MSP models that promise easy growth but often lead to low margins, outsourced complexity, and stalled businesses. Together, Josh and Ray explore why most copier dealers only convert a small percentage of clients into managed IT customers, why outsourcing the help desk breaks the economics for many MSPs, and why clarity of intent (“why”) matters more than chasing the next trend.
 
This episode is a candid look at what actually works, what doesn’t, and what MSPs and copier dealers need to rethink as disruption accelerates.
🎙 What We Cover in This Episode
 
• Why many MSPs get “lost on the way to relevance”
• The reality of the 3–5% copier-to-MSP conversion rate
• Vendor-driven strategy vs. business fundamentals
• Why outsourcing the front-line help desk hurts margins
• The difference between lifestyle MSPs and growth-focused firms
• Why fee-based assessments and consulting matter
• “Why comes first, how comes second” as an operating principle
• What mature MSPs do differently to protect value
👤 Guest Links
 
Ray Stasieczko
LinkedIn: https://www.linkedin.com/in/raystasieczko/
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https://beringmckinley.com/blog#speaker-form