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. HACE 1 DÍA

    Your VP of Sales Should NOT Carry a Quota

    A popular startup belief says your VP of Sales should “carry a bag” and close deals when they start. The logic sounds reasonable: if they can’t sell, how can they lead a sales team? But that idea misunderstands what a real VP of Sales is actually hired to do. In this episode, Ray breaks down why asking a VP to carry a quota creates a direct conflict of incentives, attracts the wrong candidates, and is usually a sign the company isn’t actually ready for a VP of Sales yet. If you're a founder or CEO thinking about hiring your first VP of Sales, this episode will help you avoid a costly mistake and understand what problem you actually need to solve first. What You’ll Learn in This Episode • Why legitimate VP of Sales candidates won’t accept roles that require them to carry a quota • The incentive conflict that happens when a VP is asked to sell while building a team • How needing a quota-carrying VP is usually a signal your company isn’t ready for one yet // 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. HACE 2 DÍAS

    The 2.5–3X Rule for Sales Rep Ramp Time

    Most MSP leaders wildly underestimate how long it takes a new sales rep to actually produce. On a recent coaching call with 15 MSPs, someone asked me a simple question: How long should it really take to ramp a full-cycle outside sales rep? The common answers—“six months,” “nine months,” “once they learn the product”—all miss the point. In this episode, I break down a rule of thumb I’ve used for years: your real ramp time is 2.5–3× your average sales cycle. That ratio captures the hidden work most leaders forget—learning the company, building pipeline, and then actually running deals through your process. If you’re hiring sales reps, planning headcount, or trying to figure out whether a new rep is actually behind—or just on a realistic timeline—this framework will change how you think about ramp time. What You’ll Learn in This Episode Why the real ramp time for a sales rep is 2.5–3× your average sales cycleThe three phases of ramp most companies underestimate: learning the company, building pipeline, and running dealsWhy using a fixed ramp number like “nine months” creates bad expectations for leadership and reps // 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

  3. HACE 4 DÍAS

    My Hair Pills Taught Me More About Business Than an MBA

    I started noticing something while I was shopping for hair loss pills — Hims, Keeps, Roman, all of them — and every single one had the exact same rule: you can only buy in five or six month blocks. No one-month trial, no cancel anytime. And once I figured out why, I realized it was one of the smartest business moves I'd ever seen. In this episode, I break down why most companies are optimizing for the sale when the really smart ones are optimizing for what happens after it, why short commitments are quietly destroying retention, and why the easiest growth strategy most businesses ignore is simply stopping the bleeding on churn. // 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

    7 min

  4. 6 MAR

    Army Ranger, Hollywood Screenwriter, Cannabis Kingpin — And the 7 Questions That Build a Real Brand

