HODL no more: Strategy hits the Wall

Hey Superheroes,

Today is the day.

SpaceX (NASDAQ:SPCX) begins trading on the Nasdaq tonight after pricing its IPO at US$135 a share overnight — a US$75 billion raise at a US$1.75 trillion valuation, making it the largest IPO in stock market history. With up to 30% of shares set aside for global retail investors (versus the usual 5–10%), this is the most retail-heavy mega-listing ever attempted. We’ll have more for you next week once the dust settles.

Macro-wise, the picture is less rosy. US CPI hit 4.2% in May, the highest reading since April 2023, with energy prices alone up 23.5% year-on-year off the back of the Iran war. The Fed has its first meeting under new Chair Kevin Warsh next Wednesday and is now expected to hold, with the next move possibly being a hike rather than a cut.

Back home, Westpac’s Consumer Sentiment Index fell to 80.6 in June, “amongst the weakest seen in the 50-year history of the survey,” with pessimists outnumbering optimists by nearly 20%. The Budget didn’t help — 70% of those surveyed gave it an unfavourable rating. NAB is now flipping its call from “next move up” to “next move down,” citing collapsing household confidence.

Here’s what else moved this week.

HODL No More: Strategy’s Reality Check

Michael Saylor built an empire on four letters: HODL. This week, that pillar cracked.

Strategy (NASDAQ:MSTR), the company formerly known as MicroStrategy and currently the world’s largest corporate Bitcoin holder, has lost 40% of its value over the past month. Shares closed at US$117.02 on Tuesday and tested the critical US$100 support level on Wednesday, having traded close to US$200 just six weeks ago.

Bitcoin slides beneath $60K

The trigger is the underlying asset. Bitcoin slid below US$60,000 this week, down roughly 25% in a month, as the broader risk-off mood from sticky US inflation and the Iran war drained crypto liquidity. For Strategy, that’s a double whammy: Bitcoin’s drop is bad enough, but it also compresses the “premium” the stock has historically traded at relative to its underlying Bitcoin holdings.

That premium typically sat at 1.5–2x the company’s Bitcoin Net Asset Value. This week it’s been compressing fast, which is why MSTR has fallen further than Bitcoin itself.

The “never sell” cracks

Then the unthinkable happened. On 1 June, Strategy disclosed it had sold 32 Bitcoins — its first sale in four years. The amount was small (around US$2.5 million worth), but the symbolism was enormous. Saylor has spent half a decade telling investors he would never sell.

To make matters worse, the CFO got involved. Strategy CFO Andrew Kang sold 1,949 MSTR shares on 9 June for US$241,362. The sale was scheduled (tax obligations on RSU vesting under a Rule 10b5-1 plan, not a discretionary call) but the timing alongside the broader sell-off didn’t look great. 

The squeeze, and the bull case

Despite the carnage, Wall Street isn’t bailing. Mizuho cut its price target from US$320 to US$265 but kept an Outperform rating, while TD Cowen sits at US$400. Of 18 analysts covering MSTR, 15 still rate it a Strong Buy — and consensus price target of US$363.62 implies a 185% upside from current levels.

Strategy still holds 845,256 Bitcoins, the largest corporate position in the world, and recently raised US$181 million via an ATM offering to buy more. The bear case is that the NAV premium keeps compressing. The bull case is a short squeeze if Bitcoin bounces. Either way, this is the most-watched stock in Saylor’s career.

OpenAI Joins the Queue

If you were keeping score on the AI listing race, it’s now three for three. SpaceX trades today. Anthropic filed two weeks ago. And on Monday, OpenAI confirmed it confidentially submitted a draft S-1 to the SEC.

The classic OpenAI announcement

OpenAI did it in OpenAI’s style. The company issued a two-sentence statement: “We recently submitted a confidential S-1. We expect it to leak so we’re just announcing it.” It added that it “has not decided on timing yet; it may be a while” and described the move as keeping its options open.

In other words: this is permission, not a date. But the runway is being cleared.

The valuation

OpenAI’s last confirmed private valuation was US$852 billion, set in its March 2026 funding round (US$122 billion raised, with SoftBank, Amazon, Nvidia and Microsoft participating). Cumulative private funding now exceeds US$170 billion. Bullish analysts at CNBC and Enterprise DNA expect the public debut to land above US$1 trillion, with a September window plausible per Axios reporting.

Annualised revenue is running around US$25 billion. Cash burn is projected at roughly US$27 billion for 2026 — meaning the company is still losing more than it earns by a wide margin.

The Microsoft re-cut

One detail worth flagging. Ahead of the filing, OpenAI renegotiated its revenue-share arrangement with Microsoft, capping total payments at US$38 billion through 2030, down from a prior trajectory closer to US$135 billion. That’s a US$97 billion shift in OpenAI’s favour — and a clear sign that the company was readying its income statement for public-market scrutiny.

With Anthropic (US$965B post-money), OpenAI (US$852B–$1T+) and SpaceX (US$1.75T trading today), the trillion-dollar IPO trio that defined 2026 is finally lined up. With three massive options on the table, retail investors will be watching closely to see how these valuations hold up in the public eye.

Some other things we’re shining the Spotlight on:

BARBEQUES NO MORE: Iconic Aussie retailer Barbeques Galore is set to wind up from 16 June after a rescue plan collapsed. All 62 company-owned stores will close, putting around 500 staff out of work, with the 27 franchise locations expected to keep trading. Founded by Max Mason in Sydney in 1977, the chain had been losing money for years — Bunnings’ in-store BBQ sales didn’t help. Gift cards are honoured until 30 June.

VINTED GETS MINTED: European second-hand fashion platform Vinted is now valued at US$9 billion after an €880 million secondary share sale, with the CEO telling CNBC the shift to second-hand consumption is “a fundamental change” that’s “here to stay.” Vinted is now pushing into the US market — its first move outside Europe — though management says the company is in no rush to IPO.

CHEMIST WAREHOUSE EYES BOOTS: Sigma Healthcare (ASX:SIG), the ASX-listed Chemist Warehouse owner, is in talks to buy UK pharmacy giant Boots for around A$14 billion. The deal would scrap Boots’ planned London IPO and hand Sigma 1,800 stores across the UK and Ireland. Sigma shares fell 5.5% on the news as investors weighed the strategic ambition against the price tag.