The Ray J. Green Show

As we head into 2026, I’ve realized that AI literacy is no longer just a productivity hack for CEOs; it is a critical defense mechanism against mediocrity. I recently caught my own team trying to pass off lazy, fluff-filled ChatGPT answers as strategic thought, and I discovered I was paying a vendor for content I could replicate instantly with a simple Claude skill. If you don’t have the hands-on technical experience to spot the difference between genuine human insight and a robotic output, you are flying blind, and I’m explaining why your inability to use these tools is bec...

As I audited my performance in 2025, I was confronted with a stark reality: every single one of my personal limitations—from "shiny object syndrome" to hidden insecurities—gets directly installed into the operating system of my business. I’ve witnessed high-potential companies stall because the founder needed to be the smartest person in the room, and I’ve learned that if you don't actively manage your own weaknesses, they become the permanent ceiling for your team. I’m unpacking why the most successful founders treat their own identity as the primary constraint to solve, and why you must constantly upgrade yo...

One of the biggest traps I fell into after leaving the corporate world was believing that I needed to lead by example, often clocking twelve-hour days just to prove a point about work ethic to my team. I’ve realized that while leading by sheer effort creates a bottleneck, leading with radical clarity is the true force multiplier that actually scales a business. I’m breaking down how I shifted from micromanaging the "how" to defining clear outcomes for the "who," a strategic pivot that has allowed me to 5X my output, escape the weeds of daily operations, and stop...

One of the biggest traps I fell into after leaving the corporate world was believing that I needed to lead by example, often clocking twelve-hour days just to prove a point about work ethic to my team. I’ve realized that while leading by sheer effort creates a bottleneck, leading with radical clarity is the true force multiplier that actually scales a business. I’m breaking down how I shifted from micromanaging the "how" to defining clear outcomes for the "who," a strategic pivot that has allowed me to 5X my output, escape the weeds of daily operations, and stop...

As we transition into 2026, I’m kicking off a dedicated series where I break down the most impactful lessons I learned, relearned, and unlearned throughout 2025. I’ve audited everything from my calendar to my AI conversation history to curate a list of high-leverage insights—stripped of all the "guru" filler—that I’ll be sharing one by one in the coming episodes. This isn't a random information dump; it’s a focused look at the specific strategies and mindset shifts that actually moved the needle for my business, serving as both a guide for you and an accountability note to my future...

Years ago, I gave my wife business advice that technically worked but ultimately led her to build a company she didn't love. She had a thriving creative business with a massive waiting list, and I convinced her to scale it, effectively turning her from an artist into a manager. In this episode, I’m sharing that story to highlight a critical lesson for every entrepreneur: just because a strategy makes financial sense doesn't mean it aligns with the life you actually want to live, and I'll walk you through how to filter the advice you receive so you don't en...

As we think about year-end planning, I want to challenge how you're setting goals. Most people set goals based on what they want: "I want more brand growth, more leads, smoother operations." I have a different outlook. Your business is a system, and systems are only capable of producing output according to what the constraints allow. So instead of saying what you want, ask: "What are the constraints keeping us from getting there?" Not getting enough leads? Sales process isn't good? Delivery isn't smooth? Write down all the problems, then identify the ONE highest-leverage constraint—the bottleneck where fixing it...

I learned a defining lesson early in my management career that I’ve lived by for the last 20 years: a cohesive team working together will always outperform a collection of highly talented individuals looking out for themselves. Whether it’s on the football field or the sales floor, the moment you prioritize collaboration and core values over individual stats, you unlock a level of performance that “stars” simply can't achieve on their own. In this video, I react to a powerful clip from Tom Brady that validates this exact philosophy, and I share how I used this approach to transfor...

I was on a coaching call with people selling IT services, and someone had an opportunity to dig deeper into what the prospect said. Another person suggested, "We could have asked 'Why is that important to you?'" The response? "I thought we weren't supposed to ask 'why' questions. It's what I heard from Chris Voss." Look, I love Chris Voss—phenomenal hostage negotiator, great book (Never Split the Difference)—and I fundamentally agree with most of what he says. He's right that "why" questions can make people defensive because we're trained from childhood that "Why did you do that...

