Bob Perkins has done things most people only read about — fighter pilot instructor, political fundraiser, the ad agency behind Apple's 1984 Super Bowl commercial, CMO at Calvin Klein, executive at Playboy, head of marketing at Pizza Hut, and turnaround CEO. He's sat on boards, built ventures inside the U.S. Chamber of Commerce, and now spends his time thinking and writing about how AI is fundamentally reshaping competition.

We got into all of it. From the real story behind the most famous Super Bowl ad ever made (and the worst one, made by the same people the very next year) to why marketing as a discipline is being consumed by AI, to a fighter pilot decision-making framework that most companies are too slow to execute. We also talked about what actually drives organizational change, why group dynamics override expertise, and what Bob would tell his 40-year-old self if he could go back.

This one went deep. If you run a business or lead a team, there's a lot here.

What you'll learn in this episode:

1. Why marketing is becoming unrecognizable — and what's replacing it
2. The real story behind Apple's 1984 ad and how it almost never aired
3. The Boyd Loop (OODA) — how fighter pilots make decisions at 500 mph and why it matters for your business
4. Why competitive advantage is shifting from planning to execution speed
5. How AI changes the feedback loop — and why that's the real unlock for sales teams
6. What stops organizations from acting on decisions they've already made
7. Why the power of the group is the most underrated force in business — and how it quietly kills change
8. Bob's advice to his 40-year-old self (and the one skill he wishes he'd developed more)

Books referenced in this episode:

1. Sapiens by Yuval Noah Harari
2. The Geek Way by Andrew McAfee
3. The Innovator's Dilemma by Clayton Christensen
4. On the Edge: The Art of Risking Everything by Nate Silver
5. The Infinite Game by Simon Sinek

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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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In this episode, I’m diving into a psychological trap that kills credibility in sales and marketing: the "Gold Delusion Effect." Drawing on research from the University of Chicago, I explain why stacking more benefits into your pitch actually makes people believe them less. It turns out that when you try to promise everything—saving time, saving money, increasing morale, and boosting revenue—you often end up being the "12-page menu" restaurant that no one trusts to make a great burger.

I share real-world examples of "zero delusion" brands like Raising Cane’s and WD-40 that have built empires by doing one thing exceptionally well. But even if you run a complex, multi-service business, I’ll show you how to use "umbrella branding" and surgical discovery to keep your message undiluted. Join me as I break down why one message per moment is the key to building real belief in your prospects.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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

In this episode, I’m tackling one of the biggest myths in business: the idea that you have to be an outgoing extrovert to be great at sales. As an introvert who has spent years in the trenches, I’ve actually found the opposite to be true. I’m making the case for why introverts—all things being equal—actually close more deals.

I dive into the fundamental difference in how we approach networking and discovery calls. While extroverts often get their "reward" just from the act of socializing, introverts are usually on a mission. We don’t have the energy to waste on small talk for the sake of small talk, so we tend to be more methodical, more intentional, and way more focused on the data points that actually move a deal forward. If you’ve ever felt like your quiet nature was a disadvantage in a loud industry, this episode is for you.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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

In this episode, I’m breaking down why we need to stop looking at success as a straight line and start seeing it for what it actually is: an exercise in 10,000 micro-failures. Inspired by a story from former NASA engineer Mark Rober about how they get a rover to Mars, I explore the concept of "mouse farts"—the tiny course corrections that keep a mission from drifting millions of miles off target.

I talk about why the difference between reaching your destination and giving up usually comes down to how you handle those inevitable moments when you've veered off track. If you’re feeling like you’ve hit a wall or made a wrong turn, join me as I explain why that isn't the end of the road—it’s just time for a little course correction.//

Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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’m currently watching a merger turn into a complete clusterfuck, and it’s a story I’ve seen way too often in private equity. It’s a classic case of an acquirer coming in, kicking the original leadership to the curb, and gutting the company because they don’t understand that value isn't always visible on a spreadsheet. In this episode, I dig into the "Doorman’s Fallacy"—the mistake of eliminating something because you can’t quantify its utility, only to realize later that it was the very thing holding the brand, the culture, and the customer experience together.

