Childhood and Early Life
Barry Diller’s beginnings were a blend of privilege and rebellion, with just enough ambition to set him apart. Born in 1942 in San Francisco, California, Diller spent his formative years in Beverly Hills, the son of a successful real estate developer. His father’s business thrived to the point of naming streets after him—Barryvale and Barrydale—a testament to the family’s status. But despite this charmed childhood, Diller wasn’t exactly a poster child for academic discipline.
At Beverly Hills High School, his attendance record was patchy. He later quipped, "I never went to school on Mondays or Fridays and rarely on Wednesdays." Not surprisingly, formal education didn’t hold much appeal for him. After a brief stint at UCLA, Diller dropped out. But he wasn’t directionless. “I always knew I wanted to get into entertainment,” he said, and academia wasn’t the path he envisioned to get there.
Instead, Diller took charge of his own education. While his peers were sitting in lecture halls, he was reading voraciously. “I read tremendously—that's how I was educated, by reading,” he once explained. It was a DIY approach to learning, one that fit his independent streak and foreshadowed the bold, unconventional career moves he would later make.
Even in those early years, Diller’s instincts were clear: He was going to find his own way—and he was going to do it on his terms.
Early Career: From William Morris Agency to ABC (1961-1974)
Diller’s journey into the entertainment world started in the most unglamorous of places: the mailroom at the William Morris Agency. He landed the job in 1961 through a family connection, but he didn’t treat it as a dead-end gig. Instead, he used his downtime to study the agency’s entertainment industry archives, soaking up knowledge like a sponge. For three years, he absorbed everything he could about the business, but eventually, he realized that being an agent wasn’t for him. Television, on the other hand, caught his eye. As Diller later put it, “I’ve always believed whatever you’re interested in, get on the widest road, not the narrowest road. And television was certainly a pretty wide road.”
In 1964, Diller took his first step into that wide road, becoming an assistant to Elton Rule, who was then running ABC’s West Coast operations. It wasn’t long before fate intervened. Rule was promoted to ABC network President, and Diller moved with him to New York City. That relocation turned out to be a pivotal moment. Suddenly, Diller found himself with a much larger role than he’d anticipated. His initial task—negotiating broadcast rights for feature films—turned out to be the perfect proving ground for his sharp instincts and fearless approach. Within a year, he was promoted to Vice President of Development at just 23.
It didn’t take long for Diller to start making waves. In 1969, he came up with the idea for the “ABC Movie of the Week,” a groundbreaking series of 90-minute made-for-TV films that redefined network programming. The concept was a hit, but what really cemented Diller’s reputation was how he handled the negotiations. Universal Studios wanted an exclusive deal to produce all the films, but Diller wasn’t about to give away that kind of control. Instead, he offered Universal a one-year exclusivity agreement. When they balked, Diller walked. ABC ended up partnering with multiple studios instead, gaining flexibility and better deals. It was a textbook Diller move: confident, strategic, and unafraid to take a risk.
Diller’s boldness didn’t go unnoticed. By 1973, he was Vice President of Prime Time Television at ABC Entertainment, a role that saw him steering some of the network’s most important programming decisions—all before turning 30. Leonard Goldberg, ABC’s Vice President of Programming, described him as a “rough, tough kid who wasn’t afraid and who had class and style.”
One of Diller’s most lasting contributions was the creation of the “novel for television,” a format we now call the TV miniseries. And the crown jewel of this innovation? Roots.
In 1977, Roots aired as an eight-part epic about slavery in America, and it was a groundbreaking cultural event. A staggering 85% of American households tuned in to at least one episode, and the finale still holds its place as the third most-watched TV episode in history (behind Mash’s finale and Dallas's Who Done It episode). But while Roots is often remembered as a singular phenomenon, it wasn’t an overnight success story. It was the culmination of something Diller had been meticulously building over years.
Before Roots came QB-VII and Rich Man, Poor Man, two early examples of long-form, serialized storytelling on television, both overseen by Diller. The strategy is encapsulated in a famous Diller mantra: “When you find a vein, thicken it any way you can.” These projects laid the foundation for what Roots would become: proof that television could deliver gripping, emotional stories on a scale that rivaled the movies.
Rise to Power at Paramount Pictures (1974-1984)
When Diller became Chairman and CEO of Paramount Pictures in 1974 at the age of 32, it was a bold leap. Coming off his success at ABC—where he’d redefined television with the Movie of the Week—Diller was already known as a sharp negotiator and results-driven leader. That reputation caught the attention of Charles Bluhdorn, head of Paramount’s parent company Gulf and Western Industries, who saw in Diller the perfect candidate to rescue a struggling studio. And struggling it was—financially adrift despite the legacy of The Godfather. For Diller, it was both a challenge and an opportunity.
One of his first moves was to build a team that would change Hollywood forever. Dubbed the “Killer Dillers,” this group of young, hungry executives helped turn Paramount into a powerhouse. Michael Eisner, who Diller had originally hired at ABC, joined as President and COO in 1976. Eisner, of course, would go on to transform Disney into an entertainment juggernaut, taking several members of the Paramount team with him. Jeffrey Katzenberg became head of Disney’s film studio, while Dawn Steel went on to make history as the first female to head a studio when she took the top job in Columbia Pictures. Then there was Don Simpson, who teamed up with Jerry Bruckheimer to redefine the blockbuster with films like Flashdance (1983), Beverly Hills Cop (1984), and Top Gun (1986).
