The Ray J. Green Show

Ray J. Green
  • 4.5 (11)
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A podcast for accomplished people (or those aspiring to be) cut through the BS, make hard choices, optimize what actually matters, and build lives worth living and businesses worth selling. Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family. This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.

  1. 7H AGO

    The Calendar System for Scaling Businesses and Taking 2-Month Vacations

    This may be one of the most important podcasts I record for you. I'm sharing my system for taking control of my calendar—and I say most important because time is your most valuable asset. When you master how to manage it, it affects everything: your business, your family time, your health. This year alone, I started MSP Sales Partners from zero to $800K, added five full-time hires and 50+ customers, created content every week without missing a newsletter or YouTube video, had dinner with my kids almost every night, traveled for two and a half months over summer, took a fully-unplugged family trip to Spain and France, and managed 90 minutes to two hours of exercise seven days a week. I attribute ruthless time management to being able to do all of that. This episode breaks down my system: shift from reactive to proactive calendar management—stop playing defense and go on offense by designing "The Perfect Week" where you map out your ideal calendar with everything that matters (prospecting time, team meetings, exercise, kids' dinners, date nights), then lock those blocks in as busy so nobody can steal them back. Every Sunday, audit how the week went versus your perfect week, identify what's off and why, then fix it for the upcoming week. I also do quarterly off-site planning to identify the major business constraint and update my perfect week accordingly. Learn how to have the hard conversations to protect your time, why managing up and down requires showing people what's in it for them, and how this prevents the slow creep back to homeostasis where your calendar gets stolen again. // 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

    17 min

  2. 1D AGO

    AI Is Making Your Team Stupid

    Is your team outsourcing their thinking to ChatGPT? In this video, I break down why relying on AI for answers is leading to "thought atrophy" and killing expertise in the workplace. While AI is an incredible tool for efficiency, it cannot replace the nuance, context, and experience that I hire my team for. I share the story of a recent project where an AI-generated response missed the mark, and I outline the 4 New AI Guidelines I’ve implemented to ensure we use technology to amplify our intelligence—not replace it. // 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

    15 min

  3. 2D AGO

    The Bezos Lesson: Enough Good Ideas to Kill Your Company

    I used to be an idea gangster with my team—I'd do drive-bys every single week. I'd read a book, get super excited about the takeaways, and come in firing: "All right team, let's execute!" They were genuinely good ideas. But we never got enough traction with any of them before I'd pop in with the next one. My COO finally leveled with me: "Dude, we gotta stop. People are exhausted. We're not doing great work. That great idea eight ideas ago? We still never saw it produce fruit, and we're on to seven more since then." Here's what I learned: every new idea has an exponential curve—it's really hard on the front end, but weeks or months later is when the curve bends and the really good shit happens. We never gave anything time to get there. Then I came across this clip of Jeff Bezos explaining it perfectly: his VP of operations told him "You have enough ideas per minute to destroy Amazon. You have to release work at the rate the organization can accept it. Every idea you release creates a backlog that adds no value—it creates distraction." This episode breaks down why good ideas can fuel your company or kill it, how I created systems (an idea bank, a dedicated filter person) to stop injecting my ADHD into the business, and why I fired a fractional client this year because we couldn't execute through their constant idea churn. Your ideas are either an asset or a liability—which one are they? // 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

    12 min

  4. 3D AGO

    I Forgot My Car Today (And Why That Makes Me Better at Business)

    True story: I forgot my car in a parking lot today. Made it all the way home. My wife asked "where's the jeep?" and my first thought was "oh shit, did someone steal it?" This isn't the first time I've forgotten a car. I have ADHD and level one autism, which means I get wildly obsessed with things I care about—it's why I learn things so quickly and see patterns in complex systems—but I also completely forget shit that's not in my focus. I've flown to the wrong cities, forgotten to eat all day, and yes, forgotten multiple cars. Extreme weaknesses always come with extreme strengths. I'm really good at systematizing complex sales models and building businesses, but I can't remember to take out the trash. This episode shares what I've learned at 45 after years of beating myself up trying to "fix" it: accepting it instead of fighting it, stopping the guilt, not trusting my memory (I tie hoodies around my waist as reminders), thinking in teams where people offset my weaknesses, and using tactics like walking, fidget toys, and no-device Sundays. I don't have this figured out—I just forgot a car—but I've created an environment where my business thrives, my marriage thrives, and I can focus on my superpowers. Sharing this in case it helps you too. // 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

