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TLDR: NFA approval is close for the prediction market product launch. Trump hopes US prediction markets thrive. Insiders and beneficial owners hold >50% of the stock, and institutional ownership is at an all-time high. ROLR $100/share isn't a meme. Short interest and CTB dropped.
**Position update.**
[Original position from Fidelity.](https://preview.redd.it/1i1i0jffz74h1.png?width=793&format=png&auto=webp&s=0d3b830ed9e2e606436ef1062724f50bad4ed150)
[Added some shares in Robinhood to test out whether I would run into wholesaler inventory issues and discrepant spread.](https://preview.redd.it/wib5mjr3x74h1.png?width=1170&format=png&auto=webp&s=d689662907693d11ba790503546ad7c2de166976)
Now for the month in review (May 3, 2026 — May 31 2026):
**Q1 2026 Earnings.**
[Sourced from Stock Titan. Down on revenues from winding down operations in unregulated markets, which came with a decrease in associated operating expenses, thus getting closer to breakeven. Dilution provided them with a higher runway. I like to say this quarter represents a \\"2nd IPO\\" wave for this company considering they're fresh off a capital raise and moving into new markets with a new leadership team in 2026.](https://preview.redd.it/7thhq7gkwa4h1.png?width=1140&format=png&auto=webp&s=2f42940018f403dfa76444ebe4f8f12b9e535957)
**Earnings Q&A highlights.**
* No launch date was communicated. Quote from CEO: "We're racing toward the finish line."
* The team is working through the prediction market product pre-launch campaign with its marketing partners, technical infrastructure, and licensing status.
* ROLR is pursuing both the Guaranteed Introducing Broker (GIB) and Introducing Broker statuses (more on this later).
* The marketing partners are key to their user acquisition strategy due to their broad reach (at the level of mainstream players like Barstool Sports) and search engine-optimized pages.
**"wHeN aRe We GeTtInG nEwS???" Here are the catalysts I'm tracking.**
For US prediction markets, go to the NFA BASIC website and search for ROLR US LLC (NFA ID: 0578141). You'll see that all the principals listed right now are approved.
There are a few events I believe still need to happen before they become completely NFA-approved.
1. Seth Young needs to pass his short track Swap Associated Person modules (requires a few hours for the training modules and exam) and the Associated Person (AP) Series 3 exam (requires a couple of weeks of studying and a couple of hours for the exam) to be approved for the Swap AP, AP, and NFA member, to which the company's NFA membership approval is contingent upon.
2. Brandon Eachus should be listed and approved as a principal, given the recent Schedule 13D. Previous principals took 1-2 weeks to be approved for reference.
3. Foris DAX FCM, LLC (CDC-FCM) needs to submit the Form 1-FR-IB Part B. It takes like 5 minutes to fill out.
That's it.
Once this happens, you'll see a green banner with "NFA Member Approved" and an 8-K filed within 4 days to disclose the material event. Then they can get their license as a GIB, start receiving the live production credentials, and launch.
[NFA BASIC showing ROLR as a Pending NFA Member.](https://preview.redd.it/cidbirsax74h1.png?width=374&format=png&auto=webp&s=ff9627ae53b029f4675768d4018c0e5df20e18b8)
They did mention in the earnings call that they are also pursuing an independent IB license. The main difference here is that they have to fulfill their own capital and accounting requirements. It takes months longer, but has no adverse effect on the launch timeline since the GIB is their priority. My guess is future proofing, in case they decide not to continue their contract with Crypto.com (CDC) and either pursue a different partnership after 2 years or become a DCM and FCM themselves to have vertical control (like Kalshi).
For their iGaming license in Alberta, visit the AGLC.ca/iGaming website and click on "iGaming Registrants..." under the "AGLC iGaming Guidance Documents" section. This page is updated every week. Currently, High Roller Technologies, Inc. isn't on the list. Similar to prediction markets, they'll likely file an 8-K within 4 days to disclose a material event should it occur. Operators go live on July 13, 2026.
https://preview.redd.it/y7v8bfme1b4h1.png?width=1367&format=png&auto=webp&s=63ae88d28737d353832d9ffcf0835818a6cb253d
For their iGaming licensing in Ontario, the latest information from the 10-K annual filing is that they're in the process of obtaining the license, having applied in May 2025, and plan to launch in the second half of 2026. I currently don't have a source to track this BEFORE it happens, but the iGamingOntario.ca/en/operator/operators website has a page to look up the current operators and gaming websites where High Roller Technologies, Inc or highroller.com may show up before an 8-K is filed.
https://preview.redd.it/n458rsyr1b4h1.png?width=1914&format=png&auto=webp&s=6c573e46dad0cd373fcacb07c8dc8fcfd9bbd552
For their iGaming license in Finland, we know that they plan to pursue a license, but there has been no further news or signals given by the company, probably because they already get revenue from Finland through their Estonian license. Monitoring the status of iGaming operators on FinnGaming.com/operators. Operators go live on July 1, 2026.
https://preview.redd.it/3stevyg72b4h1.png?width=1410&format=png&auto=webp&s=cf010801262bf8adb62c823cc635171e449d15b5
And finally, for the Altenar partnership to provide an online sportsbook within their casino product, there hasn't been any news on this since January's letter of intent.
