1. How Packy raised his first fund from his readers. 

2. What regulations he needed to navigate to comply with the SEC. 

3. Which sectors he invested his first $10M into (in just 6 months) and some of his breakout startups. 

4. Why IRR can be hilariously large in the early stages of a small fund.

5. How he manages a syndicate and a venture fund while still doing right by LPs. 

David’s been a VC for a while, but he just launched a new $2.8M fund part-time with Nat Manning. We get into why his small fund size is actually so significant and represents new possibilities in venture plus:

- How he uses his podcast and community to get dealflow
- What he thinks you need before starting your own VC fund

https://twitter.com/djrosent

Mac the VC joins the show as the first guest for Angel Season 6 to share his story and how he invests. 

https://twitter.com/MacConwell

Check out Gotham Gal Ventures: https://gothamgal.com/investments

FOLLOW Joanne: https://twitter.com/thegothamgal

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

Show notes:

1:07 Jason intros "The Gotham Gal" Joanne Wilson & they reminisce on the '90s in New York & magazines

5:04 Spotting a bubble, issues with raising above your performance, New York during the pandemic & returning to normal

11:43 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist

13:12 New York's pre-pandemic situation, healthcare detaching from employment

16:11 Rethinking education & commercial real estate, NYC's pro-development mindset, roasting Hudson Yards

24:50 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel

26:19 Impact of high-end residential real estate on NYC

29:22 Joanne's experience investing in underrepresented founders, how the industry has changed over the past 15 years, opportunity with underrepresented founders

36:16 Assure - Get 20% off your first SPV at http://assure.co/angel

37:50 Why Joanne slowed her investment pace during the peak market, sorting process with an influx of startups, portfolio management in an unsustainable market

44:47 Reasons for startup failure, advice for founders raising large amounts of capital

56:14 Family talk, NFTs & sketchy art market dealings

Check out Panoramic Ventures: https://panoramic.vc

Check out SoftBank's Opportunity Fund: https://theopportunityfund.com

FOLLOW Paul: https://twitter.com/pauljudge

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

Listen here:

Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957

Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9

Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio

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:

1:05 Jason intros Paul Judge & they discuss the Miami startup scene & the impact of investing over Zoom

11:37 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist

13:08 How Paul invests, rebranding to start Panoramic Ventures & joining the investment board at SoftBank's $100M Opportunity Fund

17:26 Are dedicated opportunity funds the right approach to maximize funding of underrepresented founders? Where underrepresented founders have an edge

24:34 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist

26:11 Jay-Z's insane Q1, why George Floyd resonated more than prior policy brutality videos

35:11 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel

36:47 Downstream investors looking for underrepresented founders

41:33 Celebrity/influencer funds impact on the future fundraising landscape

43:53 What makes it easy for Paul to invest: "What's your Olympic Team?", anti-portfolio

53:07 Paul's greatest hits as an investor, paradox of borrowing money as a rich person

1:00:20 Educating more people on entrepreneurship via reality TV, Jason's Clubhouse crusade, future of SF

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 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