Most creators focus on attention.The smart ones turn that attention into trust. And trust creates optionality. In this episode of Marketing Misfits, Norm Farrar and Kevin King sit down with Jordan DiPietro to break down how content becomes trust, how trust becomes community, and why the best communities can charge $10,000–$25,000 per year without hurting conversions.

Jordan has built at the center of some of the most influential media and community brands in the world. He spent nearly 13 years at The Motley Fool, became CEO of The Hustle before its acquisition by HubSpot, ran HubSpot’s media division, and later served as CEO of Hampton, one of the most exclusive private tech communities. This is a deep, tactical conversation on community design, pricing, trust, vetting, retention, and monetization, not theory. If you’re building a newsletter, podcast, paid community, mastermind, or founder-led brand, this episode gives you the real playbook.

What You’ll Learn

- Why attention without trust is worthless

- The difference between an audience and a community

- How The Hustle turned content into leverage

- Why newsletters are still one of the strongest trust channels

- Content → trust → optionality explained

- Community vs mastermind (and why it matters)

- How Hampton vetted members and rejected 50–60% of applicants

- Why most paid communities fail after launch

- The biggest pricing mistakes founders make

- How to decide between $1K, $10K, or $25K pricing

Guest Jordan DiPietro Former CEO of The Hustle Former Media Lead at HubSpot Former CEO of Hampton Newsletter writer, advisor, and founder coach Website & newsletter:https://jordandipietro.com/

Chapters

00:00 Content Creates Optionality

01:40 Meet Jordan D. Petro

04:24 From Motley Fool to Hustle

08:15 Are Newsletters Saturated?

12:46 Audience vs Community

15:01 Monetizing Trust Correctly

18:56 Community vs Mastermind

20:42 Vetting Members Matters

24:33 How Communities Stay Engaged

27:02 Do You Need IRL Events?

31:32 Why Founders Are the Funnel

33:49 Why Communities Fail

34:42 Pricing a $10K Community

56:38 Growing a Newsletter Long-Term

About Marketing Misfits:

Marketing Misfits features unfiltered conversations with operators, founders, and marketers who build real businesses through trust, distribution, and execution.

Hosted by Norm Farrar and Kevin King. New episodes every Tuesday.

This episode is brought to you by:

- Sellerboard: https://sellerboard.com/misfits

- House of AMZ: Elevate your brand today at https://www.amazonseo.com/

- 8fig: Get 25% off 8fig off at https://8fig.co

- Stack Influence: Use code MISFITS for 10% off at https://stackinfluence.com/

- Levanta: Get 20% off Levanta's gold plan and book your call today - https://get.levanta.io/misfits

If you’re serious about building authority, monetizing trust, and creating leverage through content, subscribe so you don’t miss future episodes.

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Most companies are using AI wrong. They think it’s about cutting staff or automating a few tasks. But the real power of AI is something much bigger. In this episode of Marketing Misfits, Norm Farrar and Kevin King sit down with Rachel Woods, one of the world’s top AI operations experts, to show how businesses are turning their internal playbooks into AI-powered systems that can run entire workflows on autopilot. Rachel previously worked on the early transformer technology behind modern AI while at Facebook, then built and sold a VC-backed startup before launching her AI operations agency. Today, she helps companies replace weeks of manual work with AI systems that run in hours.

They break down what “AI operators” really are, how agentic AI works, and why companies that fail to build internal playbooks will get wiped out as models improve. This is not theory. You will hear exactly how an agency replaced a 3-week influencer vetting process with an AI system that runs in hours, plus how Amazon sellers, agencies, and SaaS companies can apply the same playbook.

