47 acquisitions in 2025, and 25 in 2024 — but how?

Buyers and Buidlers,

Recognize some familiar faces in this photo?

Here is a small hint:

Anyway…

It’s me, Ramsey Sahyoun (Co-Founder and Head of M&A of Evergreen) and Alex (Co-Founder of RollupEurope).

And yes, we finally recorded the episode.

When I asked Ramsey—after he and his team had done over 160 acquisitions—where they want to grow the company over the next 4 years:

"We aim to 3x revenue and 4x free cash flow, to $5 billion and $1 billion by 2030. That’s not just about buying more companies. It’s three things: accelerate acquisition pace, grow organically at double-digit rates and expand margins.”

Secondly, I asked, ‘after doing 47 acquisitions in 2025 and 25 acquisitions in 2024, what is the biggest takeaway from sourcing?’

"I think 80% of our deals are proprietary. We've always believed that you can hustle and if you roll up your sleeves, you can get opportunities that other people don't see. We don't just kind of sit and let deals come to us.

Secondly, persistence. And persistence is one of our three core values at Evergreen, and a big reason for that is that I personally feel like anything worthwhile I’ve ever accomplished required a lot of persistence.

An example of this was a business we acquired in 2022, a great company out of St. Louis, called GadellNet. The guy that ran the business was someone I got in contact with in 2017, but that wasn’t the right time for them to consider selling it.

So, we continued to check in, were persistent over five years and finally in 2022 he called me on a Friday, and said ‘hey, you know my other partners are open minded to selling the business now. If you’re ready to talk about this we have to move quickly.’

This was after five years of talking to someone and getting nowhere. We ended up signing an LOI the following week and closed the deal within two months."

This, and many other great stories, in this long-awaited podcast episode with Ramsey, building what might be one of the most interesting HoldCo stories in America.

(Over 850 downloads within the first 7 hours of going live.)

Here are the links to Apple Podcasts, Spotify and YouTube.

On the surface, Evergreen is “just” a serial acquirer in technology services (think IT managed service providers and application software companies).

In reality, they are building a decentralized compounding machine.

Since starting in 2017, Evergreen has completed 160 acquisitions, grown to roughly $1.5 billion in revenue and about $250 million in adjusted EBITDA, while still putting up around 10% organic growth. Those numbers alone are impressive. Here is the story of how they are doing it, I hope you enjoy:

Links to Spotify, Apple podcasts, YouTube.

The following is the newsletter I first sent to readers right after the Serial Acquirers Conference in Stockholm, but as hundreds of new people have signed up since then, I believe it’s worth rereading, as their model works extremely well.

During our in person conversation in Stockholm, Ramsey said he’s forever thankful for Alpine Investors (they’re previous employer); when they decided to leave, Alpine stepped in to back their next project, which today is Evergreen. (note: Alpine still owns the majority.)

“It’s been one acquisition and one key hire at a time.”

Let’s describe their model, which is simple to describe but very hard to replicate.

They buy and hold businesses indefinitely. They keep the structure decentralized. They preserve the identity of the companies they acquire. And then they layer in what Jeff called the real economic engine: M&A, talent and playbook.

That triad seems to be the key.

The first leg is obvious: they are exceptional acquirers. Evergreen has built specialized M&A teams, strong relationships with founders, and a proprietary sourcing engine. The majority of their acquisitions appear to be off-market, which matters. In any roll-up, proprietary deal flow is one of the clearest signs that the company has become a preferred home for sellers rather than just another bidder in an auction.

The second leg is more important than most people realize: talent. Evergreen is not only buying companies. They are recruiting leaders, placing operators, and building a bench that can scale across the portfolio. They have placed talent in more than 80% of acquisitions. That tells you this is not a passive capital allocator. It is an operating HoldCo that understands the biggest bottleneck in scaling service businesses is usually leadership.

The third leg is the playbook. This is where serial acquirers separate themselves from ordinary consolidators. Evergreen is not trying to centralize everything. They are trying to create repeatable methods that local operators can use to grow faster, improve margins, and serve customers better. That includes go-to-market initiatives, service delivery improvements, and increasingly AI-driven experimentation inside the portfolio.

The last point stood out to me.

A lot of companies talk about AI in vague, promotional language. Evergreen’s framing was much more practical. They see AI as a tool to expand value proposition, scale service delivery, and create new revenue streams. In other words, they are thinking like operators. Use AI to automate workflows, improve ticket routing, launch advisory services, and reimagine delivery models.

Another thing I found interesting is how directly Jeff positioned Evergreen relative to the Swedish serial acquirers. At the end of his presentation, he openly acknowledged the inspiration.

The shared DNA is clear: decentralized operations, long-term ownership, strong cash flow orientation, and a belief in organic growth on top of acquisitions. But Evergreen is also building its own distinct version of the model. Unlike many of the Swedish DSAs, they are pursuing a higher-velocity M&A strategy, focused specifically on technology services, and they are reinvesting 100% of free cash flow back into growth rather than emphasizing dividends.

That makes Evergreen feel less like a copy and more like an American evolution of the model.

The current operating structure also shows real intentionality. Evergreen sits at the HoldCo level with a relatively lean team, and beneath it are focused operating groups like Lyra, Pine, and Cedar. Each has its own niche inside technology services. Lyra is a technology managed services provider for SMBs. Pine focuses on cloud ERP managed services. Cedar serves government agencies with technology solutions. This is not intentional diversification. It is a portfolio being built around adjacencies inside a broad and growing technology services market.

And that market is massive.

The slide on market opportunity framed Evergreen’s current scale against a huge global technology services TAM, supported by secular tailwinds like AI adoption, cloud migration, cybersecurity, connected devices, and increased outsourcing.

Evergreen’s $1.5B in sales, Global MSP (Managed Service Provider) $360B and Global Technology Services market being $1.4T.

That is what makes the model especially compelling: this is not a roll-up in a stagnant industry. It is a roll-up in a fragmented market that is still growing underneath them.

The performance slide may have been the most impressive part of the whole presentation.

The EBITDA chart showed a business that did not spike from one transformative deal. It climbed steadily, quarter after quarter, through phases: building the foundation, high-pace MSP M&A, expansion into multi-vertical, and now organic growth plus international scale.

Evergreen is not merely buying revenue. They are trying to build the best permanent home for technology services businesses and their leaders.

The best serial acquirers understand that their true product is not capital. Their true product is being the most attractive long-term destination for great companies, founders, and operators. That seems to be exactly how Evergreen thinks.

If they can continue to combine proprietary M&A, operator density, and playbook-driven organic growth, this could become one of the most important HoldCo stories to study in the next decade.

And probably the most exciting part for me personally, again:

The conversation with the other co-founder of Evergreen, Ramsey. (Listen on Apple Podcasts or Spotify)

Enjoy!

That’s all for this week.

Take care,

Mikk Markus / PrivateEquityGuy