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I'm an operator documenting what I've learned building revenue engines over the past decade.

CEO @ MSP Sales Partners. Managing Partner @ Repeatable Revenue. Former PE-backed CEO. Former Managing Director at the U.S. Chamber of Commerce. Spent six years building sales systems for Robin Robins (TMT, sold to PE). Built revenue engines for 100+ service businesses.

I write about what I've learned: how sales systems actually scale, the difference between activity and productivity, why hard choices matter more than hard hours, building a business without burning out.

This isn't guru content. It's lessons from the work... what I got wrong, what finally clicked, patterns I see across businesses, frameworks that actually held up under pressure.

I write for three types of people: Strategists thinking about exits and scale. business owners stuck at a plateau trying to break through. Thinkers who want to build intentional lives, not just businesses.

If you're one of those (or all 3), follow along.

Ray J. Green

6 years ago I started posting on LinkedIn because I actually enjoyed creating content. 

I also had a decent amount experience turning around sales teams & businesses using some unorthodox practices. 

So, I wrote about it. 

And wrote about leaving the C-Suite, moving my family to Cabo, and figuring out how to generate income from a Mexican beach. 

My wife and a couple friends were the only people who liked my posts. Sometimes not even them. 

But I actually enjoyed the process. And I wrote just about every day. It was easy. It was light. It was enjoyable. 

With just 3 or 4 likes per post (I don't have many friends), I even managed to get a couple clients from content. They saw a post, looked at my half-assed "optimized" profile, and hired me to give them advice. 

Shortly after that, creating content became a task. Something I had to do every day to be seen and known. To generate some business. 

Sit down. 
Think of something to write. 
Hammer out a post. 
Make it look pretty with descending lines. 
Post. 
Every day at the same time. 

It started to consume every morning. 

Then I learned that commenting on everyone else's posts helped my posts get more reach. So I'd block time every day to "engage" with people's content. A couple hours a day... on a slow day. 

Then I decided to start "batching" content, sitting down and hammering out 6 or 7 posts in one setting and scheduling them all out in advance. 

Then I started recycling content, taking old stuff, refreshing it, and adding it to a second publishing slot for the day. 

Before long, I was cranking out 21 posts a week and racking up who knows how many hours of commenting. 

For all intents and purposes, I was a machine. 

And that's before AI got added to the mix. 

But along the way, I stopped enjoying the process. 

I managed to systematize the joy out of writing. 

Content was forced. Engagement was forced. 

I wasn't sharing a viewpoint I felt strongly about. I wasn't enjoying the process. I was just "building an audience" and generating leads. 

And to some extent, that's perfectly fine. It's LinkedIn. We're all here to do business in one way or another. Myself included. We all gotta eat. 

But today I made a decision: I'm going to start spending more time doing things I genuinely love doing. And one of those things is writing for the sake of writing. 

Not for leads. Not to check a box. Not at a specific time. Not on a schedule. Not in conjunction with 7 hours of commenting on other people's posts. 

But for the joy of it. 

And hoping it adds value in one way or another to someone else here. Even if it's back to 3 or 4 likes per post. 

This post is the first stab at that. And I'm already enjoying this process a hell of a lot more. 

If you want to follow along, comment "WRITING" to receive my.... kidding. 

You'll never see another handraiser post like that from me again. But that's a post for anther day. Maybe tomorrow. But then again, maybe not. 

See you around.

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OCAS 2.0

It took me 40 months to break $40k/month as an independent consultant. If I started again, I'd do it in a fraction of the time. I created this course - and share it for FREE - to help others do exactly that: https://www.rayjgreen.com/digital-course

RJG Newsletter

Join my email list for practical advice on sales, strategy, and self-mastery from an operator, not a guru: https://rayjgreen.beehiiv.com 

Chief Executive Officer

Managing Partner

Writer & Podcaster 

Expert In Residence: Sales & Sales Management

CEO @ MSP Sales Partners | Man. Partner @ Repeatable Revenue | Ex-PE Backed CEO | Former U.S. Chamber Man. Director

When people say, “just stay consistent” or “it’s about volume,” what I hear is: work hard, cross your fingers, and hope you get lucky. 

