TThe Diary of a CEO
← All episodes
24 March 2022

Diplo: College Dropout To World's Most Iconic DJ

4Frameworks
13Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take51:00

Diplo Thinks Being Ready to Lose It All Supports Success

Diplo says he believes he could start again in another craft if music, labels, and DJing disappeared. He treats career status as a facade beside family, meaningful work, and the ability to live humbly, and suggests that comfort with starting over may support success.

  • He imagines alternatives such as carpentry or making pizza
  • The replacement career would still need to involve work he loves
  • He does not equate a smaller or less wealthy life with personal collapse
  • Family provides continuity beyond his public career

if you have that feeling inside you that you can lose everything and be okay with it

Diplo · 51:30
#resilience#identity#starting over

Explainer· 1

Explainer18:30

Diplo's Real Strength Is Conceptual, Not Technical

Diplo rejects the idea that his value comes from instrumental mastery or elite turntablism. He describes himself as someone who solves musical riddles, combines sounds, and uses improving technology to translate ideas into audio.

  • His early production workflow was technically limited and unconventional
  • He sees musical combinations as problems to solve
  • Visual audio tools fit the way his mind works
  • He contrasts his approach with technically exceptional producers and turntablists

i've always been like more of a conceptual artist

Diplo · 19:00

i'm the guy with like ideas and how do i apply those ideas

Diplo · 20:30
#creativity#music production#strengths

Story· 5

Story03:30

Why Diplo Left Film School for Real-World Practice

Diplo studied anthropology and filmmaking after community college but dropped out of Temple University. He says the film programme made him question whether formal study was moving him toward active creative work, and he now wishes he had begun making things outside school earlier.

  • His interests in culture and documentary film predated his music career
  • He became dissatisfied with learning about a business instead of working in it
  • He views the detour as part of the journey even while wishing he had left sooner

the real business is like going out and making it yourself

Diplo · 05:00
#college#filmmaking#career change
Story05:30

The Unstable Years Before DJing Paid the Rent

Diplo describes moving from social work into side-gig DJing and eventually running his own parties. The transition replaced a salary with several years of uncertain monthly income, during which he learned through small experiments, failures, mixtapes, edits, and event promotion.

  • Social work felt meaningful but bureaucracy wore him down
  • Running his own parties taught him basic business economics
  • Music income remained inconsistent for roughly three or four years by his account
  • He learned production and computing without a formal teacher

it's not a consistent paycheck music never is

Diplo · 07:30
#dj career#side hustle#income risk#learning
Story30:30

The Forced Pause That Made Diplo Reassess His Pace

Diplo says he had operated at breakneck speed and rarely refused opportunities before COVID restrictions stopped live shows. The pause gave him room to buy a house, reconsider his next steps, spend more time with his children, and work on records on his own terms.

  • He says he had been moving at extreme speed without taking a break
  • He felt pressure to keep working while his career window remained open
  • The pause shifted some attention toward family and non-work exploration
  • He still created music but stopped chasing every live event and possible success

i never said no to anybody

Diplo · 31:00

eventually i was like you know what this isn't that important

Diplo · 32:00
#burnout#covid#work life balance#family
Story41:00

Why Working With Young Rappers Changed Diplo's Mental-Health Advocacy

Diplo connects his decision to speak more about mental health with Avicii's death and his work with very young rappers. He recalls seeing rapid fame surround artists in their late teens and early twenties, several of whom later died, and feeling that young artists needed older people willing to help them navigate decisions. This is Diplo's interpretation of what he witnessed, not a clinical explanation of those deaths.

  • He names Avicii's situation as one influence on his advocacy
  • He worked with young rappers including Lil Peep and XXXTentacion
  • He says rapid public attention made modern youth feel harder to navigate
  • He tried to help some younger artists make decisions and imagined a big-brother role

i just like damn these guys all need like a big brother

Diplo · 42:00
#mental health#young artists#fame#mentorship
Story1:00:00

Diplo Says Fatherhood First Made Love Feel Undeniable

In a discussion about emotional reserve and romantic connection, Diplo says the birth of his first son gave him his first experience of love as an undeniable lifelong responsibility. He describes all three sons as the people he cares about most and says becoming a father changed his understanding of love.

