The Ray J. Green Show

I was on a coaching call with people selling IT services, and someone had an opportunity to dig deeper into what the prospect said. Another person suggested, "We could have asked 'Why is that important to you?'" The response? "I thought we weren't supposed to ask 'why' questions. It's what I heard from Chris Voss." Look, I love Chris Voss—phenomenal hostage negotiator, great book (Never Split the Difference)—and I fundamentally agree with most of what he says. He's right that "why" questions can make people defensive because we're trained from childhood that "Why did you do that?" means we're being accused of something. But here's my slightly different perspective: Chris comes from negotiating with terrorists and hostages—there's inherent conflict between the two parties. That's not consultative sales. Your prospect's money isn't being held hostage. This episode breaks down why the advice gets implemented too broadly without understanding the context. If you ask with curiosity—"Interesting, I haven't seen that before... why do you guys do it that way?"—versus accusation—"Well... what's the purpose of that?"—your tonality changes everything. I hereby give you permission to use "why" at the beginning of questions, so long as you deliver it with curiosity and not accusation. Don't overthink it. Use it strategically.//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//Follow Ray on:YouTube | LinkedIn | Facebook | Twitter | Instagram

If you're nervous when you fire up the camera, I'm going to share a piece of advice Dan Martell gave me three years ago that I absolutely did not want to hear: go live for 30 days in a row. I was terrified of video—I could write great scripts, set up the tech perfectly, get the lighting and mic just right, then hit record and completely blank. Stage fright. So when Dan told me to go live with no retakes, no edits, where if I look dumb I'm stuck with it? That was the LAST thing I wanted. But I did it anyway. And I credit that exercise for paving the way for the hundreds of videos I've created since—YouTube every week for two and a half years, LinkedIn, Instagram, webinars, VSLs, you name it. This episode breaks down why it works: (1) it eliminates excuses and procrastination—I couldn't waste time buying new lights or tweaking camera angles, I had to go live by end of day even if it was just my iPhone, (2) it's forced exposure therapy that builds tolerance to your fear, and (3) it compresses learning—30 videos in 30 days versus taking 60 weeks to publish 30 videos spreads that learning over a year. I was surprised how supportive people were, and I even got a client from it. But don't expect applause or followers—the real ROI is internal. Your only goal is to finish. Fire up a live right now, announce you're doing 30 days, and that's your first video done.//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//Follow Ray on:YouTube | LinkedIn | Facebook | Twitter | Instagram

This is probably the most unfiltered view I've posted since changing this podcast format. I saw a LinkedIn post with the hook: "My wife died at 39. Her doctors never tested the one thing that could have saved her." I started reading—retired pharmacist, tired of Western medicine, quotes, problems—and thought "this smells like a sales letter." I scroll to the bottom and there's a CTA: "Leave a note of 'Energy' below and I'll send you the clinical research." Are you fucking kidding me? Did we really just leverage someone's spouse dying as a hand-raiser post to generate leads? This made me both frustrated and nervous. This episode breaks down three critical principles: (1) Why principles matter more than tactics—understanding WHY that hook works lets you adapt it without being disgusting, rather than just copy-pasting cringeworthy garbage, (2) Trust your intuition—if something feels cringeworthy, that's a warning sign (not always a limiting belief to push through), and (3) The digital marketing landscape is changing drastically—AI makes it too easy to create fake testimonials and look real for a few grand, which means more scammers and harder differentiation. Learn why I'm shifting away from traditional online marketing playbooks toward creating authentic content that gives me energy, why following everyone else means you're using a playbook from three years ago, and how to bob when they weave instead of racing to the bottom with 72-month guarantees for 99 cents.//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//Follow Ray on:YouTube | LinkedIn | Facebook | Twitter | Instagram

One benefit of getting older? You see patterns over a longer horizon. And here's one I keep seeing in sales and marketing: people proclaiming channels are dead. Cold calling is dead—nobody answers their phone. Webinars don't work. Cold email is ruined by spam filters. LinkedIn organic content doesn't work. Canvassing is impossible. DM selling has been destroyed by automation. I've heard every single one of these channels proclaimed dead—sometimes by people I actually respect who used to crush it in that channel, then didn't evolve with it, and now their message is "it doesn't work." Here's what I know from seeing inside 500 MSPs last year: when we do attribution exercises on closed deals, every single fucking one of those "dead" channels is represented. Which means they DO work. The question isn't "does it work?" It's "do you know how to make it work?" This episode breaks down why the biggest mistake is looking for a channel that works instead of picking one and committing to making it work. Learn the cycle every channel goes through (hard learning curve → figure it out → generate results → shit changes → adapt), why that cycle is actually good because if it was easy everyone would do it, and why harder channels give you longer reward cycles. Stop saying "this doesn't work" and start saying "I don't know how to make this work yet." The reframe matters. I saw someone post "cold calling's dead" on LinkedIn and thought "God, here we go again." So that's my drop for today.//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//Follow Ray on:YouTube | LinkedIn | Facebook | Twitter | Instagram

This may be one of the most important podcasts I record for you. I'm sharing my system for taking control of my calendar—and I say most important because time is your most valuable asset. When you master how to manage it, it affects everything: your business, your family time, your health. This year alone, I started MSP Sales Partners from zero to $800K, added five full-time hires and 50+ customers, created content every week without missing a newsletter or YouTube video, had dinner with my kids almost every night, traveled for two and a half months over summer, took a fully-unplugged family trip to Spain and France, and managed 90 minutes to two hours of exercise seven days a week. I attribute ruthless time management to being able to do all of that. This episode breaks down my system: shift from reactive to proactive calendar management—stop playing defense and go on offense by designing "The Perfect Week" where you map out your ideal calendar with everything that matters (prospecting time, team meetings, exercise, kids' dinners, date nights), then lock those blocks in as busy so nobody can steal them back. Every Sunday, audit how the week went versus your perfect week, identify what's off and why, then fix it for the upcoming week. I also do quarterly off-site planning to identify the major business constraint and update my perfect week accordingly. Learn how to have the hard conversations to protect your time, why managing up and down requires showing people what's in it for them, and how this prevents the slow creep back to homeostasis where your calendar gets stolen again.//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//Follow Ray on:YouTube | LinkedIn | Facebook | Twitter | Instagram