Today’s episode is brought to you from the top of Shasta Mountain where I’m holding a virtual conversation with Woody Wiegmann, founder of the Woodside Investment Counsel. Our discussion focuses on gaining the courage to be disliked without losing your connection to community. You can find Woody on Twitter @woodywiegmann, or check his ideas out at woodsideinvestmentcounsel.com. Enjoy.

(4:23) Navigating the balance between being okay with being disliked and being an asshole; Woody shares his daily attempts at navigating this spectrum. (Quick hint: you have no idea what anyone else is thinking.)

(8:37) How our genetic programming to attempt to fit into an ingroup has led to the polarization of society and the steady disintegration we’re currently witnessing, especially in the political sphere, and once again, a metaphor we can use to parse the boundaries between seeking acceptance and living true to your core.

(16:38) The downsides to identifying with the social identity, especially at the corporate level.

(21:15) A suggestion we can practice to maintain our individual sovereignty without losing the attachment to community that gives our lives meaning, and what countries like Israel can teach us in maintaining this balance.

(24:38) Have cities made us more ungrounded? What do you think? Have you ever lived outside the city? What was the experience like for you? Leave me a comment on twitter @stewartalsopIII with your thoughts on the matter and tag your post #episodewithwoodywiegmann

(28:30) Woody’s interpretation of the US’ response to COVID-19; how America is becoming less and less habitable for the average householder.

(31:43) What is America’s future in light of the various institutional and wealth inequality crises that are steadily nearing critical mass?

(37:06) How America’s response to COVID-19 is killing capitalism and entrepreneurship in many places all over the country.

(44:50) A solution to tackling the issues we face in today’s world.

(47:43) Learning to deal with the unknown and a brilliant quote by Nicholas Nassim Taleb.