The Ray J. Green Show

Ray J. Green
  • 4.5 (11)
  • MANAGEMENT
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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. 1D AGO

    Why the Most Data-Driven Marketer in B2B Quit Marketing for Something Nobody Understands Yet

    Chris Walker built Refine Labs from $3,000 in the bank and $65K in debt to $22 million in revenue in roughly three years — 100+ employees, 350 software company clients, and arguably the most influential voice in B2B marketing. He created the "dark social" movement, redefined how an entire generation of marketers thinks about MQLs, and built a massive audience doing it. Then he walked away. Because the peak of the business was also the lowest point of his life. In this conversation, we get into what actually broke at the top, why changing your environment doesn't fix what's underneath, and what Chris means when he talks about "frequency" — stripped of the spiritual language and grounded in the engineer's brain he actually has. We debate whether you have to grind before you can transcend it, why limiting beliefs feel like facts, and why he thinks training your frequency will be as common as going to the gym within five years. We also go deep on extractive vs. regenerative systems — in business, content, social media, and relationships — and why the intention underneath your actions matters more than the actions themselves. I've been using Chris's ENCODED program for five months. I came in skeptical. I still have questions. But I can't deny what shifted. This one's worth your time whether you buy the concept or not. WHAT YOU'LL LEARN Why building a $22M company was one of the worst periods of Chris's life — and what that reveals about external vs. internal successWhat "frequency" actually means as identity + beliefs + intentions, without the spiritual languageWhy changing your job, city, or business doesn't work if you don't change the foundation underneath itThe difference between extractive and regenerative systems — in business, relationships, and how you show up as a leaderWhy limiting beliefs feel like facts, and how to spot the invisible ceiling you didn't know you builtHow the intention underneath your actions — in content, business, and life — determines the results you getWhy Chris thinks frequency training will be as mainstream as going to the gym within 3–5 years BOOKS & RESOURCES REFERENCED Shoe Dog by Phil Knight — https://a.co/d/05UhJN4T ENCODED Frequency Map — https://www.encoded.ai/ We Are Encoded Podcast — https://open.spotify.com/show/5eEzaXy4hUSqlvzD9ROqrz

    1h 31m

  2. 5D AGO

    Your Network Assessment is Costing You Deals

    Here is a short, first-person podcast description based on your transcript: Episode Description: Are your MSP prospects ghosting you after you present their network assessment? It's probably because you're treating that assessment like a discovery call—and skipping the most fundamental part of the consultative sales process. In this episode, I’m breaking down a massive mistake I see IT sellers making: presenting problems instead of uncovering pain. A network assessment gives you facts and technical vulnerabilities, but facts don't motivate buyers—feelings and business impact do. People don't pay to fix problems that aren't causing them pain. Tune in to hear why all roads lead back to discovery, and learn how to properly structure your sales process so you can stop getting ghosted and start closing at a best-in-class rate. // 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

