The Ray J. Green Show

Ray J. Green
  • 4.5 (11)
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The Ray J. Green Show is for operators and founders who are already doing the work — but know that working harder isn't the same as getting it right. Each day, Ray J. Green — investor, operator, and founder of MSP Sales Partners — brings the sales tactics, leadership decisions, and strategic thinking he's learned from leading turnarounds, advising hundreds of B2B and MSP businesses, and making his share of costly calls. Some episodes are frameworks you can use tomorrow. Some are the thinking underneath the frameworks — the part nobody teaches. Most are both. From Cabo, where he lives with his family. No hype. Just what's working, what isn't, and how to think about the difference. Visit for fresh episode daily: https://podcast.rayjgreen.com

  1. 4D AGO

    The Doorman’s Fallacy: When You Cut What You Can’t Measure

    I’m currently watching a merger turn into a complete clusterfuck, and it’s a story I’ve seen way too often in private equity. It’s a classic case of an acquirer coming in, kicking the original leadership to the curb, and gutting the company because they don’t understand that value isn't always visible on a spreadsheet. In this episode, I dig into the "Doorman’s Fallacy"—the mistake of eliminating something because you can’t quantify its utility, only to realize later that it was the very thing holding the brand, the culture, and the customer experience together. I compare the hollowed-out wreckage of this recent acquisition to my experience at the Four Seasons, where small, "unmeasurable" details like a lens cloth or a cord tie create the entire premium experience. We’re exploring why 40% of M&A deals end up as dumpster fires and how the best operators identify and protect the invisible value creators that actually drive ROI. If you’ve ever wondered why great companies fall apart after a sale, this is why. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    10 min

  2. JAN 31

    My Doctor Said There’s a Small Chance of Sudden Death

    "There is a small chance of sudden death." That’s a hell of a thing to hear from your cardiologist when you’re a guy who runs ten miles a day and feels healthy as fuck. One minute I’m "knocking the cover off the ball" on my stress tests, and the next, I’m being told I have Hypertrophic Cardiomyopathy—a condition where my heart is literally too strong for its own good. It’s a diagnosis that could have sent me into a spiral of anxiety, especially after a recent trip to the ER during a family vacation, but it actually led me to the most important mental shift I’ve ever made. In this episode, I’m sharing the raw details of my heart journey and the specific reframe that changed everything: the moment I stopped asking "Why is this happening to me?" and started asking "Why is this happening for me?" I dive into how this diagnosis actually protected my sons, empowered my team to crush it while I was out of pocket, and forced me to trade frantic intensity for sustainable productivity. I’m also walking you through a powerful exercise to help you take your own current "low point"—whether it’s in your health, your business, or your relationships—and rewrite the story in real-time. You don’t have to wait ten years to be grateful for a challenge; you can choose to see the benefit of the obstacle today. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    11 min

  3. JAN 29

    13% to 71% in 45 Days: A Real MSP Sales Transformation

    Most sales trainers will tell you that closing more deals requires a "killer instinct," better "closing techniques," or some fancy psychological methodology. But I just watched an MSP salesperson go from a 13% close rate in 2025 to a 71% close rate in just 45 days, and it had nothing to do with "mindset" or charisma. In this episode, I break down the real-world transformation of Garrick, a seller who closed $17,000 in MRR this month alone. We didn't give him a new script; we gave him a new system for how to think about the sales process. We move past the surface-level "motivational" advice to focus on the tactical shifts that actually bent the curve: stopping the guesswork on ROI by simply asking the prospect how they measure value, practicing the "money ask" until it became boring muscle memory, and learning to lead proposals with the prospect's priorities rather than our own expert biases. If your sales team is working hard but failing to convert, it’s likely not a lack of effort—it’s a lack of the system underneath the tactics. Let’s look at how to stop treating discovery like a checklist and start conducting conversations that actually lead to a close. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    23 min

