Podcasts about mid market

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Best podcasts about mid market

Latest podcast episodes about mid market

Repeatable Revenue
Chris Voss is Wrong About 'Why' Questions (And Here's Why)

Repeatable Revenue

Play Episode Listen Later Jan 1, 2026 7:54 Transcription Available


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

Repeatable Revenue
Scared of Video? Go Live for 30 Days Straight. Here's Why

Repeatable Revenue

Play Episode Listen Later Dec 31, 2025 10:00 Transcription Available


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

Repeatable Revenue
AI, Fake Gurus, and What I'll Never Do

Repeatable Revenue

Play Episode Listen Later Dec 30, 2025 15:09 Transcription Available


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

Repeatable Revenue
The Real Reason Your Marketing Channel Isn't Working (It's Not Dead)

Repeatable Revenue

Play Episode Listen Later Dec 29, 2025 8:42 Transcription Available


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

Repeatable Revenue
The Calendar System for Scaling Businesses and Taking 2-Month Vacations

Repeatable Revenue

Play Episode Listen Later Dec 27, 2025 16:59 Transcription Available


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

Repeatable Revenue
AI Is Making Your Team Stupid

Repeatable Revenue

Play Episode Listen Later Dec 26, 2025 14:34 Transcription Available


Is your team outsourcing their thinking to ChatGPT? In this video, I break down why relying on AI for answers is leading to "thought atrophy" and killing expertise in the workplace. While AI is an incredible tool for efficiency, it cannot replace the nuance, context, and experience that I hire my team for.I share the story of a recent project where an AI-generated response missed the mark, and I outline the 4 New AI Guidelines I've implemented to ensure we use technology to amplify our intelligence—not replace it.//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

Repeatable Revenue
The Bezos Lesson: Enough Good Ideas to Kill Your Company

Repeatable Revenue

Play Episode Listen Later Dec 25, 2025 12:08 Transcription Available


I used to be an idea gangster with my team—I'd do drive-bys every single week. I'd read a book, get super excited about the takeaways, and come in firing: "All right team, let's execute!" They were genuinely good ideas. But we never got enough traction with any of them before I'd pop in with the next one. My COO finally leveled with me: "Dude, we gotta stop. People are exhausted. We're not doing great work. That great idea eight ideas ago? We still never saw it produce fruit, and we're on to seven more since then." Here's what I learned: every new idea has an exponential curve—it's really hard on the front end, but weeks or months later is when the curve bends and the really good shit happens. We never gave anything time to get there. Then I came across this clip of Jeff Bezos explaining it perfectly: his VP of operations told him "You have enough ideas per minute to destroy Amazon. You have to release work at the rate the organization can accept it. Every idea you release creates a backlog that adds no value—it creates distraction." This episode breaks down why good ideas can fuel your company or kill it, how I created systems (an idea bank, a dedicated filter person) to stop injecting my ADHD into the business, and why I fired a fractional client this year because we couldn't execute through their constant idea churn. Your ideas are either an asset or a liability—which one are they?//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

Repeatable Revenue
I Forgot My Car Today (And Why That Makes Me Better at Business)

Repeatable Revenue

Play Episode Listen Later Dec 24, 2025 13:55 Transcription Available


True story: I forgot my car in a parking lot today. Made it all the way home. My wife asked "where's the jeep?" and my first thought was "oh shit, did someone steal it?" This isn't the first time I've forgotten a car. I have ADHD and level one autism, which means I get wildly obsessed with things I care about—it's why I learn things so quickly and see patterns in complex systems—but I also completely forget shit that's not in my focus. I've flown to the wrong cities, forgotten to eat all day, and yes, forgotten multiple cars. Extreme weaknesses always come with extreme strengths. I'm really good at systematizing complex sales models and building businesses, but I can't remember to take out the trash. This episode shares what I've learned at 45 after years of beating myself up trying to "fix" it: accepting it instead of fighting it, stopping the guilt, not trusting my memory (I tie hoodies around my waist as reminders), thinking in teams where people offset my weaknesses, and using tactics like walking, fidget toys, and no-device Sundays. I don't have this figured out—I just forgot a car—but I've created an environment where my business thrives, my marriage thrives, and I can focus on my superpowers. Sharing this in case it helps you too.//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

Repeatable Revenue
Why My Teams Don't Miss Targets

Repeatable Revenue

Play Episode Listen Later Dec 23, 2025 12:39 Transcription Available


I just wrapped a full day of calls with 75 MSP business owners about goal setting, and I heard all the mistakes I've made myself over 20+ years—from leading eight sales turnarounds to turning around a 40-year-old PE-backed company to its highest revenue ever. The most common mistakes? Inaccurate goals where the math doesn't map. Unrealistic goals that look good in December but are dead by March. Setting them too high so your team quietly thinks "that's never happening," or too low creating a complacent half-ass culture. Or worst of all—not setting goals at all. Here's why I'm passionate about this: the right goals manage for you, change behavior, and help people make decisions when you're not around. But bad goals make terrible people look good and great people look bad, which ruins your culture. This episode breaks down why I don't believe in "shoot for the moon, hit the stars"—that just means you're constantly missing and creating a losing culture. Learn why starting small and building a winning habit matters more than big aspirational numbers, why your goals need integrity (not pencil marks that change when you're behind), and how to rebuild momentum with bite-sized wins instead of resetting the whole target.//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

Repeatable Revenue
The Simple System That Manages Your Sales Team for You

Repeatable Revenue

Play Episode Listen Later Dec 22, 2025 10:39 Transcription Available


A friend who does M&A for MSPs asked me: if you've got a team of five hunters, what's a good hiring and firing process that keeps top performers, pushes average reps, and weeds out the bottom? Here's my answer—and it's all about having a system that manages for you. The best approach consists of two parts: First, separate your minimum standards from actual goals. Your goal might be $24K/month where commission incentives kick in, but your minimum standard is $18K—the threshold below which the business economics don't work. Top performers never notice this number. Average performers are aware of it but rarely dip below. Bottom performers struggle to hit it consistently. Second, create a clearly documented escalation policy: miss the minimum once, it's a discussion; twice in three months, written warning; three times in five months, termination. This episode breaks down why you want a standard that top performers never notice, average performers can maintain, and bottom performers systematically get rooted out—without you having to crack the activity whip every day. Learn how to adjust this for different sales cycles (like using 90-day rolling averages for MSPs), why average is actually good and you don't want high churn, and how the right system diminishes your need to micromanage while keeping the team steady and high-performing.//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

