The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More
In a Nutshell
Guy Oseary built his career on rapid, high-conviction decisions—signing artists like Candlebox and Alanis Morissette after hearing just one song—which allowed his small label to compete against majors and generated massive successes including a 30-million-copy Alanis debut. He applies the same pattern-matching and "fall in love fast" approach to tech investing, securing early stakes in Vita Coco (IPO at ~$2B) and Anthropic ($35M at $5B valuation) while amassing 26 IPOs and 86 exits overall. His 36-year partnership with Madonna reinforced a relentless forward momentum, creative risk-taking, and cross-domain thinking that treats founders like artists and prioritizes identifying talent before others do.
These notes were generated by AI and may contain inaccuracies.
Guy Oseary emphasizes that 90% of the decisions he makes happen within the first 5 minutes. He finds it frustrating when discussions extend for months over decisions that can be made quickly. His small boutique label competed against established major companies without any roster of artists, which required rapid decision-making to secure talent before competitors could offer more money or make bigger promises.
Oseary signed artists after seeing just one song or performance, including Muse and Atlantis Morris. This approach demonstrated immediate passion and belief in the artist, which was meaningful to them. He notes that hesitation could have cost him opportunities as other labels might have offered more financial incentives.
Behind Oseary sits a calligraphy piece featuring Purple Rain lyrics by Prince. He has been a fan since childhood with Prince posters on his wall. At age 12, he met Prince at the Park Hotel in West Hollywood, where Prince signed something for him with "Love God." They later became friends. Oseary had posters of Billy Idol and Prince visible from the street, which helped him connect with other artists including INXS, Billy Idol, Michael Hutchence, and Morrissey when he was young.
Before attending Beverly Hills High School, Oseary went to a school on Pico and Arlington in downtown Los Angeles. The bus ride featured music from either KDAY (LA's first hip-hop station) or K-Rock (alternative radio). This period exposed him to diverse groups including punk rockers, hip hoppers, break dancers, gang members, and graffiti artists. During this time, he absorbed various musical energies and developed his love for music.
While waiting outside a school dance for his late father, Oseary witnessed a man running past him, followed by a car. A man jumped out with a knife and asked if he was in a gang or with the fleeing person. Oseary explained he was just a kid at a school dance. This incident prompted him to tell his father he wanted to attend Beverly Hills High School, inspired partly by the TV show 90210.
Despite not living in Beverly Hills, Oseary's father arranged for someone to provide their address so he could attend Beverly Hills High School. The combination of attending both the downtown LA school and Beverly Hills High gave him unique perspective from blending two very different worlds.
Walking through the doors of Beverly Hills High felt like entering a different world with visible wealth, cars, homes with pools, and significant optionality. This inspired Oseary at age 14 to recognize he needed to work harder since he lacked the same means, money, and connections. He began focusing on music as his area of strength and passion, starting to draw music around age 15 and becoming actively involved by age 16.
Bernie Brillstein was an iconic Hollywood manager who managed SNL talents including John Belushi and Garry Shandling. At age 15, Oseary began compiling a portfolio of artists with demos, having yearbook photos taken, and creating what he called "Wise Guy Records" with a logo. He approached Beverly Hills High students asking to meet their fathers in entertainment, ultimately getting two significant meetings from approximately five asks.
Oseary met Brillstein at the 9200 building on Sunset. He played a song for him, and Brillstein offered $25,000 to put out the record if Oseary would pay it back if successful. Oseary declined the money, instead requesting three phone calls to music business people. Brillstein made those calls, though the meetings didn't lead anywhere. This encounter confirmed for Oseary that he was on the right path in music.
Freddy DeMann, who worked on Thriller with Michael Jackson and managed Madonna, became Oseary's second significant connection through his daughters Nissa and Polar. Oseary pitched himself by showing he was immersed in music and around artists. He had previously managed Ice-T's DJ Evelan and his brother Henji through the Rhyme Syndicate, securing them a record deal at age 17 with help from Steve Rifkind.
