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Cover image of Angel | hosted by Jason Calacanis

Angel | hosted by Jason Calacanis

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.

Weekly hand curated podcast episodes for learning

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The best episodes ranked using user listens.

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Ask an Angel! Jason Calacanis & Ed Roman answer questions on runway concerns, syndicate hit rates, advising best practices, founder updates, due diligence, pro-rata rights & more | Angel S2 E10

Ask an Angel! Jason Calacanis & Ed Roman answer questions on startup runway concerns, syndicate hit rates, advising best practices, founder updates, due diligence, pro-rata rights, investment legal structures & more

1hr

2 Apr 2018

Rank #1

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Super angel & syndicate leader Gil Penchina on 20 yrs & 200+ investments, learning the game & making your own rules, optimizing deal flow, minimizing failure, & enjoying the chaos | Angel S1 E2

In episode 2 of Jason's new podcast, "Angel," Super Angel & Syndicate Leader Gil Penchina shares secrets from his 20 years investing in 200+ startups, including LinkedIn, PayPal, & Cruise. Gil reveals why he became an angel, which founders & verticals to back (& which to run away from), deal flow strategies, tips for learning the game & making your own rules, how to support founders, & lessons he's learned from his greatest hits ... and failures. Thank you to Audible for sponsoring this podcast.

47mins

18 Sep 2017

Rank #2

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Andrea Zurek, XG Ventures (Facebook, Twitter) & angel since 2006, shares lessons building Google, ideal terms & valuations, solving problems & finding right combination of money, fortitude, discipline | Angel S1 E3

In "Angel" episode 3, Jason speaks with Andrea Zurek, Founding Partner of XG Ventures ("ex-Googlers"), and angel investor since 2006. Andrea, whose portfolio includes Facebook, Twitter and Box, shares how she picks companies, her ideal terms and valuations, the trouble with TAM and solo founders, deciding when to follow on, how she applies lessons from building Google to help her founders, best advice for accredited and non-accredited investors, insights on increased opportunity for women in investing, portfolio greatest hits & misses, and much more. Thank you to Audible for sponsoring this podcast.

1hr 13mins

18 Sep 2017

Rank #3

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Pete Flint, NFX Managing Partner & Trulia Founder, shares criteria for $150M seed fund, supporting persistent founders, company-building & culture | Angel S2 E9

Pete Flint, NFX Managing Partner & Trulia Founder, shares insights from entrepreneurship to investing, criteria for $150m seed fund, supporting persistent founders, company-building & culture, targeting markets ripe for disruption, & the power of data network effects

1hr 17mins

25 Mar 2018

Rank #4

Most Popular Podcasts

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Angel & syndicate leader Ed Roman on optimizing for outsized outcomes, leaning on gut & market analysis, not learning the wrong lessons, avoiding fraudulent customers, swinging for fences in SV | Angel S1 E4

In episode 4 "Angel" podcast Jason talks to angel & syndicate leader Ed Roman. Ed describes his journey from serial entrepreneur in Austin to syndicate angel in Silicon Valley, and shares strategies for optimizing for outsized outcomes, developing the right alchemy gut & market analysis, the biggest mistake investors make, his greatest hits & misses, how to tell when a founder will go 10x, how to know when you're a seasoned investor...and much more. Thanks for Audible for sponsoring this podcast.

53mins

18 Sep 2017

Rank #5

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Dave Morin of Slow Ventures shares insights from 250+ investments (Slack, Pinterest, Twitter), architecting Facebook & building Path, promoting mental health, combatting depression | Angel S3 E9

Dave Morin of Slow Ventures shares insights from 250+ investments (Slack, Pinterest, Twitter), architecting Facebook & building Path, promoting mental health with Sunrise, combatting the internet's true tax of depression & how founders can get help - Part 1

46mins

20 Jun 2019

Rank #6

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Satya Patel, Homebrew, on 80+ investments, betting on founders with mission, solving problems over building biz, funding "phases" not stages, portfolio stars, & importance of boards | Angel S2 E4

Satya Patel, Homebrew, on 80+ investments, betting on founders with mission, solving problems over building biz, funding "phases" not stages, portfolio stars, & the critical importance of boards & organizational muscle memory

1hr 18mins

4 Jan 2018

Rank #7

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Ben Narasin shares his strategy behind 80 portfolio co's (w/ 50% Series A conversions & 3 unicorns), proven thesis on successful startups & founders | Angel S1 E6

Ben Narasin has a unique view on early-stage investing, quite different than Jason's, and today on "Angel," he shares his proven thesis and dives into a track record that speaks for itself, with over half of his seed companies reaching Series A, and 3 unicorns. Ben explains what he looks for in a startup (teams factors heavily, but not exclusively), the absolute critical characteristic a founder must have to succeed, and executing on the strength of your convictions. Plus, portfolio hits, misses, regrets, and more.