If you're nervous when you fire up the camera, I'm going to share a piece of advice Dan Martell gave me three years ago that I absolutely did not want to hear: go live for 30 days in a row. I was terrified of video—I could write great scripts, set up the tech perfectly, get the lighting and mic just right, then hit record and completely blank. Stage fright. So when Dan told me to go live with no retakes, no edits, where if I look dumb I'm stuck with it? That was the LAST thing I wanted. But I...

This is probably the most unfiltered view I've posted since changing this podcast format. I saw a LinkedIn post with the hook: "My wife died at 39. Her doctors never tested the one thing that could have saved her." I started reading—retired pharmacist, tired of Western medicine, quotes, problems—and thought "this smells like a sales letter." I scroll to the bottom and there's a CTA: "Leave a note of 'Energy' below and I'll send you the clinical research." Are you fucking kidding me? Did we really just leverage someone's spouse dying as a hand-raiser post to generate leads? This...

One benefit of getting older? You see patterns over a longer horizon. And here's one I keep seeing in sales and marketing: people proclaiming channels are dead. Cold calling is dead—nobody answers their phone. Webinars don't work. Cold email is ruined by spam filters. LinkedIn organic content doesn't work. Canvassing is impossible. DM selling has been destroyed by automation. I've heard every single one of these channels proclaimed dead—sometimes by people I actually respect who used to crush it in that channel, then didn't evolve with it, and now their message is "it doesn't work." Here's what I kn...

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...

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.

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Welcome to Repeatable Reve...

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...

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 mult...

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 abou...

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 perf...

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 ho...

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...

Ray Green answers a thought-provoking question from a friend: Is there a real difference between "play to win" and "play to not lose" people, and can you build an entire team of aggressive risk-takers? In this episode, Ray breaks down why he believes there are two distinct types of "play to not lose" people - Type 1 who are well-intentioned and think through proper risk mitigation, and Type 2 who operate from fear and lack of confidence. He explains why Type 1 people are actually assets who balance out aggressive play-to-win leaders, while Type 2 people are toxic liabilities that drain your organization...

Physics defines work as force times distance times alignment. In sales, that's effort times results times whether those results actually get you what you want. I saw a junior SDR post on LinkedIn saying "sales training is a joke—just dial your face off." He's one-third right. Volume matters. But here's what gets lost: you drive to work every day, doesn't make you a Formula One racer. It's intentional volume that matters. Josh Braun responded with something so well-written I had to share it: "Drop someone in a pool with no training and they'll kick really hard, flail harder, an...

Physics defines work as force times distance times alignment. In sales, that's effort times results times whether those results actually get you what you want. I saw a junior SDR post on LinkedIn saying "sales training is a joke—just dial your face off." He's one-third right. Volume matters. But here's what gets lost: you drive to work every day, doesn't make you a Formula One racer. It's intentional volume that matters. Josh Braun responded with something so well-written I had to share it: "Drop someone in a pool with no training and they'll kick really hard, flail harder, an...

If you've got a BDR setting appointments and an outside sales rep closing deals, here's a question that comes up constantly with MSPs: Should your AE also be generating their own pipeline? In a perfect world, here's the ideal setup: your setter fills a third to half of the AE's calendar, and the AE fills the rest themselves. Why not just have marketing and the BDR handle it all? Multiple reasons. BDRs turn over—it's often an entry-level role with higher volatility, and you don't want your pipeline to have that same volatility. Different channels work at different times, an...

We just spent six weeks migrating our email newsletter from Beehiiv to Substack. Within one day of going live, I realized I'd made a mistake and had to course-correct. This episode opens up what happened, why it was a mistake, and more importantly—the framework for deciding when to pivot versus when to persevere. Because I've always struggled with this: am I being frantic and erratic by changing course? Or am I being stubborn and falling into sunk cost fallacy by staying? Here's what went wrong: Day One on Substack, I realized the audience is mostly creators writing for ot...

"Should I niche down in my prospecting to a vertical or an industry?" That question came up on an office hours call yesterday with a bunch of MSP business owners. Here's what I told them based on managing 50 different IT companies in our fractional sales program and listening to thousands of prospecting calls: Yes, you should absolutely niche down—but you don't have to rebrand your entire company to do it. Most people think going vertical means becoming "the law firm IT company" and changing everything. That's wrong. You niche at the campaign level, not the company level. This ep...

