Back then, Jon Stewart was just a talented, semitically handsome stand-up comic. For my money, his Unleavened and Chris Rock's Bring the Pain are the two best comedy specials of that decade. In 1998, CBS had an opening for a late night talk show to follow David Letterman's. This was the break Stewart was waiting for. He'd excelled as far as he could as a stand-up, his movie career was not taking off after a series of lackluster supporting roles in Big Daddy, and Playing By Heart. He needed this. Except CBS decided not to select him for this opening, opting instead for Craig Kilborn. You might remember Kilborn from Old School, where he was the womanizing p***k who seemed not at all to be acting.

Kilborn won the slot and hosted The Late Late Show, doing an absolutely predictable, uneventfully standard job at a completely conventional talk show, until he retired in 2004 to pursue becoming less significant on a full-time basis. Jon Stewart was left with Kilborn's leftovers, namely The Daily Show. It could have been humiliating to not only lose out to Kilborn but to be given the job Kilborn no longer wanted. But that's not how it panned out. Jon Stewart completely changed The Daily Show, and in doing so changed late night television.

Frederick M. Brown/Getty Images Entertainment/Getty
Pictured above: Kilborn, approximately 20 years after he no doubt bullied some kid in a lunchroom.

When Stewart took over The Daily Show, it was very much a parody of news magazine shows like Dateline. And while it certainly was home to some very talented writers and performers, they were there in the service of a show that mixed SNL Weekend-Update-style headline jokes with celeb interviews and parodies of news magazine puff pieces. Stewart made the show political, hiring Ben Karlin of The Onion and shepherding monster talents like Stephen Colbert, Steve Carrell, Jon Oliver, and Larry Wilmore to greater notoriety. Colbert (who worked under Kilborn as well) has stated that Stewart encouraged him to have a political viewpoint.

In 2009, Time magazine found Stewart to be television's most trusted journalist. Suddenly, for the first time in 40 years, the most important show in late night was not a celebrity talk show. Suddenly Saturday Night Live was not the only place for comedy writers and performers to aspire. Jon Stewart took his rejection from the standard path for a stand-up comic and completely revamped late night television, becoming this generation's Walter Cronkite and Lorne Michaels rolled up in one.

Unable to score a record deal, Jay Z started his own label, selling CDs out of his car. (For younger readers, CDs are magical downloads that exist on enchanted circles that fit into that slot on the dashboard in cars.) He then started Roc-A-Fella Records, ultimately landing a distribution deal with Priority Records and releasing Reasonable Doubt in 1996, which reached number 23 on the Billboard 200. From there, Jay Z's recording career took off, as did several of his other entrepreneurial endeavors.

How successful did Jay Z become? Well, in 2001, he plead guilty to stabbing record producer Lance Rivera, a second-degree felony, and was sentenced to only three years probation. That's success! Also, he gets to have sex with Beyonce, is a multimillionaire, and is one of the most important rappers of his generation. All because he went out on his own when the establishment said "No," much like how he also kept going when Rivera presumably said, "No, please don't stab me."

In producing Hollywood Shuffle, Townsend charged $40,000 on 15 different personal credits. He bought wardrobe on his Saks card, and in lieu of salaries, he filled crew members' cars with gas on a Mobil card. And he used the last of his credit to to host a buffet at a screening to attract a distributor, which he ultimately did. Hollywood Shuffle grossed over $5 million (50 times its budget) and established Townsend as a bankable commodity.

Zappa started his recording career on Verve Records, releasing Freak Out. This concept album about the counterculture was only the second double album in rock history, Dylan's Blonde on Blonde beating it by a week. In 1969, Zappa signed with Warner Brothers. So back up a second -- by the time Warner Brothers signed Zappa, they already had every idea of who he was. They knew they'd signed a man known for playing strange instruments, performing extended experimental jams, and making counterculture music (and lots of it). I guess they expected Frank to keep on being Frank, right? Of course not.

Digital Vision./Digital Vision/Getty Images
"We love the weird, verbose experimental stuff you're doing. Now stop it."

In the mid '70s, Zappa began recording a four-disc album called Lather, which encompassed all of his music styles: rock, pop, orchestral numbers, and long guitar solos. Warner Brothers, somehow surprised by a move that seems utterly Zappa-esque, refused to release the album. After lawsuits, they ultimately released Lather as four separate albums, but Zappa had already had enough, and left to form his own label. On Zappa Records and Barking Pumpkin Records, Zappa maintained full creative control over his music for the rest of his career, inspiring generations of musicians to do the same.

And do you know what's great about this story? Zappa's next two albums on his own label, Sheik Yerbouti and Joe's Garage, are arguably the two most accessible and successful albums of his career. Kind of makes you realize that maybe Warner Brothers shouldn't have pissed off Zappa in the first place. Some people, like Jay Z, start their own ventures because they can't get into the game. Others, like Zappa, have to leave the establishment to keep being who they are.

Anyway, in February of last year, the developers of WhatsApp, an instant messaging app, sold it to Facebook for $16 billion. Yeah. And one of the designers of WhatsApp was Brian Acton.

Now don't get me wrong, Mr. Acton was not some ridiculed scientist, tooling away in his basement with a product that no one took seriously. He was a Stanford-educated engineer and one of Yahoo's first hires in 1998. But y'know how technology goes -- it changes. And when Acton took his Yahoo money and invested it into .coms, he lost millions in the bust of the early 2000s. Faced with this setback, Acton did what all techheads did, which was look for the next big thing, which at that time was Facebook. He applied for a job.

This was before your aunt used Facebook to post recipes.

Faced with Acton's impressive resume and credentials, Facebook did the only thing they could: They turned him down. (Twitter did the same, but it's better for the story if we focus on Facebook.) After the rejection, Acton bought an iPhone and, recognizing the potential for apps, developed WhatsApp along with Jan Koum, whom Facebook had also rejected. It would have been far cheaper for Facebook to put them on the payroll and take advantage of their talent and expertise, but sometimes the establishment needs to be shown success on your own terms before it embraces you.

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