Diller had a unique philosophy when it came to hiring. “I have always believed in bringing people into your organization who are young and who are inexperienced for the job that you give them,” he once said. “And sometimes that works, and sometimes that doesn’t work.” But Diller thrived on taking chances. He believed hiring senior-level talent was a sign of failure; instead, he sought fresh energy and raw potential—qualities he could shape, just as he had been shaped by his early roles at ABC. It was a gamble, but it mostly worked, thanks to Diller’s uncanny ability to read people and put them in positions to succeed.
Under Diller’s leadership, Paramount quickly went from struggling to soaring. The studio churned out an unparalleled string of hits: Saturday Night Fever (1977), Grease (1978), Raiders of the Lost Ark (1981). These weren’t just blockbusters—they were cultural phenomena. And Diller wasn’t only about box office smashes. He also championed films with critical heft, like Ordinary People (1980), which swept the Oscars with four wins, including Best Picture.
Diller’s guiding principle was simple: the story came first. “A strong narrative is the foundation of any great film,” he believed, prioritizing exceptional scripts over the typical Hollywood formula of chasing big-name directors or stars. It was a radical approach for the time but one that paid off.
The financial turnaround was staggering. Before Diller, Paramount’s annual profits hovered around $10–$20 million, occasionally hitting $40 million in a good year. Under Diller and Eisner, those numbers skyrocketed, with the studio consistently pulling in over $100 million annually for nearly a decade.
While his blockbuster film successes are legendary, Diller’s influence extended deeply into television as well. Under his leadership, Paramount churned out iconic series like Laverne & Shirley (1976–1983), a Nielsen ratings juggernaut; Taxi (1978–1983), which racked up 18 Emmy Awards; and Cheers (1982–1993), which became one of the most celebrated sitcoms in TV history with 28 Emmys across its 11-season run.
Under Diller, Paramount defied the industry's usual boom-and-bust cycle, delivering exceptional profits year after year—an impressive feat in a business known for its unpredictability. He ran the studio with remarkable consistency, turning it into a well-oiled machine that not only generated steady financial success but also produced some of the most iconic films and TV shows of its era.
Jeffrey Katzenberg, one of Diller’s closest collaborators, once said, “He’s in the all-star league. The rest of us are like children at play compared to Barry.”
He and his team became Hollywood’s rising stars, and in my research I came across a copy of New York Magazine with Diller and Eisner on the cover under the headline: “Hollywood’s Hottest Stars.”
Departure from Paramount (1984)
But by 1984, the golden era at Paramount came to an abrupt end. The catalyst? A bitter clash between Diller and Martin Davis, the new chairman of Gulf+Western—the studio’s parent company. Davis had taken over after the sudden death of Charles/Charlie Bluhdorn in 1983 at just 56 years. Bluhdorn had been a close ally of Diller’s, but Davis was cut from a very different cloth. Known for his cold, cost-cutting approach, Davis prioritized numbers over innovation, which put him on a direct collision course with Diller’s creative ambitions.
At the heart of their feud was Diller’s vision to launch a fourth television network. He believed it was the next big leap for Paramount, but Davis wasn’t convinced. Their relationship quickly soured, with industry insiders dubbing it “one of the most sour in the industry.” According to some sources, the final straw came when Davis demanded Diller fire Michael Eisner. For his part, Davis denied giving such an order, but by then, the writing was on the wall.
Diller left Paramount in 1984, and his exit triggered a seismic shift. Michael Eisner, Jeffrey Katzenberg, and many other senior executives followed him out the door. It was an exodus that gutted Paramount’s leadership and reshaped the industry.
Davis’s tenure at Gulf+Western earned him a reputation as a ruthless manager, with Fortune magazine naming him one of “The Toughest Bosses in America.” But his hard-nosed approach came at a cost. Industry heavyweight David Geffen, a close friend of Diller, was scathing of Davis: “He got rid of the three most talented people in the world he inhabits—Diller, Eisner, and Katzenberg. That right there was one of the most monumental screwups in the history of show business. These three gentlemen have created billions of dollars in value for their companies that could have gone to Paramount. He threw them out.”
Diller’s departure marked the end of an era, but for him, it was just the beginning of another chapter. The talent he nurtured and the ideas he championed would go on to shape the entertainment industry for decades, a legacy that only underscored what Paramount had lost.
Murdoch, Diller and Fox
In 1984, Rupert Murdoch tapped Diller to become Chairman and CEO of Twentieth Century Fox, and by 1986, Diller was spearheading a bold new venture: launching a fourth national television network to challenge the long-standing dominance of ABC, CBS, and NBC.