Ray Green breaks down why both hustle culture and the "deep work only" mindset miss the mark, using a simple physics formula to explain what real work actually is. The equation? Force times Distance times Alignment. In this episode, Ray explains why effort alone doesn't equal results, why you can bust your ass and go nowhere, and why even getting results doesn't matter if they're not aligned with your actual goal. He walks through practical examples—from salespeople making calls to authors writing books—to illustrate why some people accomplish massive results while others stay stuck forever despite working just...

I just had dinner with four really successful business owners—all running businesses bigger than mine—and we got talking about sales compensation plans. Once I started sharing things I honestly take for granted after 20 years in sales leadership, they were like "we hadn't thought about that." These are very smart, very successful guys, just not from the sales world. So if they found it helpful, maybe you will too. Here's the foundation: the only purpose of your comp plan is to change behavior. Charlie Munger said it perfectly: "Show me the incentive and I will show you the outc...

I just wrapped up several hours of difficult conversations stacked back-to-back, and I want to share something that changed my entire management career: the conversations that are going to have the biggest impact on your business are the ones that are really fucking hard. There's almost a direct correlation between how difficult a conversation is and how much impact it has. Yet we avoid them—for days, weeks, months, sometimes years. I've talked to business owners who've let problems fester for years because they don't want the discomfort of a 30-minute conversation. Here's what helped me: reframing these conversations en...

I keep hearing this incomplete advice everywhere: "All sales is about the transference of emotion." It's a Tony Robbins thing, and it's not wrong—but it's dangerously incomplete. I work with a lot of MSP and IT sellers who rely purely on their tech stack, response times, and spotting network problems, thinking logic alone will close deals. Spoiler: it won't. But here's where the "emotion-only" crowd gets it wrong too. People make buying decisions emotionally—they want the transformation, the feeling, the status—but then they justify it logically. Think about wanting a sports car: you want the feeling of dri...

I had to call my wife to pick me up yesterday after re-injuring my knee by pushing six miles when my physical therapist said three. Sitting on that corner waiting for her, I realized something uncomfortable: sometimes the hardest thing you need to do is quit. We glorify resilience, grit, and stick-to-itiveness because they work... until they don't. If you've achieved success through raw determination and sheer will like I have, you've been rewarded for pushing through—which makes it even harder to stop when stopping is exactly what you need. I break down why business model problems and pr...

First-of-the-month accountability check reveals a brutal reality: a salesperson with nothing on the scoreboard, no pipeline, no meetings, and no real plan beyond "follow up with four people" and "pack boxes for Thursday's event." This episode is a wake-up call for anyone in sales responsible for generating their own pipeline. Learn why treating your time like a precious resource isn't optional—it's survival. Discover the two critical mindsets that separate top performers from struggling reps: (1) strategic calendar planning with "The Perfect Week" framework, and (2) complete ownership mentality that refuses to accept passive excuses like "this week's basically shot." If yo...

After years of struggling with content that either grew the business but burned him out, or stayed authentic but didn't generate leads, this episode reveals a new strategy that solves both problems. The challenge: three goals kept conflicting—grow the business, teach what you're learning, and actually enjoy creating content. The breakthrough? Create unfiltered content on dedicated channels (daily podcasts, raw thoughts on X) without worrying about hooks, thumbnails, or "ideal client" topics, then let the team mine that library to extract and reposition the business-growing content. Learn why quality comes from quantity, why ghostwriters and AI shortcuts weren't wo...

When a team member quoted the host's own content back to him—"focus on one thing, use one metric"—it would have actually been counterproductive. This episode clarifies a critical nuance that changes everything: yes, focus on ONE constraint (the biggest problem blocking your business), but measure it with at least TWO competing metrics. Why? Because single metrics get gamed, even unintentionally. Focus only on close rate? Sales reps start disqualifying opportunities. Only track appointments set? You get garbage meetings with terrible show rates. Only measure YouTube followers? You end up with 100,000 subscribers and 3 views per video. Learn how to i...

