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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 and challenge our thinking. This is the Paradox Podcast.

"Paradox Podcast is citizen journalism at its best. Long-form discussions of important ideas ––freely available to all."

Balaji Srinivasan
Angel Investor & Entrepreneur

"Paradox Podcast is a breath of fresh air. Kyle and his guests dig into real issues and ask the hard questions. The breadth of ideas and the depth of conversation makes every episode a must-listen."

Katherine Boyle
Partner, General Catalyst

"Had fun talking with Kyle on the Paradox Podcast. We hit a range of topics we both care about while still diving into substance. Definitely worth subscribing to!

Garry Tan
Co-founder, Initialized Capital

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    Join 30,000+ listeners for commute-length conversations with original thinkers who will push your perspective and pull you into the marketplace of ideas.

    Lex Oiler is the co-founder and CEO of Peachy. For episode #17, I chatted with Lex about how a hospital bill that bankrupted her family set her on a mission to fix the broken medical billing system, following her own path away from law school to become a product designer, leveraging twitter to find early employees, customers and investors and her non-linear journey to becoming a founder.

    Avlok Kohli (@avlok) is the CEO of AngelList Venture. For episode #16, I chatted with, I chatted with Avlok about how the startup funding ecosystem is changing, the geographic future of Silicon Valley, the launch of rolling funds, which have taken the venture industry by storm, and the launch of my seed fund, Paradox Capital, which launched January 1st and is managed on the AngelList platform.

    Mike Maples is the co-founder and partner at Floodgate Capital. For episode #15, I chatted with Mike about the process entrepreneurs should use to uncover breakthrough insights, a fishing trip with his Dad that taught him a lifelong lesson, how he stumbled into his first angel investment (Twitter), broke into venture capitaland one of the biggest issues facing our country that almost no one talks about.

    Geoff Lewis is a technology investor and founder of Bedrock Capital. For episode #14, I chatted with Geoff about the noble lies that exist all around us in society, the geopolitics of TikTok, why algorithms are the new oil, how searching for narrative violations is different from contrarianism, his quest to move from Canada to the U.S. starting at age 11 and the founders and companies he’s looking to invest in.

    Balaji Srinivasan is an angel investor and entrepreneur. He was formerly the CTO of Coinbase and General Partner at Andreessen Horowitz and also the cofounder of, Counsyl and Teleport. 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.

    Mike Solana is VP of brand 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 is one of the best follows on Twitter and you can follow him @micsolana.

    Karlyn Borysenko 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 cancel culture, understanding the motivations of people you disagree with, the importance of free speech and her experience as a liberal at a Trump rally.

    Garry Tan 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.

    Jeff Morris Jr. is an early-stage startup investor and founder at Chapter One who has invested in in companies including Lyft, Lambda School, Superhuman, Roman, Cameo and more. For episode #9, Jeff and I had a wide-ranging conversation about investing in a post-#COVID19 future, non-linear career paths in times of economic uncertainty, moving to Kansas City to break into tech and the unbundling of talent. PodcastNotes

    Sahil Lavingia = is the CEO of Gumroad and a prolific entrepeneur, writer, painter and thinker. For episode #8, we about 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 to Utah and the lessons he learned about breaking outside our ideological bubbles and engaging with people we disagree with in a friendly way.

    Katherine Boyle is a venture capitalist at General Catalyst and former reporter for the Washington Post. For episode #7, I chatted with Katherine about escalating tensions between the media and tech industries, her path to becoming a venture capitalist and the threat that declining economic mobility poses to future generations. Katherine leads investments in early stage companies with uncommon missions.

    Kamal Ravikant is an entrepreneur, investor and best selling author of three books: Love Yourself, Live Your Truth, and Rebirth. For episode #6, we chatted with Kamal about pushing into fear, the importance of forgiveness, how your mentality shapes your reality & the relaunch of his book––"Love Yourself Like Your Life Depends On It". We hope you enjoy this conversation with Kamal Ravikant.

    James Beshara is a modern day renaissance man – an entrepreneur, angel investor, podcaster, author, musician. James is a prolific creator who operates with passion and he’s probably one of the most honest entrepreneurs I’ve ever met. James founded three startups including Tilt which was acquired by Airbnb in 2017 where he was Global Head of Airbnb Music. Check out the PodcastNotes for this episode.

    Trae Stephens is a venture capitalist at Founders Fund with partners like Peter Thiel, Brian Singerman, Cyan Banister and Keith Rabois, where he invests across sectors with a particular interest in startups operating in the government space. He’s also Co-founder and Executive Chairman of Anduril Industries with Palmer Luckey, who founded Oculus, which was acquired by Facebook in 2014.

    James Beshara is a modern day renaissance man – an entrepreneur, angel investor, podcaster, author, musician. James is a prolific creator who operates with passion and he’s probably one of the most honest entrepreneurs I’ve ever met. James founded three startups including Tilt which was acquired by Airbnb in 2017 where he was Global Head of Airbnb Music. Check out the PodcastNotes for this episode.

    Jennifer Fearing is one of the most innovative and admired lobbyists in California. She left a corporate consulting career to advocate on behalf of issues that are close to her heart, especially animal issues. Jennifer successfully ran the 2008 Proposition 2 campaign (the Prevention of Farm Animal Cruelty Act). Jennifer spent eight years working for the Humane Society and in 2014 founded Fearless Advocacy

    Michael Davidson is the CEO of GenNext, an organization that recruits business leaders in the private sector, educates them on critical issues like economic opportunity, education and global security and empowers them to have a direct impact both inside and outside of government. Michael cares about the restoring the marketplace of ideas, reviving civics, and solving the leadership deficit in this country.

