A viral tweet calling entrepreneurship "just a lottery" hit my feed last week, and I had to respond. The author claimed successful entrepreneurs are lucky players who pretend their success was skill, and thousands of people ate it up. In this episode, I share my original reaction, but more importantly, I break down a powerful story from Alex Hormozi's $100 Million Leads about "The Many-Sided Die" that reframes the entire conversation. Yes, luck exists—some people roll green faster than others. But the real insight is this: you win by continuing to play. Every roll improves your odds, builds your skills, and gets you closer to success. The only guaranteed way to lose is to quit and blame your failure on everyone else getting lucky.

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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 got a cold call completely by chance while recording content, and as someone who reviews hundreds of sales calls, this was like Christmas morning. The health coaching rep did a solid job overall—good tone, professional, not pushy—but missed some critical opportunities that would've moved the deal forward. In this episode, I break down the entire call and show you what happens when a prospect quantifies where they are (I said I'm an 8.5 out of 10), why phrases like "small needle movers" kill urgency, how speed to lead matters more than you think, and the mistake of pitching another call without giving a compelling reason to show up. This is raw, real-time call coaching you can apply immediately.

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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

Ever been on a sales call where your gut tells you something's off, but you say nothing? That disconnect between what you're sensing and what you're saying is killing your deals and destroying your confidence. In this episode, I break down why ignoring red flags wastes your time and erodes your self-respect, and I share a real story where addressing the tension in a call turned a disengaged prospect into a signed client in 50 minutes. Learn how to trust your intuition, have candid conversations the right way, and why prospects will actually respect you more for it.

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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'm breaking down exactly how to handle one of the most frustrating situations in MSP sales: when you fix a break-fix problem for a prospect, mention managed services, and then get completely ghosted. The reality is they no longer feel the pain after you've solved their problem, so there's no urgency to move forward. Instead of making one or two follow-ups and giving up, I'm showing you how to build a simple five-email sequence that does the heavy lifting for you. This sequence educates them, shifts their mindset, and nurtures them from "not ready" to "let's talk" - without you having to badger them every week.

I'll walk you through exactly what to include in each email, how to make it valuable enough that they'd want to share it, and how this same strategy works for any recurring sales objection you're dealing with. One of my clients tried this and got a callback four weeks later asking about security assessments - that's how you turn qualified prospects into qualified opportunities

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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

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

//

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

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

I reveal the shocking truth about why most MSP deals actually fail - and it's not what you think. After listening to countless sales calls, I've discovered that deals don't die because of timing, price, or contract issues.

They fail because sales reps never actually ask for the sale! I know it sounds crazy, but I'm going to prove exactly how this happens and show you the simple techniques I use to avoid getting ghosted by prospects.

I'll walk you through my proven closing strategies, including the exact questions that force prospects to reveal their real objections so you can address them on the spot instead of hoping they'll magically say yes later. If you're tired of deals getting stuck in "we'll think about it" purgatory, this video will change how you close forever

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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