What you’ll learn

• What “AI operations” actually means

• Why SOPs are more valuable than software

• How AI agents differ from basic automation

• How to turn your workflows into AI playbooks

• How companies are replacing entire departments with AI systems

• How long it really takes to deploy agentic AI

• What AI will be capable of in the next 6–12 months

• How to avoid building on tools that get wiped out by model updates

• How to future-proof your business using playbooks instead of platforms

Timestamps

00:00 AI replaces a 3-week workflow

01:01 Marketing Misfits intro

02:12 The spider prank story

04:01 Meet Rachel Woods

06:46 Facebook AI background

07:31 What is a transformer?

09:29 From Facebook to startup

11:09 Why ChatGPT changed everything

12:39 What AI operations means

14:38 How AI playbooks are built

16:25 Can you trust AI agents?

18:14 AI vs downsizing teams

20:52 Automation vs true AI

26:14 How Claude rewrote software jobs

47:25 Influencer vetting case study

This episode is brought to you by:

- Sellerboard: https://sellerboard.com/misfits

- House of AMZ: Elevate your brand today at https://www.amazonseo.com/

- 8fig: Get 25% off 8fig off at https://8fig.co

- Stack Influence: Use code MISFITS for 10% off at https://stackinfluence.com/

- Levanta: Get 20% off Levanta's gold plan and book your call today - https://get.levanta.io/misfits

About the guest

Rachel Woods is the founder of an AI operations agency and the creator of The Exchange, a training platform for AI operators. She previously worked on transformer-based AI systems at Facebook and later built and sold a VC-backed startup using GPT before ChatGPT went mainstream. She now helps companies build AI systems that replace entire workflows instead of just single tasks.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Landing pages alone don’t convert like they used to. In this episode of Marketing Misfits, Norm Farrar and Kevin King sit down with Luca Borreani, founder of ZipChat.ai, to break down why conversational marketing is replacing static funnels and how AI chat is quietly becoming one of the biggest conversion unlocks in e-commerce. Consumers now spend hours talking to ChatGPT, asking detailed questions before buying. This episode explains why that behavior is bleeding directly into shopping behavior, and why brands that rely only on landing pages, FAQs, and analytics are missing what actually stops conversions. This is a deep, practical conversation about last-mile conversion, removing buyer doubt, and how chat data reveals insights that analytics never will.

What You’ll Learn:

- Why landing pages alone are no longer enough

- How conversational marketing removes last-minute buyer doubts

- Why people trust chat more than static copy

- The biggest copy mistake hurting conversions

- How small headline changes massively impact results

- Why analytics can’t reveal real buyer objections

- How chat uncovers hidden conversion blockers

- The difference between traffic and real intent

- Why product-market fit still beats everything

- How affiliate marketing sharpened modern conversion skills

Timestamps

00:00 Landing Pages Are Failing

01:40 Why Chat Converts

03:30 Meet Luca Borreani

08:00 Affiliate Skills That Matter

12:00 Copywriting Drives Conversions

21:05 The Last-Mile Problem

24:30 Conversational Marketing Wins

26:50 Analytics Miss Buyer Doubts

30:00 Training AI Conversations

33:45 Chat Reveals Hidden Objections

40:35 Why Users Trust Chat

49:45 WhatsApp Marketing Power

56:00 Agentic Commerce Future

This episode is brought to you by:

- Sellerboard: https://sellerboard.com/misfits

- House of AMZ: Elevate your brand today at https://www.amazonseo.com/

- 8fig: Get 25% off 8fig off at https://8fig.co

- Stack Influence: Use code MISFITS for 10% off at https://stackinfluence.com/

- Levanta: Get 20% off Levanta's gold plan and book your call today - https://get.levanta.io/misfits

Guest

Luca Borreani Founder, ZipChat.ai Conversion science, conversational commerce, AI marketing Website: https://zipchat.ai

LinkedIn: Luca Boreanni

Email: luca@zipchat.ai

About Marketing Misfits Marketing Misfits features unfiltered conversations with founders, operators, and marketers who actually build and scale businesses.

Hosted by Norm Farrar and Kevin King. New episodes every Tuesday.

Hosted on Ausha. See ausha.co/privacy-policy for more information.