Stop Wasting Time in Your Real Estate Business: How AI Agents Automate Bottlenecks
Show summary
Ben Frost shares insights on leveraging AI to streamline real estate and property management businesses, highlighting automation, overcoming challenges, and future growth opportunities.
Key takeaways
- AI should be judged on three outcomes for a business: saving money, making more money, or saving time — not on buzzwords.
- A vacation rental management company founder was spending 10-12 hours a week on bookkeeping; automating that workflow freed him to focus on raising capital for a syndicated boutique hotel project.
- Dead and old leads sitting in a CRM are commonly neglected by agents; automated follow-up workflows can pick these up consistently.
- AI agents can be built to underwrite off-market deals automatically against a company's specific buy box and target returns.
- Ben Frost uses AI agents in his own business to handle email triage and to answer and vet inbound phone calls (call setting), freeing him from those tasks.
- Frost recommends founders and team leaders focus their time on revenue-generating activities rather than administrative work like bookkeeping, and use agentic workflows with specific guardrails to take over those administrative tasks.
- Cascadia Group's client base extends beyond real estate to other SMB founders and team leaders, including a boutique consulting firm in Seattle tied to Bain Capital.
In this episode
- 00:00The real use case for AI: save money, make money, save time
- 02:53Ben Frost's focus: helping real estate founders leverage AI
- 03:25Examples: dead lead follow-up, deal underwriting, bookkeeping automation
- 05:33Ben's background: 23 years in tech and real estate
- 06:36Challenges founders face wearing too many hats
- 08:09Time saved: the vacation rental bookkeeping case
- 10:44How to contact Ben Frost
- 12:28Future growth plans beyond real estate
About Ben Frost
Ben Frost started his career in technology and began buying real estate about 23 years ago, running tech startups while investing in real estate on the side. He now runs Cascadia Group (cascadiagroup.io), helping founders and team leaders in real estate—including contractors, agencies, and short-term rental management companies—use AI agents to remove bottlenecks in lead follow-up, deal underwriting, and bookkeeping.
Listen to the audio
“The goal here with the real use case for AI besides all the buzzwords is you want to save a business money, make them more money, or save them time. Those are the three, the three goals at the end of the day.”
Ben Frost
“I believe that founders and team leaders should be spending their time on revenue generating tasks, not knee deep in their books all day.”
Ben Frost
“I don't really check my email that much anymore. I've got an AI agent that does that.”
Ben Frost
Questions answered in this episode
What are the main ways AI agents can help a real estate business?
Ben Frost says the real use cases for AI boil down to three goals: saving a business money, making it more money, or saving it time. Specific applications he mentions include following up on dead or old leads in CRMs, underwriting off-market deals against a company's buy box and return requirements, and automating bookkeeping tasks.
How much time can AI automation actually save a real estate business owner?
Frost gives the example of a vacation rental management company founder who was spending 10 to 12 hours a week on bookkeeping while also trying to raise capital for a syndicated boutique hotel project. His team automated that bookkeeping workflow so the founder no longer touches that part of the business and can focus on raising capital instead.
What kind of real estate businesses does Ben Frost work with?
He works with founders and team leaders in real estate including general contractors, real estate agencies and offices, and short-term rental/vacation management companies. He has also worked outside real estate, including a boutique consulting firm in Seattle connected to Bain Capital.
Why do old or dead leads in a CRM often get ignored, and how can that be fixed?
Frost explains that following up on dead or old leads is usually put by the wayside because agents don't go back and do it as they're supposed to. His team automates that follow-up process so it happens consistently without relying on agents to remember.
What is Ben Frost's own background in tech and real estate?
Frost started his career in technology and began buying real estate about 23 years ago, running his own tech startups while investing in real estate on the side. He says as a real estate developer he saw that the industry was behind on technology, so he was an early adopter of agentic AI workflows, which led to him helping colleagues and other founders with the same bottlenecks.
