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How I Audit My Year: Learned, Relearned, Unlearned
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
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Transcript
What are the lessons I've relearned? And these are really important because I want to make sure they stick. There are certain things that we learn, and then circumstances change, and for whatever reason, we stop doing the thing that we had learned previously worked or didn't work. And so understanding what those are so that I don't continue to repeat mistakes is really important.
And then the third thing is what are the things that I unlearned? What are the things that I've changed my mind on as the business has gone through? And there's a few of those as well.
So what I've done is on this reflection created this long list. And I've got a bunch of them. And the way that I do that is I look at my calendar, I look at content that I've created throughout the year, I look at the conversations that I have in AI—and I've actually this year I've prompted Claude, GPT, Gemini, others—and said, "Hey, what are some potential lessons that I've learned?" and just kind of asked it based on our conversations and the memory that you have.
And it's hit and miss with that, but there's a number of ways you can go back and pull those lessons forward. And I've got this long list. And what I'm going to do for the next number of episodes is I'm going to share a curated list of those with you one by one. Rather than just have this big long information dump that has filler and other things like "Hey, I'm at 18, I gotta make it 26, how do I split these up? How do I make it sound like more?"
can go back to at the end of:And that's going to be the next number of episodes. So this is just kind of teeing up what that's going to look like. And each day I'll drop in a new one. And again, my goal is make it as actionable as possible. So I'm not trying to give you fillers, I'm not trying to make the longest list possible, I'm not trying to make the shortest list possible. I'm giving you what I genuinely believe are the most important pieces that if I look at this going into 2027, I could come back and know these are the rock solid things. These are the ones that had the biggest impact and biggest output and most leverage for me.
So without further ado, I'm going to go ahead and start jamming on these and feel free to leave me some feedback if you have any questions or comments below. Adios.
