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

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

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

Paradox Podcast

Related tracks