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Maui, HI
Joined November 2012
At 24, I told a guy at church I wanted to buy an apartment complex. He said, "Hmm. I actually have a 24-unit I want to get rid of." It still took a year. I managed it for him first. Did the maintenance myself. Learned every unit. Then he sold it to me on seller financing. It was 60% empty. It took a couple years of hustle to fill it. But once it was full, it threw off enough cash flow that my wife and I both quit our jobs. That freedom is the only reason I could take a risk on a little startup called BiggerPockets. Which eventually led to 13,000+ units. If you want your one deal, here's the playbook: 1. Prove yourself small first. I read 100+ books my first year, did a couple house hacks and a flip with a partner. 2. Pick one clear target. Mine came from reading Ken McElroy's ABCs of Real Estate Investing. 3. Say it out loud to other investors. Deals find the people who've announced what they want. 4. Offer to manage it before you buy it. A tired owner hands seller financing to the person who's been handling his maintenance calls for a year.
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A buddy called me a few years back. "Our triathlon relay swimmer backed out. You live in Hawaii. You can swim, right?" I surf. I don't swim. I practiced once. Then jumped into Lake Coeur d'Alene for a 1.2-mile swim. Five minutes in I was flailing 20 feet from shore while grandmas passed me. I was looking for the kayak guys to pull me out. So I stopped staring at the finish line and went back to basics: Arm. Arm. Arm. Breath. I started passing people. Then I looked up. I was way off course. My 1.2-mile swim turned into about 1.7. That's real estate. Finish line = your monthly freedom number. Buoys = this year's property goals. Look up and check them. Strokes = what you do THIS week. My stroke list if you're chasing your first (or next) deal: - Talk to 3 agents - Take one old dude from your market to lunch - Analyze 12 properties - Track it If you don't track it, you don't do it. Head down. Look up at the buoys. Repeat.
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Maybe I’m just drinking the koolaid here… but it sure seems GrokBot is improving 100x faster than Claude or OpenAi. Every day it’s faster, smarter, and easier to use. Is this the singularity, @elonmusk ?
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If I lost everything tomorrow — money, properties, businesses, contacts — I still think I could get financially free again. Not because I'm special. Because after ~20 years and almost 14,000 units, I know the patterns… and the mistakes that waste years. Here's exactly what I'd do at 41 with nothing. No unfair advantages. youtube.com/watch?v=JZbfkkzd…
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It took ChatGPT about 39 seconds to spit out the "11 best rental markets" in America. I'm almost 20 years in with nearly 14,000 units across 20+ states… so I ran the list. Some of it's useful. Some of it will get you hurt. Also: $1,500 rent with $1,200 PITI is NOT $300/month. Repairs, vacancy, and CapEx still exist. Exact prompts + my take: youtube.com/watch?v=thjxUWns…
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Cash flow isn't dead. The light moved. Same $250k house that worked at pandemic rates got crushed when mortgages hit 6–7%. Meanwhile: a 10-bed co-living near Atlanta at ~$800/bed → ~$8k income (vs ~$2k as a normal rental) and over $1,000/mo pure cash flow with about $20k still in the deal. Where the cash flow actually is in 2026: youtube.com/watch?v=Mz3U8aqr…
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Watching @elonmusk launch the @Tesla Roadster with my six-year old son... will go down as a core memory for both of us. We both screamed and jumped up and down when that car flew!
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Ok… Whoa. Grok @bot inside my team’s @SlackHQ is next level cool! Now, I have different bots focused on different things… and in the right channels that my team can interact with. This is the future, now.
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Claude Artifacts are SO freaking helpful for a real estate investor. Literally… make charts and graphs and dashboards that update automatically. Email lists, rent deposits, cash flow statements, expense reporting, maintenance requests…. Whatever you care about and wanna see. You don’t need to rely on your crappy PM software anymore. Just point Claude at the Data and have it cook. Make it showcase data how YOU want to see it.
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Asking prices: down year over year for 38 straight weeks. Rents: up 2.7%, fastest pace since April 2025. Buyers are waiting. Renters are paying. If you buy on rent instead of appreciation, the math just quietly got better.
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How to buy your next rental without your W-2 getting a vote: Use a DSCR loan. It qualifies on the property's rent vs. its payment, not your tax returns.
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Underrated investor advice: Get real insurance quotes before you sign. Not last year's number. Ask the tenants what's broken. They always know. Call the property manager before the listing agent. Write the job post like an ad. Five drafts, not one. Boring wins.
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Your kids won't remember the cap rate. They'll remember whether your chair was empty at dinner.
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Would you be proud if your kid grew up to be exactly like you? Not your net worth. Your Tuesday night habits. That question has fixed more of my business decisions than any spreadsheet.
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Simple test for any deal: Can you explain it to your spouse on a napkin? If not, you don't understand it yet. Confusing isn't smart.
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Walk the property at 7am on a Tuesday. Sellers stage Saturday. Tuesday tells you the truth: parking, smell, neighbors, who actually lives there. You can't underwrite a photo.
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Underrated investor advice: Protect bedtime stories harder than you protect your IRR. I've watched guys with thousands of doors feel empty, and guys with 30 feel rich. The scoreboard isn't units. It's whether your kid still wants you in the room.
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How to actually work ON your rentals: Stop being the emergency contact for every toilet, text, and late-night deal panic. Build the system that answers before you do.
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The bubble will burst. And Ai will just continue to take over. Dont let your fear of the market make you miss out on the technology. Learn it or be left behind.
why do people think that if the ai bubble bursts, that ai is gone ai is not going anywhere
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Agreed… but it’s not like home developers are just making massive profits right now. The cost of a home is high because every single part of the build is more expensive due to inflation. And that’s gonna get worse. So we have to find a better way to build, or a different model for living.
I don’t know who needs to hear this but we need to build a ton more houses or we risk Gen Z checking out from life. Just so many young people think it’s not even worth trying for the American Dream. When the mean house price is over $400k, we got a problem.
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