Just read a post from a popular ghostwriter on how to go viral. His hack? Just have to keep posting. 

Over the weekend watched a YouTube video from a popular business guru on how to find the right growth strategy. Solution? You just have to keep trying new things until it works. 

But if you take this advice literally, and completely, you’re essentially saying “Just keep doing shit until you get lucky.”

And if you’re wired anything like me, that’s not going to fly. Not is it going to be sustainable. 

Volume does matter. Consistency does matter. 

But just like driving to the office everyday doesn’t train you to be an F1 race car driver, volume and consistency aren’t enough. 

It’s intentional volume. Combined with focused reflection and aggressive iteration. 

A critical mass of effort done on purpose. Then regularly reflected on to discern what’s working and what isn’t. And adjusting accordingly. 

Volume without intentionality and iteration is wasted energy. Or lottery ticket-type betting. 

And a good way to burn out.

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My inner critic is a loud SOB.

Good workout? 
You could've gone harder. 

Eating okay? 
Could be cleaner. 

Time with your kids? 
Could be more present. 

Productive at work? 
Could've done more.

It never stops.

I used to fight it. Try to quiet it. Tell myself that I should be easier on myself, like everyone says you should.

And you know what happened?

It made things worse.

Because then I had the critic AND a voice criticizing the critic. 

Layering noise on top of noise.

So I stopped fighting.

I realized my inner critic is a feature. Not a bug.

That voice... the one constantly pushing me... is what I credit for jumping literal generations for my family.

Growing up with divorce. Absent father. Broken homes. In a foster home at one point. Not a lot of money. Or formal education. And layers of other challenges. 

Today? Happily married. Two healthy boys who know nothing of that instability. MBA from a top school. Living in Cabo. Traveling the world.

That tough critic that pushed me said "This is not for you. You can do better. You will do better."

And I did.

Here's the nuance though.

I've learned to allow the critic to push my actions. My habits. My standards.

Without allowing it to define my worth.

I can accept that my actions will never be "enough" while also knowing that I am enough as a person.

And that's a big effing difference.

One keeps you sharp. 

The other keeps you whole.

Dropped a podcast expanding on this a bit if you're interested: https://lnkd.in/eAm7GyPn

Most salespeople treat discovery like a podcast interview.

"Tell me about your business. How many users? What's your current setup? Walk me through your IT history."

Like you're only there to gather information and collect facts.

And I promise you it's costing you deals. 

Something that's helped the hundreds of consultative sellers I've coached: 

Discovery isn't information gathering.
It's the first step of a strategic close. 

Run a bad discovery and the rest of the process is going to pay the price. 

Example for IT companies:

Bad discovery: "How many servers do you have?"

Good discovery: "How is IT accelerating your growth or holding it back right now?"

One gets you data. The other gets you business impact—the ammunition you need when you're actually trying to close the deal 3 weeks later.

The same thing happens in assessments.

Example for IT companies: 

You find cracked passwords. You find too many O365 admins. You document the vulnerabilities.

Then you present them like a checklist: "You have X problems."

But the MSPs who close? They explain why that matters: "You have cracked passwords on essential systems. Let me tell you what happened to a company last month when a disgruntled employee knew they were leaving…"

Every step in your process—from first call to final proposal—has one job: move the deal forward.

Not educate. Not inform. Not "let them think about it."

Move. The deal. Forward.

I shared a podcast on this, and why despite the stigma attached to it, it really is Always Be Closing. 

I explain why and how here: https://lnkd.in/e7SVFiVx

I wish there were more 'right' and 'wrong' calls in business. But what I've learned from 20 years of leading teams, divisions, and businesses? 

It's a lot more "good bet vs bad bet' and a lot less 'right decision vs wrong decision.' 

Regardless of whether you're running $500K business or a $500M business, when you're making high level decisions about where the business should go, you're operating with uncertainty. 

You may be 55% sure on some days. 90% sure on a good day. But that's the job description. 

The problem is, I see this crush a lot of founders. 

They go this direction. Then that direction, Start this project. Change to that project. Pick this priority. Then that priority. 

