From humble beginnings, Jeff Sine built a career as an unorthodox banker who offered unvarnished advice and tamed unruly transactions for business moguls like Masayoshi Son and Rupert Murdoch. He defied the odds and built merchant bank The Raine Group into an investing empire in its own right.
December 6, 2016 would prove a fateful day for Masayoshi Son — and, though he didn’t realize it yet, for one of his most trusted advisors as well. The SoftBank CEO had secured meetings with two ascendant stars who each represented the possibility of billions in profits.
Early in the afternoon, Masa found himself in Trump Tower in Midtown Manhattan, in a summit with Donald Trump, the soon-to-be leader of the free world, ostensibly to congratulate him on his surprising election victory.
The billionaire technology investor, known for grandiose visions and pronouncements that he backs up with even grander investment checks, was perhaps an unlikely visitor for a president-elect.
Trump, also a billionaire fluent in the art of grandiosity, was enamored with what SoftBank was proposing: Masa brought along a pitch deck — parts of it widely circulated after the fact — that outlined a potential $50 billion investment in the US that promised to create 50,000 jobs, all during the president’s first term.
An enthusiastic Trump welcomed the news, firing off two tweets in rapid succession during the meeting, including a barb at the outgoing administration, saying SoftBank “would never do this had we (Trump) not won the election!”
Advising SoftBank at the meeting was Jeff Sine, a longtime media investment banker and cofounder of The Raine Group. Sine’s appearance was no coincidence — and Trump’s braggadocious tweet was only part bluster.
The Raine Group, the media- and entertainment-focused merchant bank Sine launched in 2009 alongside Joe Ravitch, flies under the radar in investment-banking circles, overshadowed not just by behemoths like Goldman Sachs and Morgan Stanley but also high-octane advisory boutiques that regularly snag seats on the industry-league tables, like Evercore, Centerview, or Moelis & Co.
But Sine, a 35-year dealmaking veteran who held senior leadership posts at Morgan Stanley and UBS before starting his own firm, has served as consigliere to some of the most vaunted corporate titans in America while executing north of $1 trillion in deal volume. Longtime clients include Time Warner, Viacom, News Corp’s Rupert Murdoch, and Ari Emanuel, head of the entertainment juggernaut Endeavor.
Also included is the SoftBank chief executive, who in 2012 entrusted Sine with the company’s $22 billion Sprint takeover. It had been intended as a stepping stone to merging with T-Mobile and creating a true competitor to Verizon and AT&T, but regulators swatted down the tie-up in 2014.
While the Obama administration had thwarted Masa’s plans, Trump’s shocking victory changed the calculus: The deal Sine and Raine had helped orchestrate with Masa suddenly had a Republican, pro-business administration with which to retest the waters.
It’s not clear how much Trump and Masa discussed the wireless megamerger at the December meeting. Sine and SoftBank declined to comment on the meeting, and Trump’s office did not respond to requests for comment.
But the canny charm offensive resonated. Not long after Trump fired off his tweets, the future president and Masa emerged all smiles from the iconic golden elevator doors for a news conference, and Trump provided a warm, flattering introduction to “one of the great men of industry.” Aside from a few awkward questions from political reporters unfamiliar with the SoftBank CEO — they confused Masa several times for the boss of Foxconn, the iPhone manufacturer — the meeting hardly could’ve gone better.
Sine, who wasn’t authorized to discuss the details of the meeting in Trump Tower, told Insider in an interview that in the car ride over, Masa had excitedly shared details about a different meeting.
Masa had been busy that morning making good on his investment promise. Before Sine hopped in, the then-CEO of WeWork Adam Neumann had hopped out. Masa showed Sine his iPad — his preferred method of crafting term sheets — where he’d just struck a deal, with Neumann’s signature in blue and Masa’s in red: SoftBank would invest $4 billion into WeWork at a $20 billion valuation.
The now-infamous meeting had happened in less than 30 minutes. And Sine was intrigued.
‘Masa’s personal banker’
Perhaps no relationship has proved more pivotal and enduring in Sine’s career than his bond with Masayoshi Son — the mercurial gunslinger who’s pulled off some of the most astonishing technology wagers in history. While the Korean entrepreneur turned Japanese business magnate has worked with his share of advisors over the years, including the megabanks, no banker has worked on more deals or more important deals for Masa than Sine.
