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Timestamps:

00:09
Welcome Dan Smith!

00:27
Dan explains his Double Up Drive for charity.

01:35
How does Double Up choose the charities they support?

03:58
The story of how a terrible hangover and a psychedelic trip at Burning Man inspired Dan’s passion for charity.

07:36
Has he had any subsequent psychedelic trips that were similarly revelatory?  Other thoughts on the potential benefits of certain drug use.

10:26
Thoughts on weighing the benefits and risks of certain drugs vs alcohol consumption.

11:56
Run It Once Poker is holding a heads up tournament to help raise funds for the drive.

14:31
Some kind words from Dan regarding the Run It Once Poker software experience.

16:31
What is the origin of Dan’s cowboy persona and nickname?  How does he feel about it?

19:10
Dan has been playing a lot of chess lately.  How did he get into that?

21:13
We’re currently experiencing an online chess boom.  What are his thoughts on that and its comparison to the poker boom of the mid-to-late-00s?

22:38
Between poker, charity, and chess, what takes up most of Dan’s time these days?

24:46
Dan talks about feeling proud of his recent chess win over Alexandra Botez, despite there being almost no money involved.

26:41
Jamie brings up Mafia as another non-poker game that brings her a lot of joy in comparison to grinding online.  She and Dan play in the same group Mafia game.

29:08
Does Dan play any other games besides Mafia?

30:11
Has his experience with drugs and charity affected his personality?  This leads to an extended conversation about everybody’s mutual love for Andrew “LuckyChewy” Lichtenberger.

34:49
More info on the Double Up Drive.  How can you donate?  What’s the deadline?  Etc.

39:45
Dan posits a theory about how living charitably can improve your life and ultimately make you more successful.

44:29
Wrapping up.  Final plug for Double Up Drive and the related heads-up tournament on Run It Once.