It's exhausting just to watch. 

Even more exhausting to do. I know from experience. 

I recorded a 10 min podcast for any founder or business leader that's felt overwhelmed by uncertainty. And anyone that's let that uncertainty lead to perpetual pivots and indecision. 

You can tun in here: https://lnkd.in/eVNUZDuY

Years ago I gave my wife terrible business advice.

Not because it didn't work.

But because it did.

She had a custom baby bedding business doing $25K/month on Etsy. Six-month waiting list. Countless 5-star reviews. People literally begging her to make "just one more."

She asked for my input.

I looked at all the indicators and told her what any business advisor would say: "It's time to scale."

She had some resistance. "Yeah, but I love sewing."

But she pushed on.

She hired people. Built systems. Went from spending her days doing what she loved—talking to customers, designing patterns, creating with her hands—to managing quality control and dealing with employee issues.

The advice worked. The business scaled.

And she fucking hated it.

Her initial resistance? That gut instinct she had?

Spot on.

She didn't want to build a business. She wanted to do the thing she loved and get paid well for it. Those are two completely different games.

My advice was biased by what I believed a business should be. Not what her business could be for her.

I see this happen quite a bit. And I'm more aware of it having gone through my wife's experience with her. 

I recorded a podcast breaking down: 

→ Why you should pick advisors carefully (even if you love them)
→ Why product-market pull doesn't mean you should scale
→ How to filter advice so you build the right thing (for you, not for them)

Listen in here: https://lnkd.in/eCtMPwpn

"I do have to tell you, Ray, there is a small chance of sudden death."

My cardiologist. 

About a year-and-half-ago following a chance diagnosis of hypertrophic cardiomyopathy (HCM). 

I initially reacted the way you'd expect. 

"WTF am I supposed to do with that?!?!"

And, "Why in the hell is this happening to me?"

After all, I do 2 hours of cardio a day. 

In fact, my last echocardiogram shows I have 'athlete's heart.' My heart has literally grown because I've exercised it so much--in a good way. 

So how do I end up with a heart condition? 

But I had it wrong. This wasn't happening TO me. 
It was happening FOR me. 

That reframe changed how I look at this. Even with a couple ER visits in recent weeks. (Which ended up perfectly fine and just more awareness.) 

And it's reframed how I see every hardship in general. 

I break it all down in 10 min podcast here: https://lnkd.in/e3FKQD-m

The thing you're most certain about in your business is probably the exact thing keeping you capped.

Just took my kids to a Museum of Illusions in Utah. Your brain swears things are true that aren't—by design.

Same thing happens in business. 

I've spent a lot of time this past year with founders of $200M businesses. And founders of $2M businesses. 

Biggest difference between them? 

A few simple beliefs. 

I break down what this looks like in a 10 min podcast. 

Tune in to listen here: https://lnkd.in/eCpt5-i7

Our 4th graders were begging for cell phones. 

Parents made a pact: rewind the clock & meet 'em halfway. 

No smartphones... 

But they were genuinely thrilled to get these retro beauties instead. 📞✨

You know why so many salespeople waste 10 minutes talking about the weather?

Because they think being liked is the same as being trusted.

It's not.

Here's how I think about it:

If I needed brain surgery, I wouldn't pick the surgeon who makes great small talk.

I'd pick the one who asked questions that prove they've seen my exact condition 50 times before.

Likability gets you in the door. Credibility gets you the deal.

(If you are selling anything of high importance.) 

But there's the psychological trap a lot of reps fall into:

Small talk feels safer. It's comfortable. It doesn't require you to demonstrate expertise or challenge assumptions or risk saying something that might make the prospect uncomfortable.

So you hide behind it.

You talk about dogs and football teams instead of asking the question that might make them think: "Wait, maybe our current IT setup isn't as solid as we thought."

Real rapport is built on confidence, not comfort. 

Confidence that you know their industry. That you've done your homework. That you're not afraid to respectfully push back when they tell you something that's not accurate.

