Angel | hosted by Jason Calacanis - Jason Calacanis

Paige Finn of Behind Genius Ventures | Angel S6 E4 Feb 09, 2022

Paige Finn became interested in venture capital during college, but within a year and a half of graduating in 2020 she already has a fund!

In this episode you will learn:

1. How she secured her first allocation before having a fund

2. The steps she took to set up an SPV while being a non-accredited investor

3. How she raised a $1.6m fund

4. Behind Genius' investing thesis and strategy

5. The books that have most influenced her work and writing style

6. Why she wrote a picture book (for adults) called "Seed to Harvest: A Simple Explanation of Venture Capital"

Packy McCormick’s Not Boring parlay | Angel S6 E3 Feb 08, 2022

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.

David Rosenthal's $2.8M fund Kindergarten Ventures | Angel S6 E2 Feb 07, 2022

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 Conwell of RareBreed Ventures | Angel S6 E1 Feb 06, 2022

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

Joanne Wilson on spotting a bubble, NYC’s post-pandemic reset, portfolio management in an unsustainable market & more | Angel S5 E10 Mar 24, 2021

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

Paul Judge on helping lead SoftBank's $100M Opportunity Fund, future of fundraising, importance of "building your Olympic Team" & more | Angel S5 E9 Mar 18, 2021

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

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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

Garry Tan on lessons from past startup failures, power of community funnels, Alexis Ohanian's departure & more | Angel S5 E8 Mar 11, 2021

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

Matt Mullenweg on pioneering remote work, investing in open-source, crypto & more | Angel S5 E7 Mar 04, 2021

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

Reid Hoffman on the Joby Aviation SPAC, lessons from early Airbnb & Facebook bets, passing on Stripe & SpaceX, investment thesis & more | Angel S5 E6 Feb 25, 2021

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

Mark Cuban on the resurgence of retail investors, NBA's potential entry into wagering & digital assets, DeFi & much more | Angel S5 E5 Feb 18, 2021

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

Howard Lindzon on public vs. private investing psychology, "great unbundling" of index funds, Robinhood & more | Angel S5 E4 Feb 11, 2021

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

Elad Gil on his product-market driven thesis, importance of market pull, entering the "go public sooner" decade | Angel S5 E3 Feb 03, 2021

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

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

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Thanks to our partners:

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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

Intercom's Des Traynor on the importance of pricing, product-market fit metrics & more | Angel S5 E2 Jan 28, 2021

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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David Tisch shares insights from 350+ early-stage investments in companies like Plaid & Roman, importance of reputation, dealing with sharp-elbowed investors & more | Angel S5 E1 Jan 21, 2021

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

Shawn Carolan, Managing Partner at Menlo Ventures shares insights on his early investments in Uber, Roku, Siri & JUMP Bikes, adjusting his approach in response to hundreds of new venture funds with billions in dry powder & more! | Angel S4 E10 Apr 10, 2020

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

Jeff Richards, Managing Partner at GGV Capital shares lessons for founders & investors from 2008 recession & Dot-com bust, criteria for taking on venture debt, valuing companies in a down market & more! | Angel S4 E9 Apr 01, 2020

0:51 Jason gives some thoughts on quarantine & intros GGV's Jeff Richards 5:11 What will this crisis look like on the other side? Benefits of having a levelheaded approach 11:38 What has Jeff seen from his seasoned portfolio founders who went through the 2008 crisis? 16:21 What advice does Jeff give to first-time founders in his portfolio? 22:22 Investor panic & differences in opinion between independent & investor board members 25:50 What could inexperienced board advice be in a time like this? 30:45 What is GGV's typical check size, how many startups do they invest in per year, and how are their funds divvied up between early-stage & growth 33:26 Chances that current deals could be renegotiated? How can founders price themselves properly? 38:05 Jeff explains liquidation preferences 42:52 How should companies approach taking venture debt in a time like this? What is Jeff's criteria for taking venture debt? 51:11 If things are going poorly, what are some things founders can do to right the ship? Examples of great pivots that saved companies 57:58 What is Airbnb's roadmap from here on out? 1:02:12 Why Jeff doesn't get enamored with IPO valuations & why he is long tech 1:08:18 Thoughts on Zoom, anti-trust laws & more

