What if the work you think is growing your business is actually just making you feel like it is?

After disappearing for 8 years, Travis Kalanick—former Uber founder—quietly built a $15B robotics company, operating in 30 countries with thousands of employees… without PR, branding, or even LinkedIn visibility.

This forces a harder question: if you removed validation, visibility, and noise—would your business still move forward?

In this episode, Ray breaks down the hidden difference between building and performing—and why the question you’re asking might be capping your entire trajectory.

What You'll Learn In This Episode:

1. Why most founders are stuck in a “visibility loop” that feels productive—but isn’t actually moving the business forward
2. The mindset shift from “Can I do this?” to “What would it take?”—and how it changes the scale of problems you pursue
3. How removing yourself as the constraint fundamentally alters the opportunities, talent, and outcomes available to 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

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Follow Ray on:

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Most compensation plans don’t fail because they’re complicated—they fail because they’re unclear.

If you can’t name the exact behavior your comp plan is designed to drive, you’re not incentivizing performance—you’re creating confusion and misalignment.

In this episode, I break down the one question that cuts through all of it—and why getting this right changes how your team actually shows up day to day.

If you want a comp plan that drives the behaviors you actually need (not just outcomes you hope for), this episode will show you where to start.

What You'll Learn In This Episode

1. Why every comp plan is fundamentally a behavior-shaping system—not a payment structure
2. The hidden misalignment created when you pay people on outcomes they don’t control
3. How to identify the specific actions that actually move your business forward

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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:

YouTube | LinkedIn | Facebook | Twitter | Instagram

When execution starts slipping in a business—missed deadlines, dropped tasks, confusion across the team—most leaders immediately try to fix the wrong thing.

The real issue almost always comes down to one of three root causes: priorities, process, or people.

In this episode, Ray breaks down the simple framework he uses to diagnose execution problems after a recent rollout inside his own company didn’t go as planned. When you diagnose the problem correctly, the path to fixing it becomes obvious.

If your team feels busy but progress keeps stalling, this episode will help you identify the real cause so you can stop applying the wrong fix and start getting execution back on track.

What you'll learn in this episode:

• The three root causes behind almost every execution breakdown in a business

• Why leaders often misdiagnose execution problems and make them worse

• How to determine whether your issue is priorities, process, or people

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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:

YouTube | LinkedIn | Facebook | Twitter | Instagram

▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox

▸ Check out MSP Sales Partners: mspsalespartners.com

▸ Learn about our SDR Accelerator program: https://mspsalespartners.com/sdr-accelerator -

Three MSPs in our program are consistently booking 15-20 qualified appointments every month from their SDRs. And they’re using very distinct strategies — different than the standard smile and dial strategy. I asked all of them to walk me through everything.

In this video, I break down those 3 case studies and what they’re doing different. Plus the 5 most common mistakes that cause everyone else to get no ROI from their SDR investment.

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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:

YouTube | LinkedIn | Facebook | Twitter | Instagram

A popular startup belief says your VP of Sales should “carry a bag” and close deals when they start.

The logic sounds reasonable: if they can’t sell, how can they lead a sales team? But that idea misunderstands what a real VP of Sales is actually hired to do.

In this episode, Ray breaks down why asking a VP to carry a quota creates a direct conflict of incentives, attracts the wrong candidates, and is usually a sign the company isn’t actually ready for a VP of Sales yet.

If you're a founder or CEO thinking about hiring your first VP of Sales, this episode will help you avoid a costly mistake and understand what problem you actually need to solve first.

What You’ll Learn in This Episode

• Why legitimate VP of Sales candidates won’t accept roles that require them to carry a quota

• The incentive conflict that happens when a VP is asked to sell while building a team

• How needing a quota-carrying VP is usually a signal your company isn’t ready for one yet

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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:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Most MSP leaders wildly underestimate how long it takes a new sales rep to actually produce.