The relationship has been mutually beneficial. In a merchant-banking model, advisory and investing businesses feed into each other like tributaries into a rushing river, and over the past 12 years, Raine has hit some investing gushers of its own. All told, Raine is now managing $4.1 billion in assets — its highest tally ever — across several funds and has invested in more than 60 portfolio companies, including the helicopter-rental company Blade, the social-video app Houseparty, and the millennial news outfits Cheddar and Vice Media.
Raine earned back four times its investment in Vice, one of its earliest bets, when it exited around half of its stake in 2017 — well before financial woes tarnished Vice’s valuation.
“We make these bets about sectors to go deep on. We see how they get connected to the larger picture — and that’s fun,” Sine said.
The firm’s three growth-equity vehicles have had net internal rates of return of 11.7%, 34.7%, and 29% as of the end of March, according to a quarterly investor letter seen by Insider. Its best-performing fund, which launched in 2014 and raised $850 million, has more than tripled investors’ money.
Sine declined to comment on the private performance figures.
Insider spoke with 10 people who have worked with Sine throughout his career, including senior bankers and clients. They explained how Sine became one of the world’s most influential dealmakers, the origins of his relationships with Masa and other key clients, and how he built a billion-dollar business.
SoftBank declined to comment for this story.
In 25 years of advising SoftBank, Sine has earned an esteemed place in the inner circle, and he has the latitude on transactions to choose “how close I want to get to the flame.”
“Jeff is more like Masa’s personal banker because of the relationship he’s built over two decades now,” said Eric Hippeau, a managing partner of VC firm Lerer Hippeau and a former SoftBank executive whose relationship with both Masa and Sine dates more than 25 years. “Masa sees Jeff as someone who is in the family, someone who is natural for him to turn to.”
That doesn’t mean Masa always listens. While Sine was all too familiar with Masa’s bold and aggressive overtures, he knew nothing about Neumann, and Raine didn’t advise on the investment.
Four months later, at SoftBank’s March deal closing with WeWork in Tokyo, Sine got to see Neumann in action firsthand. While Masa was busy telling Neumann he needed to be more crazy — and floating valuations of several-hundred-billion dollars — Sine was quizzical.
He wasn’t buying the bombastic, weirdly messianic vision he heard from the young WeWork executive.
“That was a flame I wanted to stay away from,” Sine said. Eventually, though, he would get sucked in — but as part of a rescue mission to help Masa salvage SoftBank’s $11 billion investment after WeWork’s 2019 IPO capsized. It was one of several pivotal assignments Sine and Raine spearheaded in what became a year from hell for SoftBank.
Sine could not have known at the time that the events of 2016 would come full circle for The Raine Group four years later, in a completely different way.
A record year for Raine
In Raine’s investment-banking business, Jeff Sine was one of the top dealmakers in America in 2020.
Those deals included the long-awaited closure of the $37 billion Sprint-T-Mobile merger, which was announced in 2018 — nearly a year and a half after the meeting in Trump Tower — and finally passed muster with regulators in early 2020.
When the deal finally closed, Sine helped SoftBank sell some $20 billion worth of T-Mobile shares over the summer to raise cash to fund a stock buyback.
And Sine spent considerable time helping save WeWork from its dramatic implosion. He was tapped to join the company’s board in 2019, not long after helping negotiate a rescue package.
Raine’s business, which employees nearly 140 people in six global offices, has more than a couple of key business relationships. But such ties play an outsize role by design.
“We’re not ambulance chasers,” Ravitch told The New York Times several years ago. “Most of our advisory assignments are repeat business.”
Ravitch has signed marquee deals with the likes of the billionaires Steve Ballmer and Joe Tsai, who purchased the NBA’s Los Angeles Clippers and Brooklyn Nets, respectively, and the Fertitta brothers, who became billionaires through the UFC and the family casino business. Both founding partners have worked with power agent turned entertainment mogul Ari Emanuel since the mid-1990s.
