EP 72 – Revolutionising Group Travel with AI
June 2, 2025
Dave:
Hey everyone, Dave here with another episode of the Philly Tech Connect podcast. Today I’m speaking with Will Schmahl, a repeat founder and the visionary behind Housemother, an AI-powered app revolutionizing group travel and stay management. A former Airbnb super host and tech leader, Will combines deep industry knowledge with technical expertise to simplify travel logistics. Will, how are you doing?
Will:
Good. How are you doing today?
Dave:
I’m doing well. You guys presented, geez, maybe a year ago at our first pitch event that we did. So it was really cool kind of, you know, getting the introduction into the concept. And I suspect there’s probably been some changes over that time period. So tell us a little bit about your background in the travel space and your experience being an Airbnb super host.
Will:
Sure. So my career started out in the MarTech ad tech industry, but I’ve always been a traveler like everyone else. But really my roots in the travel industry — from an operator aspect — was having a beach house out on Fire Island, New York that I’ve shared every summer for the last 26 years with my sister, splitting the house between her friends, my friends, and our family.
That led to buying properties in Fort Lauderdale and becoming an Airbnb host. Hosting friends and family can actually be more of a nightmare than hosting strangers. You want everyone to have the best experience, and at the same time, you’re trying to avoid a logistical disaster.
Dave:
Yeah, for sure. I mean, I can imagine it’s tricky. I’ve never owned property with another individual before, especially one that you rent out to others. Even if it’s a sister, I can imagine there are conflicts. What dates does each person get? What are the rules? Was that your experience, and did it prompt the idea for Housemother?
Will:
Yeah, exactly. You hit it on the head. Housemother is all about the organization and optimization of in-stay or on-trip needs. Coordinating dates, tracking who can or can’t attend, figuring out logistics like ferry schedules, organizing groceries—all of it.
My house is on an island, with only one expensive supermarket. So planning who brings what, managing budgets, and not forgetting essentials became a big deal. That’s where Housemother came in. I didn’t want to carry all the responsibility alone and wanted everyone to be in the loop.
We don’t handle bookings like Airbnb, but travelers can search for homes or groups with open beds or rooms, match interests, message the planner (aka Housemother), and potentially join a stay. They can be billed for shared expenses through the app.
Our goal is to be booking-platform-agnostic. We’re actually raising funding to white-label our app and license it to hosts or platforms like Airbnb or Booking.com to manage group logistics post-booking.
Dave:
Very cool. It feels like the actual booking process has been solved, but what happens after booking — like managing the stay — is still very analog.
So you’re trying to handle the next step, right? Both for the property owner and for travelers?
Will:
Yeah, definitely. Our focus is to stay out of the host ecosystem — even though I’m technically a host. The tool isn’t for hosts in the traditional sense. It’s for the group on the trip.
We’re really focused on short-term rentals and seasonal homes. These have multiple weeks and lots of turnover, so the logistics get complicated. By focusing on travelers and not the booking side, we avoid bias and build a truly group-first product.
We’re now building safety and risk mitigation tools powered by AI. For example, imagine you’re on the beach and a friend gets caught in a riptide. You could trigger an SOS via voice command, and Housemother would alert your group and local emergency services — even in the appropriate language.
Dave:
That’s wild. But makes sense — keeping the tool focused on the group, not the host, gives it clarity of purpose.
I also noticed your emphasis on groups. Is that because complexity rises fast once you have more than one traveler involved?
Will:
Exactly. Most travel isn’t solo — it’s two or more people. That’s when problems and inefficiencies show up: shared costs, logistics, plans. One person missing a ride can snowball into a huge disruption.
That’s the sweet spot for Housemother. There are no tools focused on group logistics during the trip. We aim to be the first.
Dave:
Yeah, I’ve seen AI pop up in planning — like using ChatGPT to suggest places or itineraries. But that’s all pre-trip. How do you think AI can improve on-trip experiences?
Will:
Right now, AI is mostly used for fast responses and basic planning. But I see the real opportunity in on-trip data and context. Housemother is one of the first apps truly designed to be on the trip with you.
Right now, we’re still a utility—you input something, you get an output. But we’re working toward being proactive.
In the future, AI can support group travel by using real-time data. For example, if you’re in Japan, wouldn’t it be great to connect with a local community in each city you’re visiting and get relevant, real-time recommendations?
Static sources like TripAdvisor or outdated blogs aren’t cutting it anymore. Travelers want community-driven, dynamic updates.
Dave:
Right, it’s that live relevancy. Someone might mention a festival today that wouldn’t appear in a two-year-old blog post.
So what’s next for Housemother? And how can people get involved?
Will:
We’ve been quiet on marketing because we’re refining our data and user cases. With our current funding round, we’re building out a white-label solution and doubling down on real-time, on-trip optimization.
We want to surface offers and experiences (like local shops, fashion designers, wine tastings, etc.) that are underbooked — during the trip, at a discount. Think of it as filling empty seats or reservations that would otherwise go unused.
That’s how we plan to generate revenue: by capturing those missed opportunities and matching them to the right groups.
We’re looking for users to test the app, advisors, partners, especially people in real estate or hospitality.
Dave:
Awesome. Thanks so much, Will, for being on the show.
Will:
Thanks, Dave.