Did You Know Your Website is Broken?

The Real Estate Espresso Podcast

Did You Know Your Website is Broken?

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Did You Know Your Website is Broken?

Welcome to the Real Estate Espresso Podcast, your morning shot at what’s new in the world of real estate investing. I’m your host, Victor Menasce.

On today’s show, I’ve got a very simple question for you: When was the last time you actually checked, I mean really checked, whether your website was working? I don’t mean just glancing on your phone, but actually verifying that every link works, every form submits properly, every automated response fires the way it’s supposed to.

If you’re like most real estate operators, the honest answer is: not recently. And in the age of AI, that’s an incredibly dangerous oversight.

Let me paint a picture for you. It’s a Friday afternoon. You’ve got a showing, maybe a lender call, and a contractor walk-through all stacked up in the middle of your afternoon. The last thing on your mind is your property management website. And somewhere earlier in the week, a third-party plug-in that was installed a couple of years ago quietly reached end of life. The contact form stopped working.

Prospective tenants have been filling it out, hitting submit, and getting nothing. No confirmation, no follow-up, no callback, nothing. And you don’t find out until Monday when a prospect calls to say they found another place because they thought you weren’t interested.

See, that’s software churn, and it’s happening in your business — every business, by the way — whether you know it or not. And that’s the reality of modern software: it’s not static. I could give you dozens of examples. Things that worked one day stop working the next for often no apparent reason.

The tools and platforms we depend on — website builders, CRM integrations, booking systems, payment portals, tenant screening services — all of them are constantly changing beneath your feet. The APIs get deprecated. SSL certificates expire. That’s an important one that’s going to change. You’re going to have to refresh that every 47 days. The Internet authorities are changing that expiry time. Even if you bought a certificate that’s valid for 2 years, you need to re-verify it, soon every 47 days, or it’ll stop working.

Third-party services get acquired; they sunset. WordPress plugins stop receiving security updates. Payment processors change their policy. All kinds of things happen. Some of this is planned obsolescence. The vendors may tell you in advance that they’re discontinuing support for a particular feature. Most operators miss that notice because it arrives as an email like the thousands that you get, and you didn’t read it.

And then there’s unplanned outages. Your email provider goes down. Maybe Amazon Web Services goes down. Your booking calendar stops synchronizing. The investor portal throws an error at three in the morning.

In real estate, downtime has a cost that’s easy to ignore and hard to quantify until it hurts you. Every broken link is a prospect who bounced. Every failed form submission is a lead that evaporated. Every investor who couldn’t log into the portal to review a document is a relationship that got a little bit colder. It’s a broken trust.

So what do you do about it? Well, this is where AI agents can change the game. Now, I don’t mean AI in the theoretical sense or even in the sense of a chat tool. What I’m talking about is setting up an AI agent that runs a daily verification suite of your entire digital footprint.

Every morning, before you pour your first cup of espresso, that agent has already visited every page of your website, clicked every link, tested every form, checked every SSL certificate expiry, pinged your integrations, and verified that your automated email sequences are working correctly. If something’s broken, you get a notification before your first tenant does.

I mean, think about that. It means you’re a multifamily operator with maybe several hundred units. You’ve got a leasing website, a resident portal, a maintenance request system, an investor update page, a contact form — all running on different platforms, all potentially breaking independently of each other.

An AI agent doesn’t get bored. It doesn’t get tired. It doesn’t forget to check the maintenance request form because it was busy on Monday. It runs the same checklist every day at the same time with the same thoroughness.

And that’s just the beginning. You can extend those agents to monitor your business’s critical systems. Are the tools your team uses internally, are they running properly? Is your property management software accessible? Did the account integration that pushed last night’s rent payment into your bank account, did that work properly? Are all automated lease reminder emails going out on schedule? Did the scheduled backup of your document storage complete successfully?

This is what I call digital property maintenance, and it deserves the same disciplined approach that your physical property inspections do. You wouldn’t go six months without walking a property, and you shouldn’t go six months without verifying your digital systems are functional either.

And the barrier to entry is fairly low. There’s lots of tools to facilitate it, like Make and Zapier, and a growing ecosystem of purpose-built monitoring agents that can be configured without being a developer. Now, if you have a developer on a contract, that’s awesome, but you can often do a lot of this with simple tools, like cloud co-work and cloud code.

Operators who are going to win in the next decade are not necessarily the ones who have the best properties, but the ones who can execute consistently. The action you take today is to make a list of every digital system in your business. Which ones are you depending on every day? And then ask yourself: How would I know if it broke at midnight last night? And if you don’t have an answer, that’s the starting point.

Now, I run several businesses, each with their own website, each with their own business systems. For example, we had a contact form in my wife’s mental health care clinic. Someone changed a password. Nobody noticed that there was a problem, and 130 new client inquiries did not get sent to the intake staff. It went unnoticed for weeks. Most of those new clients went to other clinics. We spent marketing dollars on them. We spent Google AdWords dollars on them, and almost all found other therapists. We recovered maybe half a dozen out of the 130 by doing callbacks, but that’s a huge financial loss that could have been avoided.

That’s happening in your business, whether you know it or not. Now is the time, when it’s never been easier than ever, to create automated verification tools, and it’s irresponsible to not implement them.

As you think about that, have an awesome rest of your day. Go make some great things happen. We’ll talk to you again tomorrow.

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