Repeatable Revenue
Scale the Unscalable: My $50K Lesson from Hormozi's Team

Repeatable Revenue

Play Episode Listen Later Dec 21, 2025 15:49 Transcription Available


I spent two years scaling the wrong business and one conversation with Alex Hormozi's Chief Strategy Officer reframed everything. Here's what happened: I'd built a consulting business to $50K/month doing sales audits and fractional management, but I thought "this isn't scalable." So I pivoted—created courses, built a community, started teaching people how to turn expertise into income. I ended up in a sea of competition selling to the wrong audience at the wrong price point. His CSO said: "Dude, you solved the wrong problem. The problem wasn't 'this isn't scalable.' The problem was 'you didn't know how to scale it yet.'" He showed me around their 20,000 square foot building with 400 people and said, "We don't use the word 'scalable' here. Some things are just way harder to scale than others. That's why Alex and Leila own 50 companies." This episode breaks down what happened next: I killed the community, threw the courses on YouTube, and said "I don't teach this shit, I do this shit." We launched MSP Sales Partners doing fractional sales management—the thing I was actually great at—and spent a year refining the product before stepping on the gas. Learn why I'm intentionally running net neutral right now to build a moat nobody else will, why being picky with hiring and delaying profits creates competitive advantage, and how that subtle twist of words—"you didn't know how to scale it" versus "it isn't scalable"—changes everything.//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

Repeatable Revenue
How to Shrink a Price Objection to Almost Nothing

Repeatable Revenue

Play Episode Listen Later Dec 20, 2025 7:12 Transcription Available


I was on a coaching call yesterday with a bunch of people selling IT services, and the question came up: how do you handle price objections? When somebody says "that's expensive" or "more than we're paying now" or "higher than other bids," what do you do? I've got a really simple framework that works across any competitive selling situation—IT services, professional services, whatever. Here's how it works: First, ask "What makes you say that?" to understand if this is a negotiation tactic, a stall, or a real gap. Then clarify what it's relative to—get them to tell you the actual number they're comparing against. Here's the key move: minimize the amount psychologically. If you quoted $60K and they're at $42K, stop talking about $60K—now you're negotiating the $18K gap. Then slice it even smaller: "So we're $1,500 a month apart, or about 50 bucks a day for compliance?" That sounds way better than a $60K contract. Finally, isolate it: "If we can bridge that gap, are you ready to go ahead?" This episode breaks down the psychology of reframing price conversations so you're not defending your number—you're making the gap feel manageable relative to the benefits they want. Works across industries once you understand what we're actually doing here.//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

Repeatable Revenue
Your Defensive Employee Is Either An Asset Or A Liability

Repeatable Revenue

Play Episode Listen Later Dec 19, 2025 9:06 Transcription Available


Ray Green answers a thought-provoking question from a friend: Is there a real difference between "play to win" and "play to not lose" people, and can you build an entire team of aggressive risk-takers? In this episode, Ray breaks down why he believes there are two distinct types of "play to not lose" people - Type 1 who are well-intentioned and think through proper risk mitigation, and Type 2 who operate from fear and lack of confidence. He explains why Type 1 people are actually assets who balance out aggressive play-to-win leaders, while Type 2 people are toxic liabilities that drain your organization. Ray shares a personal story from his first CEO role about constantly fighting with his co-founder, who drove him crazy but ultimately made him a better leader by having the confidence to speak truth to power. This is about understanding the balance you need on your team, knowing the difference between healthy defensive thinking and toxic negativity, and why you don't want a team of only one type of person.//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

Repeatable Revenue
I Built a 7-Figure Stream with a Six-Pack and a Spreadsheet

Repeatable Revenue

Play Episode Listen Later Dec 18, 2025 11:30 Transcription Available


Physics defines work as force times distance times alignment. In sales, that's effort times results times whether those results actually get you what you want. I saw a junior SDR post on LinkedIn saying "sales training is a joke—just dial your face off." He's one-third right. Volume matters. But here's what gets lost: you drive to work every day, doesn't make you a Formula One racer. It's intentional volume that matters. Josh Braun responded with something so well-written I had to share it: "Drop someone in a pool with no training and they'll kick really hard, flail harder, and burn out in 20 seconds. Put them with a coach who adjusts their breathing, reach, and timing, and suddenly they move further, faster, with less effort. Top reps don't just make more calls—they make better calls." I'll share my own riptide story from last summer: I got caught surfing with my kids, swam as hard as I could, made zero progress—actually went backwards. Two surfers pulled me sideways along the shore to escape it. I could have swam all day and never made it. That's alignment. This episode breaks down why volume reveals your gaps but technique closes them, why I've wasted $30K on useless sales training but still believe in the right coaching, and why physics would say if you're booking appointments that don't convert, no work has actually been 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

Stikeman Elliott Podcast
Episode 150 - Trends in Midmarket M&A Cybersecurity Diligence

Stikeman Elliott Podcast

Play Episode Listen Later Dec 18, 2025 22:02


In the 150th episode of Views from the Market, Ira Goldstein joins Mario Nigro to discuss the evolving role of cybersecurity in midmarket M&A. As he explains, cybersecurity diligence has become a key part of deal-making, driven by the ever-increasing value of data in many business sectors. He stresses the value of hands-on technical assessments – rather than check-the-box exercises – for many organizations, as well as the importance of proactive controls and the challenges smaller firms face in allocating resources for cybersecurity. Looking ahead, Goldstein predicts increased use of AI-driven tools for risk assessment as cybersecurity awareness continues to grow.

