"Angel" hosted by Jason Calacanis - Audio on Smash Notes

"Angel" hosted by Jason Calacanis - Audio podcast.

December 28, 2019

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



Recently updated notes

Updated on March 23

Key points in this episode

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

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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

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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

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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"

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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?

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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

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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

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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

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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?

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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?

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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

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E28: "Angel" podcast: 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

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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

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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

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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

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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

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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

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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

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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

 

You already know LinkedIn as world’s largest professional network. It's ALSO a better way to find great talent. Go to LinkedIn.com/Angel and get a $50 credit toward your first job post. Terms and conditions apply.

 

The Embroker Startup Program helps startups secure the most important lines of insurance, at a lower cost, and with less hassle. For guaranteed 10% off on premiums (& up to 20% depending on quote) go to embroker.com/angel.

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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

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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

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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

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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

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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

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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

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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, & the critical importance of boards & organizational muscle memory

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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

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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.

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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.

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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.

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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!

 

  1. What’s the best way to verify the customers of a potential investment are happy with the product? - Alan
  2. When completing financial due diligence what documents should I be asking for/what am I entitled to? - Sheila
  3. How can I tell if the founder is the right fit for the company? - Mark
  4. “What is the best way to evaluate a founder for persistence?” - David
  5. If an idea sounds exciting but I don’t have any experience in the vertical how do I intelligently evaluate the opportunity? - Brian
  6. When I invest via an Angel Syndicate is my identity kept secret? Is my name on the cap table? - Kyle
  7. I have a great company for your syndicate, what’s the best way to discuss investment opportunities with you, Jason? - Marianne
  8. What is the standard carry? What is the minimum investment? - Craig
  9. Do you only accept US based companies? - Bill
  10. What opportunities are currently available for non-accredited investors? - Pam
  11. Re: closing mechanics...should I expect/demand an escrow type closing where all the $ of the round comes in at once?  - Anonymous

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In episode8 of "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 and insights from his journey, starting from his carpet-selling days and breaking into tech by hosting events at the rug store, to moving into venture capital, starting his own firm and backing massively successful companies. Pejman shares the secrets of his process, including staying disciplined, qualities he looks for in founders (desire to make a difference, combined with a healthy paranoia), conducting due diligence, handling failure, and belief in the good will of Silicon Valley, where you can be a nobody, but still make it.

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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.

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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.

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

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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.

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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.

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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.

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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.

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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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