I recorded a podcast breaking down: 

→ Why people confuse likability with trust (and how to fix it)
→ The preparation work that builds real credibility
→ How to show up as an expert, not an order taker

Listen to the whole thing here: https://lnkd.in/eDs2mfSZ

There's a name for what happens in a business when leaders have no spine. 

You know what I'm talking about. When the people responsible for making the tough calls... just don't. 

They ignore underperformance. 
Avoid difficult conversations. 
Procrastinate making hard decisions. 
Or just never make them at all. 

From a business standpoint, it's called 'management debt.' 

'Management debt' compounds just like financial debt. 

It destroys cultures. And it can stunt growth just as much as irresponsible financial debt can. 

I recorded a quick podcast breaking down: 

→ What management debt is (vs. real leadership)

→ The compounding impact it has on companies 

→ How to keep it from accumulating in yours 

Tune in here: https://lnkd.in/eT3aBrt2

One of the biggest challenges with digital marketing is remembering that the people in your feed aren’t the people buying your stuff. 

(Unless you sell products and services to online creators.) 

I’m guilty of forgetting this myself. 

I scroll here and see a bunch of people using AI in really cool, new ways. 

That gets baked into my head when creating a podcast or YouTube video on AI. 

Then I go to an event and talk to my actual customers and prospects and realize, they’re not using AI in their sales process in some of the simplest ways. 

But it’s not just with AI. It’s with all our messaging. 

We have what’s called “the curse of knowledge.” 

When we forget what it’s like to not know what we know so well. It’s a trap a lot of experts fall into. 

So, reminder (to myself as much as anyone) to spend a little more time creating for the people we want to listen. 

Not other creators.

I'm on Facebook the other day and see an ad: "Every sales expert is telling you the same lie—you need to build rapport before you sell."

The pitch? Buy my $37 course to learn how to sell without rapport.

If you read on, you'll see this supposed sales expert was making a common mistake: 

Confusing rapport with small talk. 

Rapport = trust & credibility. 

Small talk = likability. 

Talking about the weather. The local football team. The family pictures on the desk.

That might make you likable. But it doesn't make you credible.

And if you're selling anything of real importance to someone, likability only goes so far.

Think of it this way: If you need brain surgery, are you going with the doctor you like most, or the one you trust to get the job done? 

I recorded a podcast breaking down the common misconception. 

In it, I break down:

→ Why small talk doesn't equal rapport (and what does)

→ How to establish credibility in the first 5 minutes

→ The questions that prove you're an expert, not just likable

→ Why rapport is an ongoing process, not a one-time event

Listen now: https://lnkd.in/eDs2mfSZ

We all have beliefs that aren’t true. Every single one of us. 

The question is: How much are those beliefs holding us (or our business) back? 

Last week we took our beach kids on a ski trip to Utah for a few days. 

(“Dad, is that real SNOW?!?!) 

We had an unexpected delay in Salt Lake City and stopped by the Museum of Illusions—which is basically an hour and a half of mind bending experiences. 

It’s display after display of, “How in the hell is that happening?” 

And what it comes down to is your brain creates shortcuts with limited data. It stitches information together in a way that makes sense… but isn’t true. 

Like this picture. 

The tops of both of these boxes are the same size. Hard to see. But they even give you a block to hold over it to confirm. 

It’s harmless in this controlled environment. 

But what if the tops of these boxes represented a critical belief you held about something of importance that was holding you back. 

You know, the belief that: 

— “This business just doesn’t have the potential.”

— “That idea will never work.”

— “I’ve got to have [money, experience, connections, etc]  before I can do that.”

— “I’m too [young, old] to do this.” 

— “That channel doesn’t work anymore.” 

And what if it was just completely… wrong? 

An illusion that was holding you back from a monumental shift and achieving what you wanted. 

I've spent a lot of time this past year with entrepreneurs who've built $50M, $100M, $200M businesses.

I've also spent a lot of time with entrepreneurs who are struggling to get there. 

And the biggest difference I see is their belief systems. 

Founders who struggle to get to the next level typically have a belief that’s holding them back. Something they know to be true… that simply isn’t.  

A common one being that they are more essential to day-to-day operations than they really are. 