Repeatable Revenue
Sales Physics: Why Your Effort Isn't Turning Into Wins

Repeatable Revenue

Play Episode Listen Later Dec 17, 2025 8:11 Transcription Available


Physics defines work as force times distance times alignment. In sales, that's effort times results times whether those results actually get you what you want. I saw a junior SDR post on LinkedIn saying "sales training is a joke—just dial your face off." He's one-third right. Volume matters. But here's what gets lost: you drive to work every day, doesn't make you a Formula One racer. It's intentional volume that matters. Josh Braun responded with something so well-written I had to share it: "Drop someone in a pool with no training and they'll kick really hard, flail harder, and burn out in 20 seconds. Put them with a coach who adjusts their breathing, reach, and timing, and suddenly they move further, faster, with less effort. Top reps don't just make more calls—they make better calls." I'll share my own riptide story from last summer: I got caught surfing with my kids, swam as hard as I could, made zero progress—actually went backwards. Two surfers pulled me sideways along the shore to escape it. I could have swam all day and never made it. That's alignment. This episode breaks down why volume reveals your gaps but technique closes them, why I've wasted $30K on useless sales training but still believe in the right coaching, and why physics would say if you're booking appointments that don't convert, no work has actually been 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

Repeatable Revenue
The Six-Week Project I Killed in One Day

Repeatable Revenue

Play Episode Listen Later Dec 15, 2025 19:47 Transcription Available


We just spent six weeks migrating our email newsletter from Beehiiv to Substack. Within one day of going live, I realized I'd made a mistake and had to course-correct. This episode opens up what happened, why it was a mistake, and more importantly—the framework for deciding when to pivot versus when to persevere. Because I've always struggled with this: am I being frantic and erratic by changing course? Or am I being stubborn and falling into sunk cost fallacy by staying? Here's what went wrong: Day One on Substack, I realized the audience is mostly creators writing for other creators, the growth engine requires building another Twitter-like feed (the exact treadmill email newsletters were supposed to solve), and I risked diluting my most valuable asset—my list—with the wrong audience while having no analytics to detect it. I break down the exact questions I ask myself at these decision points: What core problem was I solving? Why was it really a problem? Does this actually solve the underlying issue? What will make me regret this in six months? The lesson: perpetual pivots destroy progress, but stubborn perseverance does too. Learn how to course-correct strategically instead of emotionally, and be aware of your own tendencies—I tend to pivot too quickly, maybe you stick too long.//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

Repeatable Revenue
Why Your Outbound Needs a Vertical (Not a Rebrand)

Repeatable Revenue

Play Episode Listen Later Dec 13, 2025 7:11 Transcription Available


"Should I niche down in my prospecting to a vertical or an industry?" That question came up on an office hours call yesterday with a bunch of MSP business owners. Here's what I told them based on managing 50 different IT companies in our fractional sales program and listening to thousands of prospecting calls: Yes, you should absolutely niche down—but you don't have to rebrand your entire company to do it. Most people think going vertical means becoming "the law firm IT company" and changing everything. That's wrong. You niche at the campaign level, not the company level. This episode breaks down how to compartmentalize your outbound: build a law firm-specific list, create landing pages with their language and acronyms, develop messaging that speaks to their specific IT fears and problems—all without touching your homepage or inbound script. The benefits are massive: your scripting has immediate relevance, you stand out from the 100 other calls they're getting, and you can feed patterns back into your campaigns through AI analysis of recorded calls. Learn why law firms have different IT concerns than manufacturing companies, how to stack verticals over time without getting diluted, and why this approach lets you leverage specialization into better specialization once the flywheel starts moving//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

Repeatable Revenue
Physics Explains Why Hustle Culture Fails

Repeatable Revenue

Play Episode Listen Later Dec 12, 2025 13:39 Transcription Available


Ray Green breaks down why both hustle culture and the "deep work only" mindset miss the mark, using a simple physics formula to explain what real work actually is. The equation? Force times Distance times Alignment. In this episode, Ray explains why effort alone doesn't equal results, why you can bust your ass and go nowhere, and why even getting results doesn't matter if they're not aligned with your actual goal. He walks through practical examples—from salespeople making calls to authors writing books—to illustrate why some people accomplish massive results while others stay stuck forever despite working just as hard. Ray shares how to clarify your real goal, define the right distance metrics to track meaningful progress, and apply the necessary force to actually get there. This is about understanding what real productivity looks like and making sure the time and energy you're investing is actually moving you in the right direction.//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

Repeatable Revenue
The Charlie Munger Principle Most Sales Leaders Ignore

Repeatable Revenue

Play Episode Listen Later Dec 11, 2025 17:00 Transcription Available


I just had dinner with four really successful business owners—all running businesses bigger than mine—and we got talking about sales compensation plans. Once I started sharing things I honestly take for granted after 20 years in sales leadership, they were like "we hadn't thought about that." These are very smart, very successful guys, just not from the sales world. So if they found it helpful, maybe you will too. Here's the foundation: the only purpose of your comp plan is to change behavior. Charlie Munger said it perfectly: "Show me the incentive and I will show you the outcome." This episode breaks down three critical comp plan mistakes I see constantly: (1) Long-term commissions that look generous to you but don't change behavior next week because salespeople don't think like business owners—they think in cash, not equity or 36-month payouts, (2) Perpetual residuals that create permanent misalignment as your costs go up while their incentive to do the hard work (hunting) goes down, and (3) Having hunters farm instead of separating the roles, which misallocates both money and results. Learn why you need to reward behavior closest to when it happens, why saying "I'll fix it later" is fucked up, and how to align effort, difficulty, and value with what you're actually paying for.//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

Repeatable Revenue
30 Minutes of Discomfort vs. Years of Regret - Pick Your Poison

Repeatable Revenue

Play Episode Listen Later Dec 10, 2025 7:20 Transcription Available


I just wrapped up several hours of difficult conversations stacked back-to-back, and I want to share something that changed my entire management career: the conversations that are going to have the biggest impact on your business are the ones that are really fucking hard. There's almost a direct correlation between how difficult a conversation is and how much impact it has. Yet we avoid them—for days, weeks, months, sometimes years. I've talked to business owners who've let problems fester for years because they don't want the discomfort of a 30-minute conversation. Here's what helped me: reframing these conversations entirely. When you avoid the hard talk, you're not actually avoiding discomfort—you're just reducing its intensity and spreading it out over time, sometimes forever. That nagging voice in your head saying "you know you should be doing that" never goes away until you do it. But after you have that conversation? You feel stronger, empowered, and you immediately wonder who else you need to talk to. This episode breaks down why avoiding these conversations is negligence, how to reframe the temporary discomfort versus permanent relief, and why this muscle becomes addictive once you experience the benefits. If there's a conversation you're avoiding right now, consider this your sign.//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

