EP 39: All-In’s Jason Calacanis Joins, Breaking Into Media, Tech in Journalism and the Kanye Controversy

All-In’s Jason Calacanis joins to talk about how he broke into media and how it impacted his success as an entrepreneur. Plus the origins of blogs and the early internet, tech in journalism today, his own experiences as a podcaster and interview, and finally the Kanye controversy. (0:00) Welcome Rashad (2:25) Kanye Controversy (9:32) Elon buys Twitter (13:58) Welcome Jason Calacanis (15:00) NYC and Silicon Alley (18:32) Getting into media (28:52) Web 1.0 to Web 2.0 (34:02) Tech and journalism (44:09) This week in startups (49:48) Palmer Luckey interview (56:56) Kanye on Lex Friedman (59:35) Responsibility as a public figure (1:02:53) All-In and Cartoon Avatars (1:09:23) Capturing lightning in a bottle (1:16:19) Being in the public spotlight (1:22:30) Wrap up   Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/three-cartoon-avatars/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg   Follow on Socials 📸 Instagram - https://instagram.com/cartoonavatars 🐦 Twitter - https://twitter.com/cartoonavatars 🎬 Clips on TikTok - https://www.tiktok.com/@cartoonavatars   About the Show A Saturday morning podcast hosted by Logan Bartlett (Partner and Managing Director at Redpoint Ventures) covering the tech news with his friends and other people with industry expertise. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1   Follow on Socials   📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow   About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.