Losing Your House: the Easy Way. 🏡💸

Brock's newsletter | April 3, 2026

Losing Your House: the Easy Way.

Original girlboss Sophia Amoruso describes how she almost lost two properties to foreclosure, and it's a doozy.

She moved to London, and had business managers, property managers, and accountants all watching managing her affairs— she's very successful. And yet, while randomly digging through junk mail, found a red letter from the county saying that two of her lots (out of the four on which her home sat) were going to auction.

Basically, despite her gaggle of financial advisers, she was about to lose half her home, and no one knew about it.

Just a Tiny Oversight.

I'm pretty sure she's talking about this Beachwood Canyon house she listed last year, sitting on an acre. Most large residential lots in LA are made up of multiple parcels, each with their own tax bill.

When she moved, only two out of four tax mailing addresses got updated, no one paid taxes on the other two for five years, and if you don't know what happens after five years of non-payment…the county sells your property out from under you.

As she puts it: "One accountant hadn't talked to the other, the new one didn't know there were two other parcels, and now my expensive dirt was on the LA tax assessor's website, slated for auction."

I Can Relate.

Has this kind of thing happened to me? Sort of.

Never lost a property, but things have definitely fallen through the cracks, despite my top notch accountant, bookkeeper, and team of property managers.

I once discovered I'd been paying a City of LA Gross Receipts Tax on all my rental income for a decade — only to find out from a city administrator that it only applies to three or more units. Probably sent in $10K I didn't owe. Not getting it back.

I can't even calculate the penalties I've paid on bills that went to old business addresses. I finally got a UPS box a few years ago and have spent years updating mailing addresses across hundreds of accounts.

I meet with my accountant 3-4 times a year, my bookkeeper monthly, and I get monthly statements from my property managers. Lori and I have weekly financial planning meetings where we review our accounts, investments, credit cards, and financial benchmarks. And things still get missed…

To be clear, I'm very organized. I actually like this stuff - spreadsheets and taxes and insurance and loans (well, most of the time). Which makes me wonder: how do normal people handle this?

The administrative burden of just living has become unmanageable for all of us.

Gotcha Capitalism.

Much has been written about "gotcha capitalism" - monthly charges that quietly continue long after you've stopped using a service, betting you won't check your statements. Helllooooo gym memberships and 15%-off auto-ship options.

Their profits depend on busy, distracted people. Personally, I'd be better at reviewing my statements if they weren't 5-10 pages of single-spaced, mysteriously named charges from a card Lori and I share.

Amoruso nails it:

Nobody tells you that the more you accumulate, the more administrative debt you carry. Every new property is a new set of deadlines. Every new LLC is a new jurisdiction to stay compliant in. Every new insurance policy is something else to cross-reference against the thing it's supposed to protect. The assets don't manage themselves. And the people you hire to manage them don't talk to each other.

The Solution?

She ends the piece floating the idea of a business built around solving this, but I'm skeptical it can be done.

The nitty gritty of a financial life is like parenting or health: it can't really be outsourced. And at the end of the day, you can hire all the business managers and accountants you want, but you still have to have a hand in your financial health (hello, Jonny Depp!). And the more you own, the more attention it takes.

Which is why I've always recommended an annual financial health day. Take a day off, go offsite with your partner and/or a financial advisor, and plow through everything. Start with your house and car, then work outward — every account, every policy, every LLC.

Don't skip home insurance! A lot of fire victims last year discovered too late they didn't have enough coverage.

After the fires, Lori asked me about our policy and I genuinely didn't know. I'd picked the basic plan years ago and had forgotten about it. We immediately upped our coverage.

We also just redid our estate plan (notary coming next week!), and are in the process of increasing our respective life insurance policies.

And after, tax day, we're doing our off-site - spreadsheets, policies, and financial plans to boot. We actually might need a few days…

And you should do this too! I bet you 2 lots you'll find a few things that have slipped through your own cracks…

While you're at it: check airline miles before they expire, spend gift cards, cancel the subscriptions you forgot you had. Make a plan to pay down debt, and max your retirement in the next fiscal year. Just a full financial house-cleaning, top to bottom.

Nobody's coming to do this for you. Schedule the day. I'm sure Sophia is.

-Brock

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