Sarah Guo, General Partner at Greylock Partners shares insights on Greylock's "Zero to One" investment thesis, sharpening her decision-making skills, ranking team, market & product as investment criteria & the changing landscape of VC | Angel S4 E8 Mar 21, 2020

0:52 Jason intros Greylock's Sarah Guo 3:37 How did Sarah wind up at Greylock? 5:45 Sarah explains Greylock's "Zero to One" thesis & typical term commitment of a VC 11:53 How does Sarah measure her personal performance and her portfolio's performance? What are her biggest strengths as an investor? 16:12 How does she sharpen her decision-making skills? 17:53 Ranking her investment criteria: People, Markets & Product 20:26 Balancing intensity & life outside of work, the commitment of early-stage startups 27:26 Work-life balance & how the venture landscape changed over time 35:36 Greylock's structured & what was Sarah's first investment & how did it play into her investment thesis? 43:38 Sarah's investments in work-enabling software 48:00 Sarah recommends Dylan Field of Figma join the show - episode dropping Friday! 49:22 Identifying subtle flashes of brilliance in early products 58:28 Female founders being held to a higher standard 1:02:35 Anti-portfolio: Zoom 1:10:06 Sarah turns off her virtual background and reveals her location

David Cowan, Partner at Bessemer Venture Partners shares insights on owning up to his anti-portfolio, understanding sunk cost, top traits for becoming a VC & best Founders & CEOs he's ever worked with | Angel S4 E7 Mar 18, 2020

0:53 Jason intros Bessemer's David Cowan 1:54 David explains how he got his start in Venture capital in 1992 4:22 What does Bessemer look for in a potential investor today? How has VC hiring and demographics have changed over time? 8:10 David gives an anecdote about understanding "sunk cost" 14:12 David explains how and why Bessemer started owning their anti-portfolio 16:03 Stories on passing on Facebook, Tesla, Google, PayPal, Napster & Youtube 19:13 What made Youtube standout from Napster from a regulatory perspective 24:05 David describes hearing the Twitch pitch for the first time 26:00 Consumer vs. Enterprise investing 29:42 Sales-driven culture 33:31 When is the right time to sell a company? 41:15 Anti-tech backlash... is it justified? 47:38 Who is the best Founder & CEO David has ever worked with? 52:10 Meeting Wade Foster and investing in Zapier 55:29 Are growth & product people making the best VCs today? 58:53 Thoughts on Quantum Computing 1:02:19 How is David investing in Robotics? 1:09:58 Jason ends the show by showing the trailer to David's Silicon Valley mockumentary "Bubbleproof"

Nicole Quinn, Partner at Lightspeed shares benefits of celebrity founders like Lady Gaga & Gwyneth Paltrow, insights on investing in consumer & power of "Force of Nature" product people | Angel S4 E6 Mar 11, 2020

0:53 Jason intros Nicole Quinn 1:59 Nicole & Jason describe their separate Calm investments, will it be the first mental health IPO? 8:00 Calm's I.C.E. celebrity engagement method & how it got them LeBron James 8:54 Investing in Sophia Amoruso & Girlboss: what is it about "Force of Nature" product people that attracts Nicole to invest? 16:03 Investing in Gwyneth Paltrow & Goop: what is Goop's business? What are the most profitable parts of their business? 19:42 Investing in Rothy's, and the inverse correlation between the success of e-commerce companies and how much they've raised 24:34 The magic moment of having shares transfer from private to public when a company IPOs 26:53 Changing her risk-averse mindset going from Wall Street to Venture Capital 33:28 Nicole's current investment interests, why voice assistants are crucial for retention 38:16 Investing in Lady Gaga & HAUS Labs: driving business via new product "drops", understanding how engaged a celebrity is in their business, celebrities as an acquisition channel 45:03 Dealing with Goop product blowback, the Netflix series & understanding the science behind it 50:12 Investing in Cameo & CEO Steven Galanis: celebrity selfie videos as a platform 54:44 What types of Founders does Nicole invest in? 56:54 How is Nicole's portfolio split up by stage?

