The #1 blogcast on the internet. Dave Flynn reads his weekly essays on business, creativity, and personal development so you don't have to. New episodes every Monday at WinWithFlynn.com.
The hard part wasn't getting people to trust me. The hard part was becoming a person worthy of trust.
That's the whole book—and the reason it took me 30 months to write.
eBook pre-orders are open now:
Amazon (https://amzn.asia/d/08OJP58l)
Apple (https://books.apple.com/us/book/shift-to-trust/id6814925556)
Print and audio on October 19th, 2026
Blog Post:
Why TRUST? (https://winwithflynn.com/2026/10/05/why-trust/)
Sponsors:
Shift to TRUST (https://winwithflynn.com/books/shift-to-trust/)
Passing Notes to Strangers (https://winwithflynn.com/books/passing-notes-to-strangers-book/)
31 Easy™ (https://winwithflynn.com/31easy/)
Chapters:
28 Sept 2026
#56 | Luck and Skill and Stories [blogcast]
You can’t lose a coin flip on purpose. Trust me. I've tried.
And it turns out, that’s a useful way to think about luck and skill. A golf professional needs to be able to reproduce the bad shots as well as the good ones. A poker player can lose on purpose. Most of the time. A basketball player can try to do the same.
Then we tell ourselves what happened. That’s when things get twisted.
We turn luck into skill, failure into excuses, and a streak of coin flips into evidence of genius.
Can we reproduce the result? Reverse it? Make it fail on command?
Maybe that’s where skill really starts.
Blog Post:
Luck and Skill and Stories (https://winwithflynn.com/2026/09/28/luck-skill-stories/)
Sponsors:
Passing Notes to Strangers (https://winwithflynn.com/books/passing-notes-to-strangers-book/)
31 Easy™ (https://winwithflynn.com/31easy/)
Chapters:
21 Sept 2026
#55 | Tips Are for Waiters [blogcast]
“What would Dave do?”
It’s a question I hear from friends, family, and my dozens of readers. And while I appreciate the vote of confidence, I have concerns.
People love tips. They look like shortcuts. But a tip is only useful if you understand why it works and whether it applies to you. That gives you the conviction to stick with it when things get uncomfortable.
From Jim Cramer to Siskel and Ebert to Wall Street’s favorite stock pickers, the lesson is the same: ideas on loan don’t come with conviction.
Blog Post:
Tips Are for Waiters (https://winwithflynn.com/2026/09/21/tips-are-for-waiters/)
Sponsors:
Passing Notes to Strangers (https://winwithflynn.com/books/passing-notes-to-strangers-book/)
31 Easy™ (https://winwithflynn.com/31easy/)
Chapters:
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