From Dad · September 2026

Bored? Build something.

You told me you were bored today. Good. Enjoy it. Boredom is when you start thinking about the stuff in life that actually matters. Doomscrolling doesn't get you there.

Another cure for boredom is starting a side hustle. Here are two I think could make money, with real numbers, so you can see how the math works. Who knows if they'll work? We have to try. And the most important thing: you only learn AI by actually using it.

First, proof that the bot works

I didn't write this email.

I built a bot that emails schools asking to rent their gym for B Ballers. The assistant principal at A-Tech wrote back that they were checking with the principal and that the school's teams finish around 7pm. The bot answered by itself, and an hour later the school replied, "I will speak to the Principal."

Gmail thread: the bot's reply proposing weekday evenings 7 to 10pm, then the assistant principal replying 'I will speak to the Principal'
Real screenshot Top message, Sep 11, 3:00 PM: written by the bot, not me. Bottom, 4:21 PM: the school's answer.

Look at what it did. It picked 7 to 10pm because the school's own teams finish at 7. It brought up insurance before she could worry about it. I never typed any of that. I just told the bot ahead of time what to do in each situation. The more you practice giving it rules, the better it gets at guessing what you want.

What it takes: about 1,371 emails to get one "let me ask"

Sent, no reply yet Replied "no" / wrong person A-Tech: "I will speak to the Principal"
Gmail Sent folder showing 1 to 50 of 1,371, full of gym rental emails and follow-ups
Sent folder: 1,371 emails, plus follow-ups like "Just following up on my note…"
Gmail inbox with replies from schools, several saying no or that the contact no longer works there
Inbox: most replies are "no" or "that person doesn't work here anymore." That's normal.

1,371 is the number in the Sent folder. The grey "no" dots are illustrative (the inbox shows a handful of those). A person could never send 1,371 personal emails. A bot does it in an afternoon. That's the whole edge.

Idea 1 · Gym space

Rent the gym, then fill the hours

If one school says yes, we'll have a gym on weekday nights. B Ballers won't use every hour, so we look for coaches, trainers, high school teams and AAU teams nearby who need court time, and rent it to them.

  1. Bot emails every schoolAI
    Already running. Follows up by itself and answers replies using my rules.
  2. One school says yesYou
    Send the insurance certificate, sign the permit, lock the nights.
  3. Bot finds the teams near that gymAI
    AAU programs, HS coaches, private trainers within a few miles. It builds the list and writes the pitch.
  4. Pre-sell the hoursYou
    Get 2–3 teams to commit before you pay for lots of nights.
  5. Bot handles scheduling and remindersAI

Play with the numbers

Cost per month
Money in per month
Hours booked to break even
Profit per month

Starting numbers: 3 nights × 3 hours. School gyms usually charge $30–100/hr. Brooklyn indoor courts rent to the public for $140/hr and up (for example, the Major Owens Center on GoodRun). Change anything and see what happens.

Read the permit

Some schools don't allow re-renting to another group. Ask up front. The safer setup is that B Ballers hosts the session and teams pay for their spot.

Empty hours cost money

Every hour nobody books comes out of profit. Slide "share booked" down to 40% and watch what happens. That's why you pre-sell.

Know the seasons

HS teams practice in winter. AAU runs spring and summer. Pitch each group at the right time.

Keep insurance current

Every school asks for it. Keep the certificate ready to send, like the bot did.

Idea 2 · Long Island property tax

Get homeowners' taxes lowered and keep a cut of the savings

Long Island property taxes are among the highest in the country, and they keep going up. Say a homeowner's bill went from $21,000 to $27,000. Lots of people just pay it. The government is betting you're too busy (or too rich) to notice.

Here's how it works. The county says the house is worth a certain amount, and the tax is based on that number. If you can prove the house is worth less, the tax goes down. You get paid only if you win. That's a contingency fee: a share of what you save them.

It already worked · Uncle's house, Elk Grove, California

I used AI to lower your uncle's value by $86,876 in 5 days

California's version is called a "Prop 8" decline-in-value review. The county valued his house at $746,876. AI pulled five recent sales of similar homes in his zip code ($610K–$680K, including an identical 2,659 sq ft house that sold for $656K) and filled in the county's online form asking for $650,000.

