I burned through $50,000 and four virtual assistants trying to fix my operations and tech stack, and things only got worse. The problem? I was trying to skip the hard part - actually understanding what needed to be fixed before hiring someone to fix it.

Dan Sullivan's "Who Not How" advice is brilliant, but there's a critical piece missing that cost me nine months and left my business in worse shape than when I started. The real formula isn't just "who not how" - it's "you, then who, somehow."

I see MSP owners make this exact same mistake on the sales side constantly. They hire agency after agency, SDR after SDR, trying to outsource their way out of a problem they don't fully understand. If you've burned through multiple people in the same role, the role is probably wrong - not the people.

You don't need to become an expert, but you need to understand the problem well enough to know who you're hiring for, what success looks like, and how to measure progress. Otherwise, you're just throwing money at a problem and hoping it goes away.

This was an expensive lesson for me. Hopefully you can learn it without paying the same tuition

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

I used to think "Always Be Closing" was outdated, sleazy sales advice, but I've completely changed my mind. In this video, I break down why ABC is actually the foundation of consultative selling for MSSPs and B2B sales.

The truth is, every single step in your sales process—from discovery calls to assessments to proposals—should be designed with one goal: moving the deal forward and closing the sale. I'll show you the simple framework I use to redesign sales processes, explain why most salespeople are treating discovery and assessments like information gathering instead of closing opportunities, and reveal the biggest mistake I see during proposals that kills deals.

If you're in MSP sales or any B2B selling, this reframe will change how you approach every interaction with prospects.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Discover why most MSP deals are actually won or lost during the discovery phase, not at the close! In this video, I break down how to engineer your discovery process to address objections before they even come up.

I'll show you how to plant the seeds early by asking strategic questions that uncover pain points, buying motivations, urgency levels, and decision-making processes - then use their own words as your most powerful rebuttals later. Instead of scrambling to overcome predictable objections like "it's too expensive" or "we're not ready yet" at the end, you'll learn to reverse-engineer these concerns into discovery questions that make closing feel natural and almost anticlimactic.

I'll walk you through my proven 4-step process to transform your discovery from a technical fact-finding mission into the real close of your deal

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram