Folgen
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Elan Jones and Bradley Robinson are two of the best MSP salespeople in the country — and they work at the same company. Elan sold beer and cannabis before walking into IT sales the month the world locked down, then won MSP Salesperson of the Year. Bradley came from operations and project management, had never really sold, and became a two-time national Sales Champion finalist. Neither came from tech.
This one's a first for the show: two sellers from the same shop, eCreek IT in Denver, breaking down a sales process repeatable enough to mint champions out of totally different people. We get into selling with confidence, why price objections are usually a value problem, how they keep a discovery call conversational without abandoning the checklist, the camaraderie of a two-person sales team, and where AI actually helps versus where it's just noise. If you're an MSP owner trying to build a sales engine that doesn't depend on you, this is the playbook.
What You'll Learn
• Why most price objections are really value problems from a weak discovery call
• How to keep a discovery call conversational without abandoning the checklist
• What it actually takes for an MSP owner to replace themselves in sales
• Why drive beats credentials every time (and the camping story that proves it)
• Where AI genuinely helps in sales — and where the human-first approach still wins
Books & Resources Referenced
• Myers-Briggs Type Indicator — Elan and Bradley both tested as ENTJ despite their different backgrounds. - https://www.myersbriggs.org/my-mbti-personality-type/mbti-basics/
• Calendly (referenced as "Calum"/scheduling tool) — automated meeting reminders and follow-ups. - https://calendly.com
GEO (Generative Engine Optimization) — the emerging practice of optimizing to be recommended by AI search, discussed re: getting surfaced by ChatGPT for "IT providers in Denver."
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Art Sobczak has been selling on the phone since he was 14 — starting with tickets to the Omaha police fundraising circus. Forty-plus years later: founder of Business By Phone, author of Smart Calling (three editions), host of The Art of Sales, 1,500+ trainings — including one for my first inside sales team at the US Chamber of Commerce twenty years ago.
We get into what AI actually does for prospecting, why he'll never say "this is a cold call," the Salesperson's Oath, turning gatekeepers into allies, and the four pillars that separate salespeople who execute from those who collect training. If you or your team make outbound calls, this is the masterclass.
What You'll Learn
• Why AI is the greatest assistant — and worst replacement — salespeople have ever had
• Why personalization without relevance is just spam
• The Possible Value Proposition: the opener formula that replaces "this is a cold call"
• Why permission-based openers trigger fight-or-flight in your prospect's brain
• The Salesperson's Oath: first, create no resistance
• The social engineering approach that turns gatekeepers into allies who prep your prospect before you call
• "If the music is still playing, stay on the dance floor" — why rushing to book the meeting kills live conversations
• The four pillars of top performers — and why identity beats discipline (Be-Do-Have, shades of Atomic Habits)
• The backwards math: why 6-8 meetings a month might take 8 dream prospects and a handwritten note, not 14,000 dials
▸ Get My Free MSP Sales Toolbox: https://msp.sale/yt-toolbox
▸ Join My Newsletter for Weekly Sales Strategies: https://rayjgreen.beehiiv.com
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Books & Resources Referenced
• Smart Calling: Eliminate the Fear, Failure, and Rejection from Cold Calling (3rd Edition) by Art Sobczak - https://www.amazon.com/Smart-Calling-Eliminate-Failure-Rejection/dp/111967672X
• How to Get a Meeting with Anyone by Stu Heinecke - https://www.amazon.com/s?k=how+to+get+a+meeting+with+anyone+stu+heinecke
• Get the Meeting!: An Illustrative Contact Marketing Playbook by Stu Heinecke - https://www.amazon.com/Get-Meeting-Illustrative-Marketing-Playbook/dp/1948836440
• Atomic Habits by James Clear - https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299
• Art's First 20 Seconds Formula masterclass — smartcalling.com
• The Smart Calling Report newsletter — via smartcalling.com
• The Art of Sales podcast — theartofsales.com
• Dale Dupree Podcast Episode - https://www.youtube.com/watch?v=DotK-CSfWOI
• Chris Walker Podcast Episode - https://www.youtube.com/watch?v=2o5mLPdJp2E
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Fehlende Folgen?