Watching his wife spend weeks building custom Christmas decorations from scratch—with zero blueprint and no clear plan beyond a color theme—revealed a powerful business truth. We glorify the Bezos-style crystal clear vision, thinking that's what you need to succeed. But the reality? Most wildly successful entrepreneurs will tell you their business took on a life of its own. Building a business is more art than science—more Steve Jobs ("you can only connect the dots in hindsight") than detailed master plan. This episode explores why loving the process matters more than having perfect clarity, how the process itself...

Ray Green shares why he eliminated call minimums when he took over his first sales team - and how revenue per sale doubled as a result. Most sales managers crack the whip on volume and activity metrics, but Ray argues this comes at the expense of optimizing for what you actually want: results. In this episode, he breaks down the policy change he implemented, the cultural shift required to make it work, and how he recruited differently to build a team that took ownership of outcomes instead of just checking boxes on activity. Ray introduces the Laffer Curve framework...

Can a team be made up entirely of aggressive, play-to-win people? Or do you need the balance of risk-conscious players who pump the brakes? This episode breaks down a fascinating leadership question: the fundamental difference between people who play to win versus those who play not to lose—and why it matters for building your team. Discover the critical distinction between two types of "play not to lose" people: Type 1 who intelligently mitigate risk with confidence versus Type 2 who operate from fear and low self-esteem. Learn why the best CEO partnerships involve a play-to-win leader paired with a Type 1 ri...

When a team member fed me pure ChatGPT fluff instead of their actual expertise, it was time to draw a line. As an early adopter and power user of AI, this episode reveals the exact guidelines now required for using AI in the business—from protecting proprietary knowledge on closed systems to owning every output you submit, even if AI generated it. Learn when AI is brilliant (research, refining messages, automating tasks) versus when it's a road to mediocrity (outsourcing your thinking). The uncomfortable truth: AI has all the information but doesn't really know anything, and lazy AI habits ar...

After hiring hundreds of people across 20 years—from reversing a decade-long sales decline at the US Chamber of Commerce to leading executive turnarounds—here's the uncomfortable truth nobody admits: hiring isn't just science, it's feeling. Sure, use scorecards and screening processes to get to your final candidates, but when you're looking at five people who all score between 80-85, what separates the good from the absolute killers? This episode shares the real stories: the purple-haired sales guy HR said not to hire who became the top performer, the economics grad hired without a role who helped Moneyball a 45-year-old comp...

Feeling stretched thin trying to do everything in your business? You're not alone. Many MSP owners ask how to remove themselves from sales, but that's the wrong question. Sales is the oxygen your business needs—you never fully step away from it. The real question is: how do you get your time back while keeping sales flowing? This episode breaks down the exact phases of promoting yourself through your sales organization, from doing everything yourself, to hiring your first SDR, to building a team where you operate as a true sales leader. Learn why each role funds the next, wh...

That voice in your head telling you to do better, work harder, be more—should you silence it or lean into it? Society says constant self-criticism is unhealthy, that you should learn to be content and accept yourself as you are. But what if that relentless inner critic is actually your superpower? This deeply personal episode explores how embracing (not fighting) the inner critic helped jump literal generations of family trajectory—from broken homes and instability to building the life most people only dream about. Learn the two critical mindset shifts that turn self-criticism from exhausting battle into rocket fuel...

I learned this lesson early in my management career and have lived it every day since: a great team will always outperform a group of individual stars, no matter how talented those individuals are. A real team isn't just people doing their jobs—it's a system where everyone is aligned on the same goal, willing to collaborate, share best practices, sacrifice their own time, and do whatever it takes to help the team win. In this episode, I break down why teams outperform individuals and share a powerful two-minute clip from Tom Brady about the difference between champions and st...

I just saved an MSP owner from six months of pain, tens of thousands of wasted dollars, and zero results—all in about two minutes on a coaching call. He was trying to hire a commission-only sales rep with a $40K "guarantee" and couldn't figure out why he wasn't getting candidates. The problems were massive: he expected them to close deals in 90 days when his sales cycle was 90 days, meaning they'd need three qualified opportunities on day one just to have a chance at hitting quota. Commission-only structures attract less experienced reps, create mercenary behavior, and signal to good sa...