Ajay Agarwal, Partner at Bain Capital shares insights on culture evolving from sales-driven to product-driven, why enterprise software is the ideal business, best investments & anti-portfolio | Angel S4 E5 Mar 04, 2020

0:51 Jason intros Bain Capital's Ajay Agarwal

3:17 Are we experiencing late-stage capitalism? Is capitalism broken?

8:22 Why is upward mobility stalling?

15:29 What is it about founders & startups that made him dedicate his life's work to?

18:46 What piece of knowledge got him in startups? Ajay describes gross margin & incremental costs

23:03 Two insights on why enterprise software is the best business

30:11 Mitt Romney at Bain Capital & issues with cultural appropriation

36:44 Ajay's early days at Trilogy Software, how software sales were different in the 1990s

42:23 Companies going from sales-driven culture to product-driven

46:52 Ajay describes one of his best investments: FourKites

49:13 Ajay describes the biggest miss of his anti-portfolio: Pinterest, and why some firms care about stage and some are stage-agnostic

54:57 Has Bain ever participated in every round of a companies life-cycle?

58:15 Effects of the SoftBank Vision Fund on venture capital as a whole

Sarah Tavel, Partner at Benchmark shares insights on getting recruited by Peter Fenton, disrupting VC gender norms from the inside, transitioning from operator to investor & more | Angel S4 E4 Feb 26, 2020

0:50 Jason intros Benchmark's Sarah Tavel 1:20 Aside from Slack, what other companies grew like consumer-facing but charge like enterprise? 3:19 How was Sarah recruited to Benchmark? How is Benchmark different from other major VC firms? 12:04 Limited upside of talking to the press in 2020 17:30 Growing up in NYC and going to Harvard 21:30 Jason on becoming a "Don't touch the thermostat" dad 23:58 How did the offer from Peter Fenton go down? What drew Sarah to Benchmark? 28:36 Sarah's thoughts on disrupting VC as a woman from the inside & from the outside 37:30 How going from operating to investing is trading stress for anxiety 40:51 Jason and Sarah discuss their most personal & significant investments: Calm & Pinterest 47:26 How Pinterest's business model was a mold of Facebook and Google 49:45 Jason tells regulators how to stop Google 58:14 Investing in Chainalysis & Crypto infrastructure 1:12:44 Are the best companies polarizing? 1:16:30 Investing in Hipcamp 1:29:43 Marc Andreessen asks Sarah a question

George Zachary, General Partner at CRV shares insights on cancer scare shifting his focus to investing in health-tech, passing on Google at MDV, CRISPR & "designer babies", coronavirus threat, origins of Sand Hill Road & more! | Angel S4 E3 Feb 19, 2020

0:50 Jason intros CRV's George Zachary 2:20 Passing on Google at MDV and coming to peace with the anti-portfolio 5:51 Differences between leadership & management, where Steve Jobs, Larry & Sergey fell on that scale 10:27 Why 1990's VC was sales & marketing-driven instead of product-driven as it is now 12:52 What shifted the philosophy to product-driven businesses? 18:00 Meeting Elon Musk in the 1990's and backing Zip2 21:59 What were Seed investors like in the '90s? Origins of Sand Hill Road 25:48 Elon pitching Zip2 to a conglomerate of venture firms & selling Zip2 for cash 28:07 How VCs can be conceptually right and wrong in the outcome, how X.com merged with Confinity and became PayPal 33:27 Why is it harder to 3x the massive venture funds? How is age a limiting factor in VC? 40:28 "It doesn't make a difference what you pass on. It only takes 1 company to make your career." Positive & negative feedback cycles in VC. 42:54 Battling through multiple portfolio companies dying at once 44:15 What was George's biggest investment hit, both economically & personal fulfillment? 52:37 George describes his recent health scares and how they shifted his investment focus 1:04:06 Reasons the life-expectancy in the US has gone sideways in recent years 1:07:39 Potential health-tech advancements in the near future 1:21:58 Thoughts on CRISPR & "designer babies" 1:30:27 Cell-based fish & meat 1:37:32 Potential coronavirus repercussions - what's real and what's not? 1:55:13 Jason calls for eliminating handshakes

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 Feb 11, 2020

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?

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 Feb 05, 2020

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?