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▸ Slides + every prompt from this talk (free): mspsalestoolbox.com
▸ Work with us: mspsalespartners.com
AI has changed how companies prospect, research, and communicate, but many of the world's largest technology companies continue investing heavily in human sales teams. This episode explores what AI can automate, what it still struggles to do, and why trust, judgment, and complex buying decisions continue to require skilled people.
What You’ll Learn in This EpisodeWhy automation hasn't eliminated the need for human sales conversationsWhich parts of the sales process AI handles well—and which parts it doesn'tWhat the hiring decisions of major technology companies suggest about the future of sales//
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 high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates that are 68% — a the lowest rate — and why consistency in process matters more than most sales teams realize.
What You’ll Learn in This EpisodeThe qualification mistake that causes many MSPs to leave deals on the tableWhy strong discovery creates higher close rates later in the processThe structure top performers use instead of overwhelming prospects with proposals and quotes//
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 lot of people feel stuck because they think they need more information, another strategy, or outside guidance. But often, the real problem is execution avoidance. This episode explores the growing gap between the things we know we should do and the things we actually complete — and how that gap quietly impacts business growth, health, relationships, and momentum.
What You’ll Learn in This EpisodeWhy most people already know the decisions that would improve their livesThe hidden psychological cost of carrying an unfinished “should list”How scheduling difficult tasks shifts the brain into execution mode//
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
-
When difficult decisions start showing up everywhere at once — business, marriage, parenting, finances, health — it’s easy to assume life is breaking down. But often, those seasons are actually periods of transition and recalibration. In this episode, Ray explains why hard conversations and uncomfortable decisions are usually the entry point to meaningful progress, and how avoidance quietly creates long-term dissatisfaction.
What You’ll Learn in This EpisodeWhy periods of intense pressure often happen right before major growthThe hidden long-term cost of avoiding uncomfortable decisionsHow to reframe difficult seasons as leverage points instead of warning signs//
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 high close rate is rarely the result of charisma or talent alone. When Ray reviewed the top finalists for MSP Salesperson of the Year, a clear pattern emerged: the best performers were all running nearly the same sales process. This episode breaks down the exact five-step framework behind close rates as high as 76% — and why consistency in process matters more than most sales teams realize.
What You’ll Learn in This EpisodeThe qualification mistake that causes many MSPs to leave deals on the tableWhy strong discovery creates higher close rates later in the processThe structure top performers use instead of overwhelming prospects with proposals and quotes//
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
-
Dale Dupree sold copiers for 13 years and outsold his industry average by 11x — using a crumpled piece of paper instead of a thousand cold calls. After losing his father to cancer, he founded The Sales Rebellion.
We got into why he thinks AI is making sales worse, how 20 letters outperformed a 4-person SDR team, why he'd hire a grocery bagger over a polished resume, and what servant leadership looks like when nobody's watching.
What You'll Learn
Why a crumpled letter consistently outperforms thousands of cold emailsHow an Australian SDR booked 12 meetings with 20 letters — and got written up for itThe one interview question Dale uses to identify coachable hiresWhy the SDR model fundamentally breaks relationship-first sellingWhat Dale's father taught him about leadership at 5 AM without knowing anyone was watchingResources
thesalesrebellion.comDale on LinkedIn: linkedin.com/in/copierwarrior//
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 lot of operators think the problem is execution when the real problem is unnecessary infrastructure. This episode explores the hidden cost of building custom tools, AI agents, and internal systems before questioning whether they should exist in the first place. Ray breaks down why complexity compounds faster than most businesses can support — and why disciplined simplicity is becoming a competitive advantage.
What You’ll Learn in This EpisodeWhy every new internal tool creates long-term maintenance obligationsThe “decision above the decision” most builders skip entirelyHow strong operators solve problems by reducing complexity instead of adding infrastructure//
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 salespeople think desperation only shows up in obvious pressure tactics. In reality, prospects feel it long before the close. This episode breaks down how fear, pipeline pressure, and personal financial stress quietly change the way sellers communicate — and why those shifts destroy trust even when the offer itself is strong.
