AI-powered Roll-ups: My Bingo Card for 2026
10 Predictions for where this space is headed next year
Last week I heard the news that a tech-enabled Roll-up in the Roofing space was raising capital through an Initial Coin Offering (ICO) 🤯.
This was certainly not on my AI Roll-ups Bingo Card for 2025, but it got me thinking - what are my expectations of this space in 2026? So here goes …
My 10 predictions for AI Roll-ups in 2026
1. At least 400 companies on the AI Roll-up Nexus
Let’s start with an easy one. We have ~150 companies on the list right now, and we had just started in the second quarter of 2025. I expect ~250 more companies to get added to the database next year.
2. Total capital invested in AI Roll-ups in 2026 crosses $3b
Yes, this sounds like a large number, especially when compared to the total funding raised by AI Roll-ups in 2025 so far. But it still represents only around 1 percent of total VC, and an even smaller fraction of PE capital deployed this year. My view is that AI Roll-ups will continue to grow while remaining a non-consensus category for some time. Against that backdrop, $3b feels like a reasonable first milestone for the space.
3. PE investors get into the game: at least 5 deals where PE provides follow-on capital
While AI Roll-ups have been the domain of Venture Capital so far, I feel 2026 is finally the year when PE will start figuring out a structure to partner with them. Given the low risk-appetite of PE, I predict they will get involved with AI Roll-ups during their “Growth Phase” when they have already done several acquisitions and proven that a scalable playbook exists.
4. At least 1 Venture Debt fund launches(/markets) a dedicated product for AI Roll-ups
Venture Debt funds have been very receptive to this opportunity, and I’ve been impressed at how quickly they have adopted this into their repertoire of playbooks that they fund. Still, lending to AI Roll-ups requires different guardrails and expectations compared to traditional Roll-ups. I believe at least a few Venture Debt funds will close the gap, and at least one will openly market a tailored product for AI Roll-ups
5. Launch of at least one $100m+ specialist fund dedicated to AI Roll-ups
After hundreds of conversations with founders, and investors (including the Investor Sentiment Survey), I am convinced that AI Roll-up founders need a specialist capital provider.
AI Roll-ups represent a fundamentally new value proposition for entrepreneurs seeking to transform industries through technology. The model enables sustainable scaling rather than growth at all costs, or an overreliance on financial engineering. While they may eventually be compatible with either venture or private equity capital, neither is a one-size-fits-all solution at inception. What’s missing is a dedicated fund that can provide capital purpose-built for this strategy, especially at the earliest stages.
I predict 2026 will be the year someone raises the first truly dedicated AI Roll-up fund (and I envy them!).
6. AI Roll-ups enter the physical world, with at least 5 Roll-ups heavily leveraging Drones/Robotics and Computer Vision
While we all have our eyes on LLMs, there is another powerful revolution happening in the physical world. I am looking for early-signs of new AI Roll-ups that are built on the back of these physical world technologies in 2026!
7. At least 1 AI Roll-up on each continent (except Antarctica) that has raised $50m+ capital
I strongly believe that certain geographies lend themselves especially better to AI Roll-ups, compared to others (my top pick is Europe - by a margin). Having said that, I still believe AI Roll-ups will travel far and wide, and we will have at least 1 sizable company (based on $$ raised) on every continent where humans outnumber penguins.
8. Standardized AI Roll-up Metrics become industry norms
SaaS has a Rule of 40 and the SaaS funding napkin, Crypto has a 1000 true fans, consumer/marketplaces have a virality coefficient. I believe 2026 might see a focal AI Roll-up Metric appear in a lot of fundraise decks. One would hope it’s something to do with sustainable operational efficiency/margin uplift, and not multiples expansion!
9. At least 1 video on AI Roll-ups goes viral on Instagram/TikTok with 1m+ views
I expect a Codie Sanchez-meets-Andrej Karpathy moment in 2026, where some early-to-the-game ‘Fin’fluencers start discussing AI Roll-ups; and one of them creates a breakout video!
10a. A bestseller book gets published on AI Roll-ups
OR
10b. A top-tier business school publication writes a case study on AI Roll-ups
I would assume it’s not long before a major publication like Harvard Business Review picks up on the topic. While the strategy does not exactly lend itself to mass-appeal (and we are still in the earliest stages of its evolution), another manifestation of my prediction is that a book on AI Roll-ups becomes a NYT bestseller.
So far, I’m encouraged that this category has largely been approached with a sensible growth lens rather than treated as a hype driven gold rush, and these predictions reflect that view. That said, a few of them are deliberately a bit “out there” to keep things interesting 🙂
I’m looking forward to seeing how many we can check off when I revisit this list next year. If you have thoughts on the list or believe I’ve missed an important box, feel free to DM me on X or LinkedIn.
Great read, thanks for sharing your thoughts!
Great one Sahil - agree 100%!!