Repeatable Revenue
The Most Dangerous Half-Truth in Sales

Repeatable Revenue

Play Episode Listen Later Dec 9, 2025 6:08 Transcription Available


I keep hearing this incomplete advice everywhere: "All sales is about the transference of emotion." It's a Tony Robbins thing, and it's not wrong—but it's dangerously incomplete. I work with a lot of MSP and IT sellers who rely purely on their tech stack, response times, and spotting network problems, thinking logic alone will close deals. Spoiler: it won't. But here's where the "emotion-only" crowd gets it wrong too. People make buying decisions emotionally—they want the transformation, the feeling, the status—but then they justify it logically. Think about wanting a sports car: you want the feeling of driving it, but you justify it to your wife with "special deal, waitlist, investment value." If you only appeal to emotion without giving buyers the rational argument they need to justify the purchase to themselves (or their boss, or the committee), they'll want your stuff but never commit. This episode breaks down why technical sellers need to get past logic and understand the deeper transformation buyers want, and why emotion-focused sellers need to give the logical case that enables people to say yes. You need both.//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

Repeatable Revenue
Winners Know When to Quit

Repeatable Revenue

Play Episode Listen Later Dec 8, 2025 7:02 Transcription Available


I had to call my wife to pick me up yesterday after re-injuring my knee by pushing six miles when my physical therapist said three. Sitting on that corner waiting for her, I realized something uncomfortable: sometimes the hardest thing you need to do is quit. We glorify resilience, grit, and stick-to-itiveness because they work... until they don't. If you've achieved success through raw determination and sheer will like I have, you've been rewarded for pushing through—which makes it even harder to stop when stopping is exactly what you need. I break down why business model problems and product-market fit issues can't be solved with more effort or longer hours, why pushing harder on the wrong problem makes it worse, and how to recognize when your most reliable tool (perseverance) has become a hammer making you see every problem as a nail. This is honestly as much a message to myself as it is to you—for anyone whose feedback loop of "don't quit, push harder" has become so ingrained that knowing when to pause, pivot, or walk away feels impossible.//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

Repeatable Revenue
Your Calendar Is Your Commission Check

Repeatable Revenue

Play Episode Listen Later Dec 7, 2025 10:46 Transcription Available


First-of-the-month accountability check reveals a brutal reality: a salesperson with nothing on the scoreboard, no pipeline, no meetings, and no real plan beyond "follow up with four people" and "pack boxes for Thursday's event." This episode is a wake-up call for anyone in sales responsible for generating their own pipeline. Learn why treating your time like a precious resource isn't optional—it's survival. Discover the two critical mindsets that separate top performers from struggling reps: (1) strategic calendar planning with "The Perfect Week" framework, and (2) complete ownership mentality that refuses to accept passive excuses like "this week's basically shot." If you're carrying a "shit happens to me" mentality instead of "I make shit happen," this unfiltered conversation will either light a fire under you or make you realize sales isn't for you.//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

Repeatable Revenue
The Content Engine I Can Actually Stick With

Repeatable Revenue

Play Episode Listen Later Dec 6, 2025 12:14 Transcription Available


After years of struggling with content that either grew the business but burned him out, or stayed authentic but didn't generate leads, this episode reveals a new strategy that solves both problems. The challenge: three goals kept conflicting—grow the business, teach what you're learning, and actually enjoy creating content. The breakthrough? Create unfiltered content on dedicated channels (daily podcasts, raw thoughts on X) without worrying about hooks, thumbnails, or "ideal client" topics, then let the team mine that library to extract and reposition the business-growing content. Learn why quality comes from quantity, why ghostwriters and AI shortcuts weren't working, and how this approach finally addresses the fundamental tension between authentic voice and scalable growth—especially for founders using personal brands to grow real businesses, not just creator businesses.//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

Artificial Intelligence in Industry with Daniel Faggella
The Biggest Cybersecurity Challenges Facing Regulated and Mid-Market Sectors - with Cody Barrow of EclecticIQ

Artificial Intelligence in Industry with Daniel Faggella

Play Episode Listen Later Dec 5, 2025 18:14


Today's guest is Cody Barrow, CEO at EclecticIQ. EclecticIQ is a global cybersecurity leader specializing in threat intelligence technology. Cody joins Emerj Editorial Director Matthew DeMello to discuss how AI-driven analytics and automation are revolutionizing threat detection and response in enterprise cybersecurity. Barrow also highlights practical improvements in workflow automation, early threat identification, and measurable ROI through reduced breach risks and operational efficiency. This episode is sponsored by EclecticIQ. Learn how brands work with Emerj and other Emerj Media options at emerj.com/ad1. Want to share your AI adoption story with executive peers? Click emerj.com/expert2 for more information and to be a potential future guest on the 'AI in Business' podcast!

Artificial Intelligence in Industry with Daniel Faggella
Overcoming Cloud Complexity in Mid Market Operations - with Dirk Michiels of Savaco

Artificial Intelligence in Industry with Daniel Faggella

Play Episode Listen Later Dec 4, 2025 22:27


Today's guest is Dirk Michiels, CEO of Savaco. Savaco is a Belgium-based managed service provider specializing in hybrid cloud solutions, cybersecurity, and enterprise software deployment. Michiels joins Emerj Editorial Director Matthew DeMello to discuss the transformative role of hybrid cloud architectures in enterprise data and AI strategies. He also highlights how seamless integration, enhanced security protocols, and optimized deployment workflows lead to faster innovation and measurable ROI for modern organizations. This episode is sponsored by Xurrent. Learn how brands work with Emerj and other Emerj Media options at emerj.com/ad1. Want to share your AI adoption story with executive peers? Click emerj.com/expert2 for more information and to be a potential future guest on the 'AI in Business' podcast!

Repeatable Revenue
One Constraint, Two Metrics

Repeatable Revenue

Play Episode Listen Later Dec 4, 2025 9:08 Transcription Available


When a team member quoted the host's own content back to him—"focus on one thing, use one metric"—it would have actually been counterproductive. This episode clarifies a critical nuance that changes everything: yes, focus on ONE constraint (the biggest problem blocking your business), but measure it with at least TWO competing metrics. Why? Because single metrics get gamed, even unintentionally. Focus only on close rate? Sales reps start disqualifying opportunities. Only track appointments set? You get garbage meetings with terrible show rates. Only measure YouTube followers? You end up with 100,000 subscribers and 3 views per video. Learn how to identify your true constraint, why diluting efforts across multiple initiatives kills velocity, and how to set up balanced metrics that actually move your business forward instead of just moving numbers on a dashboard.//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

Repeatable Revenue
You Don't Need a 10-Year Vision. You Need to Start Hanging Lights.