Break-fix calls can be goldmines for MSP growth—if you handle them right. The mistake most providers make? They solve the immediate problem, then try to upsell managed services when the client feels relieved and satisfied. That's like asking someone to order their next meal right after they've finished a T-bone steak. This episode reveals a simple process tweak that creates natural leverage for managed services conversations: how to bundle an assessment or diagnostic discussion into every break-fix visit, so you can uncover latent pain points and present real findings instead of relying on the client to see the va...

After a conversation with a friend who built a $200 million gym franchise empire, this episode explores the age-old debate about hard work in entrepreneurship. Is it all about grinding 80 hours a week, or can you meditate your way to success with just a few hours of deep work? The answer lies in a powerful surfing metaphor: business success isn't about choosing one approach—it's about recognizing which season you're in. Learn how to identify whether you're in a paddling phase or a wave-riding phase, and why trying to do both at the wrong time can actually sabotage your results.

Think your job in sales is to talk to people who are ready to buy? That's just order-taking, and there's not much commission in that. In this episode, I break down the three categories every MSP prospect falls into: the red zone (won't buy no matter what), the green zone (ready to buy regardless), and the yellow zone where you actually make your money. The yellow zone is where real sales happen. These prospects could say yes or no, and your job is to close the gap between where they are and where they need to be to buy...

Discover why your outbound efforts aren't generating the results you expect. This episode breaks down the critical mistake most MSPs make—only targeting the 3% of prospects ready to buy right now—and reveals two powerful systems that successful MSPs use to capture the other 97% of the market. Learn how to implement an intel-gathering system that turns every outbound call into future opportunities, and create a top-of-mind strategy that positions you perfectly when prospects are finally ready to switch providers. Real client case study included: how one MSP went from 3-4 appointments per month to 20+ using these exact strategies.

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A viral tweet calling entrepreneurship "just a lottery" hit my feed last week, and I had to respond. The author claimed successful entrepreneurs are lucky players who pretend their success was skill, and thousands of people ate it up. In this episode, I share my original reaction, but more importantly, I break down a powerful story from Alex Hormozi's $100 Million Leads about "The Many-Sided Die" that reframes the entire conversation. Yes, luck exists—some people roll green faster than others. But the real insight is this: you win by continuing to play. Every roll improves your odds, builds your sk...

I got a cold call completely by chance while recording content, and as someone who reviews hundreds of sales calls, this was like Christmas morning. The health coaching rep did a solid job overall—good tone, professional, not pushy—but missed some critical opportunities that would've moved the deal forward. In this episode, I break down the entire call and show you what happens when a prospect quantifies where they are (I said I'm an 8.5 out of 10), why phrases like "small needle movers" kill urgency, how speed to lead matters more than you think, and the mistake of pitching anot...

Ever been on a sales call where your gut tells you something's off, but you say nothing? That disconnect between what you're sensing and what you're saying is killing your deals and destroying your confidence. In this episode, I break down why ignoring red flags wastes your time and erodes your self-respect, and I share a real story where addressing the tension in a call turned a disengaged prospect into a signed client in 50 minutes. Learn how to trust your intuition, have candid conversations the right way, and why prospects will actually respect you more for it.

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I'm breaking down exactly how to handle one of the most frustrating situations in MSP sales: when you fix a break-fix problem for a prospect, mention managed services, and then get completely ghosted. The reality is they no longer feel the pain after you've solved their problem, so there's no urgency to move forward. Instead of making one or two follow-ups and giving up, I'm showing you how to build a simple five-email sequence that does the heavy lifting for you. This sequence educates them, shifts their mindset, and nurtures them from "not ready" to "let's talk" - without...

I burned through $50,000 and four virtual assistants trying to fix my operations and tech stack, and things only got worse. The problem? I was trying to skip the hard part - actually understanding what needed to be fixed before hiring someone to fix it.

Dan Sullivan's "Who Not How" advice is brilliant, but there's a critical piece missing that cost me nine months and left my business in worse shape than when I started. The real formula isn't just "who not how" - it's "you, then who, somehow."

I see MSP owners make this exact...

I used to think "Always Be Closing" was outdated, sleazy sales advice, but I've completely changed my mind. In this video, I break down why ABC is actually the foundation of consultative selling for MSSPs and B2B sales.

