I had the incredible opportunity to sit down with Kevin O’Leary, one of the sharpest minds in business and investing, during one of our past IT Sales And Marketing Boot Camps. If you’ve ever watched Shark Tank, you know Kevin is brutally honest, data-driven and focused on one thing: return on investment. His insights were not just valuable for startups pitching on Shark Tank—they are absolute gold for MSP business owners looking to scale, increase profitability and build a resilient business.
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Here are some of the biggest takeaways from our conversation, along with how you can apply them to your MSP.
Selling Yourself: The Key To Winning Deals
One of the first things Kevin emphasized was that you’re not just selling a product or service—you’re selling YOU. When he invests in a company, he’s not just betting on an idea. He’s betting on the execution skills of the entrepreneur.
In the MSP space, this is even more critical. Every MSP offers cybersecurity, cloud solutions and IT support. So why should a prospect choose your company? Because of you—your expertise, your ability to execute and your commitment to delivering results.
Focus on articulating your value proposition clearly and succinctly. Prospects don’t want to hear a laundry list of features; they want to hear how you are going to make their life easier, protect their business and ensure uptime.
Execution Is Everything
Kevin hammered home the point that execution is the most important factor in business success. Plenty of businesses had great ideas before the pandemic, but the ones that survived and thrived were those that could pivot and execute.
For MSPs, this means:
- Adapting to client needs quickly (Are you providing co-managed services as companies shrink IT teams? Are you offering cybersecurity-first solutions?)
- Optimizing service delivery (Are you leveraging automation and AI to increase efficiency?)
- Executing marketing and sales strategies consistently (Are you following up on leads, optimizing pricing, and improving customer retention?)
Kevin’s perspective aligns perfectly with what I teach: A great idea means nothing without the ability to execute. You can have the best MSP marketing plan in the world, but if you’re not following through—making the calls, running the campaigns, measuring results—you won’t see growth.
Evaluate your business execution. Do you have the right people, processes and technology in place to deliver results consistently? If not, it’s time to refine your operations.
Customer Service Is Your Biggest Differentiator
This was a huge insight from Kevin: Customer service is more important than price. He shared that businesses in the top quartile of customer service can charge more—because clients won’t leave. On the flip side, companies with poor service will lose customers even if they are the cheapest option.
MSPs, take note: Your service and responsiveness are your biggest competitive advantages. If clients feel valued, heard and taken care of, they won’t shop around based on price. But if they experience slow response times, unresolved issues or lack of communication, they’ll switch—no matter how cheap you are.
Audit your customer service experience. Are you responding to tickets fast enough? Are you proactive in communication? Are your clients delighted with your service? If not, this should be a priority.
The Two Numbers That Matter Most: Revenue & Free Cash Flow
Kevin’s investment firms track just two key numbers every week: Revenue and Free Cash Flow. That’s it. He can tell the financial health of a company by simply looking at these two metrics.
MSP owners should take note. Are you obsessing over the right numbers? Too many business owners focus on vanity metrics—like social media likes or total revenue—when the real indicators of business health are cash flow and profitability.
Start reviewing these two numbers weekly:
- Revenue: Are sales growing consistently?
- Free Cash Flow: After expenses, how much cash is left in the business?
If you’re not tracking this weekly, you’re flying blind.
The Future Is Digital—Adapt Or Get Left Behind
Kevin wrapped up our discussion by emphasizing that businesses that embrace digital transformation will win. He pointed to big brands like Nike, which now generate huge margins by selling direct-to-consumer online.
For MSPs, this means:
- Investing in automation and AI to optimize service delivery
- Embracing virtual and remote work to cut costs and increase efficiency
- Leveraging digital marketing to generate leads and close deals
Evaluate your tech stack. Are you leveraging automation, cloud solutions and remote work to maximize efficiency? If not, now is the time to adapt.
Final Thoughts: Execution And Customer Service Will Make Or Break Your MSP
This conversation with Kevin O’Leary reinforced many of the key principles I teach MSPs every day: Execution is king, customer service is your biggest competitive edge and the right financial metrics should drive your decisions.
If you want to thrive in this hyper-competitive MSP landscape, focus on selling yourself, executing relentlessly and prioritizing customer service above all else.
