The Diary of a CEOCraig David Opens Up About His Painful Rise, Fall & Redemption | E135
CHAPTERS
- 1:00 – 13:00
Bullying, ‘Johnny’ and the hidden reality of school trauma
Steven opens by reading lyrics from Craig’s 2006 track ‘Johnny’, about a bullied boy with troubled parents. Craig explains the song was his first honest expression of his own and others’ experiences with bullying in an all‑boys secondary school. He describes physical intimidation, the complexity of ‘telling a teacher’, and why music became his way to process pain without preaching.
- •‘Johnny’ was inspired by Craig’s and classmates’ experiences of bullying at secondary school in Southampton.
- •He recalls older boys physically shaking him down for money, leaving him feeling helpless.
- •He saw that reporting bullies could escalate danger outside school—waiting at gates, on buses, or from other schools.
- •His parents had their own problems; he wanted his mum to know she’d been supportive, even if the song’s lyrics sound like she wasn’t listening.
- •Writing the song coincided with his grandmother’s death and marked a shift from romantic songs to socially conscious storytelling.
- 13:00 – 29:00
Weight, body image and childhood shame as fuel
Craig talks about being overweight as a teenager and how that shaped his self‑worth. He was the empathetic friend girls confided in, not the ‘captain of the football team’ they dated. These early comparisons to societal ideals later drove his fixation on fitness and appearance, which he now sees as rooted in unexamined childhood shame.
- •He was around 14.5 stone at 14 and began worrying when his weight exceeded his age.
- •Social hierarchies at school linked desirability with athleticism and looks; he internalized that template.
- •He describes checking his reflection in shop windows, feeling his clothes didn’t fit and pitying himself.
- •Despite being ‘carrying a lot of weight’, he insists he wasn’t necessarily unhealthy then.
- •He now views that overweight period as ultimately forcing him to later unpack deep insecurities and patterns.
- 29:00 – 47:00
Parents, divorce and early models of love and relationships
Craig unpacks how his parents’ divorce when he was eight, plus a loving but fragmented family setup, shaped his views on relationships. Surrounded by nurturing feminine energy from his mum and grandma and a protective but separate father, he grew up without a living model of a working partnership. This, plus his first heartbreak, led him to keep his heart closed for years.
- •Parents divorced when he was eight; dad still picked him up weekly and immersed him in reggae and DIY work.
- •He was largely raised by his mum and grandma, gaining deep respect for women and romantic, respectful language in his songs.
- •He never saw his parents as a couple or his mum with another partner; this implicitly taught him that staying single was safest.
- •Early heartbreak (a relationship of barely a week) felt devastating because his heart was totally open; it set a lifelong defensive pattern.
- •He admits he kept women at arm’s length, sometimes entering toxic dynamics and rationalizing ‘no strings attached’, and now publicly thanks past partners for trying to reach his closed heart.
- 47:00 – 59:00
Council estate dreams, early hustle and musical DNA
Growing up on a Southampton council estate, Craig dreamed of simple upgrades like a house with a garden, inspired by his grandma’s home. He recalls his mum going into debt to make his childhood feel normal, his own entrepreneurial streak selling near‑expiry chocolate at school, and the deep musical influences from his dad’s reggae band and his mum’s soul records.
- •He clarifies that early ‘jacuzzi’ lyrics were aspirational fantasies from a two‑bed flat, not reality.
- •His grandma’s small garden became his benchmark of success as a kid.
- •He ran a mini chocolate resale business at school, leveraging timing and scarcity before the tuck shop break.
- •His dad played bass in reggae band Ebony Rockers, later honoured by a mural in Southampton.
- •His first 7-inch single purchase was Michael Jackson’s ‘Human Nature’; he also absorbed Stevie Wonder, Donny Osmond and deep reggae artists like Beres Hammond and Buju Banton.
- 59:00 – 1:19:00
From bedroom tapes to Damage and the Artful Dodger connection
Craig describes his DIY recording experiments with a Studio 100 hi‑fi system as a preteen and his first songwriting ‘break’ writing for boyband Damage at 14. He then details how DJing and MCing in local clubs led to a chance meeting with Mark Hill and Pete Deveraux (Artful Dodger), whose nearby studio became the launchpad for ‘Rewind’ and early UK garage success.
- •At 11–12 he used twin cassette decks to overdub vocals, initially copying melodies from Jodeci and Boyz II Men.
- •Winning a songwriting competition for Damage got his song ‘I’m Ready’ on a B‑side around age 14–15, giving early validation but not a career breakthrough.
