Angel - hosted by Jason Calacanis

Check out Initialized: https://initialized.com FOLLOW Garry: https://twitter.com/garrytan FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:08 Jason intros Garry Tan & they talk about Garry's Posterous regrets & lessons from failure, going from seed-stage to growth-stage founder 8:33 Garry on life as an investor, Paul Graham's original YC content/community funnel 11:04 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 12:39 Garry's YouTube experience, investing in Clubhouse & the social audio space & Jason's Clubhouse beef 20:27 Twitter spaces coexisting with Clubhouse, Twitter's recent product groove, Initialized's investment in Clubhouse 28:05 Assure - Get 20% off your first SPV at http://assure.co/angel 29:40 How accelerators get great value, Capital-as-a-Service, equity participation as newer generations' north star 36:37 Sweet spot age for founders, ISAs & community-driven learning 39:13 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 40:44 VCs moving downstream & missing the early-stage orchard, potential new models to provide value, avoiding sharp elbows as a seed investor 48:58 Garry explains Alexis Ohanian leaving Initialized & their continued bond as friends 53:55 Unicorn patterns, understanding important consumer metrics

Check out Automattic: https://automattic.com FOLLOW Matt: https://twitter.com/photomatt FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:07 Jason intros Matt Mullenweg & they discuss starting WordPress & getting into angel investing 5:47 Angel investing in the early 2000's as ecosystem building & charity, Automattic's SPAC potential, potential for individual properties to spin out 11:48 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 13:14 How WooCommerce compares to Shopify, open-source flexibility, thoughts on running a public company, difficulty of the media business 20:17 Audrey Hepburn's influence on Matt 21:30 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 23:03 Matt's first big hits as an investor, holding on to winners 28:15 Practical uses for crypto, being bullish on the technology of crypto, impact of bad actors on decentralized systems 34:30 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 35:48 Policing speech on the Internet, Trump stress test, analyzing Trump's ban 48:17 Pioneering remote work, future in a post-COVID world, advantages in competing for top talent, middle management's disadvantages due to remote work 59:37 Future of San Francisco, managing hybrid in-person / remote, tips for new founders

Check out Greylock: https://greylock.com FOLLOW Reid: https://twitter.com/reidhoffman FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:07 Jason intros Reid Hoffman & they discuss the Joby Aviation VTOL SPAC, VTOLs vs. self-driving 11:53 Assure - Get 20% off your first SPV at http://assure.co/angel 13:26 Reid on setting up the meeting between Peter Thiel and Mark Zuckerberg, hitting a 20000x+ with Facebook, opportunities for sustained growth in the big tech reaches population limitations 18:02 When business leaders should speak up on certain issues 23:50 Reinstating Trump's accounts 25:15 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 26:50 Anti-portfolio: Reid tells the story of missing on Stripe, is ownership % overrated? 36:12 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 37:31 Navigating potential portfolio conflicts 40:59 Lessons from hitting on Airbnb with his first investment at Greylock 49:15 Passing on SpaceX after an Elon pitch, returning billions to LPs in one investment 54:28 Reid's process for being a world-class investor, breaking down the Clubhouse investment 1:01:08 Investing over Zoom, future of Silicon Valley & San Francisco, Reid's next act

FOLLOW Mark: https://twitter.com/mcuban FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Show notes: 1:04 Jason intros Mark Cuban & they discuss the circumstances of their first meeting, Mark's dot-com bubble hedge, resurgence of retail investors 9:30 Mark's prescient bets, origin of Blog Maverick 12:20 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 13:39 Understanding naked shorts, how shorts could be a companies best friend 17:15 Story behind Mark venturing into the movie business, producing the Enron documentary with a day-and-date release, thoughts on MoviePass & vertical integration in the film industry, risks of investing in AI 25:14 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 26:46 How AI is starting to impact the NBA, what's changed over the past 20 years since Mark bought the Dallas Mavericks 33:40 NBA getting into wagering 36:23 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 37:55 Mark's relationship with the NBA, player-fan interaction, Porzingis trade & pairing him with Luka 44:59 Mark's original consulting business, diversity in tech, investing in Arlan 48:33 How Mark reviews cold emails, how crypto plays into the future of the NBA: smart contracts, digital assets, non-fungible tokens 57:32 How DeFi can change finance forever, Knicks talk, vaccine optimism

FOLLOW Howard: https://twitter.com/howardlindzon FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Assure - Get 20% off your first SPV at http://assure.co/angel Show notes: 1:22 Jason intros Howard Lindzon & they talk about angel investing stories from the first dot-com bubble 5:50 Creating the $ cashtag on Twitter, psychology of public vs. private investing, why VCs fled the public markets after the dot-com bust & how this relates to the SPAC movement 12:51 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 14:23 Are recent public market returns sustainable? Why hedge fund VCs have an advantage, how the Tinder swipe relates to SPACs 23:27 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 24:58 How SPACs are a hedge against paternal investing laws, why active investors should push back against "set and forget" investing, how index funds enable poor executive performance 29:51 The "Great unbundling" of index funds, how Howard invested in Robinhood 34:08 Assure - Get 20% off your first SPV at http://assure.co/angel 35:41 Howard tells a Robinhood term sheet story 39:26 Deconstructing the unprecedented Robinhood situation 48:22 Pandemic, vaccine news, optimism, how the party moved from private to public markets 55:21 Disney as a conglomerate, pure-play stocks, Apple's narrative issues, investing over Zoom, Uber's recent acquisition 1:05:50 Creating a digital wall with China, Trump's Twitter ban

