The Diary of a CEOTony Hawk: The Man With The $1.4 Billion Name! Burnout, Obsession & Regrets
CHAPTERS
- 2:00 – 8:40
Outcast Kid Finds Obsession in Skateboarding
Hawk describes discovering skateboarding at nine or ten and immediately becoming obsessed with it, despite having no role models making money from the sport. As a smaller, bullied kid who was mediocre at team sports, he found in skating a powerful sense of progression, purpose, and a misfit community that felt like home.
- •Skateboarding offered clear, incremental improvement every session compared to team sports where he felt average.
- •The culture—DIY, rebellious, punk‑infused—gave him identity and belonging as an outcast.
- •Early on there were no expectations of fame or fortune; his drive was pure obsession and self‑betterment.
- •His parents, older and emotionally distant, appreciated that skating channeled his strong‑willed “determination.”
- 8:40 – 17:10
Early Success, School Anonymity, and Being an Outcast Twice Over
By his early teens Hawk is sponsored and then turns pro at 14, yet skateboarding is deeply uncool at school. He talks about hiding his board to avoid harassment and living a strange double life: signing autographs at contests on weekends, then returning to be invisible in the school hallways.
- •He was in gifted academic classes and initially imagined becoming a math teacher.
- •Skating in the early 80s was stigmatized; he literally hid his board in bushes behind school.
- •Even as a sponsored and then professional skater, he was socially a “ghost” at high school.
- •The sense of belonging came from a small skate crew and the broader DIY skate/punk culture, not from classmates.
- 17:10 – 27:00
Becoming the Best and Facing Industry Collapse
Hawk outlines how he grew into a top‑ranked vert skater by innovating unconventional tricks at serious height, winning a huge percentage of contests in his late teens and early 20s. He then explains how the skate industry crashed in the late 80s and early 90s as parks closed, vert fell out of fashion, and many pros left the sport or got day jobs.
- •He credits his rise to fearlessly trying “circus”/avant‑garde tricks and accepting injury as part of progression.
- •By around 16 he realized he could execute difficult moves at heights few others could reach, even on unfamiliar ramps.
- •He won 73 of 103 pro contests, with another 19 seconds, during his early career dominance.
- •Street skating rose as private vert parks shut down, and Hawk decided to stick with vert for longevity after debilitating ankle injuries.
- •Most of his peers left pro skating in the early 90s when money dried up.
- 27:00 – 34:00
Dad, Nepotism Accusations, and Resilience as an Outcast
Hawk reflects on his father founding the National Skateboard Association to bring order to contests and support young skaters. That support backfired socially, as other skaters accused Tony of benefiting from nepotism, further isolating him within an already outsider culture. He describes how hostility from both mainstream peers and core skaters drove him to get even better.
- •His father organized competitions largely unpaid, out of altruism and love for his kids’ passions.
- •Tony was criticized as only being good at his home park or for doing “goofy little tricks.”
- •Accusations of favoritism made events emotionally difficult but also lit a competitive fire in him.
- •Later, during the X Games era, some skaters resented him for “hogging the spotlight,” even though he didn’t control programming.
- •Years of being the “outcast in the outcast activity” built a strong resilience to criticism.
- 34:00 – 43:40
Burnout, Stepping Away from Competition, and Redefining Winning
At the height of his dominance in the late 80s, contests became repetitive and joyless; judges scored him against his own potential, and peers assumed they were competing for second place. Facing pressure from sponsors to keep competing, Hawk walked away anyway, ultimately rediscovering his love for progression and later returning to competition with a risk‑embracing, less perfectionist mindset.
- •Burnout manifested as dread before events, sleeplessness, and feeling like a performing machine.
- •Sponsors warned that quitting contests meant career suicide in a pre‑social‑media era where rankings were everything.
- •Time away from contests helped him fall back in love with the creative, experimental side of skating.
- •On returning, he accepted not always making finals, in exchange for trying far riskier, more fulfilling runs.
- •He frames burnout as the collision of external expectations and self‑imposed pressure, even in a dream job.
- 43:40 – 51:00
Fame, Clubs, Kids, and the Emptiness of Celebrity Culture
As the X Games and his video game franchise exploded, Hawk suddenly found himself doing talk shows, red carpets, and VIP events. He recounts indulging in that lifestyle for a period, then recognizing how unfulfilling and distracting it was—especially from his responsibilities as a father—and consciously pulling back to re‑center on family and skating.
- •He “got famous by accident,” becoming the default ambassador because he could communicate both to core skaters and mainstream audiences.
- •Celebrity circles were filled with people who mainly wanted to be famous; he felt little affinity with them.
- •Late nights and appearances left him physically present but emotionally unavailable to his children.
- •The realization that fame didn’t feel as good as skating or time with family prompted a shift in priorities.
- •He now values being with his kids and having a grounded home life over invitations to prestigious events.
- 51:00 – 57:20
Aging, Peak Performance, and Skating into His 50s
Hawk unpacks how his expectations for a short pro career were upended as he continued to improve into his 30s and 40s, and now still skates in his 50s. He differentiates between his technical peak and his current phase, where he prioritizes lower‑impact technical skating to stay healthy while still challenging himself.
