Level up your copywriting w/ Sam Parr | E2226

This Week in Startups

Jason Calacanis

Technology

4.2 • 1.4K Ratings

🗓️ 20 December 2025

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

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

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

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

Transcript

Click on a timestamp to play from that location

0:00.0	Like I wasn't selling anything particularly special.
0:02.0	And so I started like Googling how to be a salesperson. And I learned about this thing called copywriting. And what I realized was if I could take my ability to sell one to one, which I eventually learned how to do and put it on paper, you could sell one to an infinite number. There was a guy named David D'Angelo. He would write these like 5,000 word emails where it was just plain text. And they were making $30 million a year selling ebooks on how to like hook up with the girl. What percentage of the lessons persist and kind of hold true in the current moment? All. So basically there's a lot of sales pages that you go to and it's just tons and tons of words. You're going to say, that doesn't work on me. That used to work then. It doesn't work nowadays. And you're going to like see like cheesy headlines and all that stuff. You're going to think none of that works on me.
0:54.5	You're wrong. It does. Long form copy typically is almost always better than short form copy. Anyone who sells a lot of anything knows all these principles. And one of the principles is that long form is better than short form. and a lot of people listening, they're not going to believe it, but they're wrong.
0:58.5	This week in startups is brought to you by Lemon.io.
1:01.3	Building a great team is essential to any business.
1:06.9	Lemon is a marketplace of vetted, experienced developers ready to take your company to the next level.
1:12.9	Get 15% off your first four weeks of developer time at lemon.io slash twist.
1:17.5	Northwest Registered Agent. Starting your business should be simple. With Northwest Registered Agent, you can form your entire business identity in just 10 clicks in 10 minutes.
1:22.9	From LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options, and more done.
1:30.4	Visit northwest registered agent.com slash twist today.
1:34.7	And Luma AI.
1:36.9	Stop guessing and start directing with Ray3 Modify from Luma AI,
1:41.3	the AI powered post-production tool.
1:43.8	Explore it at Luma Labs.A.I.S.T.T.
1:49.4	All right, everybody, welcome back to this week in startups.
1:53.6	Alex, as part of our continuing focus on helping founders build better startups,
2:00.7	I was faced with a bunch of founders asking
2:03.7	me how to write better copy because I was looking at their web pages. And I was like, my God,
2:08.1	this copy sucks. And then I looked at some of my own web pages and said, my God, this copy sucks.
2:12.8	And I was like, who's really good at this? And then I remembered my friend Sam Parr from the hustle,
2:20.0	hustle conference, hustle newsletter, my first million had obsessed about this. And I started doing
2:26.5	some chat GPT research, some Claude research, some, you know, perplexity searches. And Sam came up.
	...

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