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5 Creativity Hacks for Entrepreneurs with Jason Keath

February 18, 2026

Jason Keath is a creativity keynote speaker, author of The Case for More Bad Ideas, and cofounder of Social Fresh, the conference that helped launch the modern social media industry.

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Guest Resource

More Bad Ideas – Subscribe to Jason’s newsletter for weekly creativity strategies, stories, and AI tools.

3 Value Bombs

1. The most creative people aren’t the most inspired—they’re the most prepared. Systems and lists matter more than random genius.

2. Bad ideas are often stepping stones to brilliant outcomes. Embrace them, refine them, and keep going.

3. Scaling creativity is possible—and essential. The secret? More ideas, more iteration, and a willingness to question every assumption.

Sponsors

HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

Cape: A privacy-first mobile carrier, built from the ground up with security as the priority. If you care about protecting your digital life without giving up your smartphone, Cape makes that possible. Visit Cape.co/fire and use code FIRE for 33% off cape for 6 months today!

Show Notes

**Click the time stamp to jump directly to that point in the episode.

Today’s Audio MASTERCLASS: 5 Creativity Hacks for Entrepreneurs with Jason Keath

[1:13] – Jason shares something that he believes about becoming successful that most people disagree with.

  • Taking counterintuitive risks is often the real shortcut to success.

[1:52] – Jason shares what stops most people from being more creative.

  • It’s not time or freedom—it’s the lack of a creative process.
  • Even art school and creative agencies rarely teach creativity as a skill.

[3:06] – Jason share how to be creative when you’re short on time.

  • Use the “25 bad ideas” exercise to get unstuck fast.
  • Try the “constraint questions” technique: identify your top 10 limitations and ask, “What would need to be true to ignore this?”
  • Keep creativity lists—ideas, words, analogies, business problems—to build mental inventory.

[5:47] – Jason talks about how bad ideas really lead to better thinking.

  • Example: “20 Minute Yoga” seemed too generic; evolved into “19 Minute Yoga”—more distinct and memorable.
  • Spotify’s quirky billboard campaign “Thanks 2016, It’s Been Weird” was initially seen as a bad idea, but became a brand-defining success.

[9:58] – A timeout to thank our sponsors.

  • Cape: A privacy-first mobile carrier, built from the ground up with security as the priority. If you care about protecting your digital life without giving up your smartphone, Cape makes that possible. Visit Cape.co/fire and use code FIRE for 33% off cape for 6 months today!
  • HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

[12:24] – Jason talks about who is setting the creativity bar in business today.

  • Crocs: reinventing product innovation.
  • New York Times: now thriving in games and cooking verticals.
  • MasterCard: sonic and haptic branding excellence.
  • HubSpot & Robinhood: building media companies inside brands.

[15:21] – Jason tells that scaling does not kill creativity but amplifies it.

  • Creative success = 50–100 ideas for every 1 great result.
  • Example: SNL writes 850 jokes weekly for 15 to air; Mr. Beast advises creating 100 videos before worrying about quality.

[16:53] – Jason talks about how AI makes us creative.

  • AI is a powerful “thought partner,” not a decision-maker.
  • Best results come from giving it expert-level prompts and iterating with it.
  • Jason offers free AI creativity prompts on More Bad Ideas.

[19:07] – Jason gives his final takeaway.

  • “What if…?” is the most powerful question for creatives.
  • Stay curious. Even the weirdest idea can hold real potential if you explore it.

[19:52] – Call to action

  • More Bad Ideas – Subscribe to Jason’s newsletter for weekly creativity strategies, stories, and AI tools.

[21:15] – Thank you to our Sponsors!

  • Cape: A privacy-first mobile carrier, built from the ground up with security as the priority. If you care about protecting your digital life without giving up your smartphone, Cape makes that possible. Visit Cape.co/fire and use code FIRE for 33% off cape for 6 months today!
  • HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!

Killer Resources!

1) The Common Path to Uncommon Success: JLD’s 1st traditionally published book! Over 3000 interviews with the world’s most successful Entrepreneurs compiled into a 17-step roadmap to financial freedom and fulfillment!

2) Free Podcast Course: Learn from JLD how to create and launch your podcast!

3) Podcasters’ Paradise: The #1 podcasting community in the world!

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