1hr 14mins

24 Sep 2017

Rank #8

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Rob May, investor in 45+ co's & founder Talla & Backupify, shares dealbreakers, successful founder patterns, creating Talla's ICO & future of bots, blockchain, & crypto | Angel S2 E8

Rob May, investor 45+ co's & founder Talla & Backupify, shares dealbreakers, successful founder patterns, using scar tissue as entrepreneur to be a better angel, creating Talla's ICO & future of bots, blockchain, & crypto

1hr 9mins

18 Feb 2018

Rank #9

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Sarah Cannon, Partner at Index Ventures, shares insights on the future of work, underrated emerging startup markets, going from Obama Administration to VC, increasing upward mobility in America | Angel S4 E1

0:01 Jason intros Season 4 of Angel & Index Ventures' Sarah Cannon 3:22 How did working for the Obama administration lead Sarah into Venture Capital? 4:56 Picking a fight with Larry Summers as an intern 15:42 Choosing Harvard's MBA program over Stanford's 18:26 Getting into VC 20:27 Working at CapitalG 24:09 How was the foundation of Index built by Danny Rimer and what is Sarah's role? 31:42 What does Index focus on during a Series A and what is a partner meeting like at Index? 36:31 Thoughts on gig economy work and is there a better way to categorize freelancers and full-time workers in the gig economy? 44:54 Sarah's proposed solution for categorizing gig economy workers 46:36 Jason's thoughts on politicians evolving their views over time 50:15 Ideas to increase upward mobility in America 1:00:35 What was Sarah's first investment? How did it work out? 1:08:42 Founders getting distracted after raising large rounds of funding 1:11:05 Thoughts on emerging international startup markets like India & Australia 1:13:19 Is France an underrated startup market? 1:17:42 What is Sarah most passionate about investing in?

1hr 30mins

5 Feb 2020

Rank #10

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Part 2 Dave Morin of Slow Ventures (250+ investments inc. Slack, Pinterest, Twitter), shares insights on favorite business models & products, backing founders with a tangible sense of inevitability, the rise of two internets | Angel S3 E10

Part 2 Dave Morin of Slow Ventures (250+ investments inc. Slack, Pinterest, Twitter), shares insights on favorite business models & products, backing founders with a tangible sense of inevitability, the rise of two internets, democratization of passion, & an optimistic future with the advancement of self-care tech

57mins

24 Jun 2019

Rank #11

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Samantha Wong, Partner at Blackbird Ventures (Canva, Culture Amp), on the growth of Australia's startup ecosystem, valuations outside of SV & benefits for investors, focusing on deep tech & "science nonfiction | Angel S3 E11

Samantha Wong, Partner at Blackbird Ventures (Canva, Culture Amp), shares insights on the growth of Australia's startup ecosystem, valuations outside of SV & benefits for investors, focusing on deep tech & "science nonfiction," backing founders with an unstoppable force, & how immigration laws impact entrepreneurship

57mins

27 Jun 2019

Rank #12

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Dan Rose, Chairman at Coatue Management is leading a $700M early-stage fund, shares insights on working with Bezos & Zuckerberg during pivotal years at Amazon & Facebook, 100+ angel investments, standout founder traits & more | Angel S4 E2

0:50 Jason intros Coatue Management's Dan Rose 1:52 Dan takes Jason through getting his internship at Amazon in 1999 and meeting Jeff Bezos 6:55 What was Amazon's core business in 1999? What was it like incubating the Kindle in the mid-2000s? 10:04 How did Bezos grow as a leader and businessman during Dan's tenure at Amazon? 18:21 How does Bezos' ability to turn Amazon around in the eyes of public investors relate to Uber, Lyft and other large & unprofitable companies? How does Bezos inspire so much loyalty? 23:27 What was Amazon's company culture during Dan's tenure? How was AWS developed? 26:08 How did Dan wind up at Facebook as employee ~130? What did he see in a young Mark Zuckerberg? 32:13 Who created the original Facebook News Feed? 35:34 How did they get the ad-network to work at scale? 42:50 Where do Elon, Bezos & Zuckerberg rank in the Pantheon of Entrepreneurs? 44:06 How did the billion-dollar acquisition offer from Yahoo! fall apart? 46:42 Why launching open registration led to the billion-dollar investment by Microsoft 48:30 Insights on the Instagram deal 51:00 How Facebook bounced back from the stock dropping from $31 to $17 shortly after IPO & how Dan's experience at Amazon helped him rally the troops? 58:44 Zuckerberg's response to mistakes 1:03:01 How did Dan wind up at Coatue Management leading a $700M early-stage fund? 1:08:01 What is Coatue's strategy around data science? 1:11:20 Dan had over 100 Angel investments before joining Coatue 1:13:18 What is Coatue's new fund strategy? 1:16:09 How does Dan think of diligence in regards to early-stage companies? 1:20:25 What does Dan want to see in an ideal founder?

