Podcast Summary: Level Up Your Copywriting w/ Sam Parr | This Week in Startups, Ep. 2226

Release Date: December 20, 2025
Host: Jason Calacanis
Guest: Sam Parr (Founder: The Hustle, Hampton, My First Million Podcast)

Episode Overview

In this lively episode, Jason Calacanis sits down with Sam Parr to dive deep into the art and business impact of copywriting. Drawing on Sam’s journey from hot dog stand hustler to multimillion-dollar founder, the conversation focuses on actionable copywriting strategies, the enduring power of storytelling, the use of AI, and how copywriting principles from the past still drive business growth today. Alongside plenty of practical advice, the hosts share war stories from media, investing, and community-building, making this an essential listen for founders, marketers, and operators.

Key Discussion Points & Insights

1. Sam Parr’s Copywriting Origin Story

• Early businesses & discovery: Sam recounts running a hot dog stand in college ("Southern Sam's Wieners, as big as a baby's arm") and exploring how to sell more through copy.
  • "I wasn't selling anything particularly special...I realized if I could take my ability to sell one-to-one and put it on paper, you could sell one to an infinite number." — Sam Parr (04:19)
• Inspiration from the Internet marketing world: Learned from long-form sales letters and notorious marketers (e.g., David D'Angelo in the PUA era).

2. Timeless Copywriting Principles

• Long Form vs. Short Form
  • Both Sam and Jason stress that long-form copy STILL works—even in the age of TikTok and X (Twitter), long-form builds investment and trust.
  • "There's no such thing as too long. There's only such a thing as too uninteresting." — Sam Parr (14:31)
  • The "slippery slope" of AIDA — every word encourages the reader to continue: Attention, Interest, Desire, Action. (09:30, 12:46)
• Classic Resources:
  • Sam and Jason recommend learning from copy greats: Ogilvy on Advertising, Confessions of an Advertising Man, Joe Sugarman’s Adweek Copywriting Handbook.
  • Sam emphasizes classic direct mailers' skills: "They got incredibly good at figuring out what words convince people to buy and take action." (06:33)

3. Practical Copywriting Tactics

• Write Like You Talk
  • Use relatable, conversational language at a 4th or 5th-grade level. Reference to Warren Buffett: “If you have to look something up in a thesaurus, don't use the word.” — Sam Parr (16:14)
• Active Voice Over Passive:
  • Make sentences clear and direct: "The boy kicked the ball" (active) vs. "The ball was kicked by the boy" (passive). (16:14)
• Personal Connection
  • Write as if to one person; get intimate with their pain points.
  • Example: Paint a scenario that deeply resonates with your audience’s lived experience—e.g., describing someone always standing on the edge in photos for a weight-loss ad (09:30).
• Copywork as Training:
  • Transcribe great sales letters or book passages by hand to internalize great writing. (23:48)

4. Bridging Old-School Copy to Modern Platforms

• “Human nature is human nature…it’s been the same since the beginning of time. Certain ways to actually do this [influence action] still work.” — Sam Parr (14:31)
• Twitter “thread boys” and Instagram hooks: long-form and emotional investment thrive, even on short-form platforms.
• The goal isn’t to convert everyone—it’s to convert the right 5% highly engaged readers.

5. AI’s Role in Copywriting

• How Sam uses AI:
  • To brainstorm big hooks/ideas and to find evidence (e.g., asking ChatGPT for studies to support a concept). (18:29, 22:16)
  • AI tools like Grammarly and Hemingway are useful for editing, catching passive voice, and improving clarity, but Sam believes AI can’t replace the creative writing process itself.
  • "I use it to help me find the big idea, but it can never do a good job of writing." — Sam Parr (18:29)

6. Crafting Effective Web & Sales Pages

• Leading with Emotion, Not Features
  • Above the fold: Show a feeling or story, not just product features.
  • For startups: Empathize with customer’s pain, not just what the product does. E.g., “Taking the terror out of tax season” for a tax product. (29:23)
• About Us Pages & Authentic Founder Videos
  • The story and intention behind the company/founder matters to buyers.