The question I’m asking myself today: What am I dead certain is true… that isn’t?

How about you?

We glorify the benefits of entrepreneurship like independence, ownership, optionality. 

But those are the very things that crush entrepreneurs once they get going. 

Having an infinite number of options. 
Virtually no certainty while making huge decisions. 
But owning the outcome entirely. 

It's the freedom people think they want. 

But it drives a lot of entrepreneurs crazy once they get it. 

They can't make decisions. And when they do, the immediately doubt themselves and change directions. 

Which basically makes only one thing certain: they won't move forward.

I watched an entrepreneur change their mind on lead gen strategies 8 times recently. 

And I recorded a 10 min podcast breaking down why this happens (from experience). And how we can flip the script on uncertainty. 

Listen in here: https://lnkd.in/eujidhhV

The MSP owner on the phone with me sounded defeated.

His sales rep had just spent three weeks and 20+ hours on what looked like a perfect fit.

Discovery had uncovered real pain points. The assessment was thorough. The proposal meeting went well—good questions, engagement, positive energy.

Then... nothing.

Not a “no thanks.”
Not a “we’re going with someone else.”
Not even a “we need more time.”

Just complete radio silence after weeks of investment.

“This keeps happening,” he told me. “How do we stop bleeding time on deals that were never going to close?”

This was my response:

mspsuccess.com

Stop Chasing Dead Deals: How to Read Your MSP Prospects Before They Ghost You

Carol Malakasis

When I got hired at my first sales role, selling goat cheese door to door, I did not know what “revenue” meant. Fast forward 15 years later, I am an expert at scaling revenue for Seed - Series A startups. 

I am a NY sales vet who spent the last 15 years in startup sales. 

After my brief stint selling cheese, I co-founded a CPG brand (acquired) selling handmade Horchata to local markets and Wholefoods. 

I pivoted in tech in 2012 and found my passion in building SMB startups. I’ve been part of the founding GTM team in three high growth startups (2 exits). 

I’ve made over half a million cold calls, trained sales teams, hired and onboarded hundreds of reps, and sold over $2M in revenue. 

Since 2020, I am a GTM consultant, trainer, and coach for B2B SaaS companies. I’ve helped over 100 YC companies get to their first $1M in revenue and beyond. 

.........................................................................................

The first five years of a startup's life are the most crucial. 

During this time 90% of startups fail. 

Top reasons include lack of product market fit, poor or no sales execution, bad founding hires, burning through your runway. 

I de-risk all of the above and provide you with the tools and systems to predictably scale to Series A and beyond. 

When traction isn’t there, is it really your product or…is it you? Do you struggle with selling, lack a repeatable sales process, or need a product pivot? 

You're losing sleep over: 

🔵 Selling to the right ICP

🔵 Transitioning from inbound to outbound sales

🔵 Successfully qualifying and closing deals

🔵 Finding the right pricing model

🔵 Selling without being 'salesy'

🔵 When to hire and train a sales team

🔵 Executing a repeatable sales motion. 

That's where I come in. I audit your processes, custom build your GTM strategy, teach you how to sell (founder-led selling), and help you hire, onboard, and train your first sales team. 

My clients are able to get to their first $1M ARR and beyond, in a predictable, scalable way, and use the processes we build together for the lifecycle of their business. 

When you hire me, I am a part of your team. I am known for my directness, dedication, and aversion to BS. 


If you want to work with me, DM me. You can also book a call at https://calendly.com/malakasis ☎️

Envoy

Pavilion is powered by an international community of revenue leaders from the world’s fastest growing companies. Together, we teach new skills, forge meaningful connections, and help our companies grow. 

As an Event Host, I host Executive Salon Dinners for Pavilion and drive insightful, confidential dialogues on trending topics, growth opportunities, and strategies for overcoming challenges. 

Unlock your professional potential and level up with community-powered learning for CEOs, GTM leaders, and teams. Join today at joinpavilion.com/apply-now.

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The Battle

Ray J. Green

Carol Malakasis

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The Battle

Ray J. Green

Carol Malakasis

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Ray J. Green's LinkedIn Performance

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