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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 who will expand our thinking. This is the Paradox Podcast.

"Paradox Podcast is one of my favorite new podcasts of 2019. Kyle and Alex simultaneously hit 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 Alex and Kyle are doing with the Paradox Podcast – which feels especially relevant in today's society. Definitely worth a listen."

Jennifer Fearing
Founder, Fearless Advocacy

"Kyle and Alex aren’t only exploring paradoxes and uncovering big ideas. They’re restitching the intellectual fabric of our civic life. Strongly recommend subscribing."

Michael Davidson
CEO, GenNext Foundation

Recent episodes

We're six episodes deep and just getting started. We release new episodes every few weeks on Friday but you can subscribe to get them early. Stream the podcast on any of the following services and check out our PodcastNotes.


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.

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.

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.

Jennifer Fearing is one of the most successful, 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 PodcastNotes.org – an amazingly detailed guide to key episodes:

Next episode drops in:

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

    About the hosts

    Kyle Tibbitts

    Kyle has spent the last ten years building marketing machines for startups and currently works at Opendoor, where he was the second marketing hire. Prior to Opendoor, he worked at 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 18-month-old daughter and loves learning from smart, humble people.

    .

    Alex Khan

    Alex is an Attorney who lives in Sacramento and works at the State Capitol as the Principle Policy & Budget Consultant for the State Assembly for all Healthcare Policy. Prior to working in state government, Alex attended law school at the McGeorge School of Law at the University of Pacific. Alex lives with his wife Heather and Rhodesian Ridgeback, Justice. Kyle and Alex met at age 16 while serving as Congressional Pages in the U.S. House of Representatives in Washington D.C. during the summer of 2004.

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    What folks are saying

    ⭐⭐⭐⭐⭐
    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

    ⭐⭐⭐⭐⭐
    Must-Listen!
    "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

    ⭐⭐⭐⭐⭐
    Fantastic
    "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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