Kickoff Sessions

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


Listen Later

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

...more
View all episodesView all episodes
Download on the App Store

Kickoff SessionsBy Darren Lee

  • 4.7
  • 4.7
  • 4.7
  • 4.7
  • 4.7

4.7

3 ratings


More shows like Kickoff Sessions

View all
London Real by Brian Rose

London Real

1,196 Listeners

The School of Greatness by Lewis Howes

The School of Greatness

21,313 Listeners

The Mindset Mentor by Rob Dial

The Mindset Mentor

13,549 Listeners

Tom Bilyeu's Impact Theory by Impact Theory

Tom Bilyeu's Impact Theory

4,721 Listeners

Bedros Keuilian Podcast Show by Bedros Keuilian

Bedros Keuilian Podcast Show

2,248 Listeners

The Game with Alex Hormozi by Alex Hormozi

The Game with Alex Hormozi

4,389 Listeners

The Diary Of A CEO with Steven Bartlett by DOAC

The Diary Of A CEO with Steven Bartlett

7,165 Listeners

Modern Wisdom by Chris Williamson

Modern Wisdom

3,815 Listeners

On Purpose with Jay Shetty by iHeartPodcasts

On Purpose with Jay Shetty

27,238 Listeners

The Daily Motivation by Lewis Howes

The Daily Motivation

903 Listeners

The Mel Robbins Podcast by Mel Robbins

The Mel Robbins Podcast

20,604 Listeners

First Things THRST by Mike Thurston

First Things THRST

97 Listeners

Tate Therapy by Top G

Tate Therapy

272 Listeners

BigDeal by Codie Sanchez

BigDeal

750 Listeners

Jack Neel Podcast by Jack Neel

Jack Neel Podcast

21 Listeners