  1. AI finds comps and files the county's online form
  2. County emails: "The Assessor's Office has received your Decline-in-Market Value" request
  3. County emails the results letter: reduced to $660,000
$746,876County's value before
$660,000County's value after
−$86,87611.6% lower

At California's roughly 1.1% tax rate, that's about $950 a year saved. The county will re-check the value every year until the market comes back, so the savings can keep going. A tax company charging 50% would have taken about $480 of it. We paid $0.

Open the county's PDF letter
Sacramento County Assessor letter dated August 25, 2026: 2026 Factored Base Year Value $746,876, Owner's Opinion of Value $650,000, 2026 Prop 8 Value $660,000
Real letter Sacramento County Assessor, Aug 25, 2026

The county didn't give us all $650K we asked for, but it came close. Ask low, back it up with real sales, and the county settles near you. Long Island works the same way: different form, same idea.

How you prove it: comparable sales

Long Island example (made-up numbers). House: 4 bed, 2.5 bath, pool, 9,000 sq ft lot. The county says it's worth $2.0M. The bot finds recent sales in the same zip code with the same features:

You tell the county: similar houses sold for $1.59M–$1.66M, so this one isn't worth $2M. If they agree and drop it to $1.59M, that's a 20.5% lower value.

  1. Find the houses with the biggest increasesAI
    The tax records are public. The bot ranks homes by how much their value or tax went up.
  2. Mail each one a personal letterAI
    "Your tax went up $6,000. We can help." The bot fills in each house's numbers. Your main cost is the stamp.
  3. Homeowner signs the agreement and authorizationYou
    This lets you represent them, and says you get X% of what you save them.
  4. Bot pulls the comps and writes the filingAI
    Same zip code, same features, recent sales, lowest prices you can defend.
  5. File with the county or town before the deadlineYou
  6. Next year, bot checks the new billAI
    If it went up again, file again. A reduction usually only lasts one year, so the same clients come back every year.
Sample letter the bot would write

Dear Homeowner at 12 Maple Ln,

Your property tax went from $21,000 to $27,000 this year, a $6,000 increase. The county values your home at $2.0M. But three similar 4-bed, 2.5-bath homes with pools in your zip code recently sold for as little as $1.59M.

I'm a licensed real estate agent and I track sales in your area. I'll file your challenge for you. If we don't lower your taxes, you pay nothing. If we do, my fee is 40% of this year's savings, and you keep the rest.

If nobody challenges it this year, next year's bill starts from the higher number.

One house: what the client saves and what you earn

Value you argue for (lowest comp)
Value drops by
Tax saved this year (rough)
Client keeps
You earn

Rough math: taxes saved ≈ bill × the % drop in value. Exemptions and how the bill is split can change the real number. Most firms charge 50%. With AI doing the work, we can charge 30–40% and still make money. That's how we beat them.

At scale: a whole mailing

Clients signed
Cases won
Total saved for homeowners
Mailing cost
Your profit, year 1 (at your fee above)

The defaults are deliberately conservative. $1,462 is the average saving reported for Nassau grievances, far below our $5,535 example. About 80% of Nassau homeowners who filed in 2024 got a reduction. The 2% sign-up rate is a guess. Test it with a small mailing first and put in the real number.

Bill up ≠ value up

Sometimes the bill goes up because the school budget or tax rate went up, and the county's value of the house didn't change. A challenge can't fix that. Pick houses where the value jumped.

Comps must be fair

Use the same area, recent sales and truly similar houses. Ask for the lowest one. The county might settle in the middle, and that's still a win.

Deadlines are strict

Nassau County takes filings online starting in early January. Suffolk towns hold Grievance Day in May. Miss it and you wait a full year. Have the bot track the dates.

Tell the truth in the pitch

You don't need a license to file, but only say "licensed agent" if you are one (I am). Big firms already mail every house. Our edge is a lower fee and faster work.

What these two have in common

In both, the boring work used to need a room full of employees: finding people, writing letters, pulling sales, following up. The bot does it now. That leaves you the parts that matter: making the call, signing the deal, and deciding what to try next.

Pick one. Try one small version. Tell the bot what to do in each situation, see where it messes up, and fix the rules. That's how you learn AI: by using it.

Sources: Ownwell: Nassau grievance data · Long Island taxes among highest in US · HangTime: gym rental costs 2026 · GoodRun: Major Owens Center rate