Owen Monagan

I trade these contracts. At some point I looked at a year of my own positions and thought: what on earth do I do about taxes on this? There was no good answer. The exports are raw, the treatment is unfamiliar, and the advice that exists was written for people trading something else.

Then I asked around, and it turned out not to be my problem. Across hundreds of conversations with sports bettors and traders, the same gap came up every time: people were quietly losing money at tax time, and most of them assumed a loss was just a loss. Often it is worth something. That is the whole reason Realize exists.

I have spent years building consumer-finance and responsible-gaming products for sports bettors and traders, at Layup, always with the same goal: helping people who bet hold on to more of their own money. A prize-linked savings product. A product to offset the financial impact of betting. Realize is the same idea pointed at the one moment where the money is largest and least understood. I spoke on the technology track at SBC Summit Americas in 2026.

Layup’s banking partner is NBKC, a federally insured bank that also provides Acorns’ checking accounts. That earns a line here for one reason: a regulated bank runs real diligence before it puts its name beside yours, so it is a judgement made about us from outside the company.

We have publicly announced $2.3 million in funding, from investors including Chicago Ventures and Continental Investment Partners, and personally from the founders of Discover and Aeropay. I hold a B.A. Moderatorship in Computer Science and Business from Trinity College Dublin.

Over the years we have spent more than $100,000 on legal research at the intersection of consumer finance and sports betting, including formal opinions from Orrick on the prize-linked savings products we built. That was not tax law, and I am not going to pretend it was.

What sits behind the guides is more ordinary, and more useful to tell you about. I have sat in the rooms where the case for and against these markets is actually made, at gaming law and regulation conferences including the IAGA Gaming Summit and the NCLGS summer meeting, and heard both sides put by the people making them rather than summarised secondhand. Then I took the tax question to lawyers and CPAs who work in this area and asked what it means. That, plus the primary sources, read carefully and cited on the page, is the whole basis.

Where the treatment of these contracts is genuinely unsettled, every guide says so rather than picking the answer that sells better.

Unsettled is not the same as unknowable. There is a statute, there is case law, there is a regulatory record, and there are people who do this for a living, and the guides read them rather than stopping at “consult a professional”.

A concrete example. Whether a prediction-market contract is the same thing as a sports bet, and whether either is gambling for tax purposes, are separate questions with separate answers, and the federal and state positions are currently moving apart rather than together. A niche this fast-moving is hard for a general practice to track, which is the reason this site exists, and the reason we hand you something to take to your accountant rather than asking you to take our word for it.

So the guides keep the two apart on the page. Where something is settled, they say what the law is. Where it is not, they say there is no IRS guidance, describe how each filing route works, and show what each produces for the same year.

The tax engine and the spec it is written against. Every figure the product shows comes out of it, and I would rather that be one named person’s responsibility than a company’s.

The hard part is the year-end mark. Section 1256 treats every open position as though you sold it on the last business day of the year, so a filing needs the market value of each position on December 31, not only the trades you closed. That number is in nobody’s export, and rebuilding it by hand means looking up each position’s price for that day. We rebuild it from the venue’s own published price history, position by position, which is also what lets somebody file a year that ended before they had heard of us. Where the venue published no price that day we say so and leave the position out, rather than inventing a mark.

That is what we hand your accountant: not a view on how you should file, but the figures underneath it and a trail back to every trade behind them.

LinkedIn · TikTok, where I talk through what we are learning as we build.

What I can do is organize your trades, compute a position, show every step, and be honest about which parts of the law are settled and which are not. Take the output to someone who is qualified. That is what it is built for.

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