Road To Carry is proudly supported by Reef Pass Investors
Reef Pass is a US based investment partnership that specializes in launching serial acquisition and HoldCo platforms (most often launched by ex-PE professionals).
Reef Pass brings decades of experience building acquisition platforms and flexible mandate across incubation and growth stages with a long-term capital base.
If you've ever thought seriously about launching your own acquisition platform, I'd love to hear your thesis!
Note: this partnership does not impact editorial independence.
A few weeks ago, we sat down with Ed Brandman (former CTO of KKR) to talk about how AI is quietly changing the way PE firms themselves operate.
Today, we go one level deeper into the stack — how AI is changing the companies PE (and VC-backed) firms are actually buying.
I recently sat down with Ilia Drozdov, Co-Founder & CEO of Dwelly, a UK-based AI-powered property management platform that:
Recently raised $93 million, led by General Catalyst and Trinity Capital
Made 10+ acquisitions in under two years
Punchline? His first acquisition went from 15% to 40%+ EBITDA margins leveraging AI. But he’s got bigger ambitions—instead of optimizing margins, he’s funneling everything into growth so he can become the dominant player and eventually evolve into a tech-enabled marketplace.
This one is for anyone who has ever rolled their eyes at the phrase "AI-enabled roll-up", or anyone tempted to start one.
State of Play
If there's one thing Ilia wants you to take away from this conversation, it's this:
AI-enabled roll-ups are not "PE roll-ups with a little AI on top." They are tech companies whose go-to-market strategy happens to be acquisitions.
We talked about:
Why AI-enabled roll-ups are structurally different from PE roll-ups
Concrete operational wins in tenant screening, maintenance, and pricing
Why the first Dwelly agency went from 12% to 40%+ EBITDA (and why that's not the point)
How AI-enabled roll-ups approach integration and change management
Which fragmented services industries actually fit the playbook
If you prefer to listen to this interview, you can find it here.
If you’re new to AI-enabled roll-ups, the core thesis is entirely different from traditional private equity. Financial engineering and scaling back-office costs are secondary. The primary goal is fundamentally redesigning how a service is delivered to the end customer from the ground up.
Here is my conversation with Ilia on what it takes to build a modern AI-native acquisition platform.