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The Ray J. Green Show

The Ray J. Green Show

By: 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© 2025 RJG Consulting, LLC Economics Leadership Management Management & Leadership Marketing Marketing & Sales
Episodes
  • I Don’t Fully Buy the “Only Do What You Love” Advice
    Feb 19 2026

    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

    Show More Show Less
    12 mins
  • Why Waiting for the Right Time Kills Your Growth
    Feb 18 2026

    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

    Show More Show Less
    9 mins
  • Make the Sales Conversation Uncomfortable
    Feb 17 2026

    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

    Show More Show Less
    6 mins
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