DeMann brought Oseary in as a scout for a label he and Madonna planned to start, though it had no name yet. Oseary didn't require salary, just requesting an office and desk. His first attempted signing was Hole after discovering their song "Teenage [__]" and reaching out to their lawyer Rosemary Carroll. The story leaked to papers that Madonna was trying to sign them. He played the song for Madonna and DeMann, and they pursued the band, though it ultimately went to Geffen Records.
Oseary attended college for half a semester before dropping out after signing his first group, Henji and Evelan. His English teacher told him he could always return. He gave himself a year to make progress in the industry before committing fully. The drive came from recognizing the opportunity at Beverly Hills High and feeling he needed to maximize it, plus the fear of being discovered using a false address.
The first was the Bernie Brillstein $25,000 offer at age 16, providing external validation of his talent. The second came after finally getting his driver's license and a Honda Civic. Beverly Hills High students showed no reaction, but his old downtown LA friends were amazed and celebratory, giving him perspective that Beverly Hills was a work environment rather than a social circle.
Oseary's first real connection with Madonna came through the Hole attempt. His second attempted signing was Rage Against the Machine, which he took Madonna to see at The Limelight in New York, though they signed with Michael Goldstone at Epic. His third attempt was Candlebox, which he successfully signed. They sold 4 million albums, providing his first major success despite having no established label infrastructure.
Oseary discovered Candlebox after attending a bad party and having time to catch their showcase at the Lingerie on Sunset. Watching their performance, he visualized thousands of people singing along despite only 30 people being present. He immediately called DeMann from a pay phone declaring them "the band." The songs were so strong that the first two singles on the album came from the original demo rather than re-recordings, as they couldn't be improved upon.
Oseary explained that the muscle for fast response thinking and intuition was built in the music business. With a small boutique label competing against established companies, quick decisions were essential. When he discovered an artist he liked, he needed to move fast or risk losing them to competitors offering more money.
Oseary described meeting Alanis Morissette when she flew from London to LA with producer Glenn Ballard for a showcase. After hearing just the first song, he stopped the performance and told them they did not need to play anything else. When they expressed wanting to continue since they had traveled so far, he reiterated his conviction. This demonstrated high conviction to the artist and prevented other labels from making competing offers.
Oseary noted that in Silicon Valley, people respond better to the term "pattern matching" than "intuition," though both describe the same process. He explained that beyond recognizing good music, he was picking up on something in those five minutes that justified betting on an artist when a small label cannot afford to sign everything.
Oseary stated that signing decisions require falling in love with the artist, which cannot happen every five seconds. When Alanis walked into his office with Glenn Ballard, he did not know what to expect and initially thought they were a band. With experience, he now incorporates additional elements beyond pure gut feeling, but the foundation remains emotional connection.
In his current tech investing, Oseary combines gut instinct with pattern recognition. He also looks for whether he can help the company, visualizing what he can contribute. When the puzzle starts coming together quickly, that excites him. Additionally, he emphasizes verifying that companies deliver on their promises—ensuring the car arrives when ordered or that apartments are actually available through the platform.
Alanis Morissette played a significant role in Oseary's career as the rocket ship that took him to the next level. She appeared in his office with Glenn Ballard and played several songs, with the first being "Perfect." Oseary initially did not grasp the full power of the lyrics about earning parental love and approval, but he was immediately struck by the songwriting quality.
Oseary had no prior knowledge of Joni Mitchell and did not understand the comparisons people made to her work. To him, Alanis was simply his own version of that archetype. He was unaware of her earlier Canadian pop album that caused others to prejudge her. He had zero background or context when meeting her and Glenn Ballard.
When Alanis and Glenn walked in, Oseary thought there was a hippie group vibe. The album became a life-changing moment because everyone else in the industry passed on signing her, yet he immediately felt it in the first minute. The album sold 30 million copies and ranks among the top five debut albums of all time. Because he signed her without competition, it cemented his confidence that he was in the right position to pursue more such opportunities.
Oseary expressed pride in having played any part in Alanis Morissette's career. He noted that she continues winning awards and performing successfully. He recalled telling Freddy before the album's release that he predicted it would sell millions of albums, feeling it was a monumental record unlike anything he had heard.
