Bert claimed that Cigar Aficionado magazine launched in 1992 and single-handedly revitalized a cigar industry that had lost its popularity.
Snapshot · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Bert claimed that Cigar Aficionado magazine launched in 1992 and single-handedly revitalized a cigar industry that had lost its popularity.
Where this was said
At 18:40 · chapter starts 9:23
Bert produces two premium cigars from his backpack and the episode transforms into a cigar-smoke-filled conversation. His heartbreak over Tiger Woods is real: Tiger was a hero, a superman of golf, and watching addiction 'get all its hooks in him' is genuinely sad. But Bert's solution isn't sobriety — it's offering Tiger a seat at his table for beers. The Ruthie from The Real World comparison is both absurd and disturbingly apt. Bert then pivots to the history of cigars, revealing that Cigar Aficionado magazine launched in 1992 and engineered a cultural revival by putting celebrity smokers on its pages. MJ drinking whiskey and smoking two Cubans simultaneously becomes the image of aspirational cool Bert is chasing.
Bert loves Tiger Woods too much to want sobriety for him. He wants Tiger to get control — not quit — and openly offers himself as the world's most enthusiastic enabler. The Ruthie from The Real World comparison is genuinely alarming.
Cigars were dying until Cigar Aficionado launched in 1992 and got MJ, Arnold Schwarzenegger, and Bruce Willis puffing on camera. The industry exploded overnight. Bert's deep-dive into cigar history mid-sobriety is a thing of beauty.
Despite months of meticulous preparation, Starter Story's initial launch attracted zero users — a humbling reminder that building alone guarantees nothing.
A single Reddit link post quickly drove 100 visitors to the Starter Story website, igniting the founder's belief in social traffic.
After reformatting content as a native self-post (no direct link spam), the post exploded with hundreds of upvotes and thousands of readers.
By posting again and again with the native-content strategy, the founder's posts repeatedly hit Reddit's front page, reaching millions of readers.
Before Reddit banned his domain, the founder converted his viral traffic into an email list of tens of thousands — a self-owned audience independent of Reddit.
Redditors eventually organized a petition to ban starterstory.com posts, effectively ending the Reddit growth channel — but the email list was already built.
The Reddit attention strategy ultimately served as the foundation for a million-dollar business, proving that free distribution channels can replace paid marketing.
The key tactic was keeping content fully on-platform (no direct link spam), then adding a small link at the post's end for users who wanted more.
With a thriving email list and a self-owned audience, the founder quit his six-figure New York City salary job to go all-in on Starter Story.
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