What You’ll Learn in This EpisodeThe subtle behavioral changes prospects interpret as desperationWhy “checking in” follow-ups often communicate self-interest instead of valueHow to return to a calm, solution-oriented sales process during a slump//
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 lot of MSP owners think they’re making “safe” hiring decisions when they delay or minimize sales investment. But many of those decisions are actually driven by a hidden assumption: that sales won’t materially change the business. This episode examines how defensive thinking creates growth ceilings, why underfunded sales hires often fail by design, and how strong MSPs use sales to expand the size of the business instead of protecting the size of the budget.
What You’ll Learn in This EpisodeWhy hiring sales based only on today’s budget creates long-term stagnationHow “safe” decisions quietly reduce the odds of sales successThe difference between businesses that protect revenue and businesses that create 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
-
When marketing underperforms, the instinct is to change tactics, channels, or people. But if execution is weak, those changes don’t stick—they just create more noise. This episode reframes what looks like a marketing problem into something more fundamental: your ability to consistently turn decisions into outcomes.
What You’ll Learn in This Episode
Why fixing marketing rarely works if execution is inconsistentHow weak execution shows up as “department problems” across the businessWhat changes when execution becomes the standard instead of the exceptionFollow Ray on:
YouTube | LinkedIn | Facebook | Twitter | Instagram
//
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
-
When results drop, it’s easy to point to the market, the economy, or “how things are right now.” But that explanation comes at a cost—it shifts you out of control and into reaction. This episode examines what changes the moment you accept that narrative, and why some sellers in the exact same conditions continue to close. The issue isn’t just performance—it’s what you’ve started to believe about it.
What You’ll Learn in This Episode
How accepting external explanations quietly removes your ability to solve the problemWhy two sellers in the same conditions produce completely different outcomesWhat shifts internally before results ever show up in your pipelineFollow Ray on:
YouTube | LinkedIn | Facebook | Twitter | Instagram
//
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
-
You’re trying to build a positive culture—but performance keeps slipping, and no one is saying what needs to be said. This episode breaks down why “niceness” often replaces truth inside teams, and how that tradeoff quietly drives poor decisions and repeated losses. If your team feels good but isn’t getting better, this is the tension you’re in.
What You’ll Learn in This Episode:
Why teams default to agreement even when they know something is wrongHow avoiding conflict directly impacts execution and resultsThe hidden cost of protecting feelings over telling the truthFollow Ray on:
YouTube | LinkedIn | Facebook | Twitter | Instagram
//
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 people think sales is a role. It’s not—it’s a constant condition. This episode reframes sales as the ability to navigate other people’s motivations under real constraints, using a story that exposes how decisions actually get made in everyday life.
What You’ll Learn in This Episode:
Why “I’m not in sales” is a costly assumptionHow decisions are shaped by context, emotion, and timing—not logic aloneWhat changes when you start seeing alignment instead of persuasion//
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 PayPal's early days, customers were so pissed off about service issues that they tracked down direct lines to employees and called headquarters to yell at them. Leadership's response wasn't to fix customer service. They ripped the phones out of the wall. In this episode, Ray breaks down the Reid Hoffman story behind one of the most underrated disciplines in business: figuring out which fires to let burn. PayPal's leadership knew growth determined funding, and funding was oxygen — so they let the customer service fire rage while they stepped on the gas. Most operators can't make that call because they want to hedge, and hedging means running out of water trying to put out the wrong fire. This is for founders and operators who have more problems than resources, which is to say — all of them.
What You'll Learn in This Episode:
Why the loudest problem is almost never the right one to solve — and how PayPal identified funding as the real constraint while everything else was on fireThe triage mindset that separates operators who scale from operators who stall — and why hedging is the default trapWhat it actually takes to let a fire burn when customers are screaming and your own team is telling you it's bullshit//
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 people run Elon's algorithm in reverse. They automate first, simplify second, and never question whether the process should exist at all. In this episode, Ray breaks down the 5-step algorithm Musk developed the hard way at SpaceX and Tesla — question every requirement, delete, simplify, accelerate, automate — and why the order matters more than the steps themselves. If you're tech-friendly or systems-minded, you're probably guilty of this: falling in love with the machine instead of the output. The sin isn't skipping steps. It's running them backwards, which is how you end up with bloated automations built on processes that shouldn't exist in the first place.