How can someone contact Ben Frost or his company?
His company is Cascadia Group, found at cascadiagroup.io. He can be emailed directly at ben@cascadiagroup.io, and he is also reachable on LinkedIn under the name Real Ben Frost.
Resources and links
- Cascadia Group’s Website
- Ben Frost on Instagram
- Ben Frost’s Email Address: ben@cascadiagroup.io
Full transcript
Ben Frost (00:00)
the goal here with, the real use case for AI besides all the buzzwords is you want to save a business, money, make them more money or save them time. Those are the three, the three goals at the end of the day. So, for instance, the, vacation rental management company that we just wrapped up with them. he mentioned that this was costing him about 10 or 12 hours a week.
just this is a founder, a founder that’s in the midst of the books. And it’s just something that’s right for an agent tech workflow to take over with very, very specific guided and guard rails on it.
Michelle Tack (00:25)
a lot.
Hi, I’m Michelle Tack from Real Estate Pros podcast and I have a great guest with us today, which is Ben Frost. Ben, we’re super excited that you’re here with us today to share your knowledge of things in terms of how you can improve efficiencies and other items using your unique software that you have built. I want to ask you
⁓ If you could Ben for those that may not come from your background or from your arena to talk about, you know, what is your main focus these days and what markets you’re ⁓ operating in.
Ben Frost (02:53)
Thanks for having me, Michelle. I appreciate the opportunity. We are primarily focused on helping founders and team leaders in the real estate space understand and utilize and leverage AI to help their business and cut down the bottlenecks and the friction.
Michelle Tack (03:11)
Can you give examples of how you do that? Ben, maybe a couple of past engagements where ⁓ obviously it was sort of game changing for for those developers, etc.
Ben Frost (03:25)
Sure. One thing we’ve done is to help out contractors, general contractors, real estate agencies, offices with their lead generation and following up on dead leads or old leads in their CRMs. That’s something that’s usually put by the wayside that a lot of agents don’t go back and actually do as they’re supposed to. So we kind of automate that process. We have helped some
real estate companies with underwriting deals based on their buy boxes, their requirements and the types of returns that they’re looking for on properties, off market properties. We’ve automated lots of those. We just got done helping a short-term rental vacation management company who was knee deep in their books every week, 10 to 12 hours while they’re trying to raise funds for syndicated.
boutique hotel projects, so you can understand they’re very busy. we just really dug into their process and what was the quicksand that was holding them back and ⁓ automated that for them. And now they don’t touch that part of their business.
Michelle Tack (04:25)
That’s awesome.
What I really loved about your background is that you have a tech and a real estate background. Can you talk about that a little bit in terms of making you uniquely situated to address these challenges that, you know, owners have?
Ben Frost (05:33)
Right. I do think I’m a little bit uniquely positioned here because I started my career in technology. And as soon as I was able to started buying real estate, both about 23 years ago. and so I’ve always been, either working at a, paying W2 job in technology or starting my own, technology startups, but real estate was always a part of that,
investment goal, as you might say. And so when I started building as the developer, obviously technology is a little bit behind in those groups. So when this newer age of agentic workflows and things come up, we were the first to jump on it and optimize many parts of our business in real estate and short-term rental management.
which organically through my network and my colleagues transformed into us helping them with a lot of these bottlenecks and friction points in their business as well.
Michelle Tack (06:36)
That’s awesome. In terms of we all, as we talked about before, have challenges in our business, whether you’re Elon Musk or, you know, the new guy that’s taking over for Apple, right? Or Michelle Tak and Ben Frost. Can you talk about some of the challenges that you have today and how you’re overcoming them? Meaning an example of something that occurred and you’re able to pivot.
and resolve the situation and still retain the client.
Ben Frost (07:07)
Sure. I think like many business owners, founders, team leaders, we wear lot of hats. So we’re trying to do the marketing, the sales, the business development, the coding, what have you. so trying to keep track and keep tabs on all of those at once is always a struggle for founders.
