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 st...
Nov 02, 2021•1 hr
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 collabo...
Jun 10, 2021•55 min
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 ...
Apr 08, 2021•52 min
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...
Jan 21, 2021•49 min
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 tur...
Sep 30, 2020•1 hr 12 min
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 Capita...
Aug 26, 2020•45 min
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 ...
Jul 29, 2020•1 hr 6 min
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 ser...
May 13, 2020•58 min
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 opponent...
Apr 25, 2020•48 min
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, Flex...
Apr 15, 2020•1 hr 3 min
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 abou...
Mar 31, 2020•55 min
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 peo...
Mar 13, 2020•1 hr 2 min
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 i...
Feb 28, 2020•58 min
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 fo...
Jan 10, 2020•44 min
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 se...
Nov 15, 2019•53 min
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. milita...
Oct 31, 2019•1 hr 7 min
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 se...
Oct 18, 2019•1 hr 2 min
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,...
Oct 04, 2019•50 min
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.
Sep 19, 2019•47 min