For Sine, Masa could hardly have been a better client to have throughout Raine’s 12-year run.
SoftBank has spent $2.3 billion in the past five years for investment-banking fees, according to Refinitiv data, more than any other company. In 2018 alone the firm paid $894 million for deal advice and to procure bonds, loans, and equity investments.
Many banks earned substantial chunks of those fees, especially from arranging the billions in debt necessary to complete large transactions. But when it comes to strategic banking advice, Sine is the leader.
“It’s a marked difference in how he deals with Jeff than how he deals with commercial bankers,” a person who’s worked on deals with both men said. “He doesn’t look to them for the should-I-do-it advice. That, Jeff leads the way in.”
A late bloomer
Sine grew up mediocre, in his own words — a classic “late bloomer,” he told Insider. Born and raised in New Providence, New Jersey, his father worked for F.W. Woolworth managing department stores, and his mother was a flight attendant and a stay-at-home mom. Sine was an avid reader and passionate about baseball, but he was neither a standout student nor athlete.
His unpretentious upbringing would later help distinguish him in high finance from many of his cocksure, Ivy League-educated competitors.
Sine attended American University in Washington, DC, majoring in international studies with the intention of working for the State Department, but he opted instead for law school at the University of Southern California. He excelled, earning an offer from Sullivan & Cromwell, one of the country’s most prestigious law firms — the first person the firm had ever hired from USC’s law school, Sine was told at the time.
“That was probably the luckiest break in my life,” Sine said.
He spent two years in New York before transferring to London, where the privatization era under Prime Minister Margaret Thatcher was in full swing. As a young associate, Sine gained exposure to complex regulatory and capital-markets problems, including negotiating with the US Securities and Exchange Commission on behalf of the government of the United Kingdom regarding the 1984 public offering of British Telecom.
He worked on transactions alongside banks including Goldman Sachs and Morgan Stanley while in London, and he eventually started to bring in business, including the 1986 IPO of Mrs. Fields’ cookies. This came as a shock to some of his more experienced colleagues.
“One asked me, ‘What are you doing bringing in new business? We didn’t ask you to do that,'” Sine said. “I kind of knew at that point that it was maybe not the right entrepreneurial, culture fit.”
Instead of pursuing the partner track, the young associate jumped to Morgan Stanley in 1986, first in corporate restructuring, where he worked on the 1989 landmark sale of Manhattan’s Rockefeller Center to Mitsubishi Estate.
Morgan Stanley’s media-group head Steve Rattner left for Lazard that year, and Sine took over the team in 1991, just as the media industry was gearing up for a boom.
He’s a completely straight shooter. He’s very candid. So you know you’re getting raw advice. It’s not coming with some agenda.Ari Emanuel, CEO of Endeavor
Bowling alleys, dive bars
“All of the people I’ve met in banking — thousands and thousands of people — I can count on one hand where clients hired Morgan Stanley because of that person rather than because they wanted to work with Morgan Stanley. And Jeff was one of those people.”
That’s how one former colleague, also a senior banker, recalled Sine’s days at Morgan Stanley, where he would build a formidable and lucrative business for the firm over 15 years, garnering a reputation as a reliable and relentless deal engineer and securing relationships that continue to pay dividends decades later.
Some of the traits that made Sine successful, according to clients and former colleagues, are qualities present in nearly any senior dealmaker: He’s shrewd, indefatigable, creative, and ambitious.
But as a trained attorney, Sine was also fluent in deal structure and mechanics, and he had a bloodhound’s nose for sniffing out obstacles before they fouled up transactions.
“There are coverage officers, and there’s M&A people, and Jeff knew it all. And that’s why clients liked him. He wasn’t just wine and dine,” a former colleague recalled.
Unlike many of the star bankers of his time — pedigreed schmoozers who held MBAs and focused their efforts on elephant hunting among the Fortune 500 — Sine cast a wider net, dividing hundreds of companies to conquer among his team.
At the same time, Sine was considered something of an oddball in that era and didn’t always earn the admiration of his peers, especially in Morgan Stanley’s cutthroat culture. Whether it was background, interests, appearance, style, dress, or schooling, “the place had a bit of a look and a feel to it,” a former colleague recalled, “and he wasn’t that.”