The foundation for the Fox Broadcasting Company was laid with meticulous precision. In March 1985, Murdoch’s News Corporation purchased a 50% stake in TCF Holdings, the parent company of 20th Century Fox, for $255 million. By December of that year, Murdoch had acquired the remaining stake for $325 million, giving him full control. At the same time, News Corporation spent a staggering $2.55 billion to buy six major independent TV stations from Metromedia. These stations, located in the biggest U.S. markets, became the backbone of what would soon be Fox Broadcasting.
Regulatory hurdles added drama to the timeline. U.S. broadcasting rules required Murdoch to become a U.S. citizen in 1985 to legally own these assets. Additionally, cross-ownership rules forced him to sell the New York Post, though he later repurchased it. By March 1986, the FCC approved the Metromedia acquisitions, paving the way for the network’s launch.
The Launch of Fox Broadcasting Company
Industry insiders were skeptical. The idea of a new network entering a market dominated by the Big Three seemed far-fetched, even foolish. But Diller had a strategy. On October 9, 1986, Fox Broadcasting officially launched—not with a full lineup, but with a single late-night program: The Late Show Starring Joan Rivers. In April 1987, Fox began airing prime-time programming, starting with weekend evenings. Instead of rushing to fill a full schedule, the network carefully added nights over several years. This phased rollout defied industry norms and established a new playbook for launching networks. It was methodical, conservative, and highly effective.
Diller operated with remarkable autonomy at Fox. As he later reflected, "I never really felt I worked for Rupert Murdoch. I made decisions as if I owned the place." Murdoch himself admired Diller’s disciplined management style, once noting, "He was a very conservative manager. He would arm-wrestle movie producers for months."
Diller’s vision for Fox was simple but daring: “We were the fourth network, so we had to not be like the other three. The only thing we should do is be an alternative.” With this in mind, Fox targeted young, upscale viewers—the kind of demographic advertisers loved.
Defining Fox’s Identity
Under Diller’s leadership, Fox developed an irreverent, groundbreaking lineup of shows that became its signature.
Married... With Children (1987): A brash, no-holds-barred sitcom that turned the wholesome family TV trope on its head.
The Simpsons (1989): A cultural phenomenon that satirized the perfect family archetype with a biting, dysfunctional twist. Diller famously noted that The Cosby Show was dominating TV at the time, so he wanted something that was "100% the opposite." The Simpsons became a ratings juggernaut and merchandising powerhouse, cementing Fox’s reputation as a network willing to take risks. Reflecting on its success, Diller said, “When you find a vein, thicken it any way you can.”
Beverly Hills, 90210 (1990): A glossy teen drama that tapped into the aspirations and angst of young audiences.
In Living Color (1990): A sketch comedy show that broke boundaries with its diverse cast and fearless humor.
By 1990, Fox was no longer the scrappy newcomer—it was a major player in the television industry. Diller’s innovative programming and bold vision had not only established the network but redefined what a network could be.
His exit from Fox in 1992 sent shockwaves through Hollywood. This wasn’t just another executive shuffle—this was Barry Diller, the man widely hailed as the brightest mind in the media at the time. USC professor A.D. Murphy summed up the general sentiment perfectly, saying, “Diller is probably the most successful executive in business today.” Not "one of the most," mind you—the most. And when someone of that stature walks away, everyone takes notice.
But his reasoning was quintessential Diller: "I'm both young enough and old enough to want to own my own store. This one is owned by someone else."
The decision was about independence. “I really want to be independent,” he said at the time, emphasizing his desire to take risks with his own capital rather than someone else’s.
But his exit also reflected the shifting dynamics at Fox. Rupert Murdoch, who had previously granted Diller significant autonomy, was becoming more hands-on after relocating to Los Angeles. By 1991, Diller felt his role had changed. Reflecting on a News Corp. board meeting that year, he said, “I had the feeling I was an unwanted voice chiming in. I thought, ‘My God, I really am an employee.’”
At 50 years old, and after nearly two decades of reshaping the entertainment industry, Diller was ready to tackle a new challenge. After years of overseeing scripts, productions, and programming, he admitted, “After 18 years of reading scripts, I never wanted to see another one.” It wasn’t just about fatigue—it was about his natural restlessness. In interviews, Diller has spoken candidly about how quickly he grows bored once he’s solved the puzzle of any given challenge. For him, success isn’t about staying on top of the game; it’s about finding a new game to master.
And in true Barry Diller fashion, he was ready to jump headfirst again into the unknown.
QVC
Diller’s pivot to QVC in 1992 was a move that surprised—and puzzled—almost everyone. Here was a man who had dominated traditional media, and now he was stepping into the world of home shopping, something many in Hollywood viewed as lowbrow.
Through his Arrow Investments Inc., Diller bought a 3% stake in QVC for $25 million.
Diller’s co-investors at QVC were heavyweights in the cable industry: John Malone of Liberty Media and Brian Roberts of Comcast. Both men understood Diller’s knack for pushing the boundaries of media. Malone described QVC as a “vehicle” and said, “It’s a platform for Barry.”
Dillers interest had been sparked by something close to home: Diane von Furstenberg, his close friend and future wife, had debuted her Silk Assets collection on QVC, selling $1.2 million worth of scarves in two hours (equivalent to $2.6 million today). Over four years, her collection raked in more than $40 million. The numbers were staggering, and they hinted at QVC’s potential as more than just a shopping channel.
