Three bets that landed on May 23

Three separate decisions landed on May 23 across nearly a century. None of them paid off the way anyone involved expected — one too slowly, one too late, one not at all.

Walt Disney was 20 years old when he incorporated Laugh-O-Gram Films, Inc. in Kansas City, raising roughly $15,000 from local investors. 1 The office was on the second floor of the McConahay Building at 1127 E. 31st Street. The team included Ub Iwerks, Hugh Harman, Rudolf Ising, and Friz Freleng — names that would later define the golden age of American animation. 2

Within four months, the company was dead in practice. A sales manager signed a $11,000 contract with Pictorial Clubs, Inc. of Tennessee to produce six animated fairy-tale shorts for school screenings. Pictorial paid $100 upfront and owed the rest on delivery in January 1924. Pictorial went bankrupt before paying. 1 By late 1922, Disney had moved out of his apartment into the studio's offices. Biographer Neal Gabler later wrote that Disney was "subsisting on beans, and bathing once a week at Union Station." 1 Laugh-O-Gram filed for Chapter 11 bankruptcy in July 1923.

Disney sold his camera, spent $40 on a one-way train ticket to Hollywood, and carried an unfinished reel of Alice's Wonderland. He wrote to New York distributor Margaret Winkler pitching the film; Winkler replied, "If your comedies are what you say they are and what I think they should be, we can do business." 3 On October 16, 1923 — five months after the bankruptcy — Walt and his brother Roy signed the Alice Comedies distribution contract and incorporated Disney Brothers Cartoon Studio. That date is The Walt Disney Company's official founding day. 4 Disney later reflected: "I think it's important to have a good hard failure when you're young. I learned a lot out of that." 5

Today The Walt Disney Company carries a market capitalization of approximately $178.9 billion. 6

Mirror: Laugh-O-Gram's collapse was caused by a single contract with $100 upfront and the rest due in 14 months — standard terms for a 20-year-old who needed the work. The lesson isn't "don't take deferred payment deals." It's: one large-deferred-revenue client as your sole revenue line is an existential concentration risk. Disney had no fallback when Pictorial went under. The Alice reel that saved him existed because a dentist paid $500 in cash for a short film Disney made on the side. The cash-paying side project outlasted the flagship deal.

At SunWorld in San Francisco, Sun Microsystems science director John Gage announced Java 1.0. 7 The language had started in 1991 as "Oak," originally aimed at interactive TV set-top boxes, then pivoted to the web in 1994 when James Gosling's team saw browser-based application deployment as the real market. 8 On the same day, Netscape co-founder Marc Andreessen announced that Netscape Navigator 2.0 would ship with Java support built in — the distribution deal that turned a developer conference demo into a platform. 8

Sun's core pitch was "Write Once, Run Anywhere": Java bytecode ran on any machine with a Java Virtual Machine, sidestepping the need to write separate code for each operating system. 7 That portability directly threatened Microsoft's Windows lock-in. Microsoft licensed Java in 1996, then distributed a modified version that removed key cross-platform components (Remote Method Invocation and the Java Native Interface — the mechanisms that let Java code interact with non-Java systems without tying itself to Windows) and added Windows-specific extensions, undermining the compatibility guarantee. 9 Sun sued in October 1997. In January 2001, Microsoft paid Sun $20 million to settle and lost its Java license entirely. Sun CEO Scott McNealy called it "a victory for our licensees and consumers." 9

The platform survived Microsoft's attack but eventually passed to Oracle, which acquired Sun in 2010 for $7.4 billion, calling Java "the most important software Oracle has ever acquired." 10 Oracle then sued Google, alleging Android's reimplementation of Java APIs infringed copyright — a decade of litigation that ended in April 2021 when the U.S. Supreme Court ruled 6-2 in Google's favor. 11 As of May 2026, Java ranks third on the TIOBE programming language index at 7.94%. 12

James Gosling, who led Java's design at Sun Microsystems. 7

Mirror: Java's thirty-year run shows what happens when a platform bets on developer portability and wins the ecosystem before the incumbent reacts. But it also shows the structural fragility of open platforms: Microsoft almost weaponized the standard, and Oracle later extracted its value through litigation rather than innovation. If you're building a platform today and granting broad licenses to grow adoption, the questions worth resolving early are: what happens when a large licensee forks? And who controls the compatibility tests?

Brazil's Natura &Co agreed to acquire Avon Products in an all-stock deal valuing Avon's equity at roughly $2 billion ($3.7 billion including debt), with Natura shareholders retaining 76% of the combined company. 13 The merger would create the world's fourth-largest pure-play beauty group by revenue, crossing $10 billion annually. 13 Both stocks rose over 9% on the announcement.

What Natura was actually buying was a brand in freefall. Avon had reached a market cap of roughly $21 billion in 2004; by 2019 it had fallen to approximately $1.4 billion — a 93% decline. 14 The company had paid $135 million in 2014 to settle a Foreign Corrupt Practices Act case related to bribing Chinese officials, with total legal costs around $500 million. 14 It had been removed from the S&P 500 in 2015. It had already sold 80% of its North American business to Cerberus Capital Management, a New York-based private equity firm, in 2016. 14

The integration failed. By April 2023, S&P Global Ratings noted that "the benefits from commercial, administrative and systems synergies have been weaker than expected, raising concerns about the long-term viability of the Avon brand and business model." 15 Natura sold Aesop to L'Oréal for $2.525 billion in April 2023 to pay down debt. 16 It sold The Body Shop — purchased for roughly €1 billion in 2017 — to Aurelius, a European private equity firm, for £207 million in November 2023. 17 In August 2024, Avon's U.S. holding company filed for Chapter 11 with $1.294 billion in debt and 386 talc lawsuits. 18 In September 2025, Natura sold Avon's international operations — Europe, Africa, and Asia — to Regent LP, a U.S. private equity firm, for £1. 19

Mirror: Avon had roughly 6 million sales representatives worldwide — what Forbes analyst Kate Hardcastle described as a "micro-influencer network established long before the world had a name for it." 20 The bet Natura made wasn't crazy. What it underestimated was the gap between acquiring a network and reviving a brand whose core proposition — the Avon Lady knocking on doors — had been structurally displaced by e-commerce and social platforms years before the deal closed. Buying a distressed asset with a historic brand name and an entrenched channel is rarely a renovation project. More often, it's a salvage operation.