Other bankers chummed it up at country club golf courses; Sine invested in Broadway theater (he has three Tony awards and eight nominations as a producer.)
He was also less gifted than other dealmakers in banter or working a room, the colleague recalled.
“He’s a little bit of an awkward guy. He’s not as socially comfortable as a lot of senior bankers that can blend into any room and tell a funny story and mingle seamlessly,” the person said. “That’s not Jeff. Jeff is more likely to watch a room from the outside, read the room, and look where to engage.”
Some described Sine as aloof and at times out of touch with his junior staff and how hard they were working.
But he took care of his team, financially and in their careers, and he was keen on group building, according to those who worked with him. Sine held unpretentious team outings at bowling alleys and dive bars — Tortilla Flats in the West Village was their “unofficial clubhouse,” he said — or hosted barbecues at his home, he and former colleagues recalled.
He was also willing to share the spotlight and subsume his own ego, giving younger bankers opportunities to shine that other group heads were more likely to save for themselves — a habit that followed him to UBS and Raine.
“He had no problem putting other people on the map. He was fully secure in that,” a former colleague said. “He did not feel like to be successful he had to be the king.”
What endeared him to clients was candid, no-nonsense advice centered on solving problems. He was adept at sussing out the true decision makers in a deal and navigating their personalities.
“He’s not a banker the way a lot of bankers are — who are sometimes wrong but never in doubt. Jeff is willing to say the words ‘I don’t know,'” a person who has worked on deals with Sine said.
Ari Emanuel met Sine in the mid-1990s when they were both working with the World Wrestling Federation, now known as WWE. The relationship quickly blossomed, and Emanuel would prove a crucial ally in the formation of Raine.
“He’s a completely straight shooter. He’s very candid. So you know you’re getting raw advice. It’s not coming with some agenda,” Emanuel said. “I don’t want to speak ill of bankers, but you get a sense sometimes that you’re being played; there’s some agenda that you don’t need to know about. You never have that with Jeff.”
These talents coalesced in the mid-1990s when Morgan Stanley’s team was tasked with executing a series of transactions for an incipient Japanese technology investor looking to break into the US.
In 1994, Bill Ziff put his family’s publishing business, which included PC Magazine and several other marquee computer periodicals, up for auction. Masa, who had taken SoftBank public earlier that year and was flush with cash that he intended to deploy on a significant acquisition, coveted Ziff-Davis Publishing. For years, he had licensed titles and content from Ziff-Davis for Japanese editions.
But he was outmaneuvered by the private-equity firm Forstmann Little, which won out with a surprise $1.4 billion cash offer. But SoftBank didn’t go home entirely unrewarded. Earlier that year, in SoftBank’s Tokyo office, Masa met Sine for the first time, to discuss a potential bid for Ziff.
He hired Morgan Stanley, and, as part of the auction, Sine helped orchestrate the winning bid for the Ziff conference and trade show business for $202,072,000. Masa had just hit par, scoring a 72 on the golf course, for the first time and threw in the extra $72,000 to commemorate the feat.
“I came to New York, and I can’t tell my wife I came home empty-handed,” Sine recalled Masa telling him.
A flurry of deals followed, manned by Sine and his media team at Morgan Stanley. Several months later, in early 1995, SoftBank ponied up $800 million to buy Comdex, a computer trade show that was drawing 200,000 attendees, from Sheldon Adelson. Masa merged it with the recently acquired Ziff events unit to create the world’s largest technology trade-show business.
Masa and Sine got another crack at Ziff-Davis less than a year after their failed bid, and this time they would not be denied. SoftBank paid $2.1 billion to buy the company from Forstmann Little in fall of 1995, and at Comdex that year Masa explained he wanted to own the “infrastructure” of the computer industry and boldly predicted SoftBank would own 1,000 titles with 50 million in circulation in a decade. Morgan Stanley led the Ziff-Davis IPO three years later.
But by 1999, dozens of SoftBank investments later, that grand vision was abruptly cast aside.
Buoyed by the rising tide of internet euphoria and billions in paper gains from savvy bets on the online stock brokerage E-Trade and Yahoo, then the top website on the planet, SoftBank’s stock was soaring, tripling by midyear.
