13 episodes

Join 15,000+ listeners for commute-length conversations with original thinkers who will push your perspective and pull you into the marketplace of ideas.
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"Had fun talking with Kyle on the Paradox Podcast. We hit a variety of topics we both care about while still diving into substance."
–Garry Tan, Cofounder of Initialized Capital

"The great thing about Paradox Podcast is Kyle is not one to shy away from heady topics, and tends towards nuance over hot takes.”
–Sahil Lavingia, CEO of Gumroad
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We live in a paradoxical time where we have more comfort but less peace, more connectivity but less connection, more information but less wisdom. The purpose of this podcast is to explore these natural tensions with independent voices across tech, culture and politics who will expand our thinking.

Learn more: http://paradoxpodcast.co
Connect: https://twitter.com/KyleTibbitts

Paradox Podcast Kyle Tibbitts

    • Society & Culture
    • 5.0, 27 Ratings

Join 15,000+ listeners for commute-length conversations with original thinkers who will push your perspective and pull you into the marketplace of ideas.
_______________________________________

"Had fun talking with Kyle on the Paradox Podcast. We hit a variety of topics we both care about while still diving into substance."
–Garry Tan, Cofounder of Initialized Capital

"The great thing about Paradox Podcast is Kyle is not one to shy away from heady topics, and tends towards nuance over hot takes.”
–Sahil Lavingia, CEO of Gumroad
_______________________________________

We live in a paradoxical time where we have more comfort but less peace, more connectivity but less connection, more information but less wisdom. The purpose of this podcast is to explore these natural tensions with independent voices across tech, culture and politics who will expand our thinking.

Learn more: http://paradoxpodcast.co
Connect: https://twitter.com/KyleTibbitts

    #13 — Balaji Srinivasan — The rise of cloud cities & citizen journalism

    #13 — Balaji Srinivasan — The rise of cloud cities & citizen journalism

    Balaji Srinivasan (@balajis) is an angel investor and entrepeneur. For episode #13, I chatted with Balaji about the rise of cloud cities, the Oregon Trail generation, a decentralized model for citizen journalism, why crypto is still underrated and the best piece of advice he’s ever received. Balaji was formerly the CTO of Coinbase and General Partner at Andreessen Horowitz, he was also the cofounder of Earn.com, Counsyl, Teleport and Coin Center.

    Balaji holds a PhD in Electrical Engineering and a master in Chemical Engineering from Stanford University and teaches the occasional class at Stanford, including an online MOOC in 2013 which reached 250,000+ students worldwide. He was also the first person in my Twitter feed to sound the alarm on the global pandemic back in January, something I’m personally grateful for. Balaji is a truly original thinker who is unafraid to speak his mind and someone I’ve learned a lot from just by following him on Twitter. Hope you enjoy this conversation with Balaji Srinivasan.

    Check out the Podcast Notes for this episode: https://podcastnotes.org/paradox-podcast/balaji-srinivasan-on-the-paradox-podcast

    • 1 hr 6 min
    #12 — Mike Solana — The heresy of speaking your mind

    #12 — Mike Solana — The heresy of speaking your mind

    Mike Solana (@micsolana) is VP of brand and community at Founders Fund. For episode #12, I chatted with Mike about having the courage to speak your mind, self-censorship, the rising tide of socialism in the United States and the power the stories we tell ourselves both as individuals and societies have to dramatically alter the future we end up living in.

    Mike runs creative programming for Founders Fund, including F50, the firms annual summit and Shop Talk, the firm’s professional networking series. He’s also creator and producer of the firm’s awesome podcast, Anatomy of Next, which just went into a new season. Mike also just launched a personal podcast called Problematic which I highly recommending checking out.

    Prior to joining Founders Fund, he edited non-fiction for the Penguin Group (USA). There, he acquired and developed New York Times bestselling work in the fields of technology, politics, philosophy, and humor. Mike is one of the best follows on Twitter and you can follow him @micsolana. Whether you agree with him or not, Mike has the courage to speak his mind, his cultural commentary is next level and if nothing else he will definitely push your thinking. I hope you enjoy this conversation with Mike Solana.

    • 58 min
    #11 — Karlyn Borysenko — A liberal goes to a Trump rally

    #11 — Karlyn Borysenko — A liberal goes to a Trump rally

    Karlyn Borysenko (@DrKarlynB) is an organizational psychologist who helps organizations and teams find happiness and fulfillment at work through her company, Zen Workplace. For episode #10, Karlyn and I had a wide-ranging discussion about her experience in an online knitting group that turned her off to cancel culture, taking part in the New Hampshire primary and meeting every Democrat presidential candidate and her decision to go to a Trump rally to try and understand how her political opponents think.

