TTA’s Autumn Leaves: Oura puts off IPO, Anthropic’s IPO November (?); Sycamore Partners nearing Boots sale; telehealth support for pediatricians in youth mental health, Oracle’s Congressional spanking, more!

October 3, 2026 | by | No Comments

 

2-5 October 2026

Here we are past the first week of Fall (or Autumn). The leaves may be turning, but the healthcare/AI  IPOs aren’t, with the Oura health monitoring ring postponing its IPO indefinitely and the Anthropic AI rumored only for early-to-mid-November. Another turning is for Boots, with Sycamore Partners breaking up the Walgreens Boots Alliance combine for $9 billion. And this week’s Perspectives discusses the burden pediatricians are taking on in youth mental health and how telehealth can support this need.

For Readers: Your Editor will be on publishing leave due to travel to 21 October. ‘Best Of’ Alerts will be out weekly on Fridays and Saturdays after this week till then. Some past highlights:

  • Humanity’s Rumored Doom in 10 years at the hands of AI are Zebras, not Horses.
  • Oracle’s simultaneous strong Q1, 3,000 layoffs, and its two top execs subpoenaed by the House VA Committee for a whacking over the 170% increase in budget to cover the next three years (Congress is Fed Up).
  • How infrastructure tech needed by healthcare organizations can’t get arrested on funding, while whiz-bang consumer apps can.

Please feel free to comment on the articles and pass along this Alert. Let me know if this is worth it to you! Also check out my personal page on Substack.

IPOs, IPOs–Oura’s stalls out, Anthropic’s restarts, possibly mid-November. To everyone’s amazement!

Developing: Walgreens’ Sycamore Partners owner on final approach to sell Boots operation to Canada’s Weston family for ~$9B

Perspectives: What Meta’s settlement reveals about youth mental health, access shortages, and where telehealth can support pediatricians

More of Interest 

Oracle’s continued restructuring cuts 3K more jobs, adds $700 million while revenue grows 30%; House VA Committee subpoenas Ellison, Sicilia 19-0–and why Congress is mad at a 170% budget increase (Updated for how Congress really feels)

(Related) Revealed: Oracle’s extended VA EHRM contract increased by $17B as original ceiling reached this year; VA Indy EHR goes online

AI’s hoofbeats as Horses, not Zebras: a Gimlety view of AI’s destructive capacity (updated) (P(doom) may be conquered by F(doom), or Why Worry?

Perspectives: Digital Health Capital Keeps Rewarding What Patients See, Not What Keeps Companies Alive (Infrastructure tech can’t get funding)

Silicon Valley Bank’s take on H1 investment: among the “have and have nots”, it was “the best half in years” for health tech

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IPOs, IPOs–Oura’s stalls out, Anthropic’s restarts, possibly mid-November. To everyone’s amazement!

October 3, 2026 | by | No Comments

Is it the market, or is it something else that’s putting off the ‘sure’ IPOs? The smart money was betting that the Oura health monitoring ring would have IPO’d on Wednesday (30 Sept) for about $2.1 billion. The employees holding restricted stock units (RSU) and investors would be counting their money by now. After all, Oura has been profitable this year after breaking even in 2025, and there was real enthusiasm when it filed its SEC S-1 right before Labor Day. But on 29 September, when the offering was scheduled to price, it was postponed. Indefinitely.

The Oura press release cited “that it is postponing its previously announced initial public offering on Nasdaq, despite strong demand, due to uncertainty in the IPO market”. No new date was given. Uncertainty is a factor, but there are others specific to Oura.

If you read Endpoints, they cited the Federal Reserve raising its rates a few weeks ago, depressing demand for the rich valuation Oura was seeking; the P(doom) around AI; and Apple introducing a new Watch with improved sensors and an option to order blood tests, as Oura has. There are rumors that Apple will also develop a faceless watch that will copy everything that Oura has. That’s a lot of putting off right there.

Ace investigator Sergei Polevikov in his AI Health Uncut of 29 September digs considerably deeper. Non-subscribers to his Substack platform will see some of this but his main points are that the oversubscribing level was weak at ~4x whereas ~20x for large offerings has been the norm since 2023. Three early VCs-Forerunner, Lifeline, and Elysian Park Ventures–were seeking to exit, never a good sign, and taking $1.53 billion with them. The IPO is also being built on Oura’s promise to deliver predictive health. Whether a ring–a piece of Finnish jewelry–can deliver that and more, reliably and interestingly to a growing user base, is a real question.

What 4x versus 20x says is that this IPO is a ‘nice to have’, not a ‘must have’. No one here has FOMO–fear of missing out.

There are hardware issues–and hardware is the vast bulk of its sales with service subscriptions only 19.8% of revenue.

Last but certainly not least, Oura’s benefit in going public on Nasdaq would largely have gone to the Taxman. Little known fact unless you’ve Been There, Done That: RSUs are treated as employee pay when they vest. The tax is withheld, just like wages. It becomes the employer responsibility, not the employee’s. In net settlement, Oura pays the tax in cash from its IPO proceeds and keeps part of the shares to cover the tax. (That doesn’t count what states do with RSUs nor how laws differ internationally.)

