Zero
No. 02Gambling

The Phantom Tax

Making $0 in profit still generates a tax bill.

There is no debate: sports betting apps like DraftKings and FanDuel have completely taken over post-Covid. But if you're placing bets you need to be prepared for a nasty surprise.

Just like any other income stream, your sports betting wins are subject to federal and state taxes. But unlike trading stocks — where you can seamlessly offset your capital gains with your capital losses (i.e. tax-loss harvesting) — gambling losses are treated very differently.

With new regulation the rules have changed, and the math is incredibly frustrating.

The new 90% rule

Under new regulations, you can only deduct 90% of your gambling losses against your gains. This might sound like a minor detail, but if you take a step back, this new limitation has massive consequences. Let's look at a simple example.

A day of break-even betting

Line itemAmount
Winnings$10,000
Losses($10,000)
Net profit$0

At the end of the day, your net profit is exactly $0. You simply broke even.

However, the IRS doesn't see it that way. Because you are only legally allowed to deduct 90% of that $10,000 loss — $10,000 × 0.9 = $9,000 — the government interprets your day of betting as $1,000 of taxable gains.

What the IRS actually sees

Line itemAmount
Gross winnings$10,000
Deductible losses (90%)($9,000)
Phantom taxable gains$1,000

What's your next move?

Usually, the tax code is full of loopholes. But with this new gambling rule? There is no magic exemption. No back door. The only way to protect your wallet is to know the math before you place your bets.

Don't bet blind.

Sree TripuramalluFounder & CEO

P.S. These letters reflect personal opinion and are not investment advice.