But the bottom line wasn’t.
In May the company announced its first operating loss since going public five years earlier, hemorrhaging more than $125 million, thanks in large part to lackluster performance from Ziff-Davis.
SoftBank sold a small portion of its Yahoo stake to dull the earnings pain, but Wall Street analysts hammered the debt-laden company. They questioned its underlying health, according to media reports, and said its stock price was disconnected from reality, relying too much on unrealized investment gains and not enough on profits and cash flow.
Masa faced pressure to raise more cash, including calls to sell off his company’s stake in Yahoo Japan. But rather than divest promising young assets, Sine and Eric Hippeau, the chairman and CEO of Ziff-Davis at the time, had another solution: Sell off Ziff-Davis.
Another element added urgency. Hippeau had noticed ad sales in Computer Shopper, the company’s thickest magazine, had started to tail off.
“That was literally the canary in the mind shaft of the meltdown of internet 1.0,” Sine recalled, crediting Hippeau for recognizing the gathering storm. They needed to sell before the bottom fell out.
Unloading the media business resonated with Masa, an ardent believer in the internet revolution. In July 1999, he announced SoftBank would invest solely in internet companies going forward, and Ziff-Davis formally engaged Morgan Stanley to explore a sale.
It would prove an exceedingly complex transaction, according to accounts from several people involved in its execution. Selling Ziff-Davis to one buyer would be the natural goal. Rupert Murdoch’s News Corp, which partnered with SoftBank that summer on an internet-media joint venture, kicked the tires, considering a $1.5 billion offer before ultimately passing. Sine and his team realized bidders were vastly undervaluing the company and that it would fetch more money if it were sold as separate businesses — magazines, television, online media, events, education, and market intelligence.
So Morgan Stanley simultaneously ran six separate Ziff-Davis transactions, requiring individual due diligence and bidding processes.
At a board meeting that fall, after the first few businesses sold for cash, one person in the room recalled Masa banging his fist on the table and exhorting the Morgan Stanley team, “Good. Keep selling!”
The operation, code-named “Project Zebra,” was celebrated with a plush zebra deal toy. The entire series of deals took a little more than a year to complete, and, crucially, SoftBank kept its majority stake in Yahoo Japan, which was created as a joint venture with $3.5 million in capital when SoftBank invested in Yahoo in 1996.
“Everyone else recommended Masa sell shares of Yahoo Japan, but Jeff didn’t. And Yahoo Japan exploded,” a person familiar with the deal said. The company’s value climbed from $1.5 billion in 1999 to $45 billion within five years. Unlike its US counterpart, Yahoo Japan remains a relevant and lucrative technology company and is still owned by SoftBank.
But the happiness over completing the Ziff-Davis deals didn’t last long. By the time the final deals closed, the internet collapse that Hippeau and Sine feared was apparent to the whole world.
If you don’t help me, I’m going to pour gasoline all over myself right here and set myself on fire with this $1 lighter.Masayoshi Son
‘Deep freeze’ at UBS
Masa, who was worth $78 billion by early 2000 with a portfolio of dozens of internet companies, according to Forbes, saw his net worth collapse to $7 billion by December as the dot-com bubble began to pop and SoftBank stock cratered more than 90%.
Sine, meanwhile, saw his 15-year run at Morgan Stanley come to an end.
The bank merged Sine’s media troop with the telecoms team in 2000, and while he was nominally appointed cohead of tech, media, and telecoms, Chris Harland, the entrenched telecoms boss, was the de facto leader.
Sine, who hated the politics, had fewer loyalists among the investment-banking management team, and some senior bankers found him arrogant, according to the 2006 memoir “The Accidental Investment Banker” by Sine’s media-team colleague Jonathan Knee.
One former banker called Morgan Stanley’s ruthless banking division a “rat’s nest.”
“Everyone was pitted against each other. There was so much fighting and backstabbing back then,” the former banker said.
Disenchanted over losing his free-standing group, Sine was the odd man out, and Harland assumed sole control.
By then, Sine’s track record of building a profitable business and important client relationships had earned him admirers on the Street.
