If you could automate one thing in your investing business, what would it be?

Question

Not a big strategy question. I mean the small recurring task you dread: chasing rent, entering rehab costs, updating a deal tracker, sending contractors payment status. Which one eats the most time for you?

Alik Levin · Answer

Eric,

Claude - front office (listings, transactions, placements, due dates, financials all up, and property management monthly cycles tracking and closing, and the books, and a few more)

Grok Bot - back office (web dev, daily ops, books records updates, socials, and a few more)

ChatGPT - spill over work in when I hit limits with either of the two above

Central "app", the system of record - Atlassian Jira for tickets tracking, JSM for owners interaction - quarterly reports and repair tickets tracking visibility, and Confluence for SOPs - this is the brain off of which all the bots feed off and switch over quickly as needed.

Richard Neese · Answer

Thanks for the thought provoking question Eric! I have a construction crew and flip/rental operation in Alabama. We spend a lot of time tracking receipts invoices and cost in general and are constantly pushing towards responsible automation. QB has some great features and combining that with AI is pretty incredible with bots and what not, but not every sub contractor/handyman etc... are digitized. Scanning and organizing docs in 3 different places is a time killer. Excited to follow this thread and get some insight on other bussinesses

Matthew Tregoning · Answer

For vacation rentals, my pick would be chasing an acknowledgment after a reservation changes. An extra night or a canceled stay can affect the cleaner, access instructions and scheduled work. I’d want the update routed to the right people, with an alert if someone hasn’t confirmed it. Sending the message is the easy part; knowing the person doing the work has seen the new plan is what would save the back-and-forth.

Akansha Sharma · Answer

From the property managers I talk to: the phone. Not the hard calls, the repetitive ones. Is it still available, what's the rent, are pets OK, can I see it Saturday, my sink is dripping. They're most of the calls, and they come in while you're at a showing. Whatever you use (answering service, VA or software), the win is having them answered from your own written facts and turned into a booked showing or a written repair ticket. Disclosure: I'm building a tool for exactly this, so I'm biased.

Alik Levin · Answer

In two words - grunt work and oversight.

Examples of grunt work:

Copy/Pasting, file download/uploads? - AI's job

Parsing endless docs to get key info (HOA rent cap or AirBNB prohibition for example) - AI's job

Examples of oversight:

Writing puffy enthusiastic property descriptions and crossing the lines? AI can catch it if trained well (not legal advice!)

Submitting endless forms and sure to miss key info - AI can easily catch it if trained well.

Eric Kleinsasser · Answer

Hi Alik, What Ai model do you use for all this? Do you have a central app where you collect and organize all the data?

Stephen Schroeder · Answer

Richard, for a crew the cost line that never comes with a receipt is labor. Receipts eventually get scanned. Hours get written down from memory at the end of the day, and that number is what the job cost report runs on. By the time the flip closes nobody can say which house ate the extra two days.

What fixed it for the crews I work with was clocking in and out of each job on the phone, with GPS behind it, so the hours land on the right house while the guy is still standing in it. Then job cost is hours times rate plus the receipts, and the drive between houses shows up as its own line instead of hiding inside somebody's day. Your sub that isn't digitized still just taps a button.

I built Orca, which is the time and GPS side of that, so grain of salt. Lee's one front door for receipts plus that for hours covers most of what you described.

Lee Futcher · Answer

Hi Richard,

Running a crew and the rentals side by side means every receipt has two possible homes before it reaches the books, so I get why scanning into three places is the time killer.

The first fix I'd try isn't more software. It's one front door for paper. Every sub and handyman sends a photo of the receipt or invoice to the same single number or inbox, with the property address and the job written on it. Nobody has to go digital beyond taking a picture.

That's the part AI handles well now. It can read a crumpled receipt, pull out the vendor, amount and address, and match it to the right property and job. A person still makes the repair-versus-improvement call and handles anything that doesn't match an open job.

Cheers,Lee

Eric Kleinsasser · Answer

Yeah, that's sounds like a real time eater. Logging eats the time you'd rather spend on the phone with sellers. What you're describing is a simple rule: when a seller says "not now," the tracker sets a follow-up date 90 days out, takes them off today's call list, and puts them back on it when the date arrives. Pulling fresh comps and rent at that point is doable too. It mostly comes down to which data source you're comfortable paying for. Do you track this in a spreadsheet right now, or a CRM? And when someone says call back in 3 months, do you usually learn why (price, timing, another buyer)? That reason is usually the field worth capturing.

The challenge you are facing is exactly the kind of problems we tackle and who we built it for. I'd be happy to chat and see if there is anything we could do to help.

Muyees Ayilara · Answer

For me it's follow-up and data entry. I'm in off-market outreach in Delray - tracking owners, skips, texts, who said call back in 3 months. I spend more time logging than actually talking to sellers. If I could automate that tracker so when a lead says not now it auto bumps 90 days and pulls fresh comp/rent, I'd save 10 hours a week easy.

If you could automate one thing in your investing business, what would it be?

If you could automate one thing in your investing business, what would it be?

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