  4. JAN 28

    I Watched a Founder Change His Mind 8 Times in 3 Months

    I used to think that successful entrepreneurs had a "secret map" that gave them 100% certainty before they made a move. I spent years in planning mode, working my tail off but making zero progress because I was terrified of making the "wrong" bet. In this episode, I’m sharing a raw look at a trap I see so many founders fall into: the endless pivot. I recently worked with a business owner who cycled through three different strategies in a month, not because he lacked talent, but because he was waiting for a feeling of certainty that simply doesn’t exist in business. I’ve learned the hard way that our job isn't to find something that works—it’s to commit to making it work. We’re going to talk about escaping the "amygdala hijack," why most results live on the other side of a J-curve, and how to start thinking in probabilities rather than absolutes. If you feel like you’re rowing hard but staying in the same place, it’s time to stop looking for a guarantee and start making a bet. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    11 min

  5. JAN 27

    The $2M vs $200M Founder Difference

    I’ve spent the last year hanging out with two very different groups: founders stuck at the $1M to $2M mark and entrepreneurs running $200M empires. Do you want to know the biggest difference between them? It’s not intelligence or work ethic—it’s their belief systems. Fresh off a trip to the Museum of Illusions with my kids, I realized that many of us are running our businesses while staring at the corporate equivalent of a "mind-bending" optical illusion. We are dead certain about "truths"—that we are essential to daily ops, that a certain channel is dead, or that we lack the right connections—only to find out those "truths" are the very things capping our growth. In this episode, I’m challenging you to look at where you might be fighting reality. What is the one thing you know for sure that just "aint so"? Let’s break down the hidden illusions keeping you from the next level. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    6 min

  6. JAN 24

    The More Necessary You Think You Are, The Smaller You’ll Stay

    Two weeks ago, I ended up in the ER with a heart incident that knocked me completely out of commission. But instead of falling apart, my business didn't skip a beat—in fact, we had our best sales month in six years. In this episode, I break down the critical decision I made last year to stack my team with "A-players" and the specific system I used to find them. I also explore the uncomfortable truth about why believing you are "necessary" is actually the biggest cap on your business's growth, and how to finally get out of your own way. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    11 min

  7. JAN 23

    The Tool Making You Faster Is Making You Replaceable

    In this episode, I explain why the AI tools making you faster might actually be making you replaceable. I share a story about a 1917 hay delivery business to illustrate the fatal difference between using technology to be "lazy" versus using it to be "better." I also break down a real-world example of why I fired a ghostwriter who was using AI to cut corners, and how I built an automated system to replace—and outperform—them in less than 24 hours. Tune in to find out if you are building a gas station or just delivering hay. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    8 min

  8. JAN 17

    Most Sales Advice About Pain Is Wrong (Including Mine)

    "No pain, no deal." It’s standard sales advice for a reason: painkillers are always easier to sell than vitamins. But are there exceptions? In this episode, I break down the only two scenarios where a prospect will buy from you even if they aren't feeling active symptoms. I discuss the concept of "high-stakes latent pain" (and why a blocked artery motivates action when slightly high blood pressure doesn't) and how intense desire—like the urge to buy a Porsche 911—can create its own internal pressure to buy. If you think your prospect has "no problems" but you still want the close, you need to understand these two specific triggers. // Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru. 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

    5 min
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Trailer

4.5
out of 5
11 Ratings

About

The Ray J. Green Show is for operators and founders who are already doing the work — but know that working harder isn't the same as getting it right. Each day, Ray J. Green — investor, operator, and founder of MSP Sales Partners — brings the sales tactics, leadership decisions, and strategic thinking he's learned from leading turnarounds, advising hundreds of B2B and MSP businesses, and making his share of costly calls. Some episodes are frameworks you can use tomorrow. Some are the thinking underneath the frameworks — the part nobody teaches. Most are both. From Cabo, where he lives with his family. No hype. Just what's working, what isn't, and how to think about the difference. Visit for fresh episode daily: https://podcast.rayjgreen.com

Information

  • Creator
    Ray J. Green
  • Years Active
    2020 - 2026
  • Episodes
    238
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show