Disclaimer: Unless noted otherwise, views and analysis expressed here are the author's own and based on public sources. The article is intended for informational and entertainment purposes only. This is not financial advice. Please consult a professional for investment decisions.

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Welcome to yet another episode of the Rollup of Tomorrow series! Today’s guest is Ramsey Sahyoun, a co-founder and Head of M&A at Evergreen. This is Part II of our deep-dive on Evergreen, a multinational IT services group majority-owned by Alpine Investors. Read Part I here: MSP M&A WDYT? 7 lessons from Evergreen on scaling from 0 -> $1.5B revenue & $250M EBITDA

Ramsey and I discussed: 

You can also listen to this episode on Spotify.

Before we kick off…

Alex: Welcome Ramsey! As an opener, I'd like to talk about your and Jeff's state of mind 9 years ago, when after that fateful Berkshire Hathaway AGM, you decided to build Evergreen. What's remarkable is that you guys were very young, in your mid-20s. You didn't have an MBA. In fact, you didn't have any experience of running companies. What gave you the confidence that Evergreen was going to succeed? 

Ramsey: Alpine Investors is one of the first private equity firms to hire people directly out of university and to train them up - versus hiring from investment banking. There was always this ethos around empowering people earlier in their career, giving them the tools to be successful. After learning the Alpine Playbook, we felt it could be applied to a certain category of businesses, on a long-term horizon. That gave us confidence: we know what good looks like. There were only a couple differences, which is the permanent HoldCo versus a typical Private Equity platform. And then going a bit down market and focusing on IT services.

Further reading: Changing the Face of Leadership Through Alpine Investors’ CEO-in-Training Program

Alex: I have a lot of respect for your job as the head of M&A having spent most of my career in the industry. When I read that, in 2025, Evergreen closed 47 acquisitions, I imagine it must have taken years and years to finetune that M&A machine. Curious to hear about your early lessons: what worked and what didn't? What were the setbacks and what did you learn to do differently versus other acquirers of IT services businesses? 

Ramsey: I have a lot of thoughts on this. The M&A engine is my baby. For the first couple years my day was just talking to business owners. It was literally me finding the deals, Jeff executing the deals, and finding the CEO that we were going to put in.

And that was it. It was just the 2 of us doing that for a good chunk of time. It was then that I developed our direct sourcing engine. Right as we were starting Evergreen, I had a conversation with a successful search funder. He walked me through their sourcing engine and the KPIs that he paid attention to. How many companies they were adding to the database. How many outreaches they were doing. How many intro calls they were having. It was all very systematic and scalable. 

A lot of people take a very slow, bespoke, not metrics driven approach to sourcing - and it falls flat.

We were able to come out of the gates strong because we pushed the pace. We were doing a high-volume of conversations with business owners. Our top of the funnel has always been really strong, which has led to good investment decisions. If you just sit back and wait for acquisition opportunities, you're not going to have a great opportunity set to choose from.

Alex: I would like to double-click on that high velocity and origination strategy. The flip side of 80% proprietary deal flow is that some deals take years and years to mature. How do you approach that? Do you personally show up at people's homes and conferences and tell them, hey, I'm Ramsey, we've been chatting on and off for 5 years? Or do you do it at a high level: coach people to go out and originate deals?

Ramsey: It's definitely more the latter. Our team is doing most of the deals today. To your point, I have relationships that go back 8 years from when we started the company. Where the owner hasn't been ready to sell, but I've kept the relationship with them.

So, I still source personally a handful of deals a year, $10M of EBITDA a year or something like that. I try to get involved right around the time someone's making a decision. I can help tip the scales in our favour; that's the role I try to play. 

But as far as the methodology, it's pretty simple. We track what we call management calls, which are introductory first calls with business owners. And you can only have 1 of those per target company. And then we just check in, sometimes over a long period of time. In the early days we got lucky in that there wasn't a lot of competition. People were responding to my outreach. If we were trying to start today, with a direct sourcing engine, I would still bet on us to do it, but it would be harder for sure. It's hard to break through. 

Alex: Let's switch gears and talk about capital allocation. I read somewhere that you and Jeff are big admirers of Berkshire Hathaway, TransDigm and Constellation Software. Speaking of Constellation, they track IRRs on a deal-by-deal basis. They call them hurdle rates. And at the group level, they look at something called the “Combined Ratio”. Which is the sum of the Return on Invested Capital and Organic Growth.

Further reading: How Constellation Software wins deals and keeps talent - while remaining ultra-frugal

What do you measure to track how efficiently you allocate capital? 

Ramsey: Great question! A couple of thoughts here. A key difference between Evergreen and Constellation is that our M&A sourcing and execution is done centrally at the Evergreen HoldCo whereas at Constellation portfolio managers are responsible for both organic growth and M&A.