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 are causing thought atrophy in otherwise smart people. These framework guidelines will help you leverage AI's strengths while protecting what actually makes you valuable.

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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 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

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

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 company, and the bar conversation that led to a hire so good it changed where the host lives today. Learn why gut decisions produce outliers and how to strengthen your hiring intuition.

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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 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

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

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, why abdication kills results, and how to build a self-sustaining sales machine without losing control of your company's lifeline.

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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 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

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, including the crucial distinction between "my actions can improve" versus "I'm not enough as a person."

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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 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

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 stars. Brady says it perfectly: "Champions do what stars aren't willing to do." I've seen this firsthand—we had a "no prima donnas" rule on my team, and for ten years straight, we never missed a single goal. If you're hiring or building a team, stop looking for the best players and start looking for the best people. That mindset shift will change everything.

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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 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

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 salespeople that you either don't have money or aren't willing to invest in the role. In this episode, I break down why this approach fails, the real math behind sales ramp time (hint: it's your sales cycle times two), and what you should actually be hiring for—lead generation, closing, or both. If you're a business owner thinking about hiring sales, this will save you a fortune in mistakes.

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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 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

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 value on their own.

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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 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

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.

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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 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