- •He DJ’d as MC Fade for DJ Flash, learning crowd work, crate‑digging and showmanship (including cheeky tactics to get longer sets).
- •At a Southampton club he met Mark Hill and Pete Deveraux; Mark needed a songwriter, Craig needed a producer—an ideal partnership.
- •Their first release ‘What You Gonna Do?’ gained underground traction via vinyl promos and power radio play, leading to London PAs and growing buzz.
- 1:19:00 – 1:33:00
‘Rewind’, ‘Fill Me In’ and the euphoric wave of global fame
Craig recounts the creation and reception of ‘Rewind’, including its halftime bassline that initially confused club crowds but became its unique hook. He then moves into the explosion of ‘Fill Me In’ and ‘Born To Do It’, describing hysteria at shows, celebrity fans like Missy Elliott, Beyoncé, J.Lo, Stevie Wonder and even Michael Jackson listening to his album.
- •He instinctively knew ‘Rewind’ was special walking home with it on his Sony Walkman and blasting it through a huge sub at home.
- •Crowds initially froze at the halftime chorus bassline but that structural twist became the record’s USP and cultural signature.
- •‘Fill Me In’ debuted the same day as Destiny’s Child’s ‘Say My Name’ yet hit number one; acoustic performances on TFI Friday and Jools Holland broadened his appeal beyond garage.
- •‘Born To Do It’ sold around 7 million, with three Wembley Arena sell‑outs and intense fan hysteria (needing to be carried over Leicester Square by security).
- •At LA’s House of Blues, Missy Elliott, Beyoncé, J.Lo, Stevie Wonder and Quincy Jones all attended across three nights; Quincy told him ‘Michael’ had his album and loved it.
- 1:33:00 – 1:47:00
Expectation, misalignment and the slide into box‑ticking music
With his second album ‘Slicker Than Your Average’, Craig encountered the darker side of success: label forecasts of 10–11 million sales and disappointment at ‘only’ 3.5 million. This reframed achievement as failure in his mind, nudging him into projects he didn’t feel—culminating in the live‑leaning ‘Trust Me’ and a Motown covers album that felt like being someone else.
- •Labels assumed the follow‑up to a 7‑million‑selling debut must sell more; 3.5 million on ‘Slicker’ was framed as underperformance.
- •He internalized commercial expectations and began judging his worth by chart positions and midweek numbers.
- •By the ‘Trust Me’ album (2009), he sensed he was making music to ‘please people and tick boxes’ and moving far from his synth‑based roots.
- •The ‘Signed, Sealed, Delivered’ covers album had him singing Motown classics almost verbatim, reinforcing the sense he was abandoning his own artistic identity.
- •The marketplace responded with muted interest, mirroring his internal disconnect and leaving him out of the scene and out of contract.
- 1:47:00 – 2:08:00
Miami highs, overtraining, injury and the crash into depression
Craig moves to Miami around 2010, initially enjoying an intense period of parties, women, cars and status. But as music output dwindled and gym culture escalated, a catastrophic back injury from deadlifts caused persistent nerve pain and triggered major depression. He candidly describes dark thoughts, the limits of ‘positive reframing’, and learning to read his body’s warnings.
- •For the first 2–3 years Miami was ‘the best time’ of his life superficially: constant parties and toys, with music slipping into the background.
- •Excessive training, including deadlifts, led to a severe lower‑back blowout, causing electric‑shock‑like spasms with nearly every movement.
- •The chronic pain over 2–3 years caused despair and thoughts like ‘I can’t live my life like this’, which he identifies as his first true depressive episode.
- •He saw this as a forced confrontation with everything he’d suppressed—body image, identity, abandonment of his musical essence.
- •Rehab involved injections, targeted strengthening (multifidus, paraspinals, glutes), and a new philosophy: heed small warning aches before the body ‘amps up the sound’ into a crisis.
- 2:08:00 – 2:20:00
Men’s mental health, dropping ‘man up’ and the dark night of the soul
Reflecting on his depression, Craig criticizes the ‘man up’ narrative and links it to male suicide rates. He advocates open conversation, including with anonymous listeners, and frames recovery as a ‘dark night of the soul’ where you systematically unpack old stories and trauma rather than sweeping them under the carpet.
- •He calls ‘man up’ rhetoric deeply harmful, arguing it fuels repression that contributes to male suicides.
- •Talking is essential but only the first half; the second half is a prolonged inner journey confronting childhood wounds, identity stories and unmet emotional needs.
- •He sees his own experiences—physical pain, heartbreak, anxiety—as necessary ‘sign‑ups’ that enable him to speak authentically on these topics.