**In other news...**
If there's anything we learned from watching the markets the past month, it's that anything Trump says or touches goes tits up. The man is a modern-day Midas. For anyone who thinks that prediction markets have regulatory risk from tribal lobbyists and dominating sportsbook companies, here's the Truth Social post that pretty much puts that to rest. Keep in mind that ROLR is currently the ONLY publicly traded US prediction market pure play.
[Trump pledges to ensure prediction markets thrive on Truth Social.](https://preview.redd.it/w8hdntqjx74h1.png?width=729&format=png&auto=webp&s=46829e5787dd983d8ab34d57ad658e5477066153)
**Preparing for the June 30 annual shareholder meeting.**
The proposals don't really matter. Insiders and beneficial owners hold a supermajority, so they will all pass regardless.
What matters is the Q&A. If you are a shareholder, submit your questions or be prepared to ask them live. It seems investor relations is responsive to emails that involve losing shareholder interest due to management actions (or lack thereof). This is a time where it's completely appropriate to probe into areas where we haven't received a ton of clarity. The past couple of earnings have been wasted on questions related to the prediction markets product that you can Google.
**A refresh on the cap table and wholesaler inventory issues.**
First and foremost, ROLR institutional ownership is at an ALL-TIME HIGH. In May, the stock was picked up by big-name investors such as Vanguard, UBS, Citigroup, Jane Street, BlackRock, and Morgan Stanley, to name a few. This number will only continue to grow as prediction market exposure to portfolios becomes more commonplace.
[Sourced from Fintel, institutional ownership disclosed in May shows an increase by over 3x, an all-time high.](https://preview.redd.it/odfk7u6x2b4h1.png?width=1019&format=png&auto=webp&s=be63886a956d860b89b73fab125dd79944b1f5d5)
There were a number of filings this past month related to ownership changes, so I want to break down the current ownership structure.
* With the latest filing Schedule 13D, we know shares outstanding sit at 11,023,699.
* From the Q1 2026 13F filings, institutions own a total of 313,266 shares.
* Brandon Eachus and Michael Cribari, who have shared control over Cascadia Holding Limited and SpikeUp Media A.B., have a combined ownership total of 2,810,443 shares.
* Oskar Hornell, through OEH Invest A.B., a sister company to Cascadia, owns 2,010,631 shares.
* Jeff Smith received his share of 787,648 shares from Cascadia via the redemption agreement. A Form 144 was filed for the intent to sell 100,000 shares, but no Form 4 has been filed to confirm a sale.
* Saratoga Casino Holdings owns 357,143 shares from the Jan 9 strategic investment that are in a lockup period until July.
* The rest of the executives' and board members' vested/liquid shares
* Seth Young 12,796
* Adam Felman 11,025
* Jake Francis 5,022
* Daniel Bradtke 30,822
* Legendman Investments Limited, from 2024, held 503,731 shares, but since dilution, could have sold off without needing to report a change in ownership. Noting this one as a "highly likely holder".
* The 1,892,506 shares from the DRO in January sold at $13.21, but since then, the price has never recovered to that level, so I'm noting this stack as a group of "highly likely holders that could be lending".
I'm not going to bother with all of the RSUs, active warrants, and options awarded/unvested, but just know that there are a lot of them out there, and they can create huge buying pressure.
Adding everything up, we've got 8,835,033 shares held by insiders, institutions, beneficial owners, and likely holders. Subtracting institutions and likely holders, we have a confirmed lockdown of 6,629,261 shares or 60% of shares outstanding.
Not a float lock, but still amounting to a relatively low float of less than 5 million shares.
Somehow, IBKR is still showing 248,588 shares float (shown later in the chartexchange screenshots). Not sure if they're double-counting the insider ownership like WallStreetZen, or if they have insight into shares held that we don't.
Given the daily volume hovering at a few hundred thousand a day, combined with brokerage inventory issues and inability to fill orders, you could speculate that there are so many other holders without any orders not formally documented in the books, amounting to a float lock.
