🏠 I help people build wealth without losing their soul 🏦 BetterLife Funding 🏢 13,000+ doors ❤️ Jesus, Family, Beard 🤖 My weekly personal newsletters ↓
Maui, HI
Joined November 2012
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I was fine where I lived.
Fine. Not happy. Fine.
Then real estate bought me the option to live where I'm happiest, and I took it.
If you don't love where you live right now, you are not stuck. You're just short one thing, and it's income that doesn't care what zip code you're in.
My favorite rental lost $35,000 last year. Nobody flagged it until I asked for the report.
It's the fourplex I bought the week my daughter Rosie was born. The plan: let tenants pay it off by the time she turns 18, then hand it to her for college.
Here's EXACTLY what went wrong, and the 15 minute monthly check that would have caught it -->
If you own even one rental, put 15 minutes on your calendar the first week of every month, per property:
1. Rent collected vs rent owed. Not "occupied." Collected.
2. Every utility and fee you're supposed to bill back. Is it on the ledger?
3. Repairs this month vs your budget.
4. Any unit vacant or 30+ days behind. Ask your manager why, by name.
Two bad months in a row on any line? You call your manager that day -->
Hate spreadsheets? Upload your owner statement to ChatGPT or Claude and ask:
"Compare this to last month and to my budget. Flag anything that moved, and any utility I'm paying that should be billed back to tenants."
Takes you 2 minutes, and it never gets bored of reading statements.
Go pull last year's report on your rentals this week. Seriously. Mine was a $35,000 surprise.
What people THINK will make them rich:
- skipping a latte
- 401(k)
- 9-5 jobs
- luck
What ACTUALLY makes you rich:
- owning real estate long term
- building a business and running it well
- making asymmetric bets
- time
What do you guys think? Move in FEE instead of DEPOSIT?
Stopped charging security deposits years ago.
Best decision I made as a landlord.
Here's the math on 100 units.
Security deposit of $2,000 each.
10 tenants do $4,000 of damage. That's $40,000.
You only have $20,000 of their deposits. You eat the other $20,000.
And you hand the other 90 deposits back.
Now charge a $1,000 move-in fee instead. Not refundable.
You collect $100,000. It's yours.
Same 10 tenants. Same $40,000 of damage.
You still keep $60,000.
That's an $80,000 swing.
And tenants like it better because they need half the cash to move in.
The really aggressive players are starting to charge both. But i think that’s overkill.
I built a bookshelf over the past month, by hand, so I could turn a space bedroom of mine into reading room… so I could read more.
I could have just grabbed a book.
But sometimes I turn to working on “the container” rather than the “contents of said container.”
Sometimes it’s ok- the bookshelf was therapeutic. But many times it’s simply what Author Steven Pressfield calls Resistance in “The War of Art” (not the “Art of War.” Clever play on words. One of my favorite books.)
I’m guessing I’m not the only one who would rather work on the container than the contents.
Most real estate investors spend months building the container and never fill it.
The LLC before the first offer.
The CRM before the first lead.
The deal analyzer with more tabs than deals.
The logo. And business cards. And website.
Containers feel like progress because you can finish them. The Content is scary because someone can say no to it. Judge it. Laugh at you.
The content takes effort. Work. Time.
It’s usually hard. So we work on the container instead.
So here's the test: at the end of today, did you do anything a seller, a tenant or a lender could say no to? Did the work you did move you closer to your goal, or just set you up to do the work later?
Containers are good.
Just make sure you make time to actually “read.”
The hard money lender who told me no... was right.
I didn't listen. I found another lender and bought the duplex anyway.
Here's what it cost me (ouch!) and EXACTLY what I do now instead) -->
The Hard Money lender told me no because he thought the deal needed way more work than I was projecting.
He thought I didn't have the experience to pull off a flip that big.
He thought my ARV was too high
He said no.
I took it as a roadblock, and I went looking for someone who'd say yes.
Someone did. That was the expensive part.
So here's my checklist now -->
1. When a lender says no, ask exactly why. Write it down word for word. And respect the fact that they've got hundreds of reps, and they probably know more than you.
2. Don't shop around for a yes until you can answer that why with numbers.
3. Bring the binder. Photos, rehab budget, comps, exit plan. And pad the rehab budget by 15%.
A no from a good lender is free advice. I paid $15,000 to learn that. You don't have to.
If you just:
- Analyze one deal a week
- Close when you say you'll close
- Actually care about your tenants
You're already ahead of 99% of investors.
This is my favorite commercial ever. So much nostalgia.
'Real estate doesn't work anymore.'
That's what people say... until they see the same house run five different ways.
So stop asking IF real estate works. Ask HOW it works.
Here's EXACTLY what I mean -->
Ask yourself four things:
1. What do you actually want more of, money or time?
2. Who runs it day to day? If it's you, count your hours as a cost.
3. Is it allowed at THIS address? Check zoning and licensing first.
4. What's the plan for the empty months?
And here's the part I really want you to keep -->