
Crazy Wisdom
In his series "Crazy Wisdom," Stewart Alsop explores cutting-edge topics, particularly in the realm of technology, such as Urbit and artificial intelligence. Alsop embarks on a quest for meaning, engaging with others to expand his own understanding of reality and that of his audience. The topics covered in "Crazy Wisdom" are diverse, ranging from emerging technologies to spirituality, philosophy, and general life experiences. Alsop's unique approach aims to make connections between seemingly unrelated subjects, tying together ideas in unconventional ways.
Latest episodes

Feb 7, 2020 • 1h 2min
What narratives are running your life? - Ben Hunt: Epsilon Theory
This one is fire. As soon as he said that he named his firm after the famous Isaac Azimov book right of the beginning of the episode, I knew that this was going to be a great episode. We go deep here into the challenges we are going to face as a species moving forward and what to do about it at the family level and the society level. Follow Ben's work here: https://www.epsilontheory.com/

Feb 5, 2020 • 57min
How do you create unfair advantages? - Tyler Tringas: Founder of Earnest Captial
We also talk about the following questions: In what ways is a university a tribe? Are entrepreneurs lone wolves? Do entrepreneurs start out questioning assumptions more than most people? What are the best practices of turning a niche into a profitable and sustainable company? When does a piece of Software become mission-critical? Follow Tyler here: https://twitter.com/tylertringas

Feb 3, 2020 • 1h 15min
How is technology impacting the flow of patients in hospitals? - James Burns
James is a Physicians Assistant in Greensboro, North Carolina and gives us the lowdown on how the hospitals work on the inside and how technology is impacting hospitals. We also go into ideation on an idea that James has been exploring. Follow James on Twitter here: https://twitter.com/jdburns4

Jan 31, 2020 • 50min
What is the stress of growing up in poverty and then creating an abundant life? - Luis-Orlando Isaza Villegas
This is a special episode where I went to a small town outside of Medellin to stay with and interview Orlando about his life growing up in abject poverty and then making his way out to the US to start a whole new life filled with love, adventure, and duty. There are some real new insights here for those who are interested in my main theme of stress and creativity and the interaction between the two.

Jan 29, 2020 • 44min
Fourth Episode with Kapil Gupta
The podcast delves into the pursuit of happiness, authenticity, and understanding, challenging societal norms and exploring deeper meanings. The discussion touches on the futility of chasing experiences and the importance of self-awareness for personal growth and fulfillment.

Jan 29, 2020 • 57min
What is it like to succeed when 290 investors tell you no? - Benjamin Fernandes: CEO of NALA
Here I talk with Benjamin Fernandes about how he pitched 290 investors before finally getting into Y Combinator. We also talk about the startup scene in Tanzania compared to Africa as a whole. By the time they got into YC Benjamin had way more traction than most of the other companies in their batch and this has to do with starting the company in Tanzania and focused on the African market. This makes a startup highly underestimated but also that's where the reward is if one does make it! Follow Benjamin here: https://twitter.com/Benji_Fernandes

Jan 27, 2020 • 56min
What is the hallmark of true mastery? - Jacob Cole: CEO of IdeaFlow
This is one of the unexpected episodes I record because someone I don't know that well stays in my guestroom. Jacob needed a spot to crash in SF for the night and we have a guestroom. We decided to record this episode and very glad I did because Jacob is on to something with his company IdeaFlow. Listen if you want to understand more about how to be a true master in whatever you want to do. Follow Jacob here: https://twitter.com/jacobcole4000

Jan 24, 2020 • 49min
What does it mean to be in a community? - Jillian Richardson: Founder of Joy List
Jillian knows a lot about what it means to build a community as well as be part of a community. If you have wondered what it means to be a part of a community you will like this episode. If you are in NYC and want to find community, check out what Jillian built, a way to find community based events: https://joylist.nyc/

Jan 22, 2020 • 44min
What is the current state of Coliving? Camilo Olarte: Cofounder of Indie Studio
I've been staying at Indie Studio in Medellin, Colombia and I interviewed the owner. Indie Studio is a coliving space. Coliving, as a trend, probably started in San Francisco in the 1960's with the hippie communes and then had a resurgence in SF in the 2010's. As a business, coliving didn't quite work out in SF because of the high economic costs but in other parts of the world its clearly a viable option, particularly now that digital nomads roam the globe. Here we talk about the latest in Coliving in Latin America. Follow Camilo and his projects here: Insta - @camiloolarte1 Lokl - http://www.lokl.life/ Indie - https://www.indie.com.co/

Jan 20, 2020 • 52min
What's it like to start a company in Medellin, Colombia? - Camilo Usuga: CTO of Talos Digital
Very proud to release this episode with Camilo who shares the truth, not just the hype about the particular stresses that come from starting a company in Medellin, Colombia. We also did a later interview in Spanish which was a lot of fun. Follow Camilo here: https://twitter.com/camilo_u