CHM was packed wall to wall on March 11, 2026, to celebrate Apple’s upcoming 50th anniversary. Inspired to write his new book, Apple: The First 50 Years, after hosting CHM’s Mac at 40 event two years ago, David Pogue returned to the stage to guide the audience through five decades of ideas, innovations, people, and passion.
Pogue opened with a reminder of how Apple has grown from its roots in a garage to the behemoth it is today. Nearly a third of the people on the planet—2.5 billion—are carrying an Apple device at any given moment. The company ships 220 million iPhones a year, generates $1 million in revenue every 90 seconds, and is nearing a $4 trillion market cap.
But the night wasn’t about numbers. It was about the people behind them.
Taking the audience back to the company’s profit engine, the Apple II, cofounder Steve Wozniak shared what Apple's success meant to him in a video clip. It wasn't the financial awards but rather earning the respect of fellow engineers for his ingenious design.
But that ingenuity may never have had a chance to change the world if Bill Fernandez (Apple’s first employee) had not connected his two friends named Steve when he was in high school.
Bill Fernandez remembers introducing the Steves.
On April 1, 1976, Ronald Wayne mediated a disagreement between the two Steves and unintentionally convinced Steve Jobs that they needed to start a company in order to maintain control of their intellectual property. Wayne wrote up a partnership agreement then and there, becoming the third cofounder of Apple with 10% of the company so he could, according to Jobs, break a tie when the Steves disagreed. Twelve days later, Wayne backed out. At the event, he had a chance to explain why.
Ron Wayne explains why he pulled out of Apple.
Jobs later mailed Wayne an unsolicited $800 check—“a cheap tip,” Wayne joked. He never sold his actual stake in the company, he says, despite the myth.
A part of Apple for its entire 50 years, Chris Espinosa joined as a young teen. When his mother got tired of driving him to Homebrew Computer Club meetings, he hitched rides with Woz. Espinosa wrote the Apple II reference manual before he could legally drive. At a time when computers were strange, misunderstood machines, the Apple II debuted at the West Coast Computer Fair in 1977.
Board chair Mike Markkula coached the team to give the impression of a successful company. Espinosa remembers wearing new corduroy pants to stand in the slickest booth at the fair. Like an explosion, he said, people suddenly realized they could have computing power all to themselves.
But not everything went smoothly as the company grew. Espinosa recalled how adding a last-minute Apple II emulator to the Apple III caused it to have a tendency to overheat… badly.
Chris Espinosa describes a unique way to fix the Apple III.
Espinosa said Steve Jobs inspired fierce loyalty even when he made life difficult. Like when Jobs hired Espinosa to lead Mac publications while secretly planning to fire Jef Raskin, Espinosa’s mentor. Jobs had an ex officio role as cofounder at Apple before he latched onto the Mac project, said Espinosa. He was considered by many to be a pest, not cut out to run a company. When Jobs returned to Apple with the acquisition of NeXT, Espinosa expected more of the same. But it was different, he said. Jobs had learned.
Former Apple CEO John Sculley recalled how Jobs had courted him when he was running Pepsi with the now famous, “Do you want to sell sugar water for the rest of your life, or come with me and change the world?”
Sculley wasn’t familiar with computers, but he had been an early Apple customer, having bought 550 Apple IIs to help his bottlers to send in their weekly sales figures. That status got him inside the Mac building. Andy Herzfeld had put a demo together that included dancing Pepsi cans, one of the first examples of computer animation that Sculley didn’t understand was a big deal at the time.
Sculley remembered Apple’s early culture and the sense of being on the cusp of something extraordinary, as well as the dramatic 1985 boardroom confrontation that resulted in Jobs’ removal from the Mac division.
John Sculley takes on Steve Jobs.
Despite their disagreements, Sculley appreciated Jobs’s uncompromising standards.
There was an explosion of creativity under Sculley in the late ’80s and early ’90s, including Illustrator, PageMaker, Photoshop, and PowerPoint. He and his team also professionalized distribution and improved the Mac by making it expandable, and by 1992, it was the largest selling computer.
In the audience, Robert Brunner, Apple’s early design chief, who spearheaded the establishment of Apple’s world-class design studio, remembered the pressure of the early ʼ90s and the race to miniaturize and improve awkward portables. But despite his own accomplishments, Brunner says his legacy will always be “the guy who hired Jony Ive.”
Sculley was fired after 10 years amidst leadership disagreements about company direction. By 1996, there were 50 Mac models that no one could tell apart and 12 ad campaigns. There had been three CEOs, and the company was failing.
The Mac had never really had a modern operating system. To acquire one, Apple bought Jobs’ company NeXT and brought on him and brilliant engineers and leaders, including Avie Tevanian (software) and Jon Rubinstein (hardware).
Initially, they didn’t know what they were going to do, they just knew they needed new technology to compete with Windows 95 and other competitors. The NeXT technology worked, but it wasn’t what Mac developers wanted at the time. There was no other choice but to work it out. Tevanian describes the mixed reaction at Apple.
Avie Tevanian describes wrangling Apple engineers.
Apple’s new leadership focused on just four products (desktop consumer and pro; portable consumer and pro), and one iconic ad campaign, Think Different, with the opening line, “Here’s to the crazy ones.” In perhaps the greatest turnaround in business history, a company that was six weeks from bankruptcy became profitable at $45 million one year later.
Former Senior VP of Hardware Engineering Jon Rubinstein, who had come with Jobs from NeXT recalled (on video) the first executive staff meeting at Apple, where he and Avie Tevanian looked at each other and thought, “What are we getting ourselves into?” That turned out to be a reinvention, led by the iMac and the iPod.
Jon Rubinstein describes the creation of the iMac and iPod.
Beginning in 1998, the company frequently reinvented itself with new products: iMac, iPod, iPhone, iPad. When Jobs unveiled the iPhone in 2007, hardly anyone grasped that it would reshape the world. Espinosa said the first moment he realized its power was when he received a text message from his wife after the keynote that just said, “I want.”
Apple innovation didn’t end when Steve Jobs passed away in 2011. Tevanian noted that it simply shifted from blockbuster hardware to global software and services. The company succeeds by running faster and doing things better than the competition.
The night closed with a final question: What threads tie Apple’s entire 50-year story together? Espinosa answered without hesitation: fear and pride. Apple was always terrified of being outpaced and always proud of doing things differently. Sculley added Jobs’s most consistent belief: “No compromises.”
The event concluded with a surprise—David Pogue performing a parody song he wrote about Apple fans to the tune of Pharrell Williams' "Happy" that brought the audience to its feet.
David Pogue sings a song about Apple.
Apple at 50 | CHM Live, March 11, 2026
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