He was early to identify Murdoch as a power player, and in 1990 he helped rescue News Corp from the brink of insolvency. He shepherded the $35 billion CBS-Viacom merger in 1999, and the following year he’d be a key player along with the mergers-and-acquisitions phenom Paul Taubman on the monumental, but ill-fated, $165 billion AOL-Time Warner deal.
It didn’t take long for rivals to start courting Sine, who received a monster offer — worth roughly $10 million a year over three years — from Ken Moelis, who had just joined UBS from DLJ and was building a team.
Sine’s involvement helped convince others that Moelis was putting together a serious contender. Jeff McDermott, then a senior Salomon Brothers industrials banker whom Moelis was also wooing, had reservations, and he didn’t hide them during their monthslong courtship.
“I remember being deeply skeptical at the time. ‘Ken, foreign banks try this for a few years and then give up and retreat,'” McDermott, head of Nomura Greentech, told Insider. “It takes tenacity, and it’s hard to do.”
Moelis assured McDermott he was assembling a murderer’s row, with Jeff Sine as Exhibit A.
“I knew Jeff by reputation. I said, ‘OK, UBS isn’t screwing around,'” McDermott recalled. He joined UBS within a week of Sine, in February 2001.
The group heads, based on different continents and in different sectors, didn’t work together frequently, but McDermott described Sine as “deeply relationship oriented.”
Sine also had an eye for developing young talent.
It was Sine who pulled a young UBS research analyst named Aryeh Bourkoff — the cable and satellite TV rainmaker who now runs the boutique LionTree Advisors — to the investment-banking side. Navid Mahmoodzadegan, now copresident of Moelis & Co., came up under Sine as well. Years earlier he’d helped put Mary Meeker on the map, brokering a deal for her 1996 book, “The Internet Report.”
“Sometimes bankers get confused and get very narcissistic and egocentric, and as a result they never build a machine around them. It becomes a one-man band,” McDermott said. “He’s a team builder and not a glory grabber. He’s willing to invest and elevate people.”
An early hurdle he would have to overcome at his new home: Repairing UBS’ relationship with SoftBank.
Sine learned that someone at UBS had previously angered Masa, and the bank was persona non grata to the powerful investor, putting their relationship temporarily in a “deep freeze.”
This wasn’t a huge ordeal, initially, as Sine wasn’t sold on Masa’s latest obsession — providing cheaper high-speed internet access through a service called Yahoo BB.
Masa bullied his way into the Japanese broadband market, at one point visiting a telecom official and threatening, “If you don’t help me, I’m going to pour gasoline all over myself right here and set myself on fire with this $1 lighter.”
“He went all-in, as Masa does,” Sine said. “He was not afraid.”
Deeply entrenched in the cable industry through clients like Time Warner and Telewest in the UK, Sine said he felt the ADSL technology underlying the service wasn’t a robust competitor.
“There was not much for me to do with him at that point in time, especially since I didn’t really believe in what he was doing,” Sine said.
But he recognized mending the relationship with UBS was imperative to winning future business. So Sine arranged a meeting over dinner in San Francisco and brokered a detente.
“We got together and decided to let bygones be bygones with UBS,” Sine said.
Shortly thereafter, Sine was once again advising SoftBank on deals that reverberated across the industry, including the firm’s negotiations with Alibaba and Yahoo in 2005. Masa, who had invested $20 million in Alibaba in early 2000, orchestrated a transaction that gave Yahoo a 40% stake in the company in exchange for $1 billion and its Yahoo China assets. SoftBank and Alibaba management each retained 30% ownership stakes.
Alibaba, valued at about $4.2 billion in the deal, is worth $600 billion today — one of the greatest investing scores ever.
An unlikely duo pairs up to launch The Raine Group
One summer day in 2007 in Sagaponack, New York, Sine went fishing and wound up with an overabundance of striped bass. He drove a block over to offer some to a neighbor — Joe Ravitch, a longtime rival at Goldman Sachs. They struck up a friendship.
In early 2008, they’d work together on opposite sides of a deal. Sine and UBS represented Robert Redford and the Sundance Channel in its $500 million sale to Cablevision, which had retained Ravitch and Goldman Sachs.