    All episodes

    Check out our full library of episodes below and – an amazingly detailed guide to key episodes:

    Next episode drops in:

      We release new episodes of Paradox Podcast every few weeks or so. Have feedback on how we can improve the show or a guest recommendation? Drop us a line.

      About the host

      Kyle Tibbitts


      Kyle has spent the last ten years building marketing machines for startups and is currently the Head of Marketing at Fast. Before Fast, he was Head of Brand Marketing and the second marketing hire at Opendoor ($OPEN) and held marketing roles HotelTonight (acquired by Airbnb) and ThisLife (acquired by Shutterfly). Kyle graduated from UC Berkeley with a degree in Political Science and took 6 months off to work as an Intern in the Office of Political Affairs at the White House at 19. He lives in the East Bay with his wife and 2-year-old daughter and loves learning from smart, humble people. Connect with him on Twitter or learn more on

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      What folks are saying...

      "Paradox Podcast is one of my favorite new podcasts of 2019. Kyle simultaneously hits a broad range of topics while diving deep into much-needed nuance. Highly recommend!"

      James Beshara
      Angel Investor & Entrepreneur

      "Seeking out a wide range of perspectives feels core to what Kyle is doing with the Paradox Podcast – which feels especially relevant in today's society. Definitely worth a listen."

      Jennifer Fearing
      Founder, Fearless Advocacy

      The great thing about Paradox Podcast is Kyle is not one to shy away from heady topics, and tends towards nuance over hot takes. Worth a subscribe!

      Sahil Lavingia
      Founder & CEO, Gumroad

      "The Paradox Podcast isn't just exploring paradoxes and uncovering big ideas. It's restitching the intellectual fabric of our civic life. Strongly recommend subscribing."

      Michael Davidson
      CEO, GenNext Foundation

      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."

      WordGrl007 11/14/2019

      My favorite new podcast
      "I first found about the Paradox Podcast when I heard the James Beshara episode. Then I listened to the episode with Trae Stephens and now I’m hooked. I really like how different each guest is and I always learn something new. Looking forward to more episodes and making this part of my routine on my commute."

      monihall88 11/11/2019

      We need more of this
      "We all know the world is more complex than the narratives we’re given/pushed into by mainstream news. So glad this kind of dialogue allows for the “paradoxical” nature of the world we’re in (especially with how much more so the world is going to become)."

      supsupsuppp 11/07/2019

      Refreshing original thinkers
      "I like that this podcast has a broad variety of different guests. The conversations are wide ranging and each episode takes you into an entirely new area. I’ve listened to the first three episodes and can’t wait for more. Highly recommend. Five stars."

      linda_b1958 10/27/2019

      Deeply Resonating
      "Phenomenal start to this podcast! It’s refreshing to hear people with different opinions and life experiences openly, respectfully, and deeply discuss topics such as mental health, fear, doubt, shame, courage, faith, etc. that aren’t discussed very openly, yet pervade every aspect of every person’s existence, whether they’re a high-level executive, a first-time entrepreneur, a student or a homemaker.

      Kyle has a powerful voice literally in the way it sounds but also in the messages he speaks. I most admire his wisdom, humility, and thirst to learn and more deeply understand the human experience and to live righteously. He naturally embodies transformational leadership. ❤️"

      kettlebellG 10/26/2019

      Breaking through the noise!
      "After 3 episodes, paradox has become one of my go to podcasts. Love the perspectives being surfaced that are not always popular or well received in today’s culture."

      DudesonSuomi22 10/22/2019

      "Explores a wide range of perspectives from emerging thought leaders. Thought provoking and uncovers strong insights that can be practically applied."

      Guttles21 10/20/2019

      Intellectually Stimulating
      "Loved listening to this podcast. Very interesting discussions! Would highly recommend. Look forward to more episodes."

      Dannnnydoe 10/07/2019

      "This is the most thought provoking podcast I’ve heard in a while. The concept is unique and the content is interesting. Can’t wait for the next episode!"

      JohnLichty 10/05/2019

      Fascinating discussion!
      "The concept of this pod is brilliant. Forcing productive discussion looking at all potential sides of an issue is a refreshing approach - especially in today’s climate. Can’t wait to see where they take it from here!"

      locksley79 09/27/2019

      Love it!
      "This is 100% the podcast we need in the age of Trump, fake news, and tribalism. This has opened my mind to new ideas and I enjoy every minute of it. Love these guys!"

      HeatherLK1031 09/26/2019

      My favorite new podcast!
      "Found this on Twitter and really liked the premise. The hosts seem very reasonable, middle of the road types who are actually interested in a healthy discussion and learning from their guests. Subscribing and looking forward to more episodes!"

      MalPal1988 09/26/2019

      Intellectually Stimulating
      "Loved listening to this podcast. Very interesting discussions! Would highly recommend. Look forward to more episodes."

      Dannnnydoe 10/07/2019

      A new addition to my commute
      "Very informative and relatable. Definitely looking forward to future episodes."

      Iphonesucks2 09/26/2019

      Love the concept!
      "Love the concept of this podcast. We need more forums for open and honest debate and exploring a wide range of different viewpoints. Excited for more episodes to launch!"

      PodcastFan86 09/26/2019

      Deep, wide ranging, and concise
      "Somehow they’ve managed to be deep, wide ranging, and concise. Great intellectual spread, and a necessary space for dialogue in today’s world."

      studmigca7 09/26/2019

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