Too Old, Too Late? Arianna Huffington Proved Them Wrong at 55

Quick note before today’s story: I’m still recovering from my week at summer camp (and my poker losses…), but the free new Notes tool tradition continues (if a day late)! This week, it is “The Late Bloomers Roadmap”

At 30, Arianna Huffington had already been rejected by 36 publishers.

36!

At 40, she ran for governor of California and lost, and lost badly.

At 50, she was still seen as a public intellectual without much of a platform. By all accounts, she looked like a perpetual near-miss.

Hardly the makings of the digital media titan she was about to become.

The Rejection That Fueled Her

What most people would call humiliation, i.e., repeated failure, Arianna treated as fuel. Instead of shrinking from rejection, she used it as data, as a way to refine her message.

And by her early fifties, Arianna noticed a hole in the media landscape: The internet was exploding, yes, but trusted, curated commentary was not keeping pace.

Everyone else thought blogs were unserious. She thought they were the future.

And so she took a big swing and bet on it.

Leaning Into the Undervalued

In 2005, at age 55, Arianna Huffington launched The Huffington Post.

Critics laughed and called it a boondoggle, a blog in pajamas. The New York Times dismissed it.

But Arianna leaned into exactly what made it different. It was a mash-up of celebrity, savvy commentary, and news aggregation at a time when traditional outlets were still gatekeeping.

That difference was the breakthrough.

From Punchline to Powerhouse

Within a few years, Thw HuffPo had exploded in popularity and became one of the most visited news sites in the world.

And Arianna Huffington became a household name.

Happily therefore, In 2011, she got the last laugh when AOL bought the company for a whopping $315 million, cementing her place as one of the most successful late-blooming entrepreneurs of her generation.

Yet she was not finished.

And this is almost even more interesting (almost!)

In 2016, Arianna stepped down to launch Thrive Global, her new venture focused on well-being and burnout prevention - proof that reinvention is not just possible once, but over and over.

🛠️ Free Tool of the Week

The Latebloomers Roadmap – How did Arianna Huffington and Julia Child (and countless others) do it? Here’s a roadmap you can follow

The Takeaway

Actor Michael Caine says one of his best acting (and life) lessons occurred early in his career.

A chair got in the way of his stage entrance.

He wasn't sure what to do, and an old actor saw thew problem and told him, "Use the difficulty." “Huh?” Caine said. The other actor replied, “If it’s a comedy, fall over the chair for laughs. If it’s a drama, throw the chair against the wall in anger. Use the difficulty.”

Use the difficulty!

Steal This Strategy!

📖 Book – Thrive by Arianna Huffington 
Her case for redefining success beyond money and power.

🎥 Video – Arianna Huffington at Stanford: “We Are Drowning in Data and Starved for Wisdom” 
Her View From The Top talk on wisdom, performance, and burnout.

🌐 Website – Thrive Global thriveglobal.com
Her company focused on behavior change and well-being.

🎙️ Podcast – The Tim Ferriss Show #274 with Arianna Huffington:
Apple Podcasts | Spotify 
A wide-ranging conversation on building, health, and reinvention.

🛠️ Tool – Medium 
Low-friction publishing to start shipping ideas today.

About Steve

Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!