The truth is, every single step in your sales process—from discovery calls to assessments to proposals—should be designed with one goal: moving the deal forward and closing the sale. I'll show you the simple framework I use to redesign sales processes, explain why most salespeople are treating discovery and assessments like information gathering instead of closing oppo...

Discover why most MSP deals are actually won or lost during the discovery phase, not at the close! In this video, I break down how to engineer your discovery process to address objections before they even come up.

I'll show you how to plant the seeds early by asking strategic questions that uncover pain points, buying motivations, urgency levels, and decision-making processes - then use their own words as your most powerful rebuttals later. Instead of scrambling to overcome predictable objections like "it's too expensive" or "we're not ready yet" at the end, you'll learn to reverse-engineer...

I reveal the shocking truth about why most MSP deals actually fail - and it's not what you think. After listening to countless sales calls, I've discovered that deals don't die because of timing, price, or contract issues.

They fail because sales reps never actually ask for the sale! I know it sounds crazy, but I'm going to prove exactly how this happens and show you the simple techniques I use to avoid getting ghosted by prospects.

I'll walk you through my proven closing strategies, including the exact questions that force prospects to reveal their...

I analyze a case study of a $7 million MSP owner whose close rates were declining despite having good reps and processes. What I discovered during our audit was that they had one rep who was phenomenal at opening deals through LinkedIn prospecting and another who was excellent at closing, but both were trying to handle the entire sales cycle from lead generation to account management.

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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. Cha...

I share a crucial sales framework that can prevent you from losing deals after what seemed like successful presentation meetings. I explain the "BAMFAM" (Book a Meeting from a Meeting) strategy, which ensures you never leave a proposal meeting empty-handed without either a clear decision or a confirmed next step on the calendar.

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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...

I share how downloading a "Couch to 5K" app - despite being able to run half marathons - taught me a powerful lesson about achieving big goals in business.

After hitting a mental block that kept sabotaging my runs, I discovered that starting embarrassingly easy and building small, consistent wins creates unstoppable momentum. This same principle of breaking down massive business goals into bite-sized, achievable steps helps you develop a winning habit that compounds over time, whether you're trying to scale from $1M to $10M or launch that outbound sales operation you've been putting off.

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I recently coached an MSP seller who spent over 20 hours chasing a $5,000 deal only to get completely ghosted at the end - sound familiar? If you're tired of getting stuck in sales purgatory, chasing deals you were never going to win, I'm going to show you three specific strategies to break free and force more decisions.

First, use your discovery phase strategically to understand their actual buying process by asking the right questions about urgency, decision-making structure, and stakeholders involved.

Second, after your proposal presentation, get them to quantify their interest on a 1-10 scale...

I see ads all the time claiming that "building rapport" is a lie and you need to learn how to sell without it - but these so-called experts are completely missing the point.

In this video, I break down the massive misunderstanding around what rapport actually is in sales. It's not about small talk, weather conversations, or chatting about family photos on someone's desk - that's just likability, not rapport. Real rapport is about establishing trust, credibility, and demonstrating that you have the expertise to solve their problems.

I'll show you how to build genuine...

I inherited a commission-only sales team at the US Chamber of Commerce and had to shut down the entire division 18 months later.

In this video, I'm sharing why commission-only structures actually sabotage sales teams and can ruin your business culture. Most business owners think commission-only means hungrier, more driven reps, but that's not necessarily true. I'll break down the two major problems I've experienced with commission-only structures: how they drive away top talent who see them as red flags, and how they attract mercenaries who only care about one thing - their commission.

I was on a flight with my family when we had an emergency landing, and watching how the first responders handled the situation taught me the most important lesson about running a business: successful CEOs don't try to solve every problem at once, they identify the single most critical priority and focus all their resources on that one thing

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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 rev...

I bombed my first sales interview but still got hired, and that experience taught me the three key traits I now look for when hiring salespeople that matter more than experience or charisma.

Despite being introverted with no sales background, I went on to become a top performer and help raise over $100 million - here's what really matters in sales hiring.

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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 Com...

This episode breaks down how an MSP sales professional successfully salvaged a deal after losing control of the discovery process when a third-party consultant flipped the script and interviewed him instead of allowing him to ask questions.

Ray shares three key insights extracted from analyzing the meeting transcript and demonstrates how to use strategic questioning and positioning to regain control during the proposal stage.