- •He now prioritizes aligning actions with feelings rather than external expectations or masculine stereotypes.
- •He praises platforms like Steven’s podcast for allowing men to show 100% of themselves instead of a media‑trained, guarded 80%.
- 2:20:00 – 2:35:00
Returning to London, TS5 and the joy of cultural comeback
Craig describes coming back to the UK, immediately feeling embraced by Big Narstie, Kurupt FM, Stormzy and others at a 1Xtra performance. A spontaneous ‘Fill Me In’ remix over ‘Where Are Ü Now’ goes viral, with Justin Bieber, Skrillex and Diplo sharing it. He explains how TS5 evolved from tiny house parties to major sets at Ibiza and Glastonbury, reconnecting him with his DJ roots and the pure fun of music.
- •On returning, he felt a ‘huge hug’ from the UK scene; Big Narstie emotionally praised deep cuts like ‘Bootyman’.
- •His live mash‑up of ‘Fill Me In’ over the Bieber/Diplo/Skrillex instrumental gained viral traction within 45 minutes, with all three original artists reacting online.
- •TS5 started as small house parties in his Miami apartment; he initially played only other people’s records.
- •Guests pushed him to perform his own songs, leading to recorded sets on SoundCloud and then weekly shows on Kiss FM and Capital/Capital XTRA.
- •The format—DJing, MCing and singing his own hits—proved so unique it scaled to sold‑out club shows, Ibiza pool parties and a defining Glastonbury set.
- 2:35:00 – 2:50:00
Relationships, masculinity and choosing heart‑led living
Craig reflects on how childhood models and early heartbreak led him to avoid deep relationships and objectify women during his peak fame years. He now values emotional connection, laughter and mutual consciousness over looks, and emphasizes owning his role in past toxic dynamics. He also gently rejects his own old ‘foot on the gas’ language, advocating rest and intuition over hustle.
- •He recognizes he once chased a ‘dreamy’ ideal of love without doing the real relational work his parents’ example never modelled.
- •His longest relationship lasted about 2.5 years, yet he still kept his heart partially closed and sees that ex as a teacher.
- •Today he looks for partners who can ‘go there’, emphasize laughter, and meet him consciously, rather than just match a physical ideal.
- •He now questions hustle metaphors like ‘foot on the gas’, noting that stillness (e.g. during the pandemic) often created deeper growth and creativity than constant striving.
- •He believes the old patriarchal model of alpha, repressed masculinity is failing and being replaced by heart‑based, loving connection.
- 2:50:00 – 3:09:00
‘22’: recapturing the kid, integrating the journeyman
Approaching the release of his album ‘22’, Craig explains how the pandemic gave him the same unhurried space he had making ‘Born To Do It’. Writing at home with a giant subwoofer, collaborating with younger writers for fresh language, he aimed to blend R&B and garage with the emotional honesty of a man who has been through the highs and lows. He likens himself to Charlie in ‘Willy Wonka’, returning the everlasting gobstopper—choosing integrity over temptation and finally getting the whole factory.
- •The title ‘22’ marks 22 years since ‘Born To Do It’; he sees it as a bookend and a new chapter.
- •Lockdown allowed him to write slowly, record at home and only move when he truly felt a song, echoing his teenage process.
- •He uses a massive sub at home to ‘feel’ the music in his body, just like his early Southampton setup.
- •Working with younger artists helps him use current language so the message lands without sounding dated, while retaining his authentic voice.
- •He frames himself as a ‘journeyman’ who’s passed through tests, dropped his last hidden 10–20% of inauthenticity, and is now willing to trade old pretence for full-hearted truth, not knowing how the world will react.
- 3:09:00
Message to his 14‑year‑old self and closing reflections
In response to the previous guest’s question, Craig delivers a heartfelt ‘whisper’ to his 14‑year‑old self, promising euphoria, acknowledging upcoming hardship, and reassuring younger Craig that his older self will be there holding his hand. Steven closes by highlighting the impact of Craig’s vulnerability, and both acknowledge a genuine sense of brotherhood and the importance of modelling open, emotionally honest masculinity.
- •Craig would tell his 14‑year‑old self that everything is about to change in a beautiful way, but there will be hard times too.
- •He promises his younger self that he’ll always be there, holding his hand through the journey.
- •He hints at the coming ‘crowd going off’—a nod to his future breakout hits and performances.
- •Steven emphasizes that Craig won’t fully see the positive impact his openness will have on young men struggling with similar issues.
- •They mutually recognize a feeling of instant familiarity and brotherhood, underscoring Craig’s authenticity and emotional availability.