Diller describes having an “epiphany” the first time he visited the QVC studios. He saw something beyond the racks of products and live demos. “I had only known screens for narrative storytelling purposes,” he said. “Here I saw a screen being used at this primitive convergence of telephones, televisions, and computers.” It wasn’t just commerce—it was interactivity on a massive scale. “This is going to change things,” he thought, and for someone like Diller, who thrives on reinvention, that kind of change was irresistible.
A Leap Into the Unknown
Hollywood didn’t get it. Diller recalled that people in the entertainment industry thought he’d “lost his mind.” David Geffen, his longtime friend, admitted, “I didn’t think that was good enough, or big enough, or important enough, or classy enough for Barry.” But Diller brushed off the criticism, saying, “All they care about is status. That’s why they can’t understand why I’m doing this.”
While Hollywood sneered, Wall Street took notice. The day Diller joined QVC, its stock shot up—a clear sign that investors believed in his ability to spot and seize opportunities long before anyone else.
A Vision for QVC’s Future
Under Diller’s leadership, QVC became a serious competitor to the Home Shopping Network, and within a year revenues had hit $1.6 billion and it was one of the fastest growing businesses in the US. Diller envisioned transforming the shopping channel into an interactive entertainment and merchandising service, and as a means of getting into entertainment he went shopping for a big target- his old employer Paramount.
Diller’s foray into the bidding war for Paramount Communications in 1994 was one of the most high-stakes battles of the decade.
The Prelude: Martin Davis’s Calculated Move
By 1993, Paramount was in disarray. Under Martin Davis’s leadership, the studio had become undervalued and vulnerable to takeover bids. Davis, infamous for alienating top talent (including Diller himself years earlier), knew the writing was on the wall. Concerned that Diller—ever the opportunist—might make a play for the company, Davis acted preemptively. He reached out to Sumner Redstone, offering Paramount to Viacom in a deal that would allow Davis to stay on as CEO under Redstone’s control.
In September 1993, the merger was announced: Viacom would acquire Paramount for $8.2 billion, forming Paramount Viacom International. But Redstone’s strategy hit an early snag. Reports surfaced that he had been buying Viacom shares before the deal, triggering a regulatory scandal. Viacom’s stock price tumbled, dropping the value of the Paramount deal to $7.5 billion.
Diller Makes His Move
Sensing an opening, Diller, backed by QVC, entered the fray with a counteroffer of $9.5 billion. It was bold, audacious, and perfectly timed. Diller even sent Redstone a letter expressing hope that their friendship wouldn’t be affected, but Redstone wasn’t buying it. He saw Diller’s move as a betrayal, fueled by John Malone, the aggressive CEO of TCI, who was one of Diller’s primary allies in the bid.
What followed was a whirlwind of legal maneuvers and strategic power plays. Viacom filed an antitrust lawsuit against Malone, accusing him of monopolistic practices. Redstone went so far as to present his case to the U.S. Senate Antitrust Committee. The pressure worked—Malone eventually sold his 22% stake in QVC, leaving Diller without his most powerful backer.
The Bidding War Escalates
With Malone out, Diller turned directly to Paramount shareholders, bypassing the board entirely. He launched a tender offer, placing ads that invited shareholders to sell their shares at $80 per share, $4 above market value. It was a high-stakes gamble, but Redstone wasn’t backing down. He countered with his own tender offer, escalating the bidding war.
Diller raised his final offer to $92 per share, with a tight three-week deadline for shareholders to accept. But Redstone had one last move up his sleeve: a merger between Viacom and Blockbuster. Blockbuster’s massive cash reserves gave Redstone the financial firepower to increase Viacom’s offer to $107 per share, pushing the total deal value to over $10 billion.
The Outcome
In February 1994, Paramount shareholders accepted Viacom’s offer. Redstone had won the battle. Diller, characteristically pragmatic, summed it up with a line that became legendary: “They won. We lost. Next.” It was a classic Diller moment—clear-eyed, forward-thinking, and devoid of pettiness.
But losing Paramount left a mark. Reflecting years later, Diller admitted, “In the end, I didn’t do it. He topped our last bid, and I didn’t top that. The truth is, I should have done it, but I was chicken.”
CBS Merger
Diller’s 1994 attempt to merge QVC with CBS was another bold chapter in his career—a high-stakes play that, while ultimately unsuccessful, underscored his willingness to take on titans and reshape the media landscape. At $5.4 billion, the merger was poised to create a powerhouse that would redefine television, retail, and broadcasting. QVC shareholders were set to own 46% of the combined entity, with Diller at the helm. But in a twist worthy of a Hollywood script, Comcast’s Ralph and Brian Roberts derailed the plan at the eleventh hour.
The Comcast Counterstrike
Just as the boards of CBS and QVC were preparing to sign off, Diller’s plans unraveled. While his jet was en route to finalize the deal, the Robertses arrived with a letter containing a surprise counteroffer: Comcast would pay $2.2 billion ($44 per share) to acquire the 84% of QVC stock it didn’t already own. This bid easily surpassed CBS’s $38-per-share offer and sent shockwaves through the media world.
