How Jason Levin Made Silly a Serious Business

Jason Levin, founder of Meme Lord.com, shares how a lifetime of posting goofy content turned into a million-dollar empire and why taking your comedy seriously might just be your smartest career move.

Author

Ben Sharf
August 29, 2025

In Season 4, Episode 14 of Turning Pro, Ben Sharf talks to Jason Levin, the founder of Meme Lord.com and author of Memes Make Millions. Jason has been creating and sharing memes since he was a kid, long before he knew it could pay the bills. What started as silly Photoshop experiments and weird tweets has become a fully fledged media and software company generating over $1M a year.

Jason breaks down how staying true to his sense of humor opened doors to billionaires, investors, and big brand deals. He explains why cringe is a sign you’re ahead of the curve, how cold DMs beat cold emails, and why every founder should treat content like a digital diary. We also get into the business side: his meme marketing software, his unique hiring process, and how memes have landed him serious contracts in unexpected ways.

Listen to Season 4, Episode 14 of Turning Pro on Apple, Spotify, or YouTube.

10 Key Takeaways from Jason Levin’s Episode

  1.  Cringe Is a Phase, Not a Verdict: Everyone looks cringe until they succeed. Push through the “cringe valley” and you’ll come out respected.

  1. Consistency Compounds: Jason has written his newsletter every Sunday for over 180 weeks. Show up on a schedule, even when no one is watching.

  1. Cold DMs > Cold Emails: Direct messages let people instantly see your profile, mutuals, and personality, making them far more effective than email.

  1. Content Is a Digital Diary: Even if you never monetize, documenting your thoughts and projects creates a record you’ll value years later.

  1. Sell the Problem, Not Just the Brand: For early-stage marketing, focus memes on the problems your target audience faces, not on your company logo.

  1. Authenticity Attracts the Right People: Being fully yourself filters for the audience, customers, and investors who actually align with you.

  1. Turn Your Niche Into Software: Jason built Meme Lord’s software to solve his own pain point, tracking trending memes before they blow up.

  1. Brand Deals Can Start as Jokes: One of Jason’s biggest contracts came after he posted a competitor’s logo edited into something ridiculous.

  1. Hire From the Cult, Not the Résumé: Every person on Jason’s team came from his audience, drawn in by his content and culture.

  1. Treat Comedy Like Kobe Treated Basketball: Take the craft seriously. Reps, discipline, and high standards separate pros from dabblers.

Jason’s story is proof you can turn something playful into a serious business if you commit to it like any other craft. By blending humor, discipline, and smart business moves, he’s showing that the internet rewards those who dare to be themselves loudly and often.

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