    JP is an Army Ranger turned corporate lawyer turned Hollywood screenwriter turned cannabis operator turned branding strategist. He sold scripts to DreamWorks, Paramount, and CBS, built a dispensary from a dirt lot to $20M a year in eight months, and is a four-time Pan-American jiu-jitsu champion. He now runs Stoned Ape, a branding consultancy built around what he calls the Superhero Questions. We got into how Hollywood's shift from original stories to sequels taught him why branding comes before marketing, why most business owners can't answer "Why should anybody choose you?", why AI is creating a sea of mediocre sameness, and why his 7 Superhero Questions pull the real story out of founders who don't even know they have one. If you've ever struggled to explain why someone should pick you over the other guy, there's a framework here. ----------------------------------------------------------- What You'll Learn • Why "best product at the best price" is a feature, not a brand — and what the difference costs you • The 7 Superhero Questions and how they're designed to pull a real brand out of any founder • How Hollywood's shift from original stories to sequels and reboots is the single best lesson in brand ROI • Why JP built a $20M dispensary in 8 months by answering one question nobody else was asking • How origin stories build trust — and the specific Steve/Tacfirm example that proves it • Why AI-generated website copy is creating a "sea of mediocre sameness" that makes businesses invisible • The difference between proactive brand creation (Steve Jobs) and reactive focus-group branding — and why the focus group always produces the lowest common denominator • Why JP thinks AI search actually rewards original storytelling — and the jiu-jitsu experiment that proved it • How JP uses AI as a writing partner without surrendering point of view or creative control • Why brand is ops — and how a shitty shopping experience negates everything your marketing promised • What a near-death experience with open heart surgery taught JP about the gap between success and fulfillment • Why the Wall Street Journal is running job postings for $300K storytellers — and what that signals about where business is heading ----------------------------------------------------------- Books & Resources Referenced The Four Agreements by Don Miguel Ruiz — https://www.amazon.com/Four-Agreements-Practical-Personal-Freedom/dp/1878424319 Stoned Ape Theory by Terence McKenna (concept, popularized by Paul Stamets) — https://en.wikipedia.org/wiki/Stoned_ape_hypothesis Ray's previous episode with Bob Perkins - https://www.youtube.com/watch?v=EZf-nYlwUd4 Companies Are Desperately Seeking ‘Storytellers’ (WSJ) - https://www.wsj.com/articles/companies-are-desperately-seeking-storytellers-7b79f54e ----------------------------------------------------------- Guest Links JP on LinkedIn - https://www.linkedin.com/in/stonedape/

    1 h y 41 min

  5. 5 MAR

    What I Heard Listening to 100s of Coaching Calls

    I've been listening to a lot of sales coaching calls this week, and I keep hearing the same blind spot from managers over and over again. There are two distinct things you have to address when you're coaching someone — the person and the process — and most coaches are only doing one. In this episode, I break down why the process-only coach runs an informational boot camp that nobody acts on, and why the people-only coach just gets their team fired up to execute the wrong things with maximum enthusiasm. The real skill isn't just knowing both levers — it's knowing which one to pull with the right person at the right moment. // 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

  6. 4 MAR

    Growth, Profit, or Family — Which Are You Sacrificing?

    I came across a clip of Alex Hormozi responding to a roofer at one of his workshops — a guy doing $6 million a year who wants to get to $100 million without losing time with his family — and what Alex said applies to basically every business owner I know. In this episode, I break down why wanting it all isn't a hard formula, it's a losing one. Aggressive growth, fat margins, and maximum family time are all worthy goals, but each one has a real cost, and those costs compete with each other. Most people refuse to pick, and that's exactly why they feel stuck, guilty, and frustrated all the time. There are two paths out, and I want to walk you through both of them. // 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

    7 min

  7. 3 MAR

    Stop Selling During Discovery. Here’s What to Do Instead.

    I was coaching an MSP seller recently, and she kept asking me the same question — when I hear a problem, why wouldn't I just address it right then? It's a fair instinct, but it's also exactly what's killing deals. In this episode, I use a trial lawyer analogy to explain why the best sellers treat discovery like cross-examination — pulling information, staying patient, and never mixing the case-building with the closing argument. If you're pitching solutions mid-discovery, you're leaving facts on the table and signaling that you're there to sell, not to understand. Discovery is where you build the case. Closing is where you present it. // 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

  8. 2 MAR

    AI Slop and the Fork in the Road for Every Knowledge Worker

    I've been parting ways with service providers left and right lately, and it all comes down to the same thing — AI slop. In this episode, I break down why the vendors using AI to do the same old work faster are actually accelerating their own irrelevance, and I use a simple analogy to explain it: the hay delivery guy who got a Model T and thought he was winning. There's a fork in the road right now for every knowledge worker, and most people are picking the wrong path without even realizing it. I want to talk about what separates the people who will thrive from the ones who won't see it coming. // 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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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

Información

  • Creador
    Ray J. Green
  • Años de actividad
    2020 - 2026
  • Episodios
    257
  • Clasificación
    Explícito
  • Copyright
    © 2025 RJG Consulting, LLC
  • Mostrar sitio web
    The Ray J. Green Show