Despite starting as one of ten candidates in a compromised position, the systematic approach helped the salesperson become a finalist and ultimately win the sizable deal.

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Ray breaks down a real coaching scenario where an MSP salesperson lost a deal to an inferior provider despite proving compliance issues and security vulnerabilities.

The prospect chose to give their current provider "one more chance" instead of switching to better service.

//

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...

Shy, introverted, and autistic - I bombed my first sales interview selling knockoff perfume. But I went on to never miss a sales target for 3 consecutive years and built a 20-year career helping MSPs scale from $5M to $50M+.

If you're a technical founder who thinks you're "not cut out for sales," this video will change 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 rev...

I break down why SDRs aren't just booking appointments—they're actually closing deals every single day, and how treating prospecting like a real sale will dramatically increase your appointment-setting success.

Learn the exact framework I use to help MSP SDRs understand what they're really selling and why most people get this completely wrong

//

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 fundr...

I share a real conversation I had with an MSP business owner who was avoiding making tough decisions about an underperforming salesperson, and explain why true leadership means making difficult decisions that others may disagree with rather than letting problems persist to keep everyone happy.

//

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 nat...

We analyzed what drives SDR success after coaching 100+ reps and discovered 6 critical levers plus 1 amplifier that make the difference between crushing it and flopping.

In this video, I'll share exactly what separates high-performing SDRs from the rest so you can guarantee results in your business.

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 nat...

Ray guides viewers through creating two plan options and making a compelling recommendation to seal the deal. Subscribe for more insights on growing your business through effective sales techniques.

//

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 le...

In this episode Ray shows you how reps with all the right questions still blow the deal—and how one simple shift in how you run discovery can help you outsell competitors, even when your price is higher.

//

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.

→...

In this episode Ray shares why having too many good options might secretly be sabotaging your success—and reveals the tough decisions he made to break free. If you're juggling multiple opportunities, this might be exactly what you need to hear.

//

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...

I break down how to build a sales team that truly runs itself by implementing fundamental systems that eliminate the daily firefighting and micromanagement that drains most MSP owners.

I share my 20 years of experience showing how the right systems - from lead distribution to compensation plans - can free you from constantly making subjective decisions and dealing with team conflicts, allowing you to focus on proactive growth strategies instead.

//

Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Sm...

In this podcast, Ray reveals the real reason marketing strategies like cold calling, LinkedIn outreach, and paid ads fail for MSPs—and the mindset shift you need to make any of these strategies actually deliver results.

//

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 op...

I'm breaking down why hiring traditional salespeople can actually stall your MSP's growth in 2025, and sharing the component-based system approach that hundreds of successful MSPs use instead.

Learn how to avoid expensive hiring mistakes and build scalable sales processes that don't create key-man risk in your business

//

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...

In this episode, a CEO’s forced digital detox during a European vacation reveals how just two hours of focused work a day can unlock sharper priorities, empower your team, and expose the hidden cost of micromanagement.

//

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...

I share seven practical strategies I've learned throughout my career to help salespeople bounce back from setbacks, including taking feedback constructively, managing expectations, not taking rejection personally, focusing on controllable factors, using scripts effectively, establishing pre-game rituals, and creating an alter ego to handle difficult situations.

//

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 n...

In this episode, I walk you through the 7-part MSP sales system we use to help managed service providers grow consistently and predictably. If you're tired of relying on random referrals or stalled pipelines, this framework will give you the structure and clarity you need to scale. Let's break it down step by step.

//

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...

In this episode, I’m sharing the exact 4-step formula I’ve used to hit every meaningful goal I’ve ever set—personally and professionally.

From relationships to business to building MSP Sales Partners, this process has helped me win again and again.

If you’re in the MSP space and want to achieve big things, this is for you.

//

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...

If your MSP growth strategy doesn't make you want to chuck your computer out the window occasionally, it probably won't deliver meaningful results

I'll show you why pushing through that initial resistance leads to outsized returns while "serial starting" keeps most IT businesses trapped on a plateau.

//

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...

I explain how to create an effective compensation plan for Sales Development Representatives (SDRs) in Managed Service Provider businesses.