7. Building “Hampton”—Exclusive Community for Founders

• Hampton Model (44:49):
  • $15k/year membership; only 4% acceptance rate.
  • Small core groups of 8, led by trained moderators (46:17), focused on deep bonds and business/psychological support.
  • Mix of in-person and digital interactions.
  • Inspired by legacy organizations like YPO and Vistage, but more contemporary and startup-focused.
  • "My daughters are going to intern here. That's my goal..." — Sam Parr (49:30)

8. The Power of Story in Business Growth

• Great products alone are no longer defensible; intention and authentic narrative are critical for lasting brands (34:48).
• Personal stories (success, loss, motivation) drive connection, loyalty, and outsized value.
  • "The story matters more than anything." — Sam Parr (35:30)
• Underappreciated founders/ideas can massively outperform—never underestimate an “awkward” or unconventional builder (59:19).

9. Media Entrepreneur Wisdom

• Reflections on selling early vs. late (Hustle, Weblogs Inc.), career philosophy, and inspiration from media moguls like Felix Dennis and Ted Turner (37:47, 51:04).
  • "If you can make as much money as possible by 35, you can relax and write poetry... my goal was to make a lot of money by the age, in my case, 31, so I don't have to worry about that." — Sam Parr (61:12)

Notable Quotes & Memorable Moments

• On Long-Form Copy:
  “You want the least amount of words to be the most effective. And oftentimes, you need a lot of words to be incredibly effective.” — Sam Parr (09:30)
• On AI and Copy:
  "I use [AI] to help me find the big idea, but it can never do a good job of writing." — Sam Parr (18:29)
• On Learning Copywriting:
  "If you do [copywork] for 20 minutes a day, for 20 days, you will get better..." — Sam Parr (23:48)
• On Startups and Storytelling:
  "In today's market... the intent of the founder, the intent of the artist, why did they make this... Why did they create this product? ...Intent matters, right? Why you made the product." — Jason Calacanis (34:48)
• On Community and Moderation:
  "But finding a moderator in your city and then training them, training them in the Hampton way, that's really hard." — Sam Parr (47:17)

Timestamps for Key Segments

| Segment | Topic | Timestamp | |-------------------------------------|-----------------------------------------------------------------|-------------| | Opening, Sam’s copywriting story | Hot dog stand, discovering copywriting | 04:03–05:24 | | Classic advertising books | Ogilvy, Sugarman, Copywriting roots | 06:28–07:49 | | The Power of Long-Form Copy | AIDA, slippery slope, emotional hooks | 09:04–12:46 | | Applying AIDA, Instagram hooks | Modern hooks, emotional engagement, call-to-action | 12:46–14:01 | | Copywriting Tactics | Write like you talk, active voice, personal angle | 16:14–18:13 | | AI and Copywriting | Using AI for hooks, not for the writing itself | 18:13–19:29 | | Web Copy, “Above The Fold” advice | Leading with emotion, not features | 29:23–30:46 | | About Us pages, adding story | Power of storytelling and authenticity | 32:54–34:48 | | The necessity of founder intent | Product intent, story over tech | 34:48–36:58 | | Building Hampton community | Pricing, structure, value proposition | 44:49–46:48 | | Moderators in community | The importance and challenge of training moderators | 47:13–48:43 | | Longevity & legacy businesses | Learning from YPO, Vistage, building for 50+ years | 48:15–48:43 | | Parallels in media entrepreneurship | Selling too early, the importance of equity vs. income | 60:25–62:24 | | Closing recommendations | Favorite up-and-coming podcasts | 63:09–63:41 |

Resources Mentioned

• Books:
  • Ogilvy on Advertising — David Ogilvy
  • Confessions of an Advertising Man — David Ogilvy
  • The Adweek Copywriting Handbook — Joe Sugarman
  • How to Get Rich — Felix Dennis
• Apps:
  • Hemingway Editor (hemingwayapp.com)
  • Grammarly
• Communities:
  • Hampton (joinhampton.com)
  • YPO, Vistage
• Podcasts:
  • My First Million
  • Money Wise
  • Founders
  • How to Take Over the World (Ben Wilson)

Final Takeaways

This episode delivers a masterclass in copywriting for founders, blending practical how-to's (“write like you talk”, use copywork, personal storytelling) with business lessons from decades of media entrepreneurship. Whether building a landing page, an email campaign, or a billion-dollar community like Hampton, the skills and mindsets shared by Sam Parr—and drawn out by Jason Calacanis—remain timeless.

“Copywriting is just sales on paper... It's rooted in compelling storytelling, which is the most important thing.” — Sam Parr (47:27, 36:58)

For anyone building, selling, or communicating online: study the greats, clarify your thinking, and don’t underestimate the power of a good story.