Level up your copywriting w/ Sam Parr | E2226
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This episode of This Week in Startups features Sam Parr, founder of The Hustle (sold to HubSpot), creator of Hampton (an exclusive founder community), and host of "My First Million." Jason Calacanis brought Sam on to teach founders how to become better copywriters, exploring timeless advertising principles from the 1940s-50s that still drive conversions today. (03:00) The conversation covers everything from the AIDA framework to why long-form copy outperforms short-form, and how AI should be used strategically in writing.
• The episode focuses on practical copywriting techniques, classic advertising principles, and building authentic founder communities through storytelling and genuine connection.
Speakers
Sam Parr
Sam Parr is the founder of The Hustle, which he sold to HubSpot in 2021. He currently runs Hampton, a members-only community for high-performing founders that charges $15,000 annually and accepts only 4% of applicants. He also hosts "My First Million" podcast and "Moneywise," focusing on wealth and financial transparency among successful entrepreneurs.
Jason Calacanis
Jason Calacanis is an angel investor, entrepreneur, and host of This Week in Startups. He previously founded and sold Silicon Alley Reporter and Weblogs Inc. (sold to AOL for $30M), and has invested in companies like Uber, Robinhood, and Thumbtack. He's known for his direct communication style and focus on helping founders build better companies.
Key Takeaways
Long-Form Copy Consistently Outperforms Short-Form
Sam explains that despite common beliefs about attention spans, long-form copy almost always converts better than short-form. (08:15) He points to Amazon and Apple as examples - their product pages contain thousands of words and multiple photos because they work. The key insight is that it's not about length, but about creating a "slippery slope" where readers gradually become more invested in your message through the AIDA framework (Attention, Interest, Desire, Action). (09:52)
Write Like You Talk, But at a Fourth-Grade Reading Level
Sam emphasizes the importance of writing simply and conversationally, recommending tools like HemingwayApp.com to ensure fourth or fifth-grade reading levels. (16:21) He uses Warren Buffett as an example, noting that his famous annual letters average 18 words per sentence at a sixth-grade reading level. This simplicity, combined with powerful analogies, made Buffett famous for memorable phrases and contributed to his legendary communication skills.
Use AI for Research and Ideas, Not Actual Writing
Sam advocates for a strategic approach to AI in copywriting - use it to find compelling angles and research supporting evidence, but never let it do the actual writing. (18:38) He demonstrates this by describing how he used AI to discover the "Michelangelo effect" concept and find scientific studies to support networking arguments for Hampton. The human touch in writing creates authentic connection that AI cannot replicate.
Master Copywriting Through "Copywork" Practice
Sam recommends a technique called "copywork" where you hand-write excellent sales letters or compelling content word-for-word for 15-60 minutes daily. (23:46) This practice, similar to musicians learning by playing existing songs, helps you internalize the rhythm and structure of effective writing. He compares it to chess puzzles that make players 20% better - the act of physically writing great copy changes your brain and improves your own writing abilities.
Focus on Emotional Connection Over Feature Lists
Rather than leading with product features, Sam advises starting with the emotional experience or problem you're solving. (28:58) He suggests describing feelings so intimately that readers think you know their problems better than they do. For example, instead of listing tax software features, you might describe the stress of receiving an unexpected tax bill and wishing you'd known in advance - creating immediate emotional resonance.
Statistics & Facts
- Only 4% of applicants are accepted into Hampton, Sam's exclusive founder community. (45:19) Last month they received 2,300 applications, and everyone gets interviewed personally, with Sam watching 100% of the interviews himself.
- Vistage, a business coaching company launched in 1962, has 40,000 members paying an average of $20,000 per year, yet most people have never heard of them. (48:07) The company was previously owned by Larry Ellison and Michael Milken, demonstrating the massive scale possible in founder communities.
- Warren Buffett's famous annual letters average 18 words per sentence and are written at approximately a sixth-grade reading level. (17:04) This simple communication style contributed significantly to his fame and ability to explain complex financial concepts to ordinary investors.