With that said, one of these great things with this, agentic AI revolution that we’re all seeing here is, that’s, those are some of the first things that can be remedied with building smart workflows. so we’ve actually taken a lot of that off of our, off of our plate. I don’t really check my email that much anymore. I’ve got an AI agent that does that. Of course it had to be, trained and implemented, lead generation,
AI agent that are answering phone calls and vetting prospects, call setters, if you will. And so those are lots of ways in which challenges and then we walk the walk. So we’re trying to solve these for our own business so that we have experience to help others.
Michelle Tack (08:09)
Absolutely.
It sounds like that’s obviously providing a lot more fluidity in the business, meaning you’re smoothing out some of those bottlenecks in terms of timing, etc. From a couple of the things that you implemented, I don’t know if you have statistics and I know if you don’t, that’s fine. But how much time do you think you’ve saved from implementing those types of automation?
to your business so you can go on and do other things. What do think that looks like or cost?
Ben Frost (08:43)
yeah,
the goal here with, the real use case for AI besides all the buzzwords is you want to save a business, money, make them more money or save them time. Those are the three, the three goals at the end of the day. So, for instance, the, vacation rental management company that we just wrapped up with them. he mentioned that this was costing him about 10 or 12 hours a week.
just this is a founder, a founder that’s in the midst of the books. And it’s just something that’s right for an agent tech workflow to take over with very, very specific guided and guard rails on it.
Michelle Tack (09:42)
a lot.
Ben Frost (09:56)
And so we’re very careful about that. So we solve really specific issues that free up that time. And as I said, this client, were
They’re just in the process of raising capital for a boutique hotel project, which is where they should really be spending their time. I believe that founders and team leaders should be spending their time on revenue generating tasks, knee deep in their books all day.
Michelle Tack (10:15)
Mm-hmm.
I
absolutely concur. Regardless of what you think about Jeff Bezos, what he does is the first thing in the morning, he turns off all of his electronics and spends an hour just thinking about stuff. And it could be anything. It could be a bird. I think it’s really interesting, right? And look where it is today. Well, look, I want to make sure that folks get an opportunity to, you know,
Ben Frost (10:32)
You’re right. ⁓
Yeah.
Michelle Tack (10:44)
Go ahead and contact you. Can you give some information about your contact information so that people listening can reach out? May want to partner learn etc.
Ben Frost (10:54)
Absolutely. For specific real estate business owners, cascadia group.io is our website. I can be reached at ben@cascadiagroup.io. And that’s really the best place. I’m also on LinkedIn at real Ben Frost. So yeah, those are the great places to contact me and see if we can help anybody.
Michelle Tack (11:17)
Just for those folks that may, could you just spell out your email address for folks just to ensure the correct spelling?
Ben Frost (11:24)
Sure, Ben, like
my name, yeah, sure, B-E-N, like my name, at Cascadia, C-A-S-C-A-D-I-A, group, G-R-O-U-P, dot I-O.
Michelle Tack (11:34)
That’s awesome, Ben. I really enjoyed the conversation. Oh, the last thing I want to ask you. Where is your? What opportunities you see for you in the future? You know in your next step here. For your business.
Ben Frost (12:28)
I think it’s just growth from here on out. We’ve got the capacity to help. And we don’t only do real estate. We helped out a consulting group in Seattle that works. It’s more of a boutique consulting firm that works at Bain Capital. But just with my, you know, my organic experience in the 23 years in both real estate and technology, I tend to sort of know the issues there, whether it’s a contractor.
a real estate agency or a builder. So really, I’d love to help as many of those SMB founders and team leaders as possible.
Michelle Tack (13:05)
Well, you’ve been a pleasure to speak with for those listening. Please continue to access our podcast and subscribe. Thanks a lot, Ben.
Ben Frost (13:12)
All right, thanks Michelle.