Check out Elad's Website: http://eladgil.com FOLLOW Elad: https://twitter.com/eladgil FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist Show notes: 0:00 Start 1:05 Jason intros Elad Gil, Elad explains what he's learned since he started angel investing 10+ years ago, Internet market caps growing 10X-30X over the last decade, software's surface area 11:32 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 13:06 Understanding Clubhouse's valuation, a history of "overpriced" standout social apps, monetization options 19:01 Potential of paying it forward to black creators 25:01 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 26:32 SPACs, startups going public earlier, theories on why "stay private longer" was popular in the 2010s and why 2020s looks like the "go public faster" decade 33:11 Thoughts on selling secondary shares & selling in public markets 36:04 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 37:36 How the pandemic endgame impacts his investment thesis, Israel's incredible vaccine distribution 47:07 Elad's thesis: product-market driven OVER team driven, importance of market pull in non-obvious markets, using growth rate to determine market size 54:34 Amazon's sustained growth rate, how consumer companies accelerate at scale, big tech's best acquisitions 1:00:49 Self-driving, VTOLs, future tech epicenters, work from home

Check out Intercom: https://www.intercom.com FOLLOW Des: https://twitter.com/destraynor FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist Assure - Get 20% off your first SPV at http://assure.co/angel Show notes: 0:00 Start 1:08 Importance of charging for enterprise products from the start 6:08 Explaining the phenomenon of startups that become great companies when the idea behind them is not logical or the market is unforeseen 10:18 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 11:49 Investing in Notion - what he initially saw in the product, how UI helps Notion stand out, how angel investing & giving advice help hone his skills as an operator at Intercom 17:39 Common fundraising mistakes that founders make 21:48 Growth planning at a late-stage startup 24:26 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 25:57 How Intercom was initially pitched, the singularity of CRM platforms (Salesforce, HubSpot,Intercom, etc.), preparing for IPO & raising capital as a late-stage startup 30:52 Operating profitably, thoughts on acquisitions as a route to growth 35:02 Assure - Get 20% off your first SPV at http://assure.co/angel 36:32 Hopin's rapid rise in online events, dealing with the pandemic and being cooped up, keeping up company moral 44:13 Intercom's international offices, work from home, Slack's market penetration play, Microsoft vs. Salesforce in the 2020's 51:09 Acquisition offers, why hasn't Intercom sold yet? Pricing power in the enterprise, important product-market fit metrics 1:01:50 Thoughts on going public Subscribe to our YouTube to watch all full episodes: https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1 Subscribe to TWiST Clips for all the best moments: https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg?sub_confirmation=1

Check out BoxGroup: https://boxgroup.com FOLLOW David: https://twitter.com/davidtisch FOLLOW Jason: https://linktr.ee/calacanis Show notes: 0:00 Start 1:04 Jason intros BoxGroup's David Tisch & they discuss being an angel investor post-Great Recession & starting Open Angel Forum 7:36 David on investing his own money until 2019 & why he decided to raise from LPs, investing in 350+ companies 10:45 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 12:18 Expectations in a 350+ company portfolio 16:36 Investing in Plaid: Why he invested, how he met the founder, where do they go from here 23:22 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 24:53 Big winners for BoxGroup so far, 10% of investments driving most of the returns, huge feedback loops in early-stage investing 31:01 Dealing with bad investors in the middle tier, importance of reputation 34:46 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 36:23 How David interacts with portfolio founders regarding advice & company-building, judging the experiment & founder instead of the company itself 41:51 Ownership concentration, taking pro-rata, dealing with sharp-elbowed investors 49:38 How Lee Fixel personifies the low-profile, incredibly reputable investor 52:34 How mentality changes when investing your own money vs. other people's money, pattern recognition on founders, rarity of depth of talent 1:03:59 Thoughts on WeWork, media misalignment, anti-capitalism, big tech meaning well

0:01 Jason thanks the sponsors, guests, listeners & the team for Angel Season 4! 4:38 Jason intros Menlo Ventures' Shawn Carolan 7:26 Thoughts on the market's reaction to COVID-19, when will it get back to normal? 11:51 What advice is Shawn giving to his portfolio founders? 19:07 How has the job of a VC changed with the influx of hundreds of new funds, and what impact has the large amount of dry powder done to the industry? How has Shawn adjusted his approach in response to this? 26:07 Why paying a high price on valuation for dialed in startups (like Shawn did for Uber's Series B) is still a great bet 34:13 Shawn on passing in investing on Mahalo & Jason 36:20 What was it like having a "Force of Nature" portfolio founder like Travis Kalanick, who would destroy any obstacle in his path? What are some great founder attributes? 51:24 Shawn takes us through his Siri investment 57:55 Shawn takes us through his Roku investment 1:02:25 With the influx of Seed & Series A startups, how has Shawn adjusted how he meets founders? 1:05:00 Shawn takes us through his JUMP Bikes investment, are micro-mobility unit economics broken? 1:07:43 What will the outcomes of COVID-19 be in the startup community? 1:28:05 Shawn asks Jason how to best utilize his domain expertise to create high-quality content for Menlo Ventures