The Ray J. Green Show

Ray J. Green
  • 4.5 (11)
  • Management
  • Updated Semiweekly

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

    I felt Guilty At Work AND Home. Then I Stopped.

    When work gets demanding, you feel guilty about your family. When you pull back from work, you feel guilty about your clients and team. Ray explores why this cycle keeps founders and operators feeling like they're failing on both sides—and why the answer isn't finding the perfect daily split. What You’ll Learn in This Episode Why guilt at work and guilt at home tend to reinforce each other.How the surfing analogy helps you recognize what season you're actually in.Why continuing to paddle after you've caught the wave can create unnecessary problems.How trying to divide every day evenly can leave you mentally absent in both places.The zoom-out test Ray uses to evaluate work and family across a longer period.Why sometimes the highest-value thing you can do for the business is leave it alone. // 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

  2. 2d ago

    No, Venting Doesn't Make You Feel Better

    Complaining can feel like a release, but Ray argues that repeatedly giving voice to frustration can reinforce the very position you're trying to escape. This episode examines what complaining costs you, from the energy it takes away from solving the problem to the effect a persistent complaining habit can have on the people around you. What You’ll Learn in This Episode Why venting can reinforce frustration instead of releasing it.The three ways complaining compounds against you: lost energy, unchanged behavior, and damaged relationships.Why complaining directly to someone rarely changes their behavior.How a persistent complaining habit can eventually filter useful people out of your circle.The difference between accepting reality and pretending you like it.Why changing the words you say out loud can change how you respond to a situation. // 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. Aug 13

    The Margin Nobody Measures

    A full calendar can look like discipline, productivity, and control—until something unexpected happens and there is nowhere for it to go. After spending four days running his business from a chair beside a hospital bed, Ray examines the hidden cost of eliminating every open hour: the loss of margin on your time. What You’ll Learn in This Episode Why a completely allocated calendar can quietly eliminate your flexibility.How time margin provides the same security, optionality, and head space that financial margin provides.Why time margin can disappear without you noticing until something unexpected lands.Three ways to rebuild it: scheduling below capacity, creating real redundancy, and redesigning your ideal week from a blank calendar.Why automatically filling newly available time with more production can recreate the same problem. // 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

  4. Aug 12

    Your No Show Problem Is Good News

    A 20% appointment show rate might look like a sales failure—until you understand what came before it. This episode examines why sales systems have to be improved one constraint at a time, and why abandoning the process when the next problem appears can erase the progress you've already made. What You’ll Learn in This Episode Why a bad metric can still represent meaningful progress.How sales constraints reveal themselves sequentially as the system improves.Why fixing hiring, training, qualification, show rates, discovery, and closing in the right order matters.How quitting when the next constraint appears can create the false belief that outbound sales doesn't work. // 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. Jul 7

    What a Parenting Book Taught Me About Sales Management

    If you've had the same performance conversation more than once, the problem probably isn't your employee—it's your management system. In this episode, we explore why conversations alone rarely change behavior, how leaders unintentionally train people to tolerate accountability, and what actually creates lasting performance improvement. What You'll Learn in This Episode Why repeated coaching conversations often reinforce the behavior you're trying to stop.The leadership question that reveals what you're actually conditioning your team to do.How to create accountability through consistent actions instead of stronger words. // 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. Jul 6

    Why Being Right Loses IT Deals (And What Top Closers Do)

    He had the budget. He agreed with every problem in the assessment. Then he said $2,000/month was "too expensive" — and walked. If you sell IT or any technical solution, you've lived this. Here's the uncomfortable truth: being right about the problem has almost nothing to do with winning the deal. I just judged a national MSP sales contest, and the top closers — 68%, 72%, 76% close rates — weren't the best technical sellers in the room. Most of them didn't come from tech at all. They were winning like trial lawyers. In this video I break down the exact process they run: • Why people buy what they want, not what they need • Problems vs. pains — and why emotion closes deals, not logic • The "curse of knowledge" that turns your expertise into a liability • How to use questions as weapons, like a trial lawyer • The 5-stage process: Qualify → Discover → Assess → Present → Decide • BAMFAM — the habit that keeps deals from stalling 👉 Free templates, playbooks & scorecards in the MSP Sales Toolbox: https://mspsalestoolbox.com (new resources every month) ▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox ▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com

  7. Jul 3

    Your Sales Process Is Costing Your Deals

    Episode Summary Ever lose a deal to someone who clearly wanted your solution but refused to follow your sales process? The problem may not be the buyer—it may be the rigidity of your process. In this episode, we explore why every prospect already has a buying process, and why the best sales teams know when to guide it and when to adapt to it. What You'll Learn in This Episode Why forcing buyers into your sales process costs qualified deals.How to determine when to influence a buyer's process versus adapting to it.A practical way to gather decision-maker input without forcing another meeting. // 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. Jul 2

    Progress Is The Result

    Many business owners mistake a lack of immediate outcomes for a lack of progress. In reality, the work that creates results often happens long before the numbers improve. In this episode, Ray explains why building the conditions for success is itself meaningful progress, and how impatience causes people to abandon strategies that were beginning to work. What You’ll Learn in This EpisodeWhy foundational work often matters more than early performance metricsHow impatience leads people to skip the very steps that produce long-term resultsWhat to measure when the outcome you want hasn't arrived 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

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4.5
out of 5
11 Ratings

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
    300
  • Rating
    Explicit
  • Copyright
    © 2025 RJG Consulting, LLC
  • Show Website
    The Ray J. Green Show