The line on the bottom for Oura after the IPO? The company nets only a paltry $6.2 million because of investor payoff and employee RSU taxation. That is over 98% of the proceeds going to everyone but Oura. 

Have other IPOs been like this? Not many. Evidently a lot of pay went to RSUs spread generously around, not just executive staff. This IPO evidently is to help three major VCs exit nicely–and a ~4x oversubscription wasn’t enough.

Another Ominous Parallel with an IPO that some of us remember: Peloton, once a fitness darling. There are similarities (the enthusiasm, the unfavorable hardware issues, the imbalance between hardware and subscription revenue, unsustainable growth beyond enthusiasts) and differences (the Oura Ring is under $400, a Peloton machine over $2,000, and Oura is profitable). But you’ll have to subscribe (and you should!!) to Sergei’s Substack to see all of his finely worked out and fully buttressed argument.

Oura is not exactly hurting for financing, having raised $1.5 billion over the past decade, with a jumbo $900 million Series E last October led by Fidelity, and an undisclosed corporate round this past July led by Eli Lilly, neither of which are exiting.  Crunchbase

Will Oura IPO this year or next? This Editor cannot see anything that was cited as changing the picture if the IPO were tomorrow or in the next few months.  Also Mobihealthnews

About the Anthropic IPO, the financial press is agog with talk that its engines may restart by mid-November. The date is rumored to be 9 November. Anthropic executives will meet with investors on 14 October to build a case for a $2 trillion offering, which would be an all-time record for an IPO.

Readers know that the IPO talk, explored since May, came to a screeching halt right around 9/11 with the talk of P(doom) [TTA 17 Sept] and Federal regulation. Some believe that these ‘external brakes’ were applied because neither Anthropic nor OpenAI were ready to IPO and it was easier to create Doom than to postpone directly. But here we have it at least for Anthropic, even if the fundamentals scream “warning”! Certainly the incentive to beat OpenAI to the IPO is still there. Anthropic, which was created by OpenAI bolters, surely want to ring that bell on either Nasdaq or NYSE (another small matter to finalize) before Sam Altman. Here we go again! Yahoo Finance

Developing: Walgreens’ Sycamore Partners owner on final approach to sell Boots operation to Canada’s Weston family for ~$9B

October 2, 2026 | by | No Comments

Looks like it won’t be Walgreens Boots Alliance for much longer. Breaking yesterday in The Wall Street Journal is that Sycamore Partners, the private equity retail giant that owns WBA, is closing in on a buyer for the Boots UK and international operation. The discussed price is in the vicinity of $9 billion (£7 billion) for the Boots UK stores, brands, and other international operations in Thailand, Mexico, Germany and China. Talks are proceeding with a deal reportedly within the next few weeks (WSJ), with the Financial Times reporting as early as one week.

The prospective buyer, the Canadian branch of the Weston family, already is a giant in the Canadian food business with Loblaw, Real Canadian Superstore and other brands. They’re also experienced in the retail drug business with over a decade of owning Shoppers Drug Mart, a large national pharmacy chain. The family holding companies are Wittington Investments Limited and the public company George Weston Limited. Their last UK venture was Selfridges, which was sold in 2022 for £4 billion. Another branch of the family is an investor in Associated British Foods.

The Guardian helpfully adds that Boots has 1,800 stores across the UK and employs about 51,000 people, including about 6,000 at its headquarters in Beeston, three miles south-west of Nottingham. One wonders whether Boots will continue to sell Boots Beauty products such as No. 7 in Walgreens USA stores.

This summer, Sycamore tried and failed to sell Boots for $10 billion to Australia’s pharmacy group Sigma Healthcare. In London, a Weston buy has dashed hopes that Boots would be spun off and listed on the London Stock Exchange as reported in the FT. Those had multiplied after Boots in May appointed Alex Baldock, former boss of retailer Currys, as its new chief executive.

Walgreens bought Boots in two stages, with a 45% interest in 2012 and the remainder in 2014. The total price between cash and stock was in the vicinity of $15 to $16 billion. Yes, selling it for $9 billion along with associated debt is quite the ‘haircut’. 

Boots has been up for sale ever since the Sycamore Partners’ Walgreens Boots Alliance acquisition in March 2025 for a total value of $23.7 billion including debt, leases, and other factors [TTA 11 Mar 2025]. Sycamore took on an 83% debt level in doing so. Almost immediately, Sycamore split WBA into five parts, including Walgreens retail stores, Shields Health Solutions specialty pharmacy, CareCentrix, and VillageMD. Practices of the last have been either sold off in parts or shuttered, with Summit Health/CityMD remaining.

Yet, according to the FT, Boots is doing well. “The company reported in June that new beauty brands and the uptake of weight-loss jabs had driven up both its retail and pharmacy sales in the UK. Overall revenues rose by 3.2 per cent to £7.5bn in the year to the end of August 2025. Pre-tax profits jumped by a quarter to £337mn, driven by the reversal of impairment charges.”