- •Initially, no one viewed pro skating as a viable long‑term job; he never expected to still be doing it past 20.
- •His technical peak combined dangerous high‑impact moves with complex, technical tricks in his late 30s/early 40s.
- •Public perception shifted from “you’re pretty good for your age” as a kid, to “you still skate?” in midlife, back to “good for your age” in his 50s.
- •Serious injuries like a broken femur have reinforced the need to adjust focus toward lower‑impact tricks.
- •Skating is no longer his entire identity; it’s a cherished, compartmentalized part of a broader life.
- 57:20 – 1:06:40
Mastery, Style, and the 12‑Year Quest for the 900
The conversation turns to mastery and the metaphorical lessons of skateboarding. Hawk explains how style emerges even in standard tricks, then details his 12‑year battle to land the 900, culminating in the famous 1999 X Games moment where he either wanted to land it or be carried out on a stretcher.
- •He sees skating as a metaphor for life: persistence, self‑belief, and risk‑taking in the face of repeated failure.
- •True mastery requires both focus and openness to influence, collaboration, and leaving your creative bubble.
- •Style is the fluid, individual way you execute a trick—so distinctive he can identify skaters by silhouette.
- •The 900 was difficult because you’re blind to your landing twice; early attempts often ended in injuries like broken ribs.
- •At the 1999 X Games, consistent speed and good takeoff led to a mid‑air realization about shifting weight backward, then “splitting the difference” to finally land the trick.
- 1:06:40 – 1:16:00
Tony Hawk’s Pro Skater: The Biggest Bet of His Life
Hawk walks through how he chose Activision/Neversoft over another more technical skating game project, prioritizing accessibility for non‑skaters. He then recounts turning down a $500,000 royalty buyout just before launch, a decision that became the most lucrative financial call of his life as the franchise sold around a billion dollars’ worth of games.
- •He picked Activision because their early build felt intuitive and fun even to a non‑skater, which he felt was crucial for mainstream adoption.
- •A rival project aimed for hyper‑realistic mechanics, which he believed would limit accessibility and appeal.
- •Weeks before launch, Activision offered a flat $500k to buy out future royalties; coming from lean years, the sum felt enormous.
- •Because his finances were stable enough, he chose to gamble on royalties instead.
- •The game’s runaway success transformed his financial life and introduced skateboarding to kids globally who’d never seen the sport.
- 1:16:00 – 1:22:40
Imposter Syndrome, Failure, and the Business Behind the Brand
Hawk and Bartlett explore identity, self‑doubt, and the myth of an unbroken success story. Hawk admits to imposter twinges but says repeated cycles of rise and fall have grounded him. He outlines his current business ecosystem—from Birdhouse and apparel to the Skatepark Project—and openly acknowledges failed ventures and relationships as integral to his learning curve.
- •He relates to imposter syndrome but says it’s now “more of a whisper” thanks to a long track record of tangible work.
- •Business failures came from timing issues and operating outside his true expertise, teaching him to be more selective.
- •He’s involved in apparel, boards, investments, and a foundation that builds skateparks in low‑income areas.
- •He views both skating and business errors as data for growth rather than reasons for shame.
- •Despite continued commercial success, he expresses genuine surprise and gratitude that people still care about his work.
- 1:22:40 – 1:32:00
Therapy, Intimacy Fears, and Rewriting Family Patterns
The discussion shifts to Hawk’s inner life: his fear of intimacy, the impact of a cold but functional childhood home, and how therapy helped him confront compulsive behaviors. He talks about practicing vulnerability with his kids and wife, worrying about repeating generational patterns, and discovering that true bravery lies in sharing feelings.
- •His parents felt like “roommates,” and his father never said “I love you,” leaving Hawk emotionally guarded.
- •He identified compulsive behaviors and intimacy fears in his 40s and sought therapy to realign his actions with his values.
- •He worried about passing emotional distance on to his children and consciously worked to change that pattern.
- •Deliberately telling his kids he loves them and being vulnerable makes them feel seen and strengthens their bond.
- •He credits his wife as a grounded partner who isn’t impressed by fanfare, acts as his sounding board, and helps him navigate fatherhood and intimacy.
- 1:32:00
Giving Back, Cobain’s Board, and Final Reflections on Legacy
In the final segment, Hawk answers audience‑style reflection questions, revealing both personal gestures and large‑scale philanthropy. He shares the story of buying a Kurt Cobain‑painted skateboard, reproducing it, and donating proceeds to mental health and skatepark causes, and reflects on legacy, humility, and the role of his family in keeping him grounded.
- •He surprised his wife with a new car but also sees “doing for others” in larger projects.
- •Hawk bought an original Kurt Cobain hand‑painted board, verified it with Cobain’s daughter Frances, and released 500 replicas.
- •Proceeds from those boards are split between the Jed Foundation for suicide prevention and the Skatepark Project.
- •He’s acutely aware of how his game introduced skating worldwide and is grateful but grounded about that impact.
- •Bartlett shares how Tony’s game inspired him to buy a board as a child, underscoring Hawk’s cultural influence.