Trading212 and Robinhood have been specifically called out for having difficulties filling market buy orders and/or limiting the number of shares you can hold. If this is posing a problem for anyone anywhere else, it would be appreciated if you could comment on it.
[Trading212 showing that a user can't own more than 7,953 shares of ROLR.](https://preview.redd.it/8kikjl2tx74h1.png?width=1036&format=png&auto=webp&s=1a431d83ea479e68a8cb0f62a056828f8218a548)
**The math behind ROLR $100 or a billion-dollar market cap. It isn't a meme.**
The math is simple. The following estimates are based on the most conservative baselines.
Let's say ROLR hits the CEO's target (from various interviews) of $250MM in annual B2C iGaming and online sportsbook revenue across Alberta, Finland, and Ontario. That is calculated based on the global gambling sector being about $700B annually, with the online share at about $200B annually, and Ontario, Alberta, and Finland markets representing about $5B of that online share (or 2% of the global online share). If High Roller can capture 5% of the 2% global opportunity, that's a $250MM topline business, up from $30MM topline in 2024. Aside from increased marketing spend, the product has been built and does not require additional operating costs.
And let's say they capture 1% of the $10B revenue for prediction markets at maturity and take a 40% cut from contract fee revenue in a B2B context. That would amount to $40MM in annual revenue.
There are two ways I see us calculating a market cap from this:
1. Sum-of-the-parts revenue multiple
2. Blended EBITDA multiple
For the first case, iGaming operators typically trade at a 2x revenue multiple, and prediction market providers trade at a 5.5x revenue multiple. The implied valuation/market cap would then equal $720MM (250,000,000 \* 2 + 40,000,00 \* 5.5).
For the second case, using the baseline 22% margin for mature B2C iGaming operators and 65% baseline margin for a B2B contractual prediction market feed, you get a total blended theoretical adjusted EBITDA of $81MM (250,000,000 \* 0.22 + 40,000,000 \* 0.65). Mature gaming and exchange tech companies typically trade at a blended forward 10x to 14x EV/EBITDA multiple. Happy path, let's say the market environment favors a growth premium and we trade at a 14x multiple. That would put the valuation at $1.13 billion.
Based on the valuation range provided from those calculations, ROLR shares would trade at $65-$100/share, given that the shares outstanding remain the same (again, ignorant of share awards or further dilution).
In truth, nobody knows what revenue they will actually make or what multiple the market will want to pay at maturity. I mean, the consensus seems to be that SpaceX is a burning pile of garbage fundamentally/financially, yet somehow a trillion-dollar company on its way to fast-track inclusion into the indexes post IPO, so anything goes.
What I do know is that on The Business Roundup podcast episode with Melissa Bill and Seth Young (CEO of High Roller), ROLR is not planning for 2nd place. They want to be THE leader. Their executive team and board bring leadership experience from the very same incumbents they plan to take down. Also in the episode, along with a bit of research on ASX history, Seth Young was the CIO who took PointsBet from a $5MM valuation in 2018 to a $5B valuation in 2021. A literal 1000 bagger in 3 years.
That is the nearly $400k bet.
**An update on short interest and cost to borrow (CTB).**
Daytraders and longs gave shorts an out to take profits over the past month. Given the small float, short squeeze opportunities are common, and the stock will copefully have SPCE-level hype on the next catalyst.
[chartexchange short interest showing 421,559 as of the May 15, 2026 settlement date.](https://preview.redd.it/h7ghnyf0y74h1.png?width=717&format=png&auto=webp&s=5ef7e661eb783ea163918981ad298423e1249f3a)
[chartexchange CTB showing 55.65 APR and 45,000 shares available to borrow as of 5\/29.](https://preview.redd.it/tex9fbr3y74h1.png?width=527&format=png&auto=webp&s=6466999c07d05b93ca3090fc0ef251c23b3c752b)
[Robinhood daily short interest hovering around 5% for the past trading week.](https://preview.redd.it/5jc0o6may74h1.png?width=1170&format=png&auto=webp&s=a75485b8cd9e3122d1b3d8403ce69d4e5cf94751)
**Technical analysis.**
[Sitting above daily MA150 and MA200 sitting in discount and consolidating between $5 and $6 for the past couple of weeks proving to be a great accumulation zone. MACD is at the start of a curl upward and RSI is neutral. Filled the daily gap from April 14.](https://preview.redd.it/cnth6uk0ab4h1.png?width=1110&format=png&auto=webp&s=90bf85a1e0a25a889dd75c8f1993dc4a27c2a38a)
*All of the content in this post is my own, non-AI-generated opinions and assumptions based on months of research. This is not financial advice, and I am not a financial advisor.*