What it means for Walgreens? Sycamore gets a quick cash infusion, allowing them to focus on revitalizing the US retail operation which had fallen on difficult times over the past three years. An indicator is a late September report that it slowed store closures from a projected 700 this year to less than 100, stabilizing total locations at about 8,000. Drug Store News Walgreens does not own a pharmacy benefit management (PBM) operation, a debit which now may be to its benefit as PBMs face financial and regulatory headwinds.

Both Sycamore and Weston were remaining mum about the deal to the press. Yahoo Finance UK, Axios

Perspectives: What Meta’s settlement reveals about youth mental health, access shortages, and where telehealth can support pediatricians

October 1, 2026 | by | No Comments

TTA has an open invitation to industry leaders to contribute to our Perspectives non-promotional opinion and thought leadership area. Today’s topic concerns youth mental health–and how specialized telehealth can provide remote psychiatric backup to assist pediatricians in making critical treatment decisions. The author, Andy Flanagan, is CEO of Iris Telehealth, where he draws on experience as a three-time CEO and senior leadership roles at Siemens Healthcare, SAP, and Xerox to guide the company’s mission of improving behavioral health outcomes for patients and clinicians.

Meta’s $16.7 billion settlement with a coalition of state attorneys general puts a number on something health systems have felt for years without a dollar figure attached. Youth mental health has become a public health infrastructure problem, and the infrastructure absorbing most of the impact isn’t behavioral health. It’s primary care.

New survey data from Iris Telehealth shows that when a child starts struggling with attention, mood, or behavior, 42% of parents try home strategies first. Another 23% bring the issue to a teacher or school counselor. Only 11% go directly to a mental health professional. Everyone else eventually lands somewhere else first, and for most families, that somewhere is a pediatrician’s office.

Pediatricians are absorbing psychiatric decisions that used to require a specialist referral, and telehealth can put that backup in the room with them instead.

Pediatricians have become the default specialist

Sixty percent of parents in our survey said their pediatrician or healthcare provider is where they get information on supporting their child’s behavioral or emotional health, ahead of friends and family, online resources, and school staff combined.

The same pediatrician parents go to for guidance is often the one prescribing the medication that guidance leads to. Among parents whose children have taken medication for a behavioral or emotional challenge, 44% said a pediatrician wrote it. Only 38% said a child psychiatrist did.

A prescription for a child’s mood or attention shapes how they sleep, eat, and function every day. Pediatricians are handling more of that decision themselves, and a child psychiatrist is rarely in the building to weigh in alongside them.

Fewer pediatricians will be available right when more families need one

The pediatricians absorbing this load today are about to become scarcer. A study published this year projects that pediatrician demand will grow 2% between 2025 and 2037, while the supply of pediatricians actually available to see patients drops by more than 10% over that same period.

Workforce adequacy, the measure of how well supply meets demand, falls from 92.3% today to 81.2% by 2037. Families in non-metropolitan areas and the South will feel that gap hardest, and general pediatrics is already projected to rank 14th out of 21 medical specialties for workforce adequacy by then.

At the same time, the number of families raising a mental health concern at a pediatric visit keeps climbing. A JAMA Network Open study of 1.8 million children’s insurance claims found that visits involving a mental health diagnosis rose from 5.7% in 2014 to 9.7% in 2023. Anxiety drove most of that increase, with related visits climbing more than 250% over the decade.

For a pediatric practice, that means fewer providers on staff and more children walking in with a mental health concern attached to their visit, a combination that leaves less time and specialized support for each one. Parents aren’t asking to skip straight to medication, either. Only 7% think it should be the first step, and 45% want skill-building tried before it. What they don’t have is a clear signal for when to move from that skill-building to professional guidance, the equivalent of a pediatrician tracking height and weight at every visit regardless of symptoms.

Integration bridges the pediatric access gap that primary care can’t close alone

Pediatricians shouldn’t have to become child psychiatrists. What they need is specialist support embedded directly into the visits already on their calendar. By integrating telebehavioral health clinicians into existing primary care workflows, health systems put expert guidance right at the point of care — specifically when specialists make critical prescribing decisions. The pediatrician is no longer left managing complex cases in isolation simply because the nearest child psychiatrist is half an hour away, or completely non-existent in their county.

AI plays a valuable, supporting role in this integrated model that’s strictly focused on efficiency. Used for triage support, ambient documentation, and identifying potential referrals, AI lightens the administrative burden that often makes specialist collaboration hard to sustain. It supports the clinical team, but it never makes clinical decisions.

While policy shifts, like Meta’s recent settlement over youth app safety, target the digital environment straining kids’ mental health, regulatory fixes don’t solve the immediate clinical access crisis. That requires accessible, expert care. Telebehavioral integration gives health systems the scalable infrastructure needed to support pediatricians today, starting with the very next patient on the schedule.