The Ray J. Green Show

Ray J. Green
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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. 6 HRS AGO

    More Value = Less Trust (Here’s the Research)

    In this episode, I’m diving into a psychological trap that kills credibility in sales and marketing: the "Gold Delusion Effect." Drawing on research from the University of Chicago, I explain why stacking more benefits into your pitch actually makes people believe them less. It turns out that when you try to promise everything—saving time, saving money, increasing morale, and boosting revenue—you often end up being the "12-page menu" restaurant that no one trusts to make a great burger. I share real-world examples of "zero delusion" brands like Raising Cane’s and WD-40 that have built empires by doing one thing exceptionally well. But even if you run a complex, multi-service business, I’ll show you how to use "umbrella branding" and surgical discovery to keep your message undiluted. Join me as I break down why one message per moment is the key to building real belief in your prospects. // 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

    13 min

  2. 1 DAY AGO

    Introverts Close More Deals Than Extroverts

    In this episode, I’m tackling one of the biggest myths in business: the idea that you have to be an outgoing extrovert to be great at sales. As an introvert who has spent years in the trenches, I’ve actually found the opposite to be true. I’m making the case for why introverts—all things being equal—actually close more deals. I dive into the fundamental difference in how we approach networking and discovery calls. While extroverts often get their "reward" just from the act of socializing, introverts are usually on a mission. We don’t have the energy to waste on small talk for the sake of small talk, so we tend to be more methodical, more intentional, and way more focused on the data points that actually move a deal forward. If you’ve ever felt like your quiet nature was a disadvantage in a loud industry, this episode is for you. // 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

  3. 2 DAYS AGO

    Success Is 10,000 Micro-Failures in a Row

    In this episode, I’m breaking down why we need to stop looking at success as a straight line and start seeing it for what it actually is: an exercise in 10,000 micro-failures. Inspired by a story from former NASA engineer Mark Rober about how they get a rover to Mars, I explore the concept of "mouse farts"—the tiny course corrections that keep a mission from drifting millions of miles off target. I talk about why the difference between reaching your destination and giving up usually comes down to how you handle those inevitable moments when you've veered off track. If you’re feeling like you’ve hit a wall or made a wrong turn, join me as I explain why that isn't the end of the road—it’s just time for a little course correction.// 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

  4. 3 FEB

    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

  5. 31 JAN

    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

  6. 29 JAN

    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

  7. 28 JAN

    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

  8. 27 JAN

    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
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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
    241
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show