I walk through a three-step process for building a comp plan that maximizes ROI while avoiding issues like high turnover and underperformance, complete with practical examples and a downloadable template.

//

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 inc...

Drawing from my 15+ years of sales management experience, I'll show you how to design a comp plan that attracts top talent, motivates your sales team, and maximizes your ROI.

Whether you're struggling to retain great salespeople or want to supercharge your sales performance, these insights will help you build a compensation strategy that truly works.

//

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 sal...

I break down the four common sales problems MSPs face and provide clear guidance on whether you need a BDR, SDR, closer, or simply sales training to solve your specific challenge.

//

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 group...

▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox

▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com

Hey, I’m Ray Green. I’m a strategic growth specialist for B2B companies.

Since this is social media and anyone can claim anything, here’s a quick rundown of my background:

Former Managing Director of National Small & Midsize Business at the U.S.

Chamber of Commerce, where I doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, a...

In this video, I break down how Hilton, Airbnb, and VRBO's advertising war demonstrates effective differentiation strategies that MSPs can use to stand out and command premium pricing.

//

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 t...

I reveal the five critical elements that separate top-performing MSPs from the rest. I'll show you why owning your pipeline, focusing on process over outcomes, mastering discovery, selling with conviction, and maintaining a winning mindset are essential for reaching the top 1% of sales performance.

//

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...

Learn how to build a predictable stream of qualified appointments without becoming a full-time sales manager. Ray Green, with 20 years of sales experience and 15 years in sales leadership, shares a proven program to help IT business owners effectively recruit, train, and manage SDRs.

//

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 sal...

Learn how to communicate value, optimize calendar availability, create effective booking funnels, confirm appointments strategically, and use the BAMFAM (Book A Meeting From A Meeting) principle to maximize your sales process efficiency.

//

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 inves...

▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox

▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com

Hey, I’m Ray Green. I’m a strategic growth specialist for B2B companies.

Since this is social media and anyone can claim anything, here’s a quick rundown of my background:

Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where I doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national...

Learn how to build a predictable stream of qualified appointments without becoming a full-time sales manager. Ray Green, with 20 years of sales experience and 15 years in sales leadership, shares a proven program to help IT business owners effectively recruit, train, and manage SDRs.

//

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 sal...

In this episode, we break down Alex Hormozi's 4 biggest business risks for companies under $10M and apply them specifically to IT companies and MSPs

I share real-world examples from my experience working with IT companies and provide actionable strategies to mitigate these risks. Whether you're running an MSP or scaling a tech business, these insights will help you build a more resilient company

//

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. Cha...

Going beyond its reputation as just a recruitment platform, I break down five critical areas where companies are leaving money on the table: unoptimized profiles, ineffective content strategies, poor connection approaches, missed conversation opportunities, and failure to integrate LinkedIn into broader marketing efforts.

//

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 sal...

As the former Managing Director of the US Chamber of Commerce and a CEO for investor groups, I've helped numerous IT companies scale their sales, and I’ve been through this journey myself. I’ve learned these 7 keys through hard-fought experience, so watch and take control now!

//

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-buil...

After training over 250 IT salespeople and analyzing real performance data, I've discovered 7 key patterns that separate top IT sellers from everyone else.

//

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 busin...

Want to know who's visiting your B2B website? I'll show you the free tool that reveals exactly who's looking at your pages - and how to set it up in 5 minutes.

//

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 inves...

How over-niching cost me high-value clients and referrals. I'll share the feedback that changed my entire approach to brand building and market targeting.

//

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...

How to scale an IT company from $9M to $29M. I'm opening up my complete sales audit framework that I use to create growth plans for high-performing MSPs.

//

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 t...

Learn the exact process I use to help IT companies scale their monthly recurring revenue

//

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 P...

Two sales reps, same leads, same tools, radically different results. After leading sales teams at the US Chamber of Commerce, I'll reveal why some reps consistently outperform their peers by 2X.

//

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 group...

Ever wondered if you're working too hard for too little return in your business? In this powerful episode, host Ray Green shares a harrowing personal story that changed his entire approach to entrepreneurship. After nearly losing his life in a riptide, Ray discovered a profound truth: sometimes swimming harder isn't the answer – you need to change direction entirely.

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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 s...