Comcast had many reasons for scuppering the CBS bid. The proposed merger threatened Comcast’s influence over QVC, a company they had heavily invested in because it would reduce its stake from 15.5% to a mere 4.9% in the new entity. The proposed merger could also shift QVC’s focus from cable to network broadcasting. By acquiring QVC outright, Comcast could protect its stake and take full control of a valuable asset.
There was also an underlying tension between Diller and Comcast. Within the Roberts family, there was speculation that “Diller might have been using QVC as a springboard for himself.” Whether that fear was warranted or not, Comcast wasn’t willing to take the risk.
The Fallout
The reaction in the media was explosive. Industry veterans marveled at the drama of it all, with one source summing it up: “Hollywood couldn’t have written a script like this. All these cable-cum-broadcasting people, they have three traits: they’re phenomenally greedy, they’re phenomenally jealous, and they’re filled with a lot of hate for their competitors.”
For Diller, the setback was disappointing but not entirely unexpected. “It isn’t a complete surprise,” he said when the Robertses revealed their counteroffer. “I’m surprised a bit at the lateness of it, but it doesn’t come as a surprise, given our previous discussions. I don’t consider it as an act of evil of any kind.” True to form, Diller stayed measured and pragmatic, even as his plans unraveled.
Diller scrambled to find higher bids for QVC, reaching out to telecommunications companies and other cable operators in a last-ditch effort to outmaneuver Comcast. But the effort fell short. By the end of 1994, Comcast had completed its buyout of QVC for $2.2 billion. Diller walked away with a $130 million windfall but had to shelve his ambitions for a QVC-CBS merger.
The Legacy of the Paramount and CBS Bid
Diller’s foray into these high-profile battles—first with Paramount and then with CBS—cemented his reputation as a fearless strategist willing to challenge the industry’s most powerful players. Though he didn’t prevail in either case, his resilience, composure, and ability to think big left an indelible mark.
Years later, Jeffrey Katzenberg reflected on Diller’s knack for thriving against the odds: “The betting at Fox was 1,000 to 1 that he wouldn’t succeed with the network. He did. Then at his height, he walks away from it and lands on a thing called QVC. Everyone laughed behind his back. And he hits a grand slam at QVC.”
And despite the failed bids QVC was a success under Diller- while only there for 2 years, its market cap had gone from $833 million to $2.2 billion
The Beginnings of IAC
In 1995, Diller made what looked like a small, unassuming move: with backing from Liberty Media’s John Malone, he acquired Silver King Broadcasting, a collection of UHF stations with a small stake in the Home Shopping Network (HSN). Not exactly a headline-grabber at the time, but as Diller would later say, this was the seed from which IAC, his massive media and internet empire, would grow.
Once Diller had Malone’s financial support in his corner, he didn’t waste time playing it safe. By 1996, he orchestrated a $1.3 billion deal through Silver King to take over HSN, cementing his dominance in the home-shopping market. And then, in 1998, he pulled off another audacious move, acquiring Universal Studios’ television assets—USA Network, the Sci-Fi Channel, and Universal Television’s domestic production and distribution arms—for a cool $4.1 billion. At that point, Silver King rebranded itself as USA Networks, Inc., signaling that Diller had officially arrived as a media mogul.
But Diller wasn’t one to sit back and admire his empire. In 2002, he sold USA Networks’ broadcast entertainment assets to a Vivendi joint venture for $11.7 billion. While he stayed on as CEO of Vivendi Universal Entertainment, this sale marked a turning point for him. By this time, he’d already started venturing into a new world: online business. Back in 1997, he had begun investing in companies that would one day dominate the internet landscape. He described his methodology as "colonizing offline businesses into online businesses"
His strategy was simple: spot the potential, acquire or develop the business, help it grow, then spin it off into a standalone company. By 2005, after selling IAC’s 5.4% stake in Vivendi Universal for $3.4 billion, Diller doubled down on internet-focused businesses. His experience at QVC had given him a critical insight—people were surprisingly willing to interact with screens to make purchases. With the internet still in its early stages, he saw a gold mine in sectors like concert tickets, travel, and dating.
And, as we’ll see with companies like Ticketmaster, his instincts were spot on.
Ticketmaster
In 1997, IAC stepped in and bought 50% of the ticketing company for $210 million, banking on the idea that ticket sales and local information services could be a killer combination.
In 1998 he merged Ticketmaster with CitySearch, creating Ticketmaster Online-CitySearch—a move aimed at dominating both the ticketing and online local services markets. Then, in 2003, he doubled down again, shelling out $736 million to buy the remaining half of Ticketmaster. And the investment? It paid off in spades. Ticketmaster’s revenue ballooned from $743 million in 2003 to a staggering $1.24 billion by 2007.
Then came 2008, and the classic Diller playbook: spin it off. Just two years later, it merged with Live Nation, forming Live Nation Entertainment. For Diller, it was yet another masterclass in spotting potential, nurturing it, and knowing when to let it soar.
Expedia
The Entry
In 2001, while many companies were still reeling from the post-9/11 uncertainty, Diller made a bold move. IAC paid $1.5 billion to buy a controlling stake in Expedia from Microsoft. For most, travel seemed risky at the time, but Diller’s rationale was simple: “If there is life, there’s travel.” And he was right.
