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First things first, I did something I am not proud of.

I skipped an issue of this newsletter.

I am sorry for missing last week. I missed engaging with you all, and not seeing your responses in my inbox felt strangely heavy. But the pause was in service of something greater - two beautiful events that reminded me why this platform exists in the first place.

Previously, Huntsman sophomore Elyse Lin broke down the proptech market from a fresh Gen Z perspective. You can read that piece here. This week she is back with the second installment and a full market map outlining where early stage investors should be paying attention.

Layered on top of her qualitative view, the numbers underscore just how quickly AI and automation are reshaping the space. Recent estimates put the global proptech market on track to roughly double over this decade, with AI‑enabled solutions growing even faster. In parallel, surveys show that a clear majority of real estate executives expect AI to transform the industry within the next five years, and that adoption of AI‑powered tools for tasks like predictive maintenance and energy management is already becoming the norm.

Taken together, Elyse’s market map and the latest data point to a simple conclusion for early stage investors: the next wave of outsized returns is likely to cluster where workflow automation and AI directly touch P&L—reducing operating costs, compressing leasing cycles, and unlocking new revenue streams in previously analog corners of the value chain.

If you want a downloadable copy of the map, send a note to [email protected]

Written by Elyse Lin. Elyse is currently a sophomore in the Huntsman Program at the University of Pennsylvania.

In real estate, one thing I often hear is that “real estate is a people business.” Transactions have traditionally been face-to-face, pen-and-paper, and driven by networks. Brokers were often friends of friends; rentals were found through newspaper listings or a serendipitous stroll past a “For Lease” sign.

But today, like most industries, real estate is being transformed into an algorithm business.

Each stage of the property lifecycle, from acquiring building permits to screening tenant pets,  is being modernized by technology. Yet, because of the physical nature of real estate, many blank spaces in proptech remain question marks. Below is an overview of firms to keep an eye on in this new AI era.

Acquiring permits, drawing floor plans, and managing construction delays have long been pain points in development, often stemming from miscommunication. Many proptech startups are now attempting to tackle these developmental inefficiencies.

PermitFlow, for example, streamlines the lengthy permitting process; Resolve and OpenSpace enhance visualization and spatial planning; ArchiLabs is building a “ChatGPT for Revit,” Autodesk’s flagship design software. The goal is clear: reduce the small missteps that can derail entire projects and make construction as seamless as software development.

When people think of proptech, they often think of transaction-driven companies like Zillow and Redfin. Features such as Zillow’s home price estimator and Redfin’s 1% agent model have already begun to reshape how homes are bought and sold.

Now, the next wave of disruption comes from AI-powered real estate agents, such as Ridley and Homli, which aim to let sellers list, market, and close deals entirely on their own. With more consumers comfortable with self-service (case in point: self-checkout at grocery stores), it’s unsurprising that home selling is becoming another “DIY” experience (with, of course, the added benefit of saving on commission.)

Editor’s note: This newsletter first featured Ridley in July (read here). Last week, the company announced a $6.3 million seed round led by Fifth Wall.

Landlords often wear many hats: accountant, salesperson, maintenance coordinator. Unsurprisingly, this segment of proptech is seeing, perhaps, the most rapid innovation.

Data-driven platforms like Keyway and CoStar help landlords set optimal rent rates; Whale simplifies security deposits through mobile payments; Baselane and Zuma automate rent collection; Measurabl supports ESG compliance; and Haven AI handles predictive maintenance. Together, these tools form an all-star digital team that allows landlords and investors to manage properties more intelligently and efficiently.

Interestingly, experience-based proptech was the most underrepresented segment in my research. While firms like PetScreening verify tenant pets, Bilt Rewards gamifies rent payments, and Spaceflow enhances amenity operations and community engagement, there are far fewer companies here than in management or transactions. This could signal a gap in proptech still waiting to be filled, or simply a space that is inherently less suited to technological disruption. 

One notable player, Homeroom, focuses on younger tenants by facilitating roommate matching, digital rent payments, and in-app landlord communication, speaking to younger generations’ preference for convenience and digitized living experiences

As real estate has historically been viewed as a traditional, low-tech industry, and AI represents the latest frontier of innovation, the intersection of the two in proptech can feel like a juxtaposition. But if anything, it signals the dawn of a new era for real estate; an opportunity for real estate to evolve without losing its human core.

Proptech isn’t about replacing relationships, but about re-engineering how we collaborate, communicate, and create greater value in our various spaces. Hopefully, this new era invites the industry to be both high-tech and still remain a “people business.”

Proptech is not about replacing relationships, but about re-engineering how we collaborate, communicate, and create value in the spaces we share. And at Bear and the Bull, we want to champion exactly that spirit: independent analysis, rising voices like Elyse’s, and deep dives that help us see the future more clearly. If you would like to help make more work like this possible, consider a subscription.

🎧 A new Money Memories episode is live, featuring Grant from Affinity Credit Union. It is the first time I have brought someone from the credit union world onto the show, and his story is a thoughtful look at financial wellbeing, family dynamics, and how early money memories shape entire careers.
👉 Listen on NPR, Apple, Spotify, or wherever you listen to podcasts

🖊️ It was a busy period for fintech coverage, here’s the stories that I am pleased to share:

👉 Read on Forbes

💬 The 5 Questions With format has proven to be one of the most popular additions to this newsletter. I will be highlighting more founders and executives in the coming weeks. If you would like to be featured, simply reply to this email.

📌401(k)s Are Minting a Generation of ‘Moderate Millionaires

📌How Pokémon cards became a stock market for millennials

There will also be some structural changes coming to this newsletter to ensure I can continue delivering high-quality insight, research, and a wider range of voices across this platform.

I always welcome your feedback. And don’t forget to click on the link below!

Till next week,
Ilona