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 Jun 27, 2019

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

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 Jun 24, 2019

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

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 Jun 20, 2019

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

Ryan Hoover, Founder of Weekend Fund & Product Hunt, shares lessons from building his early-stage fund, harnessing excitement for new markets, betting on founders with unique perspectives | Angel S3 E8 Jun 08, 2019

Ryan Hoover, Founder of Weekend Fund & Product Hunt, shares lessons from building his early-stage fund, harnessing excitement for new markets, betting on founders with strong perspectives & unique qualities, & bringing his expertise & passion for creating communities to venture capital

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 Jun 01, 2019

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

Ben Ling of Bling Capital (prev. Khosla Ventures), shares strategies from 100+ investments & 9 unicorns, qualities of great founders & teams, startup valuations, market opportunities, Google's early days, future of AR/VR | Angel S3 E6 May 27, 2019

Ben Ling of Bling Capital (prev. Khosla Ventures), shares strategies from 100+ investments & 9 unicorns, qualities of great founders & teams, assessing market opportunities, the art of startup valuations, Google's early days, the future of AR/VR, & lessons from leading change in consumer behavior

Chris Redlitz, General Partner of Transmedia Capital, shares success of The Last Mile program, insights from investing in 90+ startups, nurturing networks & deal flow, evolution of syndicates | Angel S3 E5 May 21, 2019

Chris Redlitz, General Partner of Transmedia Capital, shares success of The Last Mile program teaching tech to incarcerated populations, insights from investing/advising in 90+ startups, nurturing networks & deal flow, evolution of syndicates, urgency of smart money first, & backing founders with passion, presence & perseverance

Mitch Kapor, Partner at Kapor Capital, shares results of their first-ever Impact Report, investing with purpose to close gaps &, insights on Uber's IPO, fixing the gig economy | Angel S3 E4 May 13, 2019

Mitch Kapor, Partner at Kapor Capital, shares stellar return results of their portfolio's first-ever Impact Report, investing with purpose to close gaps & back entrepreneurs with distance traveled, insights on Uber's IPO, fixing the gig economy, promoting diversity in Silicon Valley & creating long-term value v. short-term gains

Matt Ocko, Managing Partner of Data Collective, invests in deep tech with an algorithmic edge, shares decision-making in difficult markets, building a world-class team & taking risks to create a utopian future | Angel S3 E3 May 06, 2019

Matt Ocko, Managing Partner of Data Collective, invests in deep tech with an algorithmic edge, shares decision-making in difficult markets, building a world-class team, state of Seed in 2019 & taking risks to create a utopian future

Charles Hudson, Managing Partner of Precursor Ventures, shares strategies on the great rewards & risks of pre-seed, analyzing market structure vs. size, importance of mobilization to increase | Angel S3 E2 Apr 29, 2019

Charles Hudson, Managing Partner of Precursor Ventures, shares strategies on the great rewards & risks of pre-seed, betting on founders with unique insight, analyzing market structure vs. size, importance of mobilization to increase SV diversity, & the art of making early deals without data

500 Startups Co-founder & Managing Partner Christine Tsai shares lessons from her fund's 10 unicorns & 2200+ startups, what it takes to be a successful founder, 26% women-led portfolio, hits/misses | Angel S3 E1 Apr 22, 2019

500 Startups Co-founder & Managing Partner Christine Tsai shares lessons from her fund's 10 unicorns & 2200+ startups across 74 countries, what it takes to be a successful founder, achieving a 26% women-led portfolio, greatest hits/misses, & strong leadership through adversity

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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 Apr 02, 2018

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

Pete Flint, NFX Managing Partner & Trulia Founder, shares criteria for $150M seed fund, supporting persistent founders, company-building & culture | Angel S2 E9 Mar 25, 2018

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

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 Feb 18, 2018

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

Clara Brenner, Urban Innovation Fund shares insights from ~50 investments focused on solving our biggest challenges, importance of tenacity, momentum & more | Angel S2 E7 Feb 08, 2018

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

Arjun Sethi, Social Capital on bringing skills as a founder (MessageMe, Lolapps) & Yahoo head of growth to early-stage investing | Angel S2 E6 Jan 28, 2018