The Growth
Expedia took off. By 2004, it was thriving. Under IAC’s umbrella, it went on an acquisition spree, adding Hotels.com, Hotwire, TripAdvisor, and eLong, a Chinese travel company. One by one, these brands expanded Expedia’s footprint, turning it into a global travel giant.
The Leadership Moves
Then there’s Dara Khosrowshahi (say it with me: cos-row-sha-hi). He joined IAC—then known as USA Networks—back in 1998 and rose through the ranks to become CFO by 2002. Three years later, in 2005, Diller made another gutsy call: he spun off Expedia and handed the CEO role to Khosrowshahi.
It was sink or swim—and Khosrowshahi swam.
Expedia thrived. By 2018, it owned over 45 travel-related businesses, including Travelocity, Trivago, and Orbitz. As for Khosrowshahi, his success at Expedia paved the way for his next big move: in 2017, he became CEO of Uber, stepping in to stabilize the company after its turbulent Kalanick era.
Today, Expedia is valued at $24 billion, a testament to Diller’s vision, and interestingly over the last few months there have been stories in the press that Uber under Khosrowshahi could buy Expedia.
Online Dating
Diller’s foray into online dating wasn’t the result of some carefully crafted master plan—it all began with a nudge from his son, Alexander von Furstenberg. It was the late 1990s, and von Furstenberg pointed his father toward the fledgling online dating market. Diller later described the moment, saying:
“So there was a tiny little company in Texas called Match.com, because I’d said, ‘This is something the internet can do.’ So we bought this little tiny thing, and then it went where it went.”
There’s no report on how much IAC paid, but whatever it was, it was a steal considering what Match would grow into.
Match.com wasn’t just a one-off for Diller. It became the cornerstone of a broader strategy that turned IAC into the heavyweight champion of online dating- and again, harking back to his motto- “When you find a vein, thicken it any way you can.”.
Under his leadership, IAC snapped up a series of platforms, including OkCupid, PlentyOfFish, Hinge, and Tinder. As usual, Diller’s playbook came into play: nurture, scale, and spin off. In 2015, Match Group, built around Match.com, went public.
By 2018, Match Group owned over 45 dating-related businesses. With a total investment of $1.6 billion Match Group’s market cap reached $20 billion by 2019- this success cemented Diller’s reputation as a trailblazer in the digital world.
However sluggish growth over the last few years has seen its value drop to just over $8 billion at the start of 2025.
The Growth of IAC in the 2000s
The 2000s marked a period of rapid transformation for IAC, shaped entirely by Diller’s distinct business style. He wasn’t interested in building an empire for the sake of prestige or size—he wanted to understand and grow each business, then step aside when the time was right.
“I don’t like conglomerates,” Diller said plainly. “They’re inefficient. As soon as it got to a stage where I thought it really needed the light of being independent, being on its own, that was a healthy thing.” In every interview, Diller’s focus on the thrill of transformation, not possession, shines through.
By the mid-2000s, IAC was thriving, with revenue hitting $6.2 billion in 2005, largely thanks to its online travel and ticketing businesses. That same year, Diller’s compensation package made headlines—it topped $295 million, with $289 million coming from exercised stock options, earning him the title of the highest-paid CEO.
Industry giants noticed his prowess. Billionaire investor Mario Gabelli said:
“He understood the dynamics of the digital world early among the media moguls, and he captured it.”
And David Geffen added:
“Barry always has a plan. I’ve never seen him be anything but successful. To bet against him would be a fool’s errand.
But of course when you invest in so many different businesses you’re going to experience some failures.
Ask Jeeves
In 2005, IAC purchased Ask Jeeves for $1.85 billion. The goal was to compete in the search engine market, but the timing was disastrous. Google had already locked down dominance in the space, leaving Ask Jeeves floundering. IAC rebranded it as IAC Search & Media, but the company never managed to capture significant market share.
Investment in Aereo
Starting in 2012, IAC led multiple funding rounds for Aereo, investing over $90 million in total. Aereo offered live broadcast TV streaming for $8 a month, using thousands of tiny antennas to capture individual signals. The design avoided retransmission fees, which Diller called “the first potentially transformative technology” capable of delivering broadcast TV over the internet.
Aereo launched in New York City and expanded to major U.S. markets, challenging the cable TV industry’s traditional model. Broadcasters, however, argued that Aereo undermined their business by bypassing retransmission fees.
The legal battle escalated to the Supreme Court. In June 2014, the Court ruled that Aereo’s business model was illegal. Diller didn’t mince words, calling it “a big loss for consumers.” He acknowledged defeat, saying, “We did try, but it’s over now.” Aereo immediately suspended service and filed for bankruptcy in November 2014. In March 2015, TiVo purchased Aereo’s trademarks and customer lists for $1 million.
The Daily Beast
In 2008, Diller, through IAC, launched The Daily Beast alongside Tina Brown, a powerhouse editor who had run The New Yorker and Vanity Fair. The vision was to create a sharp, digital-first tabloid.