    Karlyn came on my radar when my dad told me about a viral medium essay she wrote called “I’ve been a Democrat for 20 years, here’s what I experienced at a Trump Rally” which has been read by over 3 million people. I didn’t read the article initially but when I heard Karlyn interviewed on a talk radio program I occasionally listen to, DMed her on Twitter and she agreed to come on the podcast. What could be more paradoxical than a registered Democrat going to a trump rally?

    We also talked about the importance of shared values like free speech, thinking for yourself and attributing good intent to you those you disagree with. We recorded this conversation in March as COVID19 was ramping up so we also offered up from fresh takes on how the world was shifting that may or may not age well and that’s ok. It was nice to escape Silicon Valley and talk to someone from a completely different part of the country. I hope you enjoy this episode with Karlyn Borysenko.

    • 48 min
    #10 — Garry Tan — Building the world you want to live in

    #10 — Garry Tan — Building the world you want to live in

    Garry Tan (@garrytan) is a designer and engineer turned early stage investor as a Managing Partner and co-founder at Initialized Capital. While recording from our coronavirus bunkers, Garry and I chatted about building the world you want to live in, how refugee ancestors has influenced his worldview, navigating the idea maze as a founder, his $200M mistake and how parenthood has changed his life. In 2019, Tan was listed at #21 on the Forbes Midas List having invested in Instacart, Coinbase, Flexport, Plangrid, Hellosign and many others. Prior to founding Initialized, Garry was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies and more than a thousand founders.

    He was cofounder of YC-backed blog platform Posterous (Top 200 Quantcast site, acquired by Twitter in 2012). Before that he was employee #10 at Palantir, where he was a founding member of the engineering team for Palantir's financial analysis product, and also designed Palantir's logo. He has a BS in Computer Systems Engineering from Stanford and you can find him on his weekly startup vlog on YouTube and Instagram and his videos are packed with valuable advice for entrepreneurs.

    Garry is incredibly talented and insightful and I think what struck me most about our conversation is how humble, thoughtful and empathetic he is. Hope you enjoy this episode with Garry Tan.

    • 1 hr 3 min
    #9 — Jeff Morris Jr. — Investing in a post-COVID19 future

    #9 — Jeff Morris Jr. — Investing in a post-COVID19 future

    Jeff Morris Jr. (@jmj) is a full time angel investor and the founder of Chapter One who has invested in in companies including Lyft, Lambda School, Superhuman, Roman, Cameo and Branch Metrics. For episode #9, Jeff and I had a wide-ranging conversation about the impact this global coronavirus pandemic is having on millions of lives, the types of new companies and products that might be built to address new challenges and what investing in a post-COVID19 future might look like.

    We also talked about career-related path dependence in time of rising uncertainty, the unbundling and distribution of talent out of Silicon Valley and the importance of family. Prior to becoming a full-time investor, Jeff was was previously the VP of Product, Revenue at Tinder. In the role, he led the revenue team to the #1 top grossing app in the App Store and directed one of the top grossing products in mobile history. Jeff is a super talented investor and operator and is always sharing really interesting insights on Twitter @jmj. Hope you enjoy this episode with Jeff Morris Jr.

    Check out the PodcastNotes for this episode: https://podcastnotes.org/paradox-podcast/jeff-morris-jr-kyle-tibbitts-covid-19/

    • 54 min
    #8 — Sahil Lavingia — Escaping your own ideological bubble

    #8 — Sahil Lavingia — Escaping your own ideological bubble

    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.

    • 1 hr 2 min

Customer Reviews

5.0 out of 5
27 Ratings

27 Ratings

TahoeSublime ,

Paradox Podcast

Truly excellent podcasts!!!!
I learn several things of critical importance from every podcast.
The guests are amazing and Kyle asks amazing questions.
These podcasts are a more than excellent intersection of the economic side of Silicon Valley and the individual stories behind each guest.

ovlov90 ,

Ovlov90

Just got back from torching the local 5g tower (it dont work here anyways) and dislexically read ParodyPodcast. But long story I feel when this is “all over” its time to hit the iron cause lots will be red hot. Gods Providence is real.

WordGrl007 ,

PARADOX - "the conversation" made real

"We need to have a conversation about ..."? This empty call has become cliche, reinforcing the reality that there is in truth little meaningful conversation to be heard. Paradox Podcast actually IS that conversation--real, dynamic, engaging. Great guests and production, thoughtful questions, fresh ideas and intriguing debate. Nothing boring, banal or cliche here.

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