What You'll Learn in This Episode:
Why automating first locks in the wrong process — and Musk's rule that if you're not adding back 10% of what you deleted, you haven't deleted enoughHow smart people create invisible requirements nobody challenges — and why Step 1 is questioning the rules themselvesWhy tech and systems-minded operators fall in love with the machine instead of the output — and how to reverse itElon Musk explains his 5-step algorithm for running companies
https://youtu.be/tdf3luOCNks?si=WGPPvOsJmW99btKk
An Ultimate Guide to Elon Musk's Algorithm
https://geekway.substack.com/p/an-ultimate-guide-to-elon-musks-algorithm
//
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
-
Michael Jordan earned about $90 million from his entire NBA career. Last year alone, he made $300 million — almost all of it from Nike, because of one clause his mom pushed for before he ever played a pro game: a 25% royalty on any shoe sold with his likeness. In this episode, Ray breaks down three decisions that dwarfed entire careers — Jordan's royalty, Bill Gates' non-exclusive license on QDOS that built Microsoft, and George Lucas trading $500K of his directing fee for Star Wars merchandising rights. The pattern isn't luck. These decisions never announce themselves as the big one — and most founders miss them because they're too buried in small stuff to notice.
What You'll Learn in This Episode:
How Jordan's mom turned a $2.5M shoe deal into a multi-billion dollar empire — and the one-line carve-out Bill Gates used to build MicrosoftWhy decision fatigue on small stuff is costing you the decisions that actually move the needleHow to create the headspace required to recognize high-leverage moments when they show up//
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
-
"Wait until you're at $3-5M before hiring an SDR" — Ray heard this from an attendee at a Dallas event who'd been given the rule by an EOS-type advisor. His problem with it: that rule treats the SDR as an expense you need to afford, not a revenue multiplier that helps you generate the money in the first place. "I can't afford to make more money until I've made a certain amount of money" doesn't hold up. At MSP Sales Partners, Ray's first two hires were SDRs — because when you're starting a business and need to drive demand, you hire the person who creates revenue, not wait until revenue shows up on its own.
The bigger lesson goes beyond SDRs. Business isn't paint-by-numbers, and most "rules" are just someone projecting their personal experience onto every business. Whether to hire — and when — depends on your demand, your constraints, and what role actually multiplies output at your stage.
What You'll Learn in This Episode:
Why the $3-5M SDR rule treats a revenue multiplier like a fixed expense — and why that logic breaks downHow Ray's first two hires at MSP Sales Partners were SDRs, and what he learned when organic demand changed the equationWhy most business "rules" are overgeneralizations built on one person's experienceThe real question to ask before hiring an SDR: what's the core constraint in your business right now?//
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
-
One of our Fractional SDR Management customers — an MSP owner — came to Ray with a show rate hovering just above 40%. The appointments were coming in, but half of them weren't showing up. Ray walked him through the exact diagnosis: go back and listen to the calls, figure out if the bookings are soft commitments or locked-in appointments, and then implement a 5-step pre-call process that covers everything from value-driven confirmation emails to same-day no-show recovery. The part most people miss? Garbage appointments don't just waste time — they push your real prospects further out on the calendar, and more time between booking and meeting always means a lower show rate.
If you're running SDRs or BDRs and your show rate is below 60%, this episode walks through exactly where to look and what to fix.
What You'll Learn in This Episode:
Why a low show rate is almost always a booking quality problem before it's a follow-up problemHow "garbage" appointments silently destroy close rates on your good prospectsThe 5-step pre-call process Ray walks every Fractional SDR Management client throughWhy a value-driven confirmation email outperforms a standard calendar inviteThe no-show recovery window — and why speed matters more than the script//
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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