#259 Pat Flynn - 15 Years of Online Business Advice in 65 Mins

Kickoff Sessions

Watch This NEXT: https://www.youtube.com/watch?v=HlK2P76_ZZs
Not many people know this, but Pat Flynn is the reason I started my podcast.
Back in 2020, I was broke, clueless, and desperate for a way out, I bought a $60 microphone.
That mic? It came from an affiliate link on Pat Flynn’s website.
I binged watched every piece of content Pat had:

• How to start a podcast
• The best mics and software
• Editing tools I’d never used before

Fast forward to 2025, and I just recorded episode 258 of my podcast—with Pat Flynn himself.
In this episode, Pat shares the lessons, failures, and surprises from 15 years of building online businesses—including generating over $10M in revenue.
We talk about:

• How he built and grew Deep Pocket Monster to 1M subscribers
• The importance of emotional connection in your content
• Why small, vibrant communities are the future of business
• The reality of staying relevant in a changing landscape

Is it blind luck? Or the compounding effect of 15 years in the game?
Pat breaks it all down.
If you’re building a content business or just starting out, this is an episode you can’t miss.
Check out Pat’s YouTube: https://www.youtube.com/@patflynn/
My Socials:
Instagram - https://www.instagram.com/darrenlee.ks
LinkedIn - https://www.linkedin.com/in/darren-lee1

(00:00) Preview
(00:30) Importance of Serving Your Audience
(03:03) How to Create Raving Fans
(07:02) The Power of Consistency and Experimentation
(12:38) Will AI Take Over Online Media?
(17:56) Why Video Podcasts Do Better
(19:13) The Benefits of Podcasting
(23:19) Pat Flynn’s Short-Form Content Strategies
(28:29) Short Form vs Long-Form Content
(34:02) The Art of Storytelling and Emotional Engagement
(36:39) Building Community
(39:17) Starting as a Newcomer in a Niche
(42:03) Understanding People and Building Loyalty
(45:57) Transitioning to Community-Based Learning
(51:52) Investing in Startups
(59:18) How to Get Sponsorships and Build Relationships
(01:02:01) The Importance of Thumbnails

Support the show

Chapters

1. Building a Loyal Online Community (00:00:00)

2. Creating Authentic Connections in Podcasting (00:10:21)

3. Enhancing Podcasting With Video Content (00:17:22)

4. Growth Strategies in Podcasting and YouTube (00:21:37)

5. Story Selling in Building Community (00:34:02)

6. Community Building and Podcast Guest Booking (00:41:28)

7. Advising Startups for Success (00:49:48)

8. Navigating Brand Partnerships and Online Visibility (00:54:30)

9. Mutual Appreciation in Podcasting (01:03:25)