1hr 30mins

11 Feb 2020

Rank #13

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Jeff Clavier, Uncork Capital, on pioneering micro VC, lessons from 200+ investments & 5 funds, strategizing at Seed for Series A crunch, risky ICOs, & the hard-won wisdom of always be raising | Angel S2 E3

Jeff Clavier, Uncork Capital, on pioneering micro VC, lessons from 200+ investments & 5 funds, strategizing at Seed for Series A crunch, risky ICOs, & the hard-won wisdom of always be raising

1hr 16mins

23 Dec 2017

Rank #14

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Arlan Hamilton, Backstage Capital on being a self-taught VC, creating a rocket ship to fund 64+ underrepresented founders in just 2yrs, launching an upcoming studio, & mastering the art of disciplined investing | Angel S2 E5

Arlan Hamilton, Backstage Capital on being a self-taught VC, creating a rocket ship to fund 64+ underrepresented founders in just 2yrs, launching an upcoming studio, & mastering the art of disciplined investing

53mins

18 Jan 2018

Rank #15

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Clara Brenner, Urban Innovation Fund shares insights from ~50 investments focused on solving our biggest challenges, importance of tenacity, momentum & more | Angel S2 E7

Clara Brenner, Urban Innovation Fund shares insights from ~50 investments focused on solving our biggest challenges, importance of tenacity, momentum, culture to scale & positive communication with investors

1hr 10mins

8 Feb 2018

Rank #16

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Mamoon Hamid, Partner at Kleiner Perkins & expert early investor (Slack, Box, Intercom) on evolving from growth to venture, lessons from Social Capital, great founder qualities, complementary teams, & winning formulas | Angel S3 E7

Mamoon Hamid, Partner at Kleiner Perkins & expert early investor (Slack, Box, Intercom) on evolving from growth to venture, lessons from founding & leaving Social Capital, great founder qualities, wisdom of complementary teams, & winning formulas

1hr 3mins

1 Jun 2019

Rank #17

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Ask An Angel! Jason Calacanis & Brian Alvey answer investor questions on picking startups, evaluating founders, due diligence, syndicates, terms & more | Angel S1 E9

Ask an Angel! It's a special episode of "Angel," with Jason Calacanis & Brian Alvey (Clipisode, LAUNCH) candidly answer the burning questions of investors and those aspiring to be. Picking startups, evaluating founders, due diligence, Syndicates ins/outs, deal terms and a lot more. Listen and learn! What’s the best way to verify the customers of a potential investment are happy with the product? - Alan When completing financial due diligence what documents should I be asking for/what am I entitled to? - Sheila How can I tell if the founder is the right fit for the company? - Mark “What is the best way to evaluate a founder for persistence?” - David If an idea sounds exciting but I don’t have any experience in the vertical how do I intelligently evaluate the opportunity? - Brian When I invest via an Angel Syndicate is my identity kept secret? Is my name on the cap table? - Kyle I have a great company for your syndicate, what’s the best way to discuss investment opportunities with you, Jason? - Marianne What is the standard carry? What is the minimum investment? - Craig Do you only accept US based companies? - Bill What opportunities are currently available for non-accredited investors? - Pam Re: closing mechanics...should I expect/demand an escrow type closing where all the $ of the round comes in at once?  - Anonymous

1hr

14 Nov 2017

Rank #18

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Dave Samuel, Freestyle Capital, on joy & risk of early-stage, qualities of ideal founder, team & product, portfolio faves, & focused investing as a former entrepreneur | Angel S1 E7

On Episode 7 of "Angel," Jason talks to Freestyle Capital co-founder Dave Samuel, a former founder (Spinner, Brondell) who brings his entrepreneurial focus to investing. Dave shares what qualities he looks for in startups & products, his love for building teams & companies, the trouble with B2C, raising money in a financial crisis, early internet days including founding & selling the internet's 1st music service to AOL, his innovative smart toilet, why he became an investor, and much more.

1hr 25mins

9 Oct 2017

Rank #19

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Matt Brezina, investor in 65+ startups (Dropbox, Cruise) & founder (Xobni, Sincerely) shares strategies for backing relentlessly resourceful founder-builders & bringing operational value in return | Angel S1 E10

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.

1hr 31mins

30 Nov 2017

Rank #20