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!

 

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

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