  3. FEB 20

    Dave Rendall: Why "Eat That Frog" Terrible Productivity Advice

    Dave Rendall has spoken on every inhabited continent for the last 20 years — Microsoft, AT&T, the US Air Force, the Australian government, Fortune 50 companies. He has a doctorate in organizational leadership, he's a former stand-up comedian, and he wrote The Freak Factor, a book that argues the thing everyone calls your biggest weakness is actually the foundation of your biggest strength. Before all of that, he ran nonprofits that helped people with disabilities find employment. He's also an ultramarathon runner and Ironman triathlete who competes in between keynotes. This one was personal. My son was diagnosed with dyslexia and ADHD, and I was diagnosed with Level 1 autism — all around the same time. Dave's video on weaknesses being strengths changed how my wife and I parent our kids. We've been in each other's orbit for six years — he MCs the events I speak at — but we'd never sat down and gone deep like this. We got into why "normal" doesn't actually exist, why your best employees probably have the most anxiety, the survivorship bias problem with reframing disabilities as superpowers, why "Eat That Frog" is terrible advice for entrepreneurs, and why most businesses are accidentally destroying their best people by trying to fix them. If you're a business owner, a parent, or someone who's ever been told something is wrong with you — there's a lot here. What You'll LearnWhy "normal" is a fake target — and what Todd Rose's The End of Average reveals about the myth of the average personThe Paul Orfala paradox: the Kinko's founder says "everyone should have dyslexia" — how to hold that alongside the real struggles of learning differencesWhy the survivorship bias argument against neurodiversity as a superpower is actually backwards — and what self-fulfilling prophecies have to do with itHow anxiety tested off the charts for Dave — and why elevated anxiety is what separates your best employees from your worstThe Dunning-Kruger connection: why the most competent people feel the most inadequate, and why that drives performanceWhy "Eat That Frog" creates a frog-eating job — and how to design a business where you never eat frogsWhat Faster Than Normal by Peter Shankman teaches about reframing ADHD as a speed advantage, not a deficitWhy partnering with people strong where you're weak isn't just nice — it's structurally necessary for neurodiverse entrepreneursThe real reason business owners burn out — and why it has nothing to do with how much work they're doingHow Dave's "affiliation" principle works in practice — the insurance agent story that almost ended in a firing and became a case studyWhy the first thing most schools, therapists, and managers do — focus entirely on weaknesses — is the exact wrong approachWhat the StrengthsFinder philosophy gets right that most management training misses Books & Resources ReferencedThe Freak Factor by David Rendall — Buy on AmazonThe Freak Factor for Kids by David Rendall — Buy on AmazonPink Goldfish 2.0 by Stan Phelps and David Rendall — Buy on AmazonFaster Than Normal by Peter Shankman — Buy on AmazonThe End of Average by Todd Rose — Buy on AmazonQuiet: The Power of Introverts in a World That Can't Stop Talking by Susan Cain — Buy on AmazonSensitive: The Hidden Power of the Highly Sensitive Person by Jenn Granneman and Andre Sólo — Buy on AmazonMessy: The Power of Disorder to Transform Our Lives by Tim Harford — Buy on AmazonFirst, Break All the Rules: What the World's Greatest Managers Do Differently — Buy on AmazonEat That Frog! by Brian Tracy — Buy on Amazon (referenced as counter-example)Dave Rendall's website: drendall.com Peter Shankman's Faster Than Normal podcast// 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

    52 min

  4. FEB 19

    I Don’t Fully Buy the “Only Do What You Love” Advice

    In this episode, I’m challenging the popular advice that you should "only do what you love" by exploring why friction is often a necessary data point rather than a signal to quit. While finding your flow is the ultimate destination, I’ve found that the path to success—whether you're a NASA engineer or a founder—inevitably requires grinding through tasks that drain your energy just to reach the next level. I break down how to distinguish between high-value flow and simple dopamine-seeking avoidance, offering a three-question framework to help you decide when to delegate, when to drop a task entirely, and when you just need to embrace the "mouse fart" course corrections required to get your business off the ground. Chris Walker podcast: https://open.spotify.com/show/5eEzaXy4hUSqlvzD9ROqrz?si=09ac9ae5cfde4157 Dave Rendall YouTube Channel: https://www.youtube.com/drendall Dave Rendall Website: www.drendall.com Justin Welsh Website: https://www.justinwelsh.me/ // 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

    12 min

  5. FEB 18

    Why Waiting for the Right Time Kills Your Growth

    I made the biggest hire in my business this week—and the numbers today didn't justify it. I did it anyway. Not out of gut instinct, but because a big bet is a forcing function. The moment I committed, every meeting and every project on my calendar had to justify its existence. Waiting for the safe moment feels smart, but it just gives you permission to drift. Here's what I see with businesses that plateau: early on, every entrepreneur makes bold bets because the math is simple—huge upside, little to lose. But once momentum builds, the internal math quietly flips from "what do I have to gain" to "what do I have to lose." You still say you want to scale, but the decisions tell a different story. You lose the forcing function, you lose the focus, and you stall. If you've been sitting at the same revenue number for a while, ask yourself: when's the last time you made a commitment that actually scared 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