Oseary has worked with Madonna for 36 years. He cited a Variety quote where he said she mentored him and pushed him to work hard, stating he did not know anything until she grabbed him by the hand and showed him. Beyond the obvious lessons like her extraordinary work ethic, commitment to craft, and passion, there are deeper learnings he only recognized in retrospect.
Madonna is described as the greatest identifier of talent, finding painters, designers like Frida Kahlo, and musicians early in their careers. The most significant impact on Oseary was her lack of walls around her thoughts—she does not see constraints or think "I can't do that." This influenced him to avoid compartmentalizing himself into categories.
Oseary reflected on how traditional record labels would have placed him in a specific department—R&B, jazz, rock, reggae, pop, or hip-hop. His experience with Madonna allowed him to never think in limited ways. He sees how technology and music work together, applying lessons from one domain to the other.
Oseary applies his music industry approach to technology investments. He views founders as rock stars who have music they want to share with the world. His job is to identify that founder before others do and help reach their audience by telling their story, growing their base, and thinking about their first and second singles—all within a musical framework.
After signing bands and running the record label for years, Oseary decided to start a film company with Madonna. He had a blank canvas with no context about how the film industry worked. His approach was to bring independent producers under one roof, housing them and covering expensive back-office functions like legal costs that burden independents.
The film company model provided support to producers who would otherwise bear all costs alone. This structure led to films including Twilight and Percy Jackson. Mark Morgan ran the operation effectively, but complications arose. At the same time the film business was taking off, Oseary and his partner Angela took on managing Madonna and her Confessions tour, which was the biggest-selling record that year.
Oseary explained that managers vary widely in their approach. His style is creative—he gets involved in ideation and building concepts rather than only handling logistics. When he began working with Madonna on Ray of Light, he was not yet her manager but was her partner at Maverick Records. He found producer William Orbit and director Jonas Åkerlund, contributing creatively before formally managing her.
Oseary showed Madonna a provocative video by Jonas Åkerlund for the band Prodigy, which he had signed. She immediately wanted Åkerlund to direct her first video. He also showed her Chris Cunningham's $30,000 video for Aphex Twin's "Come to Daddy," and she selected Cunningham to direct "Frozen." This back-and-forth creative energy defined their working relationship.
Oseary noted that Madonna does not rest on past accomplishments or celebrate her achievements in a self-congratulatory way. She simply keeps moving forward to the next day. This approach has required fighting through significant challenges rather than merely maintaining relevance, and she has broken ground for others who followed.
Oseary's entry into investing began on a plane to Milan for the MTV Awards when he read about Sky Dayton, who founded EarthLink and was worth $100 million at a young age. Upon returning, he tracked Dayton down for lunch at the Four Seasons. Dayton mentioned Bill Gross, who had started an incubator called Idealab and launched three billion-dollar companies in one year.
Oseary visited Idealab in Pasadena and loved the concept of multiple ideas under one roof, reminiscent of a record label with various artists and projects. He could walk between different companies and offer help where useful. After working there for a year, someone he trusted mentioned that Bill Gross was one of their greatest investments.
Oseary called Bill Gross wanting to invest in Idealab. Gross offered to put in money on his behalf as thanks for the work done. When Oseary asked what that would be worth and was told the amount, he felt it was insufficient. He requested to invest more of his own money. Gross agreed, but this occurred right before the dot-com crash.
Oseary planned three investments: Idealab with Bill Gross, Research In Motion (BlackBerry)—he was the first person from Hollywood to understand BlackBerrys and bought 400 units to distribute in the industry, making a deal with Jim Balsillie to be an advisor—and Vitamin Water, brought to him by his friend Seth Rossky. He never completed the deals for BlackBerry or Vitamin Water.
Idealab collapsed with the bubble burst. Oseary lost all his money—the majority of his savings concentrated in one investment. He thought about the loss constantly for the next two years. Both the BlackBerry and Vitamin Water opportunities became massive successes. He learned the importance of diversification.
