Opollo MSP Marketing Podcast

James Vickery, CEO of Benchmark365 and veteran of the MSP space, shares raw, battle-tested lessons from his 23-year journey—from starting a modest IT firm in Sydney to scaling a help desk powerhouse supporting MSPs across the globe.

Through thousands of strategy calls with MSP owners at every stage of growth, James has identified patterns, pitfalls, and scalable plays that set high-performing MSPs apart from those stuck in survival mode. Whether you're bootstrapping your first few clients or navigating the messy middle between $2M and $10M, this episode is a tactical guide to getting unstuck—and moving with purpose.

💥 What You'll Learn:

1. The $1M Wall—And Why Most MSPs Crash Into It

Most MSPs hit a ceiling around $1M revenue, not because of technical limitations, but because of a lack of sales infrastructure. James breaks down the biggest mindset and operational shifts needed to build a repeatable, scalable growth engine.

2. Why Sales Isn't Optional (Even If You Hate It)

James explains why sales should be your first investment—not your last—and how technical founders can reframe their discomfort with selling into a strategic advantage.

3. How US MSPs Think Differently

Operating out of Australia with a client base that's mostly American, James shares his unique insights into why US MSPs grow faster—and what others can learn from their mindset and appetite for risk.

4. The Death Spiral of Commoditization

From Reddit pricing threads to cookie-cutter service stacks, James unpacks how MSPs are unintentionally driving themselves into a price war—and how to stand out by offering value-led solutions (hint: AI plays a big role).

5. Projects vs. Recurring Revenue: Striking the Balance

Why smart MSPs lead with professional services (cloud, VoIP, AI enablement) to win deals—and how poorly executed projects are often the number one reason clients churn, even if support is solid.

6. The Power of Simplicity in Scaling

The best MSPs keep their offer tight: one stack, one price, and clear outcomes. James explains how clarity accelerates sales—and why "more services" often means more confusion.

7. Who You Hire Will Make or Break You

Drawing from his own hiring mistakes, James shares how AI helped him define—and source—the right talent for his team. From Tier 3 techs to service delivery managers, the key is ownership, not just output.

8. Out of Time? Make Some.

Still doing tickets at 8 am and expecting to build a pipeline by noon? James shares the habits that got him out of the weeds—including waking up at 5 am to hustle sales before the workday swallowed him whole.

9. From Lone Wolf to Peer Power

You're not supposed to do this alone. James shares why peer groups are the #1 growth hack no one talks about—and how they create accountability, mentorship, and momentum.

🧠 Insightful, strategic, and full of actionable takeaways—this conversation is a blueprint for MSPs who are done with stagnation and ready to build real, sustainable growth.

Whether you're at $500K dreaming of $2M, or stalled at $3M trying to unlock your next phase, this episode will challenge how you think, operate, and sell.

In this eye-opening episode of the Opollo Podcast, Steven Morey is joined by Ford Winslow, CEO of ICE Cybersecurity, to unpack the harsh truths, trends, and opportunities at the intersection of managed services and cybersecurity. With over 25 years in the cyber game—long before "cyber" was even a thing—Ford brings clarity to one of the most misunderstood and under-leveraged parts of the MSP model: security.

If you're still bundling cyber like it's an upsell or checkbox item, this is your wake-up call.

🧠 What You'll Learn:

1. Why Most MSPs Get Cyber Wrong

Ford outlines the three fatal flaws MSPs make when offering cybersecurity—and why “et it and forget it” won't cut it in 2025.

2. Cyber Is a Process, Not a Product

You can't just tap on an MDR and call it a day. Real cybersecurity is a continuous, high-touch service—and a strategic value-add when done right.

3. The SOC Question: Build, Buy, or Partner?

How about building your own Security Operations Center? Ford explains why most MSPs shouldn't and how to choose outsourced SOC models that fit your business without killing margin or trust.

4. The Kaseya & ConnectWise Conundrum

As more MSPs fall into the trap of commoditized stacks, Ford discusses the risks of vendor lock-in, switching costs, and why differentiation is more important than ever.

5. How to Make Cyber Your Competitive Edge

From offering compliance assessments (CMMC, HIPAA, ISO 27001) to embedding security into go-to-market strategies, Ford shares battle-tested ways MSPs are turning cyber into real revenue.

6. When Compliance Creates Windfall

A real case study: how one MSP helped their client win a massive ISO 27001 contract—and tripled their recurring revenue in the process.

