I’ve always taught that systems are the key to scaling, but looking back at 2025, I realized that my obsession with efficiency actually trapped one of my businesses in a state of stagnation. I made the critical mistake of building a rigid delivery infrastructure for a thousand clients when we only had ten, effectively prioritizing process over product-market fit and making it a nightmare to pivot when we received early feedback. In this episode, I’m explaining why building systems too early creates a dangerous "efficiency trap," and why my strategy for 2026 is to embrace the mess and do things manually until the volume absolutely screams for automation.

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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:

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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 becoming the single biggest vulnerability in your leadership toolkit.

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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

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 your internal software if you want your business to scale beyond your current capacity.

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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

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 being a prisoner to my own company.

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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

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 self.

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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

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 end up successfully building a business that makes you miserable.

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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

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 changes throughput dramatically. This episode breaks down why identifying the one constraint is really fucking hard (you'll feel FOMO, you'll want to tackle three problems instead of one), and why most sub-eight-figure businesses can only solve one constraint at a time. I just went through this exercise myself this morning, and here's an example: if your sales process is leaking shit everywhere, does it make sense to 10X your brand growth and leads first? No—because you're just wasting that effort. Fix the conversion constraint before the lead growth constraint. Learn how to audit constraints, discipline yourself to pick the one with greatest impact, and put all the wood behind that arrow instead of diluting effort across 27 problems.

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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 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 transform a cutthroat, toxic environment into a championship team that broke records for a decade straight.

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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