Newsletter for reference: https://www.aboutamazon.com/news/company-news/amazons-original-1997-letter-to-shareholders

For years, I preached that a crystal clear vision was the non-negotiable foundation of any successful company, often citing Jeff Bezos's prophetic roadmap for Amazon as the gold standard. But in 2025, I unlearned that rule and embraced the "Steve Jobs approach"—trusting the process, iterating in real-time, and connecting the dots looking backward. In this episode, I’m discussing why you don't need a perfect ten-year plan if you genuinely love the art of building, and how a passion for the daily grind can serve as a powerful substitute for a crystallized vision when navigating the inevitable frustrations of entrepreneurship.

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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

For six years, I’ve used my personal brand to drive millions in revenue, but I kept hitting two major walls: I became the bottleneck when client work piled up, and I burned out from repetitively talking about the same niche topics. My breakthrough this year was finally decoupling my personal identity from my business’s identity—allowing me to create content about whatever I’m obsessed with (like neurodiversity or general entrepreneurship) while my team mines that content to extract and repackage the specific pieces needed for our marketing. This shift has not only made content creation fun and sustainable again but has also removed the "assembly line" feeling and uncapped our growth potential.

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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

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

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

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

//

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