After completing three consecutive Madonna tours, Oseary recovered the money he had lost. With a window before the next tour cycle, he decided to try investing again, believing he was skilled at identifying talent and ideas. Seth Rossky called about a coconut water company called Vita Coco in New York.
Oseary's Brazilian wife meant coconut water was already familiar in his household—his first son's early words included "agua de coco." Madonna's trainer would source fresh coconuts in every tour market. Oseary noticed other health-conscious people drinking coconut water and cut out a New York Post article featuring Gisele Bündchen drinking from a coconut. When Seth called about Vita Coco, Oseary already had the article on his desk as a to-do item.
Guy flew out to meet founder Mike Kurban when the company had a $35 million valuation. He went in with full commitment, bringing Madonna, Demi Moore, Matthew McConaughey, and Anthony Kiedis into the deal because they were all healthy people who drank coconut water. He positioned the opportunity as something to scale aggressively. The company went public at approximately $2 billion and reached a $4-5 billion market cap. Guy described his approach as being all in immediately rather than thinking through the opportunity gradually.
Chris Rock, Matthew McConaughey, and Woody Harrelson have all described Guy as a great curator of people. Guy traces this back to his teenage years when he found himself among a group of hustlers and creatives. He positioned himself as the responsible one in the group, noting that he doesn't drink or do drugs, which made him a safe zone for others. Working with Madonna gave him credibility that helped build trust.
Over time, his house became a gathering place where people could congregate and feel safe. He avoids photos and cameras at events, emphasizing that safety and support have always been core to how he operates. Guy identifies talented friends the same way he identifies great companies to invest in, and he actively works to bring them together.
Guy hosts dinners frequently. When landing in New York, he often organizes dinners with 15-20 friends to stay connected. He checks in on friends regularly rather than letting a year pass without contact. He grew up primarily with his father after his older sisters left home, making his friends his entire support system before he had his own family.
Guy works with family in multiple ways. He has been beside Madonna for 36 years. Anthony Kiedis from the Red Hot Chili Peppers is the godfather of his first son. The entire band—Flea, Chad, and John—are considered family. He maintains an open-door policy, giving friends his number for when they need support.
Guy invested $35 million at a $5 billion valuation into Anthropic. The last round reached approximately $965 million. The investment thesis began when ChatGPT launched on his father's birthday. Guy compared the moment to first hearing Nirvana's "Smells Like Teen Spirit"—a moment that stopped him in his tracks. He became obsessed, showing ChatGPT to every artist and actor he encountered.
Guy called Ashton Kutcher and declared they needed to invest in OpenAI. They had previously built success during the iPhone and App Store era when companies could scale like never before. Guy identified a three-month window to deploy capital into foundational AI models, believing these would become the infrastructure everything else plugs into. They raised a dedicated AI fund and deployed 80% of the capital within three months.
Ashton spoke with Sam Altman and secured an allocation to OpenAI. Guy reached out to contacts at Salesforce Ventures—John Simari and Paul Drews—after learning they were investing in Anthropic. A headhunter friend told him everyone was going to Anthropic and nowhere else. Dario Amodei and his team came to Guy's home and completed the deal. Guy described himself as locking in completely once he identifies an opportunity worth pursuing.
Guy has achieved 86 exits and 26 IPOs. He described himself as a generalist investor who occasionally creates thematic funds when a compelling idea emerges. He emphasized that he is not based in Silicon Valley but operates from Hollywood, bringing narrative, marketing, strategy, media, partnerships, and storytelling to companies on his cap table. He looks for founders who see his involvement as an advantage.
Guy expressed concern about AI companies built on top of artists' music without compensating creators. He cited a company valued at $5-10 billion built entirely on the world's music without paying artists a dollar. He noted that every two weeks, more AI-generated music is created than exists on Spotify today. Guy has met repeatedly with the leadership of these companies, including Mikey, hoping they establish systems for artists to opt in or opt out and receive payment when their work is used.