Later that year, Ravitch approached Sine about starting their own company. Both had seen the potential, at Goldman and Morgan Stanley, for heady profits from a merchant-banking approach. The name “Raine,” a portmanteau of Ravitch and Sine, was the brainchild of Ravitch’s ex-wife.
Wall Street competitors were surprised to see the pair team up, and they were dubious about Raine’s prospects.
“People were like, ‘What? I didn’t even realize you were close to Joe Ravitch,'” a former Morgan Stanley banker said.
“Many people had a fair amount of skepticism, including me, about their ability to raise significant capital in the first instance and then deploy it effectively, given that neither Jeff nor Joe had any credible track record on investing,” a senior Wall Street executive told Insider.
The pair had more in common than met the eye, including a mutual business relationship with Ari Emanuel.
Ravitch that year had been quietly advising Emanuel on Endeavor’s Trojan horse merger with William Morris, and Emanuel was keen to get in on the ground floor at Raine.
In 2008, Endeavor invested roughly $10 million and gave Sine and Ravitch office space in its New York headquarters.
As Endeavor continued an acquisition spree, Raine became a de facto advisor.
“I looked smart after talking to him,” Emanuel said of Sine, adding that Sine was “very steady and very creative” in solving complex transactions.
Emanuel, meanwhile, helped generate deal flow for Raine, including roles on the $2 billion LA Clippers acquisition in 2014 by Steve Ballmer and the sale of a $400 million equity stake in the English soccer club Manchester City at a $3 billion valuation in 2015.
The Endeavor exec also had budding relationships in Abu Dhabi and secured a $100 million investment to launch Raine’s private-equity fund from Mubadala, the Emirati sovereign wealth fund, according to The New Yorker. Emanuel similarly cajoled Marc Andreessen and the Silver Lake managing partner Egon Durban into investing in Raine’s private-equity fund.
Sine continued to draw work from SoftBank in Raine’s early days, especially related to the company’s complicated interests in Yahoo and Alibaba. That included tense negotiations over Alibaba’s spinoff of Alipay — now Ant Group and recently valued at over $300 billion — which erupted into a public spat with Yahoo in 2011.
In 2012, Masa tapped Sine to marshal his most ambitious US acquisition yet: The $22 billion buyout of Sprint.
The investment vision from the get-go, however, hinged on merging the floundering company with T-Mobile. It was an intricate transaction, with regulatory, tax, foreign investment, and geopolitical hurdles.
“It had just about every issue you could think of,” a person who worked on the deal said.
Despite a media blitz to curry favor, the Federal Communications Commission and the Justice Department signaled in 2014 they wouldn’t approve the deal. The merger was put on ice, and Sprint lost half its value within two years of SoftBank’s acquisition.
Sine nonetheless earned respect for his work, continuing to draw mandates from SoftBank.
“To maintain a relationship with Masa after what that deal took out of people emotionally, he had the respect of Masa. And you can’t ask for much more than that,” a person who’s worked with Sine and Masa said. “He thought Jeff advised him really well.”
An even more high-stakes challenge loomed on the horizon.
The year from hell
After years of lavishly spending SoftBank’s $100 billion Vision Fund and driving startup valuations to stratospheric heights, Masa’s most high-profile investments started to crumble in 2019.
In May, Uber’s initial public offering flopped, which some considered one of the largest IPO debacles in history.
Then WeWork happened. Once viewed as a nearly $50 billion coworking juggernaut, the company’s IPO collapsed and proved more of an Adam Neumann cult of personality, hopped up on pixie dust and tequila.
The coronavirus added to SoftBank’s pain, further eroding the value of its portfolio companies. The company posted a loss of more than $17 billion in May 2020 — its first loss in 15 years.
Investors, including the feared activist Elliott Management, were taking Masa to task and admonishing him to reduce debt and buy back stock.
While many worked to right the ship for SoftBank, Masa once again tapped Sine to help provide solutions.
That’s how Sine got sucked into the WeWork fray. The biggest obstacle to the coworking giant’s solvency in Sine’s view was Neumann, according to a person familiar with his thinking, and while Neumann had built an undeniably powerful brand, Sine found him chaotic and frightening.