    14 min

  5. 4D AGO

    Why My Teams Don't Miss Targets

    I just wrapped a full day of calls with 75 MSP business owners about goal setting, and I heard all the mistakes I've made myself over 20+ years—from leading eight sales turnarounds to turning around a 40-year-old PE-backed company to its highest revenue ever. The most common mistakes? Inaccurate goals where the math doesn't map. Unrealistic goals that look good in December but are dead by March. Setting them too high so your team quietly thinks "that's never happening," or too low creating a complacent half-ass culture. Or worst of all—not setting goals at all. Here's why I'm passionate about this: the right goals manage for you, change behavior, and help people make decisions when you're not around. But bad goals make terrible people look good and great people look bad, which ruins your culture. This episode breaks down why I don't believe in "shoot for the moon, hit the stars"—that just means you're constantly missing and creating a losing culture. Learn why starting small and building a winning habit matters more than big aspirational numbers, why your goals need integrity (not pencil marks that change when you're behind), and how to rebuild momentum with bite-sized wins instead of resetting the whole target. // 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

    13 min

  6. 5D AGO

    The Simple System That Manages Your Sales Team for You

    A friend who does M&A for MSPs asked me: if you've got a team of five hunters, what's a good hiring and firing process that keeps top performers, pushes average reps, and weeds out the bottom? Here's my answer—and it's all about having a system that manages for you. The best approach consists of two parts: First, separate your minimum standards from actual goals. Your goal might be $24K/month where commission incentives kick in, but your minimum standard is $18K—the threshold below which the business economics don't work. Top performers never notice this number. Average performers are aware of it but rarely dip below. Bottom performers struggle to hit it consistently. Second, create a clearly documented escalation policy: miss the minimum once, it's a discussion; twice in three months, written warning; three times in five months, termination. This episode breaks down why you want a standard that top performers never notice, average performers can maintain, and bottom performers systematically get rooted out—without you having to crack the activity whip every day. Learn how to adjust this for different sales cycles (like using 90-day rolling averages for MSPs), why average is actually good and you don't want high churn, and how the right system diminishes your need to micromanage while keeping the team steady and high-performing. // 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

    11 min

  7. 6D AGO

    Scale the Unscalable: My $50K Lesson from Hormozi’s Team

    I spent two years scaling the wrong business and one conversation with Alex Hormozi's Chief Strategy Officer reframed everything. Here's what happened: I'd built a consulting business to $50K/month doing sales audits and fractional management, but I thought "this isn't scalable." So I pivoted—created courses, built a community, started teaching people how to turn expertise into income. I ended up in a sea of competition selling to the wrong audience at the wrong price point. His CSO said: "Dude, you solved the wrong problem. The problem wasn't 'this isn't scalable.' The problem was 'you didn't know how to scale it yet.'" He showed me around their 20,000 square foot building with 400 people and said, "We don't use the word 'scalable' here. Some things are just way harder to scale than others. That's why Alex and Leila own 50 companies." This episode breaks down what happened next: I killed the community, threw the courses on YouTube, and said "I don't teach this shit, I do this shit." We launched MSP Sales Partners doing fractional sales management—the thing I was actually great at—and spent a year refining the product before stepping on the gas. Learn why I'm intentionally running net neutral right now to build a moat nobody else will, why being picky with hiring and delaying profits creates competitive advantage, and how that subtle twist of words—"you didn't know how to scale it" versus "it isn't scalable"—changes everything. // 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

    16 min

  8. DEC 20

    How to Shrink a Price Objection to Almost Nothing

    I was on a coaching call yesterday with a bunch of people selling IT services, and the question came up: how do you handle price objections? When somebody says "that's expensive" or "more than we're paying now" or "higher than other bids," what do you do? I've got a really simple framework that works across any competitive selling situation—IT services, professional services, whatever. Here's how it works: First, ask "What makes you say that?" to understand if this is a negotiation tactic, a stall, or a real gap. Then clarify what it's relative to—get them to tell you the actual number they're comparing against. Here's the key move: minimize the amount psychologically. If you quoted $60K and they're at $42K, stop talking about $60K—now you're negotiating the $18K gap. Then slice it even smaller: "So we're $1,500 a month apart, or about 50 bucks a day for compliance?" That sounds way better than a $60K contract. Finally, isolate it: "If we can bridge that gap, are you ready to go ahead?" This episode breaks down the psychology of reframing price conversations so you're not defending your number—you're making the gap feel manageable relative to the benefits they want. Works across industries once you understand what we're actually doing here. // 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

    7 min
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4.5
out of 5
11 Ratings

About

A podcast for accomplished people (or those aspiring to be) cut through the BS, make hard choices, optimize what actually matters, and build lives worth living and businesses worth selling. Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family. This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.

Information

  • Creator
    Ray J. Green
  • Years Active
    2020 - 2025
  • Episodes
    100
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show