Dopey 601: Kevin O’Leary on Obsession vs Addiction vs Greed, Getting Rich, Feeling Empty, PLUS a dude loses a balloon of heroin up his butt in jail...Dopey 601: Kevin O’Leary on Obsession vs Addiction vs Greed, Getting Rich, Feeling Empty, PLUS a dude loses a balloon of heroin up his butt in jail...
Dopey: On the Dark Comedy of Drug Addiction
Timestamp notes 00:02:42 — Dave introduces the Kevin episode, celebrates his Ben Stiller commercial, and shares a message about reaching out for help. 00:07:37 — Limited merch and DopeyCon updates. 00:12:25 — Adam calls in with a story about receiving heroin during jail visits. 00:14:28 — Unable to hide a balloon of heroin the usual way, Adam swallows it. 00:16:54 — The balloon finally passes. There are no gloves. 00:19:16 — Dave reacts and starts reading responses to Garrett McClendon’s episode. 00:26:17 — A listener marks episode 600; Dave prepares to bring in Kevin. 00:29:55 — Kevin O’Leary joins Dopey: Shark Tank, the American dream, and what viewers don’t see in a pitch. 00:34:40 — Kevin on his harsh reputation and his intolerance for bad business ideas. 00:37:00 — Drugs among the wealthy and Kevin’s longevity routine. 00:43:54 — The job that made Kevin decide he wanted to be his own boss. 00:48:35 — Kevin recalls working with people coming out of prison. 00:50:50 — Why he thinks pursuing wealth as a symbol of status leads to misery. 00:53:14 — “We’re rich as piss. What do we do now?” Success, emptiness, and a failed attempt to retire. 00:55:28 — John Mayer, guitars, watches, photography, and the problem of having too little time. 01:04:53 — Alcohol and Kevin’s memories of a college roommate’s drinking. 01:07:17 — Practice, consistency, Jane Fonda, and the decision to drink less. 01:11:55 — Drugs, sobriety, and the responsibility of performing for an audience. 01:14:12 — Kevin’s current work on data centers and power projects. 01:21:23 — Mark Cuban, Shark Tank investments, and a memorable cupcake pitch. 01:26:07 — Favorite records, Steely Dan’s Aja, and the sound of a great stereo. 01:33:13 — Marriage, sex addiction, and the start of “This or That.” 01:35:31 — Guitars, gold, Rogan, the Knicks, Trump, and Kevin’s fellow Sharks. 01:40:35 — Dave invites Kevin to DopeyCon and they wrap the interview. 01:43:02 — Dave’s recovery message and the rest of the Patreon comments. 01:45:28 — Behind the scenes: Kevin sets up his own camera and sends Dave an edited recording. 01:47:51 — Spotify listeners react to Garrett’s story. 01:55:02 — Dave clears up Aja versus Asia, launches the worst AA text contest, and signs off. 01:57:00 — Jake’s banjo cover of “Good So Bad.” 02:01:17 — “Forever in Debt.”
2:03:47•25 Sept 2026
Greed, Heroin Balloons and Getting Sober: Kevin O’Leary Meets Dopey
Episode Overview
- If you’re struggling, reach out to someone, and if you’re doing well, reach out to people who might be struggling.
- Treat alcohol as a dangerous drug and recognise how often it sits behind jail time and ruined lives.
- After getting sober and starting work again, aim to save around 20% of your income and regularly invest it in a stock index.
- Cut back on buying things you don’t need and use that money to build a financial safety net for the future.
- Hobbies and creative passions like music, photography or sport can help fill the space that addiction once occupied.
“"Alcohol is a poison. It’s a poison that would not be allowed today if it had just been invented."”
What drives someone to seek a life without alcohol? This Dopey episode throws you straight into that messy question, mixing a wild jailhouse heroin tale with a surprisingly candid chat about money, obsession, and booze from Shark Tank’s Kevin O’Leary. Dave kicks things off with his usual mix of dark humour and straight talk, reminding the "Dopey nation" to "reach out for help or reach out to help" and sharing messages from listeners hanging on by a thread.
You’ll hear about limited merch, Narcan, fentanyl test strips, and the upcoming DopeyCon, all wrapped in that familiar blend of chaos and care. Then comes Adam’s unforgettable story from county jail: contact visits, balloons of heroin, failed attempts to "put it in the hoop", swallowing the stash, coffee and Metamucil, trash bags over toilets, and finally sifting through his own faeces bare-handed to find the balloon so he and others could get high.
It’s disgusting, funny, and brutally honest – classic Dopey. The episode shifts gears when Kevin O’Leary joins. He talks about obsession versus addiction and greed, insisting that real entrepreneurs are driven by passion, not status.
He describes the moment he refused to scrape gum off an ice cream parlour floor and realised "there are people in the world that own the store and there are people that scrape the shit off the floor" – and he wasn’t going to be the latter.
Kevin calls alcohol "a poison" and describes friends and colleagues wrecked by alcoholism, yet also shares how he’s trying to limit his own drinking, protect his sleep, and focus on health, family and creative hobbies like guitar and photography. He offers practical advice for people rebuilding after addiction: take 20% of your pay, stop buying "shit you don't need", and consistently put it into a stock index.
It’s a strange, hilarious, and raw mix of jailhouse dope, big money, and recovery reality. Where do you see yourself in that triangle of obsession, addiction, and greed?
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