Two years later, in 2010, The Daily Beast merged with Newsweek. The idea was to pair the Beast’s digital swagger with Newsweek’s gravitas. But the partnership flopped. By 2013, Diller had sold Newsweek, leaving The Daily Beast back where it started—an IAC property, standing on its own.
Financially, though, it was a mess.
By 2023, IAC started looking for a way out. They brought in an advisory firm to scout potential buyers, even exploring talks with The Ankler, a Hollywood-focused media company, but nothing stuck.
In April 2024, Diller opted for a reset instead. He brought in heavy hitters Ben Sherwood, formerly the head of Disney-ABC Television, and Joanna Coles, ex-chief content officer at Hearst Magazines, to lead the turnaround. Sherwood and Coles acquired about half of The Daily Beast, with IAC retaining the majority. Sherwood stepped in as CEO and publisher, while Coles became chief creative and content officer.
At the time, The Daily Beast was on track to lose $9 million in 2024. But Sherwood and Coles rolled out a plan focused on subscriptions, advertising, and events to chart a path to profitability. Diller, for his part, sounded optimistic, saying:
“These are tough times for digital journalism, but the combined experience, expertise, and energy of Ben and Joanna have made me an optimist about their ability to make The Beast an enduring and successful enterprise.”
Vimeo
Vimeo’s transformation into a billion-dollar business owes much to Diller’s instinct for recognizing potential and his willingness to trust young talent. Vimeo entered the IAC family in 2006 almost by accident, part of a $26 million acquisition of Connected Ventures, the parent company of CollegeHumor. At the time, Vimeo was a rudimentary web player for CollegeHumor’s sketches—not exactly a game-changer.
For years, Vimeo floundered. Even IAC’s CEO Joey Levin admitted, “We debated selling it, and even shutting it down.” The platform offered a higher-quality video experience for creators than YouTube but struggled to find scale or a viable business model.
Everything changed when Anjali Sud joined Vimeo in 2014 as head of marketing. Sud spotted something others hadn’t: a growing number of small businesses and marketing teams were using Vimeo to host videos for social media and web campaigns. “They were so diverse, it had to be a trend,” she said.
Sud proposed a radical shift. Instead of competing with YouTube in the content wars, Vimeo would reposition itself as a publishing platform for creators and businesses. Her idea contradicted Levin’s existing strategy, but Levin and Diller listened. Diller’s hallmark culture of empowering young leaders gave Sud the freedom to test her vision.
When the results rolled in, the transformation was undeniable. Sud was promoted to CEO in 2017 at just 32 years old. By 2024, Vimeo had 1.4 million paid subscribers, $104 million in annual sales, and a market cap of over $1 billion. True to Diller’s philosophy, Vimeo was spun off as a separate company in 2021.
Sud later reflected on her journey, saying, “I’m the perfect example of that strategy and I’m obviously a beneficiary of it. But I also am a really big believer in it as a philosophy.”
Diller and Scott Rudin
For years, Diller and Scott Rudin were a formidable team in entertainment, producing major Broadway hits like To Kill a Mockingbird and Carousel. Diller’s involvement went beyond financing—his name as co-producer helped attract top-tier talent and resources. Together, they delivered culturally significant productions that dominated Broadway. IAC also financed several of Rudin’s critically acclaimed films, including Uncut Gems, Eighth Grade, and Lady Bird.
But in April 2021, the partnership faced a seismic shake-up.
That’s when The Hollywood Reporter published an exposé detailing Rudin’s alleged abusive behavior. The claims included verbal and physical abuse, gaslighting, and fostering a toxic workplace. The backlash was immediate. Rudin announced he was stepping away from his projects, effectively ending his reign over Broadway and much of Hollywood.
While others distanced themselves, Diller defended Rudin. He claimed he had never witnessed the alleged behavior and argued that Rudin was “too valuable a resource” to cast aside permanently. He also criticized what he called “cancel culture,” insisting that tough management shouldn’t automatically equate to abuse.
Diller’s remarks sparked their own controversy. Critics accused him of downplaying the harm Rudin’s employees endured, reigniting debates about power dynamics in the entertainment industry.
Rudin, meanwhile, vanished from public view. By 2024, his name surfaced briefly when he sold his Manhattan townhouse for $20 million, but he remained out of Broadway and film. The scandal left a lasting mark on Diller’s reputation, underscoring the complexities of loyalty and accountability in the upper echelons of entertainment.
Insider Trading Allegations
On March 9, 2022, The Wall Street Journal revealed that Diller, David Geffen, and Alex von Furstenberg were under investigation by the SEC and DOJ for alleged insider trading. The scrutiny stemmed from their trading of Activision Blizzard options just days before Microsoft’s announcement of its acquisition.
Diller, who has a longstanding friendship with Activision CEO Bobby Kotick, categorically denied any wrongdoing, stating, "It was simply a lucky bet." He emphasized that neither he nor his associates had any prior knowledge of the impending acquisition, asserting, "We acted on no information of any kind from anyone."
The trio netted about $60 million in profits.
By 2024, the investigation wrapped up without any charges being filed. Speaking after the conclusion, Diller said, “There was no insider trading, and nobody acted on any insider information. The investigation showed that.”
