In "Angel" episode 10, Jason talks with Matt Brezina, angel investor in over 65 startups, including Dropbox, Cruise & Ring, and also founder of Xobni & Sincerely. Matt shares how & why he got into investing, his critical formative time in YC, the lasting influence of Paul Graham, meeting Drew Houston (failing to hire him, but succeeding in investing in Dropbox down the road...), learning sales from his mom, mistakes letting ego interfere with business, why he loves Twitter, the future of transportation, his belief in the power of founder-builders and investing in their careers...and much more.

Matt Brezina, investor in 65+ startups (Dropbox, Cruise) & founder (Xobni, Sincerely) shares strategies for backing relentlessly resourceful founder-builders & bringing operational value in return | A

In this series, Jason Calacanis pulls back the curtain on how early-stage startups get funded by interviewing angels and VCs about their investment strategies, biggest hits, anti-portfolio, and more.

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Packy McCormick turned his massive newsletter into a Not Boring Fund I in 2021, and has since invested $10M into startups. In this episode you will learn: 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.   

Packy McCormick’s Not Boring parlay | Angel S6 E3

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

David Rosenthal's $2.8M fund Kindergarten Ventures | Angel S6 E2

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

Mac Conwell of RareBreed Ventures | Angel S6 E1

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

Joanne Wilson on spotting a bubble, NYC’s post-pandemic reset, portfolio management in an unsustainable market & more | Angel S5 E10

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

Matt Brezina, investor in 65+ startups (Dropbox, Cruise) & founder (Xobni, Sincerely) shares strategies for backing relentlessly resourceful founder-builders & bringing operational value in return | A

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