He compared the situation to Napster, where he met with Sean Parker hoping the platform would find a way to compensate artists before it was shut down. Spotify succeeded by giving people access to all music cleanly without illegal downloads. Guy stated that fair use is not fair when building commercial businesses on artists' work. Madonna has been explicit that she does not want her music trained on by AI systems.
Guy is working on a platform he plans to announce in coming months. The platform allows him to ask other investors what companies they are evaluating. Two of his three current identified opportunities came through conversations on this platform. He also reads daily and spends significant time on X to stay informed about emerging ideas.
Guy and Ashton invested in Bitcoin at $22 and sold at $250, believing they had made ten times their money. Guy described missing the opportunity to invest in SpaceX after visiting with Anthony Kiedis. He was so impressed by the concept of building rockets that he did not ask about the business model or investment opportunity. He noted that Ashton tends to move forward without dwelling on misses, while Guy uses them as motivation to not repeat the same oversight.
Guy discussed the physical and mental demands of back-to-back Madonna tours. Around 10-12 years ago, the pace became overwhelming. He was changing personally, having children, and felt he was losing himself. The schedule of moving to a different city every other day caused him to miss family time and neglect other responsibilities.
On the first three tours, 240 shows were performed with an average of 80 shows each, missing only three total. One miss was due to illness, and two were missed for a 40th birthday celebration spent at home with friends in the house rather than performing in Seattle. Each tour involves different cities and hotels, requiring complete compartmentalization to function effectively. Blocking out thoughts of home and family is necessary, as dwelling on them causes emotional pain during extended time away.
The approach resembles how actors manage three-month film shoots away from home. In recent years, touring commitments have decreased. There was a period managing Red Hot Chili Peppers, U2, and Madonna simultaneously, with all three on tour. Decisions about where to be are guided by major market priorities—New York and London shows are never missed. During off periods in the calendar, opportunities arise to join specific tours in locations like New Zealand with Madonna or other destinations with U2 or the Peppers.
Management responsibilities are taken seriously and remain a consistent focus. The work is cyclical in nature. Red Hot Chili Peppers have no album or tour scheduled for the current or following year, creating windows for creative development. Artists require time to write songs and create albums. These cycles create periods of intense focus followed by breathing room. Madonna typically needs recovery time after completing a cycle before determining next steps. New artists are not being actively signed, which provides balance while maintaining creativity through other channels.
Creativity does not pause during off cycles. Technology developments and new relationships are continuously explored. When Madonna returns to an active cycle, accumulated ideas and connections from the downtime can be applied. The approach to forward momentum mirrors Madonna's philosophy of not resting on past achievements and continuing to advance.
Friends do not spend extensive time discussing professional activities. Work is rarely discussed with his wife. The pattern of continuous forward movement has been influenced by 36 years of working with Madonna. When recounting past events to children or others, many accomplishments surface that had been forgotten. Upon waking each morning, the feeling persists that nothing has been accomplished yet and more must be done. There is an awareness that pausing to appreciate achievements would be warranted, but the momentum continues regardless.
Visualization includes eventually being on the beach with friends. Many friends share the perspective that surviving the period and being able to pursue what they love is remarkable. A quote from Josh Kushner resonates: success means being excited to go to work and excited to go home. This balance is valued and not taken for granted. Hard work stems from recognizing that opportunities are not guaranteed. Efforts are made to bring friends and others into the network to share access to events, people, and opportunities.
After 20 years with Ashton Kutcher, the partnership is transitioning. The AI fund investments including OpenAI and Anthropic, along with SPVs throughout the growth trajectory, represent exceptional outcomes. The question was posed about what would bring enjoyment and fulfillment for the next decade. Different visions emerged among the three partners—Ashton, Guy, and Effie. Ashton's vision is supported both financially and energetically, though it differs from Guy's direction. Sound will continue to be built with Effie. The decision emerged from mutual support rather than conflict, with acknowledgment that some crossover collaboration may occur on shared interests. This represents another chapter following previous transitions from record label work to music management to crypto to film.
The conversation concluded with acknowledgment of the journey and ongoing opportunities ahead. Contact information was provided as Instagram and X under the handle XGOSEARY without apostrophe.
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