Arjun Sethi, Social Capital on bringing skills as a founder (MessageMe, Lolapps) & Yahoo head of growth to early-stage investing, being candid, overcoming hubris, taking methodical risks, & the critical importance of rapid-learning, resilient teams

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 Jan 18, 2018

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

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 Jan 04, 2018

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

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 Dec 23, 2017

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

BoldStart Founder Ed Sim on 20 years, 50+ enterprise investments, how family history shaped his VC approach & more | Angel S2 E2 Dec 17, 2017

BoldStart Founder Ed Sim on 20yrs seeding 50+ enterprise co’s, how his father’s fleeing N. Korea shaped his VC, NYC deep tech, & being 1st dollar in to help move founder-product fit to product-market fit to self-sustainability.

Urban.us Shaun Abrahamson & Stonly Baptiste seed & support startups improving cities, solving climate, housing, waste, transportation | Angel S2 E1 Dec 10, 2017

As populations grow, and climates change, could cities be our salvation? With the right infrastructure, urban areas or megaregions can be the most carbon & economic efficient habitations. But cities face countless problems, in housing shortages, broken transportation, overflowing waste, and more. With Urban.us, Shaun Abrahamson & Stonly Baptiste seed startups solving for challenges to make our cities better and our futures more hopeful. Shaun & Stonly talk to Jason about what they're working on, why cities are so critical, what they look for in startups, which problems they are tackling, 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 | Angel S1 E10 Nov 30, 2017

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.

Ask An Angel! Jason Calacanis & Brian Alvey answer investor questions on picking startups, evaluating founders, due diligence, syndicates, terms & more | Angel S1 E9 Nov 14, 2017

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

Pear VC Founding Managing Partner Pejman Nozad shares lessons from selling rugs as an immigrant to seeding 100+ co's & 6 unicorns, staying disciplined & backing founders who want to make a difference | Angel S1 E8 Oct 31, 2017

On today's "Angel," Jason sits down with Pejman Nozad, Founding Managing Partner of Pear VC. Pejman came to the U.S. from Iran with nothing, and eventually became one of the most successful angel investors ever, seeding 100+ startups including 6 unicorns. Pejman reveals lessons & insights from his journey, starting from his carpet-selling days & breaking into tech by hosting events at the rug store, to moving into venture capital, starting his own firm & backing massively successful companies.

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 Oct 09, 2017

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.

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 Sep 24, 2017

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.

"Angel" hosted by Jason Calacanis - Audio Sep 18, 2017

In this series, Jason interviews angels about their investment strategies and pulls back the curtain on how early-stage startups get funded.

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 Sep 18, 2017

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.

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 Sep 18, 2017

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.

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 Sep 18, 2017

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.

Premiere: Cyan Banister, angel investor now Founders Fund VC, shares portfolio hits/misses, deal flow strategies, finding founder-product fit & backing startups that change human behavior | Angel S1 E1 Sep 18, 2017

Welcome to the first episode of the “Angel” podcast. In this series, Jason interviews angels about their investment strategies and pulls back the curtain on how early-stage startups get funded. In E1, Cyan Banister, former angel investor (Uber, Thumbtack) now Founders Fund Partner, shares with Jason her portfolio successes & brutal losses, her formula for choosing successful startups & founders, and her journey from angel investor to VC. Thanks to Audible for sponsoring this podcast.

Zach Coelius, founder-turned-angel & Syndicate leader with a $1b exit after only 2yrs investing, shares insights on advising, hustling, deal flow, & the thrill of first market validation | Angel S1 E5 Sep 09, 2017

In today's episode of "Angel," Jason welcomes Syndicate leader Zach Coelius, Triggit founder who, only after 2yrs as an angel, has already enjoyed a $1b exit (Cruise, bought by GM). Zach shares his insights as a founder-turned-investor, including finding deals & deal-breakers, hustling & other techniques to be a better investor, advising your way onto the cap table, what stage of product development is the most exciting, the skinny on AngelList funds, his (tremendous) hits & (very few) misses, and, from personal experience, the great respect & empathy he has for entrepreneurs ("startups are like rocket ships into the walls of your incompetence"). Thank you Audible for sponsoring this podcast.

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