Repeatable Revenue

Play Episode Listen Later Dec 3, 2025 8:19 Transcription Available


Watching his wife spend weeks building custom Christmas decorations from scratch—with zero blueprint and no clear plan beyond a color theme—revealed a powerful business truth. We glorify the Bezos-style crystal clear vision, thinking that's what you need to succeed. But the reality? Most wildly successful entrepreneurs will tell you their business took on a life of its own. Building a business is more art than science—more Steve Jobs ("you can only connect the dots in hindsight") than detailed master plan. This episode explores why loving the process matters more than having perfect clarity, how the process itself reveals options you couldn't have predicted, and why energy to push through inevitable frustrations comes from one of two sources: either a vision so clear it pulls you through, or genuine love for the creative journey itself.//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

The Fiftyfaces Podcast
Episode 337: Jo Natauri of Invidia Capital: On Efficiency and Executive Talent - Unlocking Value in Mid-Market Healthcare

The Fiftyfaces Podcast

Play Episode Listen Later Dec 2, 2025 26:34


Jo Natauri is Founder and managing Partner of Invidia Capital Management, a healthcare focused private equity firm founded in 2024, with a focus on middle-market buyouts in North America. She was formerly Global Head of Healthcare Investing in the Merchant Banking Division of Goldman Sachs.We start by discussing Jo's path to investment banking and how she chose the business side of healthcare over policy. We discuss her long period of apprenticeship and then leading investments while at Goldman Sachs and her decision to strike out in her own firm. Jo explains the diversity within healthcare, from biotech to hospitals, and the permanent base of demand that makes it a good sector to invest in.  She discusses her core beliefs, including avoiding investments that increase drug prices or target vulnerable populations, and discusses the opportunity set that excites her in the middle market arena. When it comes to mentors Jo has had some legendary investors within her circle and cites the apprentice nature of the investment business as a key aspect to be remembered and observed across the seniority spectrum. Series 5 of 2025 is kindly sponsored by Diamond Hill. Diamond Hill invests on behalf of clients through a shared commitment to its valuation-driven investment principles, long-term perspective, capacity discipline and client alignment. An independent active asset manager with significant employee ownership, Diamond Hill's investment strategies include differentiated US and non-US equity, alternative long-short equity and fixed income.

Repeatable Revenue
I Made 40% Fewer Calls And Hit Quota Every Month (Here's How)

Repeatable Revenue

Play Episode Listen Later Dec 2, 2025 19:43 Transcription Available


Ray Green shares why he eliminated call minimums when he took over his first sales team - and how revenue per sale doubled as a result. Most sales managers crack the whip on volume and activity metrics, but Ray argues this comes at the expense of optimizing for what you actually want: results. In this episode, he breaks down the policy change he implemented, the cultural shift required to make it work, and how he recruited differently to build a team that took ownership of outcomes instead of just checking boxes on activity. Ray introduces the Laffer Curve framework for understanding when increased volume starts decreasing results, shares how his team went on to hit their numbers for 10 consecutive years, and explains why this approach is more critical than ever as AI threatens to replace volume-based sales roles. This isn't about having no standards - it's about having the right standards on the things that actually matter.//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

Repeatable Revenue
The Most Dangerous Person on Your Team Isn't a Risk-Taker

Repeatable Revenue

Play Episode Listen Later Dec 1, 2025 11:49 Transcription Available


Can a team be made up entirely of aggressive, play-to-win people? Or do you need the balance of risk-conscious players who pump the brakes? This episode breaks down a fascinating leadership question: the fundamental difference between people who play to win versus those who play not to lose—and why it matters for building your team. Discover the critical distinction between two types of "play not to lose" people: Type 1 who intelligently mitigate risk with confidence versus Type 2 who operate from fear and low self-esteem. Learn why the best CEO partnerships involve a play-to-win leader paired with a Type 1 risk calculator (like the CFO who fought like cats and dogs but made the organization stronger), and why Type 2 players create toxic opportunity cost that kills long-term growth.//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

Repeatable Revenue
AI Is Making Your Team Dumber (If You Let It)

Repeatable Revenue

Play Episode Listen Later Nov 29, 2025 14:29 Transcription Available


When a team member fed me pure ChatGPT fluff instead of their actual expertise, it was time to draw a line. As an early adopter and power user of AI, this episode reveals the exact guidelines now required for using AI in the business—from protecting proprietary knowledge on closed systems to owning every output you submit, even if AI generated it. Learn when AI is brilliant (research, refining messages, automating tasks) versus when it's a road to mediocrity (outsourcing your thinking). The uncomfortable truth: AI has all the information but doesn't really know anything, and lazy AI habits are causing thought atrophy in otherwise smart people. These framework guidelines will help you leverage AI's strengths while protecting what actually makes you valuable.//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

Repeatable Revenue
Why HR Would've Blocked My Best People

Repeatable Revenue

Play Episode Listen Later Nov 28, 2025 12:22 Transcription Available


After hiring hundreds of people across 20 years—from reversing a decade-long sales decline at the US Chamber of Commerce to leading executive turnarounds—here's the uncomfortable truth nobody admits: hiring isn't just science, it's feeling. Sure, use scorecards and screening processes to get to your final candidates, but when you're looking at five people who all score between 80-85, what separates the good from the absolute killers? This episode shares the real stories: the purple-haired sales guy HR said not to hire who became the top performer, the economics grad hired without a role who helped Moneyball a 45-year-old company, and the bar conversation that led to a hire so good it changed where the host lives today. Learn why gut decisions produce outliers and how to strengthen your hiring intuition.//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

Repeatable Revenue
How to Stop Being the Bottleneck in Sales (Without Abandoning It)

Repeatable Revenue

Play Episode Listen Later Nov 27, 2025 11:53 Transcription Available


Feeling stretched thin trying to do everything in your business? You're not alone. Many MSP owners ask how to remove themselves from sales, but that's the wrong question. Sales is the oxygen your business needs—you never fully step away from it. The real question is: how do you get your time back while keeping sales flowing? This episode breaks down the exact phases of promoting yourself through your sales organization, from doing everything yourself, to hiring your first SDR, to building a team where you operate as a true sales leader. Learn why each role funds the next, why abdication kills results, and how to build a self-sustaining sales machine without losing control of your company's lifeline.//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

Repeatable Revenue
Your Inner Critic Isn't a Bug. It's a Weapon.

