Bert Kreischer Teaches You How to Tell a Good Story
The hilarious comedian breaks down the moment he learned what hard work really is.
Bert Kreischer is a wildly successful comedian, a wildly successful entrepreneur, and is just plain wild. From hosting multiple podcasts and running a production company with his wife, LeeAnn, to launching a new Netflix show, Free Bert, and building the vodka brand Por Osos Vodka with his buddy Tom Segura, Bert has turned chaos into an empire. He was recently a guest on our show, How Success Happens, where he was hilarious and surprisingly soulful, and also had to be quick on his feet when he got an unexpected call-in from the Mayor of Flavortown himself, Guy Fieri.
Watch the full episode above or listen below, and read on for Bert’s most powerful insights to help your personal success take off in three, two, one!
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Three Key Insights
1. “You Don’t Understand Work Until You Find Your Passion.”
Bert says he wasn’t always a hardworking guy. In fact, as a six-year senior at FSU, he had no direction and no clue what hard work actually meant. The turning point came when he discovered comedy—something he was genuinely passionate about. “Once I found comedy, I understood all those people who worked hard in school. I understood what they were doing.” Before that, he was just a party guy throwing legendary fraternity events. But once passion entered the picture, everything changed.
Takeaway: You can’t force hard work without passion; first discover what genuinely excites you, then apply yourself to mastering it.
2. “Bust Your Ass in Business So You Can Take Your Kids on Vacation.”
Bert chased the big house for years, thinking that was the ultimate prize. But reflecting on his journey, he realized the truth: “It’s not about the big house. It’s about the experiences with your family and being able to do cool stuff with your kids, do cool stuff with your wife, be able to afford to send them to college.” His favorite house he’s ever owned wasn’t the biggest—it was a 1,100 square-foot home that “smelled like family” and “sounded like family.” Even after making $33 million in a single year, Bert discovered something shocking: “I guess my bills are paid. I don’t think I’d notice a difference between a hundred million and 10 million.”
Takeaway: Build your business empire for the personal freedom it brings, not to accumulate status symbols.
3. “A Good Story Always Starts With a Great Ending.”
Bert revealed the secret to compelling storytelling—and it’s the opposite of what most people think. “A good story starts with a great ending,” he explained. Once you know where you’re going, the journey to telling that story becomes clearer.
Beyond the ending, a great story needs what Bert calls a great hook. “You need a great moment in that story that really cues your listener to lean in,” he said. But here’s where most entrepreneurs get it wrong: Bert insisted that a great story doesn’t need to be big to be impactful. “Just find a small funny moment.”
Related: Author Susan Orlean Says to Trust Your Instincts (and Your Weirdest Ideas)
When it comes to capturing stories from his daily life, Bert’s approach is pretty laid back. He doesn’t obsess over note-taking. “I write some stuff down, I’ll put it in my notes just to remind me, but for the most part, it’s jarred from my memory when I’m sitting around a room talking.” Bert says, ultimately, he is a storyteller at heart, not a joke writer. “I love jokes, but it’s just not my passion. I’m not a mathematician guy.”
Takeaway: Master storytelling by knowing your ending first, and remember that the most powerful stories come from real, relatable moments—not manufactured “messages.”
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3.5 “When the Mayor of Flavortown Calls, You Answer.”
Bert received a surprise call-in — the first in How Success Happens history. When long-time friend Guy Fieri heard Bert was being interviewed, he busted in to get the answers to some very pressing questions.
Takeaway: Just watch or listen to the show — there’s no way to explain in words the magic that transpired between these two greats.
Two Great Ways to Learn More
- Follow Bert Kreischer @bertkreischer, check out his numerous podcasts at bertbertbert.com, and watch his new show, Free Bert, on Netflix.
- Read this Entrepreneur.com story that breaks down the art of telling your brand’s story.
One Question to Ponder
Here’s the question burning in our minds after talking with Bert:
“What’s the one moment in your life when you realized you weren’t actually pursuing work—you were pursuing your passion?”
Send your answer to howsuccesshappens@entrepreneur.com, and we might just feature it on a future episode of How Success Happens. We want to hear from you!
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.
Bert Kreischer is a wildly successful comedian, a wildly successful entrepreneur, and is just plain wild. From hosting multiple podcasts and running a production company with his wife, LeeAnn, to launching a new Netflix show, Free Bert, and building the vodka brand Por Osos Vodka with his buddy Tom Segura, Bert has turned chaos into an empire. He was recently a guest on our show, How Success Happens, where he was hilarious and surprisingly soulful, and also had to be quick on his feet when he got an unexpected call-in from the Mayor of Flavortown himself, Guy Fieri.
Watch the full episode above or listen below, and read on for Bert’s most powerful insights to help your personal success take off in three, two, one!
