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.