Repeatable Revenue

Play Episode Listen Later Nov 26, 2025 11:47 Transcription Available


That voice in your head telling you to do better, work harder, be more—should you silence it or lean into it? Society says constant self-criticism is unhealthy, that you should learn to be content and accept yourself as you are. But what if that relentless inner critic is actually your superpower? This deeply personal episode explores how embracing (not fighting) the inner critic helped jump literal generations of family trajectory—from broken homes and instability to building the life most people only dream about. Learn the two critical mindset shifts that turn self-criticism from exhausting battle into rocket fuel, including the crucial distinction between "my actions can improve" versus "I'm not enough as a person."//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

Repeatable Revenue
Why Tom Brady Wouldn't Hire Your ‘Top Performer'

Repeatable Revenue

Play Episode Listen Later Nov 25, 2025 12:20 Transcription Available


I learned this lesson early in my management career and have lived it every day since: a great team will always outperform a group of individual stars, no matter how talented those individuals are. A real team isn't just people doing their jobs—it's a system where everyone is aligned on the same goal, willing to collaborate, share best practices, sacrifice their own time, and do whatever it takes to help the team win. In this episode, I break down why teams outperform individuals and share a powerful two-minute clip from Tom Brady about the difference between champions and stars. Brady says it perfectly: "Champions do what stars aren't willing to do." I've seen this firsthand—we had a "no prima donnas" rule on my team, and for ten years straight, we never missed a single goal. If you're hiring or building a team, stop looking for the best players and start looking for the best people. That mindset shift will change everything.//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

Repeatable Revenue
How I Killed a $40K Commission-Only Disaster in 2 Minutes

Repeatable Revenue

Play Episode Listen Later Nov 24, 2025 13:31 Transcription Available


I just saved an MSP owner from six months of pain, tens of thousands of wasted dollars, and zero results—all in about two minutes on a coaching call. He was trying to hire a commission-only sales rep with a $40K "guarantee" and couldn't figure out why he wasn't getting candidates. The problems were massive: he expected them to close deals in 90 days when his sales cycle was 90 days, meaning they'd need three qualified opportunities on day one just to have a chance at hitting quota. Commission-only structures attract less experienced reps, create mercenary behavior, and signal to good salespeople that you either don't have money or aren't willing to invest in the role. In this episode, I break down why this approach fails, the real math behind sales ramp time (hint: it's your sales cycle times two), and what you should actually be hiring for—lead generation, closing, or both. If you're a business owner thinking about hiring sales, this will save you a fortune in mistakes.//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

Repeatable Revenue
The Worst Time to Sell Managed Services (And How to Fix It)

Repeatable Revenue

Play Episode Listen Later Nov 23, 2025 8:20 Transcription Available


Break-fix calls can be goldmines for MSP growth—if you handle them right. The mistake most providers make? They solve the immediate problem, then try to upsell managed services when the client feels relieved and satisfied. That's like asking someone to order their next meal right after they've finished a T-bone steak. This episode reveals a simple process tweak that creates natural leverage for managed services conversations: how to bundle an assessment or diagnostic discussion into every break-fix visit, so you can uncover latent pain points and present real findings instead of relying on the client to see the value on their own.//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

Repeatable Revenue
The $200M Lesson: Are You Paddling... or Riding the Wave?

Repeatable Revenue

Play Episode Listen Later Nov 22, 2025 4:57 Transcription Available


After a conversation with a friend who built a $200 million gym franchise empire, this episode explores the age-old debate about hard work in entrepreneurship. Is it all about grinding 80 hours a week, or can you meditate your way to success with just a few hours of deep work? The answer lies in a powerful surfing metaphor: business success isn't about choosing one approach—it's about recognizing which season you're in. Learn how to identify whether you're in a paddling phase or a wave-riding phase, and why trying to do both at the wrong time can actually sabotage your results.//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

Repeatable Revenue
The 3 Types Of MSP Prospects (You Make Money In The Middle)

Repeatable Revenue

Play Episode Listen Later Nov 21, 2025 11:10 Transcription Available


Think your job in sales is to talk to people who are ready to buy? That's just order-taking, and there's not much commission in that. In this episode, I break down the three categories every MSP prospect falls into: the red zone (won't buy no matter what), the green zone (ready to buy regardless), and the yellow zone where you actually make your money. The yellow zone is where real sales happen. These prospects could say yes or no, and your job is to close the gap between where they are and where they need to be to buy. When you understand this, objections and pushback become part of the job instead of frustrations. This mindset shift will transform both your results and your experience in sales.//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

Future Finance
DualEntry's Co-founder Santiago Nestares shares why Mid-Market CFO are ditching Legacy ERPs

Future Finance

Play Episode Listen Later Nov 19, 2025 36:34


In this episode of Future Finance, hosts Paul Barnhurst and Glenn Hopper talk with Santiago Nestares, co-founder and CEO of DualEntry, about the reinvention of ERP systems through AI-native design. After scaling a global e-commerce business to over $100 million in revenue, Santiago experienced the frustrations of legacy finance systems firsthand. That pain sparked the vision for DualEntry: an ERP platform built from the ground up for the AI era.Santiago Nestares is the CEO and co-founder of DualEntry, an AI-native ERP platform. Before DualEntry, he co-founded Benitago, a leading Amazon brand aggregator. His experience running a multi-entity, high-growth business exposed the inefficiencies in traditional finance systems, inspiring him to build a next-gen ERP solution from scratch.In this episode, you will discover:Why legacy ERP systems are fundamentally broken, and how AI changes the gameHow DualEntry enables 24-hour ERP data migrationThe role of AI in journal entries, reporting, and reconciliationHow auditors are embracing automation and AI for compliance and accuracyWhy ERP systems must evolve beyond just being "AI-enabled" to truly AI-nativeSantiago Nestares joins Paul and Glenn to reveal how DualEntry is transforming ERP for the AI era. From eliminating painful migrations to building systems finance teams actually enjoy using, Santiago makes it clear: the future of ERP is AI-native, fast, and built with users in mind. ERP doesn't have to be a burden. With the right tools, it can become a strategic advantage.Join hosts Glenn and Paul as they unravel the complexities of AI in finance:Follow Santiago:LinkedIn: https://www.linkedin.com/in/santiago-nestares/Website: https://www.dualentry.com/Follow Glenn:LinkedIn: https://www.linkedin.com/in/gbhopperiiiFollow Paul:LinkedIn - https://www.linkedin.com/in/thefpandaguyFollow QFlow.AI:Website - https://bit.ly/4i1EkjgFuture Finance is sponsored by QFlow.ai, the strategic finance platform solving the toughest part of planning and analysis: B2B revenue. Align sales, marketing, and finance, speed up decision-making, and lock in accountability with QFlow.ai. Stay tuned for a deeper understanding of how AI is shaping the future of finance and what it means for businesses and individuals alike.In Today's Episode:[01:36] - Lessons from Scaling to $100M & ERP Frustrations[03:37] - Why ERP Migrations Are So Broken[07:47] - How DualEntry Raised a $90M Series A[10:51] - AI-Native vs. AI-Enabled ERP Systems[18:23] - Challenges and Realities of 24-Hour ERP Migration[23:26] - Why Building a Mid-Market ERP Is a Bold Move[28:18] - Using AI in Audits & Real-Time Reporting[31:45] - Rapid-Fire AI Questions[35:52] - Final Reflections & Wrap-Up

