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Sahil Lavingia (@shl) is the CEO of Gumroad and a prolific entrepeneur, writer, painter and thinker. For episode #8, I chatted with Sahil about the challenges of building startups and his viral essay “reflecting on my “failure" to build a $1B company”. We also escaped the world of tech and startups to talk about moving from San Francisco to Provo, Utah – the most conservative and religious city in America and lessons he learned about breaking outside our ideological bubbles and engaging with people we disagree with in a friendly way. Lastly, we offered up some very amateur political analysis on the 2020 Presidential Race including some surprising similarities between Trump and Bernie. Full disclosure, we recorded this episode the week before Joe Biden’s South Carolina and Super Tuesday comeback so take it with a grain of salt. Sahil is a fascinating individual and I really loved how wide ranging the conversation was. I hope you enjoy this episode with Sahil Lavingia.

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