Sine initially helped behind the scenes, navigating the $10 billion rescue package in October 2019 that gave SoftBank control of the company. Days later, Sine officially joined WeWork’s board of directors.
“Jeff has been parachuted in by Masa in a lot of places. Sometimes it’s formally like WeWork. Sometimes it’s behind the scenes,” a person who has worked on deals with both men said. “He wants Jeff’s analysis of what’s going on. But there are times where he says, ‘Good advice, Jeff — I’m not doing it.'”
In April 2020, Sine’s second attempt at a Sprint-T-Mobile merger closed, freeing up capital for SoftBank’s buyback campaign. Raine helped orchestrate the sale of two-thirds of SoftBank’s T-Mobile stake for $21 billion.
He was also tapped to help sell Arm, the British semiconductor firm owned by SoftBank, to the US chipmaker Nvidia, fetching roughly $40 billion in a deal announced in September.
The deals helped facilitate a stunning $23 billion in stock buybacks, helping double the company’s share price over the past year.
They have definitely done way better than people give them credit for on both sides of the ledgerJonathan Knee, professor at Columbia Business School
A billion-dollar company?
The Raine Group’s fortunes will likely continue to hinge on longstanding relationships Ravitch, Sine, and other partners have cultivated.
“He much more prefers to have, as he does at Raine, a shorter list of clients he can go much, much deeper with and solve problems for,” a former Morgan Stanley colleague said of Sine.
In 2021 thus far, Sine has continued to solve problems, helping WeWork sign a deal to go public via at a $9 billion valuation, as of March. In April, the Spanish-language media companies Univision and Televisa announced a $4.8 billion merger, and Raine invested $125 million to facilitate the transaction alongside SoftBank and other investors.
Emanuel, who remains personally invested in Raine, took a second shot at an IPO after a failed bid in 2019, with Endeavor going public at the end of April at a valuation north of $10 billion. Raine advised on that as well.
Endeavor also bought one of Raine’s portfolio companies, Reigning Champs, in January for $200 million.
But Raine’s success in proprietary investing has made it less reliant on fees from marquee investment-banking clients.
In its growth-equity business — it also runs smaller venture funds and a hedge fund — the firm scored one of its biggest home runs when DraftKings began trading on the Nasdaq last year. Raine first invested $40 million in 2014, and its $100 million stake grew to more than $1 billion.
Three more portfolio companies have gone public this year. The food-delivery software provider Olo, which secured $40 million from Raine in 2016, went public in March, and Raine’s stake is now worth about $1.4 billion. In February, the fitness company Beachbody went public via SPAC, and the Polish mobile-gaming company Huuuge held its IPO in Warsaw.
The future looks bright as well.
As he did at Morgan Stanley and UBS, Sine has helped groom the next generation of leaders at Raine. Jason Schretter, who came over with Sine from UBS, started as a vice president and now runs the European operations. Colin Neville started as an associate in 2009 and now manages the firm’s sports practice.
The firm is laying the groundwork for its fourth growth-equity fund, according to the investor letter seen by Insider, and it also started raising capital for a fund dedicated to early- and midstage gaming companies.
Many boutique investment banks have capitalized on their success, and rewarded early investors, with an IPO. Evercore, Houlihan Lokey, Moelis, and PJT have fetched multibillion-dollar valuations. Perella Weinberg Partners earned a $975 million valuation when it went public via SPAC.
Sine hasn’t given much thought to an IPO or what his successful company might be worth. One investor in the firm estimated its value in the neighborhood of $1.5 billion.
“Things are worth what people are willing to pay for them,” Sine said. “And we’re not trying to sell.”
Critics say the inherent conflicts — advising companies that you’re also invested in — make it a tough business to grow. But Sine and Raine have already far exceeded expectations.
“They have definitely done way better than people give them credit for on both sides of the ledger,” said Jonathan Knee, Sine’s former Morgan Stanley colleague who is now a professor at Columbia Business School.
While Raine’s narrow focus and merchant model might limit its growth prospects, Knee added: “That doesn’t mean you can’t make a lot of money and have a lot of fun.”