Repeatable Revenue
You're Only Selling to 3% of Your Market (Here's How to Capture the other 97%)

Repeatable Revenue

Play Episode Listen Later Nov 19, 2025 11:46 Transcription Available


Discover why your outbound efforts aren't generating the results you expect. This episode breaks down the critical mistake most MSPs make—only targeting the 3% of prospects ready to buy right now—and reveals two powerful systems that successful MSPs use to capture the other 97% of the market. Learn how to implement an intel-gathering system that turns every outbound call into future opportunities, and create a top-of-mind strategy that positions you perfectly when prospects are finally ready to switch providers. Real client case study included: how one MSP went from 3-4 appointments per month to 20+ using these exact strategies.//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

Repeatable Revenue
Why "Entrepreneurship Is Just Luck" Is the Dumbest Take on the Internet

Repeatable Revenue

Play Episode Listen Later Nov 14, 2025 15:36 Transcription Available


A viral tweet calling entrepreneurship "just a lottery" hit my feed last week, and I had to respond. The author claimed successful entrepreneurs are lucky players who pretend their success was skill, and thousands of people ate it up. In this episode, I share my original reaction, but more importantly, I break down a powerful story from Alex Hormozi's $100 Million Leads about "The Many-Sided Die" that reframes the entire conversation. Yes, luck exists—some people roll green faster than others. But the real insight is this: you win by continuing to play. Every roll improves your odds, builds your skills, and gets you closer to success. The only guaranteed way to lose is to quit and blame your failure on everyone else getting lucky.//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

The SaaS CFO
Markup AI Raises $27M To Help Enterprises Put Guardrails on Their Content

The SaaS CFO

Play Episode Listen Later Nov 13, 2025 19:49


On this episode of The SaaS CFO Podcast, Ben Murray welcomes Matt Blumberg, CEO of Markup AI, to discuss his remarkable journey through the tech startup world. With over two decades of leadership experience—including building moviefone.com, scaling Return Path to $100 million in revenue, and leading executive search disruptor Bolster—Matt Blumberg brings a wealth of insight into startup growth, business transformation, and adapting to evolving technology. In this conversation, Matt Blumberg shares the story behind Markup AI, a company redefining how businesses safeguard their content using AI-powered “content guardian agents.” He discusses the recent rebranding from Acrolinx, the impact of large language models on both product and customers, and their transition into a new API-first, consumption-based business model. Listeners will hear lessons about navigating private equity ownership, fundraising for transformative pivots, and crafting multi-pronged go-to-market strategies—from enterprise sales to developer-driven adoption. Tune in for an honest look at leadership, innovation, and what's next for Markup AI in the dynamic world of SaaS and AI content management. Show Notes: 00:00 "AI Guardian for Perfect Content" 03:51 Acrolinx's AI Evolution 09:33 "Defining AI Content Guardians" 11:18 Private Equity Risks in Mid-Market 13:57 AI Adoption Strategies in Enterprises 18:44 "AI Growth and Rebrand Focus" Links: SaaS Fundraising Stories: https://www.thesaasnews.com/news/markup-ai-raises-27-5-million-in-funding Matt Blumberg's LinkedIn: https://www.linkedin.com/in/blumbergmatt/ Markup AI's LinkedIn: https://www.linkedin.com/company/markupai/ Markup AI's Website: https://markup.ai/ To learn more about Ben check out the links below: Subscribe to Ben's daily metrics newsletter: https://saasmetricsschool.beehiiv.com/subscribe Subscribe to Ben's SaaS newsletter: https://mailchi.mp/df1db6bf8bca/the-saas-cfo-sign-up-landing-page SaaS Metrics courses here: https://www.thesaasacademy.com/ Join Ben's SaaS community here: https://www.thesaasacademy.com/offers/ivNjwYDx/checkout Follow Ben on LinkedIn: https://www.linkedin.com/in/benrmurray

Lead(er) Generation on Tenlo Radio
EP151: Mid-Market Growth With Scalable Data & AI Strategy

Lead(er) Generation on Tenlo Radio

Play Episode Listen Later Nov 13, 2025 42:23


Mid-market leaders are facing a once-in-a-generation opportunity with AI, and this episode shows how to capitalize on it.  John Powers, former CIO and Chief Transformation Officer at Deloitte and now Executive in Residence at Mod Op, shares practical ways to turn AI, data strategy and governance into real competitive advantage. He explains why smaller, more nimble companies can finally “punch above their weight,” how to spot the fastest wins and where custom, company-specific AI beats off-the-shelf tools. You'll hear how John partnered with Mod Op to stand up data leadership, why engineering the way you communicate makes AI dramatically more effective and how to rethink work so teams spend less time on administrative tasks and more time on growth.  If you're done “checking the AI box” and ready to drive measurable outcomes, this conversation gives you a clear path forward. Leader Generation is hosted by Tessa Burg and brought to you by Mod Op.  About John Powers: John is an accomplished senior advisor with decades of success driving transformation for global multi-nationals, now bringing that experience and expertise to Mod Op Strategic Consulting clients. As Deloitte's Global Chief Transformation and Chief Information Officer he led enterprise-wide IT cloud migrations, modernized cybersecurity governance and implemented zero-trust principles to bolster resilience, while reducing cost, and improving service delivery. His experience in strategy, digital transformation, inorganic growth and organizational effectiveness is now dedicated to leveraging AI and Big Data to drive growth and profitability. John can be reached on LinkedIn or at John.Powers@ModOp.com.  About Tessa Burg: Tessa is the Chief Technology Officer at Mod Op and Host of the Leader Generation podcast. She has led both technology and marketing teams for 15+ years. Tessa initiated and now leads Mod Op's AI/ML Pilot Team, AI Council and Innovation Pipeline. She started her career in IT and development before following her love for data and strategy into digital marketing. Tessa has held roles on both the consulting and client sides of the business for domestic and international brands, including American Greetings, Amazon, Nestlé, Anlene, Moen and many more. Tessa can be reached on LinkedIn or at Tessa.Burg@ModOp.com.

