Lex Oiler (@hotgirlintech) is the 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.

Full disclosure, my fund Paradox Capital, is an investor in Lex’s company and after you listen to this conversation I think you’ll understand why it was an easy decision for me. $45B of medical debt is currently in collections and Peachy is building an entirely new platform that puts patients at the center, helps doctors get paid faster and helps patients easily pay medical bills while improving their credit.

This was a fun and informative discussion and got me excited to interview more founders on the podcast going forward.I hope you enjoy this conversation with Lex Oiler.

#17 — Lex Oiler — The accidental startup founder

David Sacks (@DavidSacks)is the co-founder and general partner at Craft Ventures. For episode #18, I chatted with David about why the best founders create movements not just startups, what he looks for when making investments, the rise of censorship and war on free speech in the United States, the decline of institutional trust and independent thinking in our culture and the rise of political homelessness for folks in the center.

Prior to founding Craft Ventures, David founded enterprise collaboration company Yammer, which was one of the fastest-growing SaaS startups in history and acquired by Microsoft for $1.2B. David first got involved in the technology industry in 1999 when he joined PayPal and became COO and has since become  a prolific investor having invested in over 20 unicorns. He co-hosts the All In Podcast, one of my absolutely favorites, and full disclosure is an LP in my fund Paradox Capital.

I’ve enjoyed every episode of Paradox thus far but this was one of my favorite conversations because it felt like we were able to break down the insanity of the last year and David’s cultural commentary and insights have been absolutely incredible to follow. I hope you enjoy this episode with David Sacks.

#18 — David Sacks — Movements and the battle for the future

LIMITED-TIME OFFER: Go to wander.com/kyle, download the app and create an account to enter to win a free Wander Trip and you can also become a Wander Founding Member for $100 and unlock benefits like:

* Get $100 credited toward your first stay
* Limited edition founding member hoodie
* Early access to Wander Homes before everyone else
* A potential opportunity to invest in the company

For episode #19, I chatted with John Andrew Entwistle, founder and CEO of Wander.com, about the challenges of starting and scaling companies, building the future of life, work and travel, cultural pitfalls in early-stage startups, the importance of writing down life lessons and how immigrants can save America. Prior to starting Wander, John Andrew was the CEO and Co-Founder of Coder.com, on the Forbes 30 under 30 list and a Thiel Fellow.

This is a very special episode because a few weeks back I announced that I joined Wander’s founding team as CMO after initially investing in the company back when Wander was just John Andrew, an idea and an incredible domain. You might be wondering – what is Wander? It’s a network of smart homes in inspiring places that you can book for you next workcation, vacation or anything in between and control every aspect of the experience from your smartphones — from unlocking the door to setting the temperature to turning on the fireplace to adjusting lights and even accessing the Tesla in the garage. Our approach is entirely different from traditional travel options because we own and operate 100% of the homes on our platform and we believe that by owning both the bits and the atoms we can deliver a truly superior guests experience.

We just launched last week and want our early believers to join us on the ground floor. For a short period of time, you can become a Wander Founding Member for $100 and unlock benefits like:

* Get $100 credited toward your first stay
* Limited edition founding member hoodie
* Early access to Wander Homes before everyone else
* A potential opportunity to invest in the company

We’re also giving away a free Wander Trip for you and up to 3 friends for 3 nights. Just go to wander.com/kyle download our app and create an account to enter for free. This episode is a little different than most in all the right ways. I hope you enjoy this conversation with John Andrew Entwistle.

#19 — John Andrew Entwistle — Traveling into the future

Michael Davidson (@MPDavidson) is the CEO of GenNext (@gen_next), 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 is a super sharp guy who cares about the restoring the marketplace of ideas, reviving civics, and solving the leadership deficit in this country.

#1 — Michael Davidson — Looking beyond gov't to solve big problems

Jennifer Fearing (@jenniferfearing) is one of the most successful, innovative, and admired lobbyists in California. She left a lucrative 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, also known as the Prevention of Farm Animal Cruelty Act. She has led successful efforts to ban the sale of ivory and shark fin soup, to ban the use of hounds when hunting bears and bobcats, and championed numerous other issues related to animal welfare. 

Jennifer spent eight years working for the Humane Society of the United States and in 2014 founded Fearless Advocacy, a lobbying firm dedicated to advancing the public policy agendas of causes she believes in. Clients include Pew Charitable Trusts, Pesticide Action Network, Defenders of Wildlife, the California Association of Nonprofits, Oceana, California Wildlife Officers Foundation and more. A graduate of UC Davis and Harvard’s Kennedy School, Jennifer has been featured on the Capitol 100, an annual list of the most impactful people in-and-around California government.