On a recent coaching call with 15 MSPs, someone asked me a simple question: How long should it really take to ramp a full-cycle outside sales rep? The common answers—“six months,” “nine months,” “once they learn the product”—all miss the point.

In this episode, I break down a rule of thumb I’ve used for years: your real ramp time is 2.5–3× your average sales cycle. That ratio captures the hidden work most leaders forget—learning the company, building pipeline, and then actually running deals through your process.

If you’re hiring sales reps, planning headcount, or trying to figure out whether a new rep is actually behind—or just on a realistic timeline—this framework will change how you think about ramp time.

What You’ll Learn in This Episode

1. Why the real ramp time for a sales rep is 2.5–3× your average sales cycle
2. The three phases of ramp most companies underestimate: learning the company, building pipeline, and running deals
3. Why using a fixed ramp number like “nine months” creates bad expectations for leadership and reps

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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 started noticing something while I was shopping for hair loss pills — Hims, Keeps, Roman, all of them — and every single one had the exact same rule: you can only buy in five or six month blocks. No one-month trial, no cancel anytime. And once I figured out why, I realized it was one of the smartest business moves I'd ever seen. In this episode, I break down why most companies are optimizing for the sale when the really smart ones are optimizing for what happens after it, why short commitments are quietly destroying retention, and why the easiest growth strategy most businesses ignore is simply stopping the bleeding on churn.

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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

JP is an Army Ranger turned corporate lawyer turned Hollywood screenwriter turned cannabis operator turned branding strategist. He sold scripts to DreamWorks, Paramount, and CBS, built a dispensary from a dirt lot to $20M a year in eight months, and is a four-time Pan-American jiu-jitsu champion. He now runs Stoned Ape, a branding consultancy built around what he calls the Superhero Questions.

We got into how Hollywood's shift from original stories to sequels taught him why branding comes before marketing, why most business owners can't answer "Why should anybody choose you?", why AI is creating a sea of mediocre sameness, and why his 7 Superhero Questions pull the real story out of founders who don't even know they have one. If you've ever struggled to explain why someone should pick you over the other guy, there's a framework here.

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What You'll Learn

• Why "best product at the best price" is a feature, not a brand — and what the difference costs you

• The 7 Superhero Questions and how they're designed to pull a real brand out of any founder

• How Hollywood's shift from original stories to sequels and reboots is the single best lesson in brand ROI

• Why JP built a $20M dispensary in 8 months by answering one question nobody else was asking

• How origin stories build trust — and the specific Steve/Tacfirm example that proves it

• Why AI-generated website copy is creating a "sea of mediocre sameness" that makes businesses invisible

• The difference between proactive brand creation (Steve Jobs) and reactive focus-group branding — and why the focus group always produces the lowest common denominator

• Why JP thinks AI search actually rewards original storytelling — and the jiu-jitsu experiment that proved it

• How JP uses AI as a writing partner without surrendering point of view or creative control

• Why brand is ops — and how a shitty shopping experience negates everything your marketing promised

• What a near-death experience with open heart surgery taught JP about the gap between success and fulfillment

• Why the Wall Street Journal is running job postings for $300K storytellers — and what that signals about where business is heading

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Books & Resources Referenced

The Four Agreements by Don Miguel Ruiz — https://www.amazon.com/Four-Agreements-Practical-Personal-Freedom/dp/1878424319

Stoned Ape Theory by Terence McKenna (concept, popularized by Paul Stamets) — https://en.wikipedia.org/wiki/Stoned_ape_hypothesis

Ray's previous episode with Bob Perkins - https://www.youtube.com/watch?v=EZf-nYlwUd4

Companies Are Desperately Seeking ‘Storytellers’ (WSJ) - https://www.wsj.com/articles/companies-are-desperately-seeking-storytellers-7b79f54e

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Guest Links

JP on LinkedIn - https://www.linkedin.com/in/stonedape/