IAC's Portfolio as of 2025
IAC’s current portfolio showcases Diller’s strategy of focusing on digital, media, and technology investments that prioritize steady growth over high-risk, dramatic gambles:
Dotdash Meredith: Created in December 2021 through the merger of IAC’s Dotdash with Meredith Corporation’s National Media Group, it’s now a major player in both digital and print publishing with a market cap of $2.6 billion
Care.com: Acquired in February 2020 for $500 million, this online platform connects families with caregivers. However, its value has stagnated over the past four years.
Angi Inc. (formerly ANGI Homeservices): A home services marketplace where IAC maintains a majority stake, slated to be spun off in 2025 and has a market cap of just under a billion dollars
MGM Resorts International: By 2024, IAC’s 20% stake in MGM Resorts was valued at over $2.4 billion, reflecting a long-term investment strategy.
Turo: A peer-to-peer car-sharing platform in which IAC invested $250 million. Its stake is now valued at just under $1 billion.
Diller’s approach here is clear: focus on strategic growth over time, avoiding the flashiness of enormous, risky bets.
Financial Performance
IAC has faced ups and downs financially in recent years:
2023 Revenue: $4.37 billion, a 17% decline from $5.24 billion in 2022.
Long-Term Growth: Despite short-term challenges, IAC’s revenue growth is evident compared to 2019’s $2.5 billion.
This fluctuation aligns with Diller’s broader philosophy—success comes in cycles, but the trend over time matters more than year-to-year changes.
But overall Diller's strategy has proven remarkably successful. From its initial value of $250 million in 1995, IAC has created an equity value of approximately $60 billion spread across ten publicly traded media and internet companies8.
Political Activities and Controversies (2016–2020)
Diller has never held back on politics, particularly when it came to Donald Trump.
On Trump’s Campaign: In 2015, Diller dismissed Trump’s presidential bid as “reality television as politics,” calling him a “self-promoting huckster” who found a “vein of meanness and nastiness.”
Trump’s Retort: True to form, Trump fired back on Twitter: “Little Barry Diller, who lost a fortune on Newsweek and Daily Beast, only writes badly about me. He is a sad and pathetic figure. Lives lie!”
Diller’s disdain wasn’t limited to Trump himself. He criticized business leaders who backed Trump solely for economic reasons, particularly hedge fund billionaire John Paulson:
“I heard him talk [about Trump] for 20 minutes and … he never talked about the character of the person. What he and others do is refuse to talk about the character of Trump.”
Diller didn’t spare Democrats either. He was critical of Obama’s business policies, wary of Elizabeth Warren’s economic stances, and even withdrew his support for Biden’s re-election campaign in the summer of 2024.
On Campaign Spending: Diller expressed disgust over how U.S. political campaigns had devolved into negativity and astronomical spending:
“I’m ashamed how much we tolerate spending $2 billion for commercials that are entirely negative.”
True to his character, Diller’s take on politics was sharp, unfiltered, and unapologetic—he called it as he saw it, whether friend or foe.
Personal Life
Diller has been married to fashion icon Diane von Fürstenberg since 2001, but their story stretches back much further—they first dated in 1975.
Normally, we don’t cover people’s personal lives unless they become part of the business story. And in Diller’s case, the speculation around his sexuality was weaponized during one of the messiest chapters of Disney’s corporate history. In 1997, Michael Eisner, then under pressure to name a successor at Disney, used Diller’s private life as part of a ploy. Eisner wrote a letter to the Disney board “recommending” Diller as a candidate, knowing the board would reject him. The letter included the line:
“The fact he [Diller] is a homosexual should have no weight,” fully aware it would carry weight. This sneaky maneuver, documented in James B. Stewart’s DisneyWar, was a low blow. Whether Diller is gay, bisexual, or straight is entirely irrelevant—it’s nobody’s business. True to form, Diller never engaged with the narrative, choosing dignity and silence over spectacle.
A League of His Own
Diller’s presence in Hollywood is unmatched. As Jeffrey Katzenberg, who worked under him from 1973 to 1984, put it:
“Even in the hyperbole of Hollywood, where there’s a new flavor every week, Barry is in a league in which he really does not have any peers.”
Daniel Melnick, a producer and poker buddy, once said, “Barry will take big chances looking for a big win and will stay in a hand longer than he should, hoping to buy a card. He’s fearless, and you can’t bluff him out.” That combination of risk-taking and unshakable confidence became a hallmark of his career.
Diller’s abilities are a rare mix of creative vision, analytical sharpness, and practical know-how. Michael Ovitz summarized it best:
“In this business, there are good analytical, practical, and creative minds, but very few who combine all three. Barry can read a balance sheet, read a script, and forward-think.”
Even his fiercest rivals begrudgingly respect him. Michael Fuchs, who spent years clashing with Diller over pay cable, once said:
“Barry’s most valuable asset is his fearlessness in confronting. He’s like a hot knife through butter. That’s powerful if you face someone who doesn’t like confrontation.”
Diller’s intellect, integrity, and refusal to shy away from challenges have cemented his status as an unparalleled figure—not just in Hollywood, but in business at large.