Des Bishop has built one of comedy’s most unlikely careers — a native New Yorker who became a household name in Ireland, then learned Mandarin well enough to headline stand-up shows in China, and later moved back to the U.S. to start over from scratch. His new special, “Bridge and Tunnel,” is streaming now on Hulu and YouTube. Des joined us on How Success Happens to talk about his wild career and share his advice with anyone trying to chase their dream — we’ve broken down 5 highlights of his insights to help fuel your own success.
Listen Now
Subscribe now: Apple | Spotify | YouTube
1. Throw Yourself Into the Deep End
Des’s very first stand-up set wasn’t a five-minute open mic — it was a 20-minute opening slot in Cork City, because the club “was so cheap, they decided to not book an opener.” His only experience was doing some bits at a joke competition two weeks earlier. “I mean, I’m sure there was a decent four or five minutes in there. A lot of it was rubbish. But I didn’t die, you know?” he says. “My only memory from that was I couldn’t wait to do it again.”
2. Force Yourself Out of Your Comfort Zone
After becoming famous in Ireland and building a following performing in Mandarin in China, Des made a deliberate choice in 2018 to rebuild his career from zero in the U.S. “I set myself a goal. I said, ‘I’m not gonna live off any money that I make outside of the United States,’” he says. He played “tiny crowds in cities” where “people had no idea who I was” — on purpose. “It was a great exercise, but it was not easy. And it did make me a way better stand-up comedian.”
Subscribe to the free How Success Happens Newsletter for weekly inspiration.
3. Redefine What “Risk” Actually Means
Des doesn’t count a bombed joke as a real risk — that’s just “the occupational hazard of needing new material.” The real risk, he says, is choosing what to talk about in the first place: “Am I ready to take the heat for having strong opinions on a particular topic?” That’s the risk-taking that actually matters to him, more than “‘Oh, this joke might not land.’”
4. Stop Resisting the New Platform
Des admits he “railed against the dying of the light” when social media took over comedy, worried about “burning” his best bits by posting them. For years, it went nowhere: “I’m posting loads of shit. It’s not going anywhere, and it’s really time-consuming.” Then one clip about mindfulness broke through — “it got 14 million views on my account,” he says, with reposts pushing it toward “100 million views” total. “Nothing I’ve done has come even close to that.”
5. Turn Being an Outsider Into Your Edge
Des built his early Irish fame on being “this guy that came to Ireland and saw Ireland through my unique eyes” — a built-in outsider’s perspective he later repeated in China. “Part of it is that I’ve been good at being a fish out of water,” he says, “but that’s a blessing and a curse” since it can also cap how wide an audience follows you. Even so, it’s given him a distinct voice everywhere he goes.
Learn More
Follow Des Bishop on Instagram at @desbishop, and stream his special, Bridge and Tunnel, now on Hulu and YouTube.
More on these themes from Entrepreneur.com:
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.
Des Bishop has built one of comedy’s most unlikely careers — a native New Yorker who became a household name in Ireland, then learned Mandarin well enough to headline stand-up shows in China, and later moved back to the U.S. to start over from scratch. His new special, “Bridge and Tunnel,” is streaming now on Hulu and YouTube. Des joined us on How Success Happens to talk about his wild career and share his advice with anyone trying to chase their dream — we’ve broken down 5 highlights of his insights to help fuel your own success.
Listen Now
Subscribe now: Apple | Spotify | YouTube
1. Throw Yourself Into the Deep End
Des’s very first stand-up set wasn’t a five-minute open mic — it was a 20-minute opening slot in Cork City, because the club “was so cheap, they decided to not book an opener.” His only experience was doing some bits at a joke competition two weeks earlier. “I mean, I’m sure there was a decent four or five minutes in there. A lot of it was rubbish. But I didn’t die, you know?” he says. “My only memory from that was I couldn’t wait to do it again.”