Level up your copywriting w/ Sam Parr | E2226

Level up your copywriting w/ Sam Parr | E2226

Author: Jason Calacanis December 20, 2025 Duration: 1:06:13

This Week In Startups is made possible by:


Luma AI - https://lumalabs.ai/twist


Northwest Registered Agent - https://www.northwestregisteredagent.com/twist 


Lemon IO - https://lemon.io/twist



Today’s show: 


DID YOU KNOW… most of the tried and true techniques devised by marketing gurus in the ‘40s and ‘50s still apply today?


On TWiST, we’re joined by online marketing expert Sam Parr, host of “My First Million” and founder of Hampton. He’s sharing all of his top tips and tricks for making your writing more compelling, and converting your readers into new customers.


In this essential pod for any and all founders, hear Jason and Sam run down their list of the best-ever marketing books, why there’s no such this as “too long” only “too uninteresting,” when to use AI and when to rely on your own brain, why you’re the average of your five best friends, and lots more deep insights.


Timestamps:


(00:00) Sam Parr of The Hustle, Hampton, and My First Million is here to teach us how to become better copywriters


(03:59) How Sam got interested in the (then-shady) world of internet marketing


(06:26) Why Sam recommended THESE advertising books to Jason


(08:15) All the principles that ad execs developed in the ‘50s still work!


(09:43) Glengarry had it right; the magic of A.I.D.A.


(11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist


(14:30) There’s no such thing as “too long,” just “too uninteresting”


(16:15) The goal is to write at a 4th grade reading level


(18:12) Why Sam only uses AI for “The Big Idea,” not the actual writing


(19:37) Why you’re the average of your five best friends


(21:14) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!


(22:15) Using AI to dig in and research, to make your writing more interesting


(23:42) CopyWork: The technique that helped Sam fine tune his writing


(28:41) Avoiding “The Feature Death March”


(30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist


(32:00) Words are better than images, but videos are better than anything


(34:43) Why stories make such a huge impact


(37:36) Sam and Jason are both obsessed with the book “How to Be Rich”


(43:02) First World Problems are still problems!!


(44:31) Why Sam launched Hampton and what it takes to get in


(47:10) Why scaling a community is so much harder than launching


(51:04) The lessons founders can take from Ted Turner


(58:36) What Jason likes best about My First Million


(1:00:28) It’s never too early to get your first $10 million


(1:04:07) How accurately did Producer Claude guess what Sam was going to teach us?


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Follow Lon:


X: https://x.com/lons


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Follow Alex:


X: https://x.com/alex


LinkedIn: [https://www.linkedin.com/in/alexwilhelm/


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Follow Jason:


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LinkedIn: https://www.linkedin.com/in/jasoncalacanis/


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Thank you to our partners:


(11:19) Luma AI - Stop guessing and start directing with Ray3 Modify from Luma AI, the AI-powered post production tool. Explore it at: https://lumalabs.ai/twist


(21:14) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!


(30:56) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist



Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 100

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