“Shark Tank” star Kevin O’Leary once shared a story about how Steve Jobs’s passion for fonts helped turn “The Oregon Trail” series of strategy computer games into an educational hit and gave him a business lesson he still uses today.
When Jobs Geeking Out Over Fonts Changed Everything
O’Leary recalled in a social media post last month that Jobs personally convinced his team to rewrite The Oregon Trail for the Macintosh by showing off scalable fonts that made screens look artistic and almost “organic.”
“I saw it with my own eyes, Jobs was obsessed with fonts,” O’Leary wrote. “Scalable, artistic, educational — he saw beauty and business in one stroke.”
“That vision made Oregon Trail on a Mac feel like a movie. And we sold millions. I didn’t just watch that happen. I learned, and I brought that lesson into everything I do now,” he stated.
In the video, the investor stated that Jobs’s pitch was so convincing that O’Leary’s company agreed to rework the game despite the hefty development costs.
“We were negotiating … whether it was 12 or 14 or 20 million to start from scratch on Oregon Trail and rewrite it,” he explained. “But we needed to sell millions of copies, which we did.”
See Also: Kevin O’Leary Says Steve Jobs Was ‘Not A Nice Guy’ But Taught Him A Success Formula That Elon Musk Now Uses
The Oregon Trail And Apple’s Education Empire
The anecdote ties back to the deep connection between Apple and the Minnesota Educational Computing Consortium, which was funded by the state of Minnesota and is the group behind The Oregon Trail.
By the late 1970s, MECC and Apple shared a vision of putting computers in every classroom, using games like The Oregon Trail, Number Munchers and Lemonade Stand to hook kids on technology.
Jobs himself said in a 1995 Smithsonian interview that schools buying Apple IIs loaded with MECC software “was one of the things that built” Apple II. With Apple’s help, MECC’s titles became staples of American education throughout the 1980s and 1990s.
O’Leary’s company SoftKey bought MECC in 1995, along with other educational tech firms, acquiring popular titles like Oregon Trail, Carmen Sandiego and Reader Rabbit.
SoftKey then acquired The Learning Company and adopted its name. In 1999, O’Leary sold The Learning Company to Mattel.
The Business Lesson That Stuck With O’Leary
For O’Leary, the episode was more than a nostalgic memory. He said Jobs’s ability to merge art with science — and to persuade partners to take risks — taught him a lesson about innovation and business that he carried forward.
“Jobs had that brilliance between art and science to bring that forward and convince people like me to follow him,” O’Leary said in a video he attached to the post. “I didn’t let that lesson go unlearned. I definitely think about that all the time.”
The Legacy Of Fonts And Innovation
In a 2011 CNN article, Simon Garfield, the author of “JUST MY TYPE: A Book About Fonts,” argued that Jobs’ overlooked legacy was giving people the freedom to write with style.
Before the Macintosh in 1984, most word processors offered only one bland typeface. Jobs, inspired by calligraphy classes he stumbled into after dropping out of Reed College, insisted on including multiple scalable fonts in the Mac, making typography accessible to everyone.
Working with designer Susan Kare, he introduced bitmap fonts named after cities like Chicago, Geneva, and Venice, each reflecting a distinct typographic character.
This innovation transformed “font” from a niche printing term into part of everyday language, paving the way for expressive digital writing and design.
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Disclaimer: This content was partially produced with the help of Benzinga Neuro and was reviewed and published by Benzinga editors.