I compare the hollowed-out wreckage of this recent acquisition to my experience at the Four Seasons, where small, "unmeasurable" details like a lens cloth or a cord tie create the entire premium experience. We’re exploring why 40% of M&A deals end up as dumpster fires and how the best operators identify and protect the invisible value creators that actually drive ROI. If you’ve ever wondered why great companies fall apart after a sale, this is why.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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

"There is a small chance of sudden death."

That’s a hell of a thing to hear from your cardiologist when you’re a guy who runs ten miles a day and feels healthy as fuck. One minute I’m "knocking the cover off the ball" on my stress tests, and the next, I’m being told I have Hypertrophic Cardiomyopathy—a condition where my heart is literally too strong for its own good. It’s a diagnosis that could have sent me into a spiral of anxiety, especially after a recent trip to the ER during a family vacation, but it actually led me to the most important mental shift I’ve ever made.

In this episode, I’m sharing the raw details of my heart journey and the specific reframe that changed everything: the moment I stopped asking "Why is this happening to me?" and started asking "Why is this happening for me?" I dive into how this diagnosis actually protected my sons, empowered my team to crush it while I was out of pocket, and forced me to trade frantic intensity for sustainable productivity. I’m also walking you through a powerful exercise to help you take your own current "low point"—whether it’s in your health, your business, or your relationships—and rewrite the story in real-time. You don’t have to wait ten years to be grateful for a challenge; you can choose to see the benefit of the obstacle today.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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

Most sales trainers will tell you that closing more deals requires a "killer instinct," better "closing techniques," or some fancy psychological methodology. But I just watched an MSP salesperson go from a 13% close rate in 2025 to a 71% close rate in just 45 days, and it had nothing to do with "mindset" or charisma.

In this episode, I break down the real-world transformation of Garrick, a seller who closed $17,000 in MRR this month alone. We didn't give him a new script; we gave him a new system for how to think about the sales process. We move past the surface-level "motivational" advice to focus on the tactical shifts that actually bent the curve: stopping the guesswork on ROI by simply asking the prospect how they measure value, practicing the "money ask" until it became boring muscle memory, and learning to lead proposals with the prospect's priorities rather than our own expert biases.

If your sales team is working hard but failing to convert, it’s likely not a lack of effort—it’s a lack of the system underneath the tactics. Let’s look at how to stop treating discovery like a checklist and start conducting conversations that actually lead to a close.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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 used to think that successful entrepreneurs had a "secret map" that gave them 100% certainty before they made a move. I spent years in planning mode, working my tail off but making zero progress because I was terrified of making the "wrong" bet.

In this episode, I’m sharing a raw look at a trap I see so many founders fall into: the endless pivot. I recently worked with a business owner who cycled through three different strategies in a month, not because he lacked talent, but because he was waiting for a feeling of certainty that simply doesn’t exist in business.

I’ve learned the hard way that our job isn't to find something that works—it’s to commit to making it work. We’re going to talk about escaping the "amygdala hijack," why most results live on the other side of a J-curve, and how to start thinking in probabilities rather than absolutes. If you feel like you’re rowing hard but staying in the same place, it’s time to stop looking for a guarantee and start making a bet.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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’ve spent the last year hanging out with two very different groups: founders stuck at the $1M to $2M mark and entrepreneurs running $200M empires. Do you want to know the biggest difference between them? It’s not intelligence or work ethic—it’s their belief systems.

Fresh off a trip to the Museum of Illusions with my kids, I realized that many of us are running our businesses while staring at the corporate equivalent of a "mind-bending" optical illusion. We are dead certain about "truths"—that we are essential to daily ops, that a certain channel is dead, or that we lack the right connections—only to find out those "truths" are the very things capping our growth.

In this episode, I’m challenging you to look at where you might be fighting reality. What is the one thing you know for sure that just "aint so"? Let’s break down the hidden illusions keeping you from the next level.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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

Two weeks ago, I ended up in the ER with a heart incident that knocked me completely out of commission. But instead of falling apart, my business didn't skip a beat—in fact, we had our best sales month in six years. In this episode, I break down the critical decision I made last year to stack my team with "A-players" and the specific system I used to find them. I also explore the uncomfortable truth about why believing you are "necessary" is actually the biggest cap on your business's growth, and how to finally get out of your own way.

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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