#2 — Jennifer Fearing — The good lobbyist

James Beshara (@JamesBeshara) 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 has angel invested in dozens of startups like Gusto, Mercury Bank, Halo Top Ice Cream, Bolt and many others, including several multi-billion dollar companies, and is now a full-time angel investor. 

This year, he launched the Below The Line podcast which is, without any exaggeration, my favorite new podcast of 2019. James is an advocate for mental health, a lover of philosophy, a beacon of honesty in the tech community and someone who always willing to help–he’s personally been very helpful in the launching of this podcast and now as our third guest. James has a book coming out next month called Beyond Coffee which you can check out at beyondcoffeebook.com and you call follow him on Twitter @JamesBeshara.

Check out the PodcastNotes for this episode: https://podcastnotes.org/2019/10/25/james-beshara-entrepreneurship-mental-health-creativity-paradox-podcast/

Show notes:
• 1:05 Introduction of James Beshara
• 2:18 Background of how the Paradox Podcast came to be
• 5:50 Why James is bullish on podcasts
• 8:24 Why radical honesty is a core part of James' life
• 15:45 Why James, a Catholic Texan, has gravitated to eastern philosophy and how meditation has impacted James' life
• 26:08 The genesis of James' serial creativity
• 28:56 Fact vs Fiction: the reality of being a founder
• 46:35 Why nuance still matters in the age of sound bites
• 52:10 How James became an angel investor and leveraged his own life challenges to help a new generation of founders
• 1:00:59 preview of James Beshara episode two available 11/1/19

#3 — James Beshara — Mental health is wealth (part 1)

Trae Stephens (@traestephens) 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. Anduril is a defense technology company focused on developing autonomous systems for U.S. military and is by far one of the most interesting, and for some controversial, new startups in the last two years. In our conversation Trae described it as a real-life Stark Industries from Ironman.

Previously, Trae was an early employee at Palantir Technologies, where he led teams focused on growth in the intelligence/defense space as well as international expansion, helping large organizations solve their hardest data analysis problems. Prior to Palantir, Trae worked as a computational linguist within the United States Intelligence community. He began his career working in the office of then Congressman Rob Portman and in the Political Affairs Office at the Embassy of Afghanistan in Washington, D.C. Trae is a publishing a paper on Just War Theory In the Age of Technology later this month and you can follow him on Twitter @traestephens. Our conversation with Trae was a wide-ranging and illuminating. We hope you enjoy the episode.

Read Trae's latest piece: The Ethics of Defense Technology Development: An Investor’s Perspective
https://medium.com/@traestephens/the-ethics-of-defense-technology-development-an-investors-perspective-45c71bf6e6af

#4 — Trae Stephens — Just warfare in the age of technology

James Beshara (@JamesBeshara) 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 has angel invested in dozens of startups like Gusto, Mercury Bank, Halo Top Ice Cream, Bolt and many others, including several multi-billion dollar companies, and is now a full-time angel investor.

This year, he launched the Below The Line podcast which is, without any exaggeration, my favorite new podcast of 2019. James is an advocate for mental health, a lover of philosophy, a beacon of honesty in the tech community and someone who always willing to help–he’s personally been very helpful in the launching of this podcast and now as our third guest. James has a book coming out next month called Beyond Coffee which you can check out at beyondcoffeebook.com and you call follow him on Twitter @JamesBeshara.

Check out our PodcastNotes from part 1: https://podcastnotes.org/2019/10/25/james-beshara-entrepreneurship-mental-health-creativity-paradox-podcast

#5 — James Beshara — Mental health is wealth (part 2)

Kamal Ravikant (@kamalravikant) is an entrepreneur, investor and best selling author of three books: Love Yourself, Live Your Truth, and Rebirth. For this episode, we talked to Kamal about fear, forgiveness and how your internal mentality can shape your external reality. Kamal was born in India but immigrated to the United States where he and his brother were raised by a single mom in a rough neighborhood Jamaica Queens. He spent countless hours at the library where he developed an early love for books –– which became his refuge and inspired him to become a writer.

This week Kamal is re-launching an expanded version of his book “Love Yourself Like Your Life Depends on it”. He sent Alex and I an advanced copy and I think the message of the book couldn’t more relevant for the world we live in. After hitting rock bottom when his startup during the .com boom completely fell apart, he made a commitment to change his life by reprogramming his mind and that’s the focus of his book. We hope you enjoy this episode with Kamal Ravikant.