  • He describes himself as emotionally guarded in relationships
  • He distinguishes uncertain romantic love from his bond with his children
  • Parenthood created a responsibility to help another person become a better human
  • He says the same commitment extends to all three sons

the first time i understood love was when i had children

Diplo · 1:01:00
#fatherhood#love#relationships

Q&A· 1

Q&A54:00

The Career Advice Diplo Plans to Demonstrate, Not Explain

Asked what advice he would give his sons about success, Diplo says he would take them on the road. He wants them to see the gym, press, promoter dinners, performances, appearances, travel, and studio sessions that sit behind the visible concert.

  • He prefers showing the daily process to giving an abstract success speech
  • The glamorous performance is only one part of a tightly managed schedule
  • He cites George Foreman Jr.'s account of learning by seeing his father's work firsthand

this is what i do every day just so you know

Diplo · 54:30

i can actually show them that

Diplo · 55:00
#career advice#parenting#work ethic

Takeaway· 5

Takeaway01:30

The Advantage Diplo Says He Got From His Father's Discipline

Diplo says his father's demanding idea of discipline became useful only when he was older. He credits persistent application toward a goal, rather than exceptional technical ability, as an important part of his progress as a DJ and songwriter.

  • He was expelled from schools, including military school, during adolescence
  • He later recognised discipline as a lesson inherited from his father
  • He distinguishes sustained application from technical virtuosity

i always apply myself to find a goal

Diplo · 03:00
#discipline#work ethic#career development
Takeaway35:00

The Management Relationship Diplo Kept for Two Decades

Diplo credits a long-standing team with supporting both his ambition and his ability to remain himself. His first manager initially worked without pay, pushed him to think beyond local success, and became the start of a management journey that Diplo says remained stable for about 20 years.

  • His first manager believed there was more potential beyond local DJ success
  • Diplo describes his broader team as a family with his interests in mind
  • He warns that management can impose the wrong vision on a young artist
  • He values people who believe in the artist while leaving room for individuality

it's important to find people you know that really believe in you but also let you be yourself

Diplo · 36:30
#management#creative identity#team
Takeaway46:00

Why an Hour on the Couch Can Matter More Than a Big Trip

Diplo says his energetic idea of fatherhood can overwhelm children who sometimes want ordinary time rather than another activity. He is learning that sitting beside his son while he watches cartoons or plays Minecraft may create a more meaningful connection than arranging an extraordinary trip.

  • He wants to pass on discipline but admits he is still learning how
  • His children sometimes experience his high-energy plans as a disruption
  • He distinguishes being physically there from being with them on their terms
  • Ordinary shared attention can be more memorable than elaborate experiences

i gotta like be their their their friend too

Diplo · 47:00

they actually remember this time and on the couch with me a lot more

Diplo · 47:30
#fatherhood#presence#parenting
Takeaway48:30

How Diplo Stops Every Show Becoming an Emotional Peak

Diplo says repeated performance highs and lows would be unhealthy for him, so he treats touring as a job and tries to keep his response steadier. He still values gratitude after an exceptional show, but avoids drinking while DJing and describes learning to wind down after late performances. These are his personal practices, not medical advice.

  • A touring schedule can include hundreds of performances by his account
  • He tries not to make each night the biggest party of his own life
  • He avoids routinely drinking while working
  • Post-show adrenaline can make sleep difficult

you have to have gratitude for that

Diplo · 49:00

you can't just live like every night's like the biggest party of your life

Diplo · 50:00
#performance#touring#recovery#sustainability
Takeaway1:01:30

Diplo's Answer to Why He Exists

Asked why he exists, Diplo answers in terms of joy, inspiration, music, cultural exploration, and adding something new to the world. The answer frames creativity as a contribution: making something that was not present before.

  • He hopes to bring joy and inspiration
  • He connects his purpose with new music and cultural exploration
  • He treats creation as adding a new thing to the world

add something to the world that wasn't there before

Diplo · 1:01:30
#purpose#creativity#music