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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For the majority of my 20-year career, small-time M&A was decidedly uncool.

Now all of a sudden, everyone is chasing $0.5M EBITDA technical services contractors and accountancies.

The usual buyers - lower middle market PE and search funds - are competing for deal flow with Silicon Valley’s brightest minds.

Is this just another instance of the “AI” buzzword attracting capital, or is there more to it? What are “AI rollups”- and which ones should you be backing (if any)?

You’ve come to the right place to figure this out. Since 2023, at RollupEurope we have published 100+ deep-dives on serial acquirers of just about everything, everywhere. Software, car washes, coffee shops, anaesthesiology practices, e-commerce brands.

We’ve developed a deep understanding of the “DNA” of successful buy and build strategies. Whilst AI rollups have their nuances, I believe many of the patterns are the same, and we can learn a lot from the successes of others.

Note: this article first appeared as a guest post on The Odin Times - a blog of the investment platform Odin.

Odin lets anyone, anywhere launch and run a private investment firm online, and work with over 10,000 VCs, angels and founders globally. You can launch an SPV or fund vehicle in less than a day. Find out more here.

1. The thesis: what are AI rollups - and why should they work in theory?

Not long ago, I posed this very question to two thought leaders in the AI rollup space: Cyrus Hessabi from Shore Capital (back then at OpenOcean) and Sahil Patwa from Unbound. Cyrus’ and Sahil’s answers informed my article Missed out on crypto, tempted by AI rollups?

You can dig into the details there, but TL;DR:

• AI rollups are technology holding companies that grow by acquiring distribution through M&A (rather than through sales). In theory, in the markets they target, it is cheaper and faster to grow this way - rather than to sell tech to incumbents that are often SMBs

• AI rollups work best in stable, regulated industries where customer relationships are sticky and switching costs are high

• The two-step playbook goes like this.

  • One, find industries with
    a) high quality revenue (recurring, high cash generation) and
    b) high volumes of repetitive, labor-intensive workflows.

  • Two, automate these workflows with AI, in order to unlock genuine productivity gains for human employees (more customers served per FTE etc.).

For me, the distinction between “AI enabled” rollups and the traditional kind lies in the extent to which the operating models of the acquired businesses are disrupted.

If you’re ripping up the tech stack, re-educating (or firing) the workforce etc. - then chances are you’re running the AI playbook to justify the mayhem.

Some examples of this from a few different industries:

• Property management:

  • Buena 🇩🇪 - raised $58m from 20VC and GV announced July 2025

• Lettings agencies:

  • Dwelly 🇬🇧 - recently closed series B led by General Catalyst

• Marketing agencies:

  • 2X 🇺🇸 - Insight Partners led a growth round announced March 2025

• Accountancies:

  • Crete 🇺🇸 (backed by Thrive) is planning to spend $500m on acquisitions in the coming years.

  • Integral 🇩🇪 - raised €12m from General Catalyst & Cherry Ventures

  • Bhub 🇧🇷 - raised $55m from Valor Capital, Hedosophia and others

• Wealth Management:

  • Savvy 🇺🇸 - recently raised a $72m series B from Industry Ventures, Thrive

  • Clove 🇬🇧 - from Paddle founder Christian Owens & Trouve cofounder Alex Loizu, launched with $14m in pre-seed funding from Accel, Kindred and Air Street

• Call Centres:

  • Crescendo 🇺🇸 - secured a $50m series C from General Catalyst

There are many more, from the above industries and others.
You can access the full list here - kudos to Sahil for maintaining it!

What makes AI rollups, in theory, a smart approach for these industries?

The incumbents have a poor understanding of technology. They’re extremely fragmented markets. Finally, there is a large volume of fairly repetitive “human in the loop” workflows that LLMs - in theory - can eat.

However, make no mistake, an AI rollup is not a normal startup. Executing on the AI rollup playbook requires a unique set of people and skills.

2. Execution: the 3 types of rollups, the metrics they target, and the skillsets required to run each one

When I worked for a ride hailing platform, the most impressive individuals I came across were city launchers.

These people were like paratroopers. They would land behind the proverbial enemy lines, mount surprise assaults, plant the flag and, after 100 days or so, fly off to the next operation.

In the rollup world, dealmakers are city launchers. They develop the equity story. They raise money. They source and close deals. And then exit.

They tend to come from investment backgrounds and excel at Type 1 - aggregators.

• Focus on a single industry - think dental practices or HVAC

• Acquire multiple businesses fast

• Have a clear and relatively short (3-5 years) exit strategy

For example, Simago built and exited a $600 million radiology rollup in less than three years, while the founders were still in their early 30s.

Charles-Henry Beglin, the man who built Simago, strongly believes that the founding team (he doesn’t believe in solo founders) must include at least one person with a PE or Corporate Development background.

Why? Two reasons:

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