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

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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

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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

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FOLLOW Mark: https://twitter.com/mcuban

FOLLOW Jason: https://linktr.ee/calacanis

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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

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FOLLOW Howard: https://twitter.com/howardlindzon

FOLLOW Jason: https://linktr.ee/calacanis

Thanks to our partners:

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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

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Check out Elad's Website: http://eladgil.com

FOLLOW Elad: https://twitter.com/eladgil

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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

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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

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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

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