Purchase Kamal's book, Love Yourself Like Your Life Depends On It, here: https://www.amazon.com/gp/product/0062968726/ref=dbs_a_def_rwt_bibl_vppi_i0

#6 — Kamal Ravikant — Your mentality shapes your reality

Katherine Boyle (@ktmboyle) is a venture capitalist based in San Francisco and former journalist. 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 Boyle is a partner at General Catalyst, a bi-coastal venture capital firm where she leads investments in early stage companies with uncommon missions. She's invested in the likes of Anduril Industries, Nova Credit, Spring Discovery and co-leads General Catalyst's seed platform. Prior to becoming an investor, she was a reporter at The Washington Post, and is passionate about the future of media.

#7 — Katherine Boyle — Untangling tensions between media & tech

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.

#8 — Sahil Lavingia — Escaping your own ideological bubble

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/

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

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.

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

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.

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

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.

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

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

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

Geoff Lewis (@justGLew) is a technology investor and founder of Bedrock Capital. For episode #14, Geoff and I chatted 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. that started at age 11 and the types of founders and companies he’s looking to invest in. In 2019, Geoff was named as one of the Top 100 Venture Capitalists in the world by CB Insights and The New York Times. 

Previously, as a Partner at Founders Fund for over five years, Geoff was an early lead investor in companies including Lyft, Wish, Privateer Holdings, Nubank, and RigUp. Prior to joining Founders Fund in 2012, Geoff was a founder himself. As Co-Founder & Chief Executive Officer of Topguest (acquired), he created a loyalty software platform that counted United Airlines, Hilton Worldwide, and Virgin America as clients. Geoff is someone I’ve enjoyed getting to know online and offline. His “Temperature Check” vlog on YouTube is fantastic and his insights are both thought provoking and original. Subscribe to Geoff's YouTube channel: https://youtube.com/geofflewistv

#14 — Geoff Lewis — Noble lies and narrative violations

Mike Maples (@m2jr) is the co-founder and partner at Floodgate Capital and was one of the original “super angels”.  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), how he broke into venture capital after being a founder, and one of the biggest issues facing our country that almost no one talks about. We even turned the tables and Mike fired some questions my way.

Mike has been on the Forbes Midas List since 2010 and was also named one of the “8 rising stars” by Fortune Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.) Some of Mike’s investments include Twitter, Twitch.tv, ngmoco, Weebly, Chegg, Bazaarvoice, Spiceworks, Okta, and Demandforce. Mike is the host of an amazing podcast called “Starting Greatness” and freely shares his insights on Twitter @m2jr. Mike is someone I’ve really enjoyed getting to know over the past year and he is compassionate and big hearted as he is insightful and wise. I hope you enjoy this episode with Mike Maples.

#15 — Mike Maples Jr. — Backcasting to build the future

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 is managed on the AngelList platform. Prior to joining AngelList, Avlok was a repeat founder. One of his startups, Fastbite, was acquired by Square in 2015.

You might be asking: what is a rolling fund? A “Rolling Fund” is a new type of investment vehicle that allows fund managers to invest in private companies at their discretion ion behalf of investors (often referred to as “limited partners”), who contribute to the fund on a quarterly subscription basis. A few of the benefits of rolling funds are the ability to continuously fundraise, more flexibility to fund managers and LPs and the ability to do marketing publicly around your fund.

This was a very informative discussion and it got me really excited about the future of building, operating and investing in startups.I hope you enjoy this conversation with Avlok Kohli. 

—————————————————————

Are you a founder of a startup? Do you need funding for your startup? The good news is I’ve launched a seed fund called Paradox Capital. The mission is to arm founders beneath and beyond Silicon Valley’s radar with early checks and expert advice to build the next great companies anywhere.  If you’re an early stage founder, reach out to me at paradox.vc or send me a DM on Twitter and let’s chat. Now let’s get back to this episode.

#16 — Avlok Kohli — An angel investing revolution

Join 35,000+ listeners for commute-length conversations with original thinkers who will push your perspective and pull you into the marketplace of ideas. 
_______________________________________

"Paradox Podcast is citizen journalism at its best. Long-form discussions of important ideas, freely available to all." — Balaji Srinivasan, Angel Investor & Entrepreneur

"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

"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
_______________________________________

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.

Seed fund: http://paradox.vc
Podcast: http://paradoxpodcast.co
Connect: https://twitter.com/KyleTibbitts

Paradox Podcast

Pinned to spotlight

Popular tracks