    9 min

  6. FEB 17

    Make the Sales Conversation Uncomfortable

    One of my coaching clients said something on a discovery call that took serious guts: "From my selfish standpoint of wanting to sell you services, I can absolutely bring you a proposal. But I don't think you're going to be ready to buy. I'm not seeing a big enough problem for us to solve." That one candid line completely changed the dynamics of the deal. The prospect opened up, revealed the CIO's days were numbered, that he was spending $340K a year across three internal IT people, and that the CIO had been slow to respond despite the owner pushing the initiative. All roads lead to discovery—and this is what I mean by that. Every question I get from sellers about stalled deals, pricing objections, unexpected decision makers, or lack of urgency can be traced back to what we didn't learn in discovery. Most sellers stop at the surface level. They ask their scripted questions, get standard answers, and move on to the next checkbox. They never pull on the thread. This episode breaks down why digging deeper in discovery requires emotional intelligence and courage that most sellers never develop, how being candid and challenging a prospect who gives surface-level answers can completely reframe the problem you're solving—from IT issues to a fundamental business problem worth hundreds of thousands—and why the seller who gets to the real pain differentiates themselves from everyone else competing for the same deal. If you don't know the real problem you're solving, your prescription won't be credible. Keep digging. // 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

  7. FEB 16

    Start Here: Who This Podcast Is For (And Who It’s Not)

    I introduce my daily podcast for operators and founders who need sharper thinking around decisions that don't come with playbooks. As an investor, operator, and founder of MSP Sales Partners and Repeatable Revenue Ventures, I explain why this show focuses on how to think before deciding what to do. I challenge the common pattern of jumping straight to tactics without examining the underlying assumptions that shape every business decision. This episode establishes the show's core premise: that getting the frame right makes the decision easier, and that real-world business requires context, not just guru advice. I outline what listeners can expect from the daily format and who will benefit most from this approach to thinking through sales, strategy, hiring, leadership, and the moments when you're the only one willing to acknowledge something isn't working. // 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

    3 min

  8. FEB 13

    Bob Perkins: He Marketed Playboy, Pizza Hut & Calvin Klein. Here's What He Thinks Kills Most Companies.

    Bob Perkins has done things most people only read about — fighter pilot instructor, political fundraiser, the ad agency behind Apple's 1984 Super Bowl commercial, CMO at Calvin Klein, executive at Playboy, head of marketing at Pizza Hut, and turnaround CEO. He's sat on boards, built ventures inside the U.S. Chamber of Commerce, and now spends his time thinking and writing about how AI is fundamentally reshaping competition. We got into all of it. From the real story behind the most famous Super Bowl ad ever made (and the worst one, made by the same people the very next year) to why marketing as a discipline is being consumed by AI, to a fighter pilot decision-making framework that most companies are too slow to execute. We also talked about what actually drives organizational change, why group dynamics override expertise, and what Bob would tell his 40-year-old self if he could go back. This one went deep. If you run a business or lead a team, there's a lot here. What you'll learn in this episode: Why marketing is becoming unrecognizable — and what's replacing itThe real story behind Apple's 1984 ad and how it almost never airedThe Boyd Loop (OODA) — how fighter pilots make decisions at 500 mph and why it matters for your businessWhy competitive advantage is shifting from planning to execution speedHow AI changes the feedback loop — and why that's the real unlock for sales teamsWhat stops organizations from acting on decisions they've already madeWhy the power of the group is the most underrated force in business — and how it quietly kills changeBob's advice to his 40-year-old self (and the one skill he wishes he'd developed more) Books referenced in this episode: Sapiens by Yuval Noah HarariThe Geek Way by Andrew McAfeeThe Innovator's Dilemma by Clayton ChristensenOn the Edge: The Art of Risking Everything by Nate SilverThe Infinite Game by Simon Sinek // 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

    1h 16m
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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
    249
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show