Heads Up Adviser
Fortune 100 Health Secrets: Steal These Strategies for Your Mid-Market Clients

Heads Up Adviser

Play Episode Listen Later Nov 11, 2025 34:04


Lee Lewis explains the "grass is greener" paradox: large employers feel they're too bureaucratic to innovate, while mid-market employers feel they lack the scale. He reveals how a new model is breaking down these barriers, bundling Fortune 100-level solutions and making them accessible to the mid-market for the first time.Tune in to understand:Why the "Show-Up" model is the only effective way to implement Direct Primary Care.How hospitals use infusion therapy as a "streaming revenue" machine and how to stop it.The groundbreaking impact of psychedelic therapies on addiction and mental health costs.How to bring the most powerful health strategies to your clients, regardless of their size.LEARN MOREHealth Transformation Alliance: https://www.linkedin.com/company/health-transformation-alliance/Heads Up Adviser: https://virtuealliance.com/heads-up-adviser/Show Sponsor Virtue Health: https://virtuealliance.com/CONNECT ON LINKEDINLee Lewis: https://www.linkedin.com/in/leewlewis/John W. Sbrocco: https://www.linkedin.com/in/johnwsbrocco/

Repeatable Revenue
LIVE Sales Cold Call Review (Spotting 6 Mistakes)

Repeatable Revenue

Play Episode Listen Later Nov 7, 2025 20:02 Transcription Available


I got a cold call completely by chance while recording content, and as someone who reviews hundreds of sales calls, this was like Christmas morning. The health coaching rep did a solid job overall—good tone, professional, not pushy—but missed some critical opportunities that would've moved the deal forward. In this episode, I break down the entire call and show you what happens when a prospect quantifies where they are (I said I'm an 8.5 out of 10), why phrases like "small needle movers" kill urgency, how speed to lead matters more than you think, and the mistake of pitching another call without giving a compelling reason to show up. This is raw, real-time call coaching you can apply immediately.//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

The SaaS CFO
Aleph Raises $47M to Raise the Stakes in FP&A Software

The SaaS CFO

Play Episode Listen Later Nov 6, 2025 23:36


Welcome to another episode of The SaaS CFO Podcast! This week, Ben Murray sits down with Albert Gozzi, the co-founder and CEO of Aleph, an innovative AI-driven FP&A platform transforming how finance teams operate. Originally from Argentina, Albert Gozzi shares his journey from Procter & Gamble to Bain, and later as a startup CFO, where he experienced firsthand the frustrations of spreadsheet-heavy workflows in finance. Together, they dive into the founding story of Aleph, its mission to streamline financial data and workflows, and how the company's AI-powered solutions are empowering finance and FP&A teams to work smarter and faster. In this episode, you'll get insider insights on Aleph's rapid fundraising journey—having recently closed a $30 million Series B and totaling $47 million to date. Albert Gozzi candidly discusses what investors look for at each funding round, the nuances of scaling go-to-market efforts, lessons learned from dozens of investor rejections, and why finding product-market fit is just the beginning. Plus, they uncover how Aleph's unique approach to implementation and pricing is winning fans among CFOs in mid-market and private-equity-backed businesses. If you want a behind-the-scenes look at building and scaling a modern SaaS finance platform, this is the episode for you. Tune in to hear the latest on Aleph's roadmap, practical advice for SaaS founders, and where the future of FP&A is headed. Show Notes: 00:00 "AI-Powered Financial Data Management" 03:59 "Flexible Platform for Mid-Market" 08:18 "Road to Series C" 11:01 "Importance of Market Repeatability" 16:19 "Fast Implementation Drives Success" 20:24 "CAC Payback: A Cautious Metric" 22:14 "Doubling Down on AI Advancements" Links: SaaS Fundraising Stories: https://www.thesaasnews.com/news/aleph-raises-29-million-in-series-b Albert Gozzi's LinkedIn: https://www.linkedin.com/in/albertgozzi/ Aleph's LinkedIn: https://www.linkedin.com/company/getaleph/ Aleph's Website: https://www.getaleph.com/ To learn more about Ben check out the links below: Subscribe to Ben's daily metrics newsletter: https://saasmetricsschool.beehiiv.com/subscribe Subscribe to Ben's SaaS newsletter: https://mailchi.mp/df1db6bf8bca/the-saas-cfo-sign-up-landing-page SaaS Metrics courses here: https://www.thesaasacademy.com/ Join Ben's SaaS community here: https://www.thesaasacademy.com/offers/ivNjwYDx/checkout Follow Ben on LinkedIn: https://www.linkedin.com/in/benrmurray

Managing Marketing
Abe Kasbo And Anton Discuss The Responsible Use Of Digital Marketing For Mid Market Advertisers.

Managing Marketing

Play Episode Listen Later Nov 4, 2025 51:17


Abe Kasbo is the founder and CEO of Verasoni. An independent marketing communications advisory firm based in New Jersey. Abe discusses why he published his latest book, Irresponsibly Digital.  He challenges mid market leaders to confront the unchecked excesses and missed opportunities of today's digital-first landscape.  Abe discusess the importance of accountability, understanding customer behavior, and the need for courage in marketing strategies. He emphasizes the significance of storytelling in marketing, the pitfalls of social media engagement, and the resurgence of traditional media.  From Pet Rocks to Trump; OpenAI to Amazon. Abe and Anton traverse the clickocracy, challenges and opportunities facing marketers today. Listen on Apple: https://podcasts.apple.com/au/podcast/managing-marketing/id1018735190   Listen on Spotify: https://open.spotify.com/show/75mJ4Gt6MWzFWvmd3A64XW?si=a3b63c66ab6e4934   Listen on Stitcher: https://www.stitcher.com/show/managing-marketing   Listen on Podbean: https://managingmarketing.podbean.com/    For more episodes of TrinityP3's Managing Marketing podcast, visit https://www.trinityp3.com/managing-marketing-podcasts/   Recorded on RiversideFM and edited, mixed and managed by JML Audio with thanks to Jared Lattouf.