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 unco...
Nov 29, 2025•14 min
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 ...
Nov 28, 2025•12 min
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...
Nov 27, 2025•12 min
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 peop...
Nov 26, 2025•12 min
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 pow...
Nov 25, 2025•12 min
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-on...
Nov 24, 2025•14 min
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-...
Nov 23, 2025•8 min
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 ph...
Nov 22, 2025•5 min
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 wher...
Nov 21, 2025•11 min
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 ...
Nov 19, 2025•12 min
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. B...
Nov 14, 2025•16 min
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 ur...
Nov 07, 2025•21 min
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 ...
Oct 31, 2025•12 min
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, sh...
Oct 24, 2025•22 min
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 ...
Oct 17, 2025•16 min
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 salespeopl...
Oct 10, 2025•15 min
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 objection...
Oct 03, 2025•17 min
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 t...
Sep 26, 2025•13 min
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. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. About Ray: → Former Managin...
Sep 19, 2025•14 min
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. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. About Ray: → Former Managing Director of National Small & Midsize Business at th...
Sep 12, 2025•14 min
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 try...
Sep 05, 2025•15 min
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 ...
Aug 29, 2025•13 min
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 t...
Aug 22, 2025•3 min
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 r...
Aug 15, 2025•13 min
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 // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. About Ray: → Former Managing Director of National Small & Midsize Bu...
Aug 08, 2025•14 min
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. // Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green. About Ray: → Former Managing Director of National Small &...
Aug 01, 2025•13 min
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, t...
Jul 25, 2025•19 min
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 ...
Jul 18, 2025•13 min
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 ...
Jul 11, 2025•15 min
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 ...
Jul 04, 2025•18 min