7. Industry Opportunities in 2025 and Beyond

Biggest wins are happening in:

• Department of Defense contractor space (CMMC)
• Healthcare and adjacent nonprofits
• Vendors servicing highly regulated or publicly traded companies

🎯 Who This Episode Is For:

• MSPs scaling into security services
• IT providers are tired of selling commoditized solutions
• Founders looking to add high-margin services without overbuilding
• Sales teams are struggling to differentiate in crowded markets

In this episode of the Opollo Podcast, Steven Morey sits down with Derek Morgan, the brain behind Referral Marketing Ideas and creator of the Referral Marketing Formula - a proven framework helping business owners tap into their existing networks to generate consistent, high-quality leads without relying on cold outreach.

With over 30 years of sales experience across financial services, tech startups, and enterprise sales, Derek knows firsthand how painful and unproductive the traditional lead generation grind can be. That’s why he built a system to make referrals scalable, predictable, and profitable.

🔥 What You’ll Learn:

✔ The Big Missed Opportunity

Why most businesses ignore their biggest growth lever: the existing relationships in their CRM, customer base, and vendor networks—and how to activate them.

✔ Referrals vs. Referral Marketing

Random “word-of-mouth” referrals aren’t a growth strategy. Derek breaks down how to build a referral engine that delivers consistent leads.

✔ How to Turn Clients Into Deal-Making Connectors

Derek’s referral-first mindset shows you how to approach client conversations so you can unlock vendor, advisor, and supplier networks—with zero awkwardness.

✔ Real ROI from Two Coffees

Hear how one follow-up reactivated a dormant contact and led to $11.2M in business. The opportunity cost of not following up might be the most expensive part of your sales strategy.

✔ Why TSPs (Not Just MSPs) Win Big With This Model

Learn how forward-thinking MSPs moving toward a Technology Service Provider (TSP) model can use referrals to become growth partners—not just service vendors.

Featured Guest: Derek Morgan

Derek is the founder of Referral Marketing Ideas and creator of the Referral Marketing Formula, a system designed to help small and medium-sized businesses build revenue-generating partnership networks.

He’s also the creator of the Partnerships Builder Fast Start Program ($97 USD), which gives you step-by-step training, tools, and nine custom AI prompts to launch a referral program in days, not months.

Bonus: Affiliates can also promote the program and earn commissions of up to 50%. Learn more here:

👉 Affiliate Program Info

👉 Apply to be an Affiliate

Guest: Kevin Hughes, Head of Sales & Marketing at Ascentient

Host: Steve Morey

Episode Overview

In this episode, we dive deep into the fast-evolving world of IT managed services and explore how AI is reshaping the landscape. Kevin Hughes from Ascentient shares his 11-year journey in the IT industry, from sales admin to leading sales and marketing, and how his team is embracing automation and AI to transform operations, elevate customer experience, and future-proof their business.

What You’ll Learn

• Laying the Foundation with Automation: Why Ascentient prioritized automation before diving into AI, and how it set the stage for scalable innovation.
• Identifying AI Opportunities: How internal surveys revealed tedious, repetitive tasks that could be automated or enhanced with AI.
• Human-First AI Approach: Kevin’s perspective on using AI to amplify human connection—not replace people—by freeing staff to build relationships and support business growth.
• Real-World AI Use Cases:
  • Leveraging Microsoft Copilot and Microsoft's emerging AI agents to boost productivity and provide 24/7 “digital co-pilots” for clients.
  • AI-driven improvements in aviation security, facial recognition, and optimized flight routing.
• Overcoming MSP Hesitation: Why some MSPs are hesitant to adopt AI, and Kevin’s advice for overcoming fear and experimenting boldly.
• Partnerships Driving Innovation: How Pax8 is helping Ascentient build a practical AI roadmap alongside Microsoft.
• Vertical-Focused Strategy: Kevin’s plan to roll out AI solutions industry by industry, starting with logistics and expanding to healthcare, aviation, and manufacturing.

Key Takeaways

• Start small with automation to create a solid foundation for AI.
• Use employee and client feedback to find high-impact use cases.
• AI is a tool to enhance, not replace, human work.
• Early adoption gives MSPs a competitive edge—hesitation risks falling behind.
• Collaborating with technology partners can accelerate your AI journey.

Episode Highlights

• [02:00] Kevin’s career journey and Ascentient’s automation-first approach
• [05:30] Identifying opportunities for AI from employee feedback
• [07:30] Why some MSPs fear AI—and why that’s dangerous
• [09:30] Insights from the Pax8 AI conference
• [12:00] AI breakthroughs in aviation and security
• [15:20] A vertical-based strategy for implementing AI