▸ 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.

//

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

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

//

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 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

//

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.

//

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.

-----------------------------------------------------------

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

-----------------------------------------------------------

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

-----------------------------------------------------------

Guest Links

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

I've been listening to a lot of sales coaching calls this week, and I keep hearing the same blind spot from managers over and over again. There are two distinct things you have to address when you're coaching someone — the person and the process — and most coaches are only doing one. In this episode, I break down why the process-only coach runs an informational boot camp that nobody acts on, and why the people-only coach just gets their team fired up to execute the wrong things with maximum enthusiasm. The real skill isn't just knowing both levers — it's knowing which one to pull with the right person at the right moment.

//

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 came across a clip of Alex Hormozi responding to a roofer at one of his workshops — a guy doing $6 million a year who wants to get to $100 million without losing time with his family — and what Alex said applies to basically every business owner I know. In this episode, I break down why wanting it all isn't a hard formula, it's a losing one. Aggressive growth, fat margins, and maximum family time are all worthy goals, but each one has a real cost, and those costs compete with each other. Most people refuse to pick, and that's exactly why they feel stuck, guilty, and frustrated all the time. There are two paths out, and I want to walk you through both of them.

//

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 was coaching an MSP seller recently, and she kept asking me the same question — when I hear a problem, why wouldn't I just address it right then? It's a fair instinct, but it's also exactly what's killing deals. In this episode, I use a trial lawyer analogy to explain why the best sellers treat discovery like cross-examination — pulling information, staying patient, and never mixing the case-building with the closing argument. If you're pitching solutions mid-discovery, you're leaving facts on the table and signaling that you're there to sell, not to understand. Discovery is where you build the case. Closing is where you present it.

//

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 been parting ways with service providers left and right lately, and it all comes down to the same thing — AI slop. In this episode, I break down why the vendors using AI to do the same old work faster are actually accelerating their own irrelevance, and I use a simple analogy to explain it: the hay delivery guy who got a Model T and thought he was winning. There's a fork in the road right now for every knowledge worker, and most people are picking the wrong path without even realizing it. I want to talk about what separates the people who will thrive from the ones who won't see it coming.

//

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

Chris Walker built Refine Labs from $3,000 in the bank and $65K in debt to $22 million in revenue in roughly three years — 100+ employees, 350 software company clients, and arguably the most influential voice in B2B marketing. He created the "dark social" movement, redefined how an entire generation of marketers thinks about MQLs, and built a massive audience doing it. Then he walked away. Because the peak of the business was also the lowest point of his life.

In this conversation, we get into what actually broke at the top, why changing your environment doesn't fix what's underneath, and what Chris means when he talks about "frequency" — stripped of the spiritual language and grounded in the engineer's brain he actually has. We debate whether you have to grind before you can transcend it, why limiting beliefs feel like facts, and why he thinks training your frequency will be as common as going to the gym within five years.

We also go deep on extractive vs. regenerative systems — in business, content, social media, and relationships — and why the intention underneath your actions matters more than the actions themselves.

I've been using Chris's ENCODED program for five months. I came in skeptical. I still have questions. But I can't deny what shifted. This one's worth your time whether you buy the concept or not.

WHAT YOU'LL LEARN

• Why building a $22M company was one of the worst periods of Chris's life — and what that reveals about external vs. internal success
• What "frequency" actually means as identity + beliefs + intentions, without the spiritual language
• Why changing your job, city, or business doesn't work if you don't change the foundation underneath it
• The difference between extractive and regenerative systems — in business, relationships, and how you show up as a leader
• Why limiting beliefs feel like facts, and how to spot the invisible ceiling you didn't know you built
• How the intention underneath your actions — in content, business, and life — determines the results you get
• Why Chris thinks frequency training will be as mainstream as going to the gym within 3–5 years

BOOKS & RESOURCES REFERENCED

Shoe Dog by Phil Knight — https://a.co/d/05UhJN4T ENCODED Frequency Map — https://www.encoded.ai/ We Are Encoded Podcast — https://open.spotify.com/show/5eEzaXy4hUSqlvzD9ROqrz