Angel | hosted by Jason Calacanis

Latest Episodes:

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

Show notes

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

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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

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

Show notes

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

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

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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

Show notes

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

Show notes

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

Show notes

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

Show notes

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

Show notes

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

Show notes

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

Show notes

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

Show notes

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