This Week in Startups

This Week in Startups

By Jason CalacanisTechnology
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This Week in Startups episodes

  • Breaking down Ryan Breslow’s YC critique + Spotify’s solution & Joe Rogan’s response | E1374
    Over the weekend Bolt CEO Ryan Breslow wrote a big thread on why he thinks Y Combinator isn't worth it. We break it down point by point and assess the validity of the claims (7:07). Right before we started recording, news broke that Breslow was leaving the CEO role to assume the executive chairman position, so we cover that too (2:11). Then, we cover Joe Rogan’s expla-nology (explanation/apology) video regarding his COVID-related interviews that have upset many. We react to his response, Spotify's new COVID policy and reflect on the risks to Spotify’s business overall (44:32).
    1 hr 24 min
  • VC Sunday School: startup investing in a down market + Emily Kirsch of Powerhouse Ventures | E1373

    Jason says, "fortunes are made in the down market and collected in the up market." In today's VC Sunday School Jason and Molly discuss how a down market impacts early-stage investors (01:45). You will learn:


    1. Risks to VC fundraising when valuations are down

    2. If your investing process should vary depending on market conditions

    3. How a down market impacts future returns

    4. Why founders should have 18 months of runway

    5. How founders can turn a down market into an advantage


    Then, Molly chats with Emily Kirsch, Managing Partner of Powerhouse Ventures for a This Week in Climate Startups segment (25:53). Emily is a climate investor and they discuss:


    1. Why Powerhouse is focused on software

    2. Climate change's potential impact on GDP

    3. How financial tools enabled the solar revolution

    4. Regulations impacting climate investing

    5. How different climate tech investors work together

    6. The imbalance between climate tech founders and companies


    (00:00) Molly and Jason intro the show (01:45) VC Sunday School: how a down market impacts the early-stage (05:45) Risks to VC fundraising when valuations are down (09:37) Should investors standards change depending on market conditions? (12:24) Bubble. Get one month free of a no-code plan at https://bubble.io/twist (13:53) How a down market impacts future returns (18:55) Why founders should have 18 months of runway (21:21) How founders can turn a down market into an advantage (23:46) Jason and Molly intro Emily Kirsch (24:34) Coda - The all-in-one doc for teams, get a $1,000 credit at https://coda.io/twist (25:53) Emily Kirsch Managing Partner of Powerhouse Ventures (29:11) Why Powerhouse is focused on software (34:31) Fellow - Sign up and get $1000 in credits at https://fellow.app/twist (36:16) Climate change's potential impact on GDP (37:50) How financial tools enabled the solar revolution (39:58) Regulations impacting climate investing (44:17) How different climate tech investors work together (55:24) The imbalance between climate tech founders and companies

    Check out Powerhouse: https://www.powerhouse.fund/ventures

    FOLLOW Emily: https://twitter.com/emilykirsch FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood


    1 hr
  • Packy McCormick's Not Boring parlay: Angel S6 E3 + Producer Rachel visits Miami Hack Week | E1372

    Today's guest is Packy McCormick of Not Boring, for Episode 3 of Season 6 of Angel. Packy 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.

    As Packy signs off we check in with Producer Rachel who went down to Miami Hack Week and spoke to one of the organizers of Tap House for an "OK Boomer" segment.


    (00:00) Molly introduces the show (01:43) Jason and Molly chat with Packy McCormick (04:40) Packy's editorial philosophy (08:06) How Packy used the 506c designation (10:38) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/angel (11:41) Using a parallel fund structure (15:33) How media-first investors can optimize their fund structure (20:50) LinkedIn Jobs - Go to https://linkedin.com/angel and post your first job for free. (21:57) Not Boring Fund II goals (24:42) How responsibilities change as check size increases (27:45) Managing Venture LPs and a Syndicate simultaneously (29:08) Embroker - Get an extra 10% off insurance for your business at https://Embroker.com/twist (30:25) Does it matter what time you enter the market as a VC? (37:04) IRR (internal rate of return) versus and multiple on cash (46:25) Packy's weekly cadence for investing and writing (51:39) OK Boomer - Rachel Reporting from Miami Hack Week

    Check out Not Boring: https://www.notboring.co

    FOLLOW Packy: https://twitter.com/packym

    FOLLOW Rachel: https://twitter.com/_@rachelbraun

    FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

    1 hr 3 min
  • $TSLA earnings breakdown & 2022 IPOs to watch with TechCrunch's Alex Wilhelm | E1371

    Alex Wilhelm from TechCrunch joins Molly and Jason for a full episode. First, they breakdown Tesla's Q4 2021 earnings including its consistently increasing Model 3 production, profitability and charger network growth (3:08). Next up, they discuss why Alex thinks the IPO window is closed for most startups. We wrap with a review of some of 2022's most anticipated IPOs including Discord, Reddit, Stripe, Impossible Foods, Chime and Instacart (24:45).

    (00:00) Jason & Molly intro the show (01:49) Welcoming Alex to the pod (03:08) Tesla's Q4 2021 earnings (08:45) Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout! (10:14) Tesla's growing supercharger network (14:34) Comparing valuations and EV offerings of automakers (19:56) Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist (20:59) Long distance road trips in EVs (24:45) Is the IPO window closed? (30:41) Assure - To get 20% off your first Special Purpose Vehicle (SPV) visit https://Assure.co/twist (32:19) Do public market investors have the ability to stomach speculative companies? (36:09) Stripe - Potential 2022 IPO (40:49) Discord - Potential 2022 IPO (47:46) Reddit - Potential 2022 IPO (57:33) "Yes, No, IPO" Impossible foods, Instacart, Chime, Gopuff

    FOLLOW Alex: https://twitter.com/alex FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

    1 hr 12 min
  • $TSLA earnings breakdown & 2022 IPOs to watch with TechCrunch’s Alex Wilhelm | E1371
    Alex Wilhelm from TechCrunch joins Molly and Jason for a full episode. First, they breakdown Tesla's Q4 2021 earnings including its consistently increasing Model 3 production, profitability and charger network growth (3:08). Next up, they discuss why Alex thinks the IPO window is closed for most startups. We wrap with a review of some of 2022's most anticipated IPOs including Discord, Reddit, Stripe, Impossible Foods, Chime and Instacart (24:45).
    1 hr 12 min
  • MSFT adds $10B, Stripe mafia memes, Spotify: platform or publisher, Scratchpad case-study | E1370

    We break down Microsoft's amazing earnings (quarterly revenue is up $10B year-over-year) and assess if Satya Nadella is the greatest big tech CEO right now (2:32). Then, we follow-up on the Stripe Mafia thread yesterday from the Bolt CEO (20:59) and we talk about Neil Young asking to have his music removed from Spotify over Joe Rogan's COVID conversations, which prompted a discussion of Spotify's new headache is it a publisher or a platform (37:40)? And, we talk about Scratchpad raising $33M, which led to Jason's request for new types of startups: beautiful interfaces for giant clunky products.


    00:00 Jason and Molly intro the show 02:32 Microsoft's amazing earnings 09:29 Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist 10:04 Is Satya Nadella the greatest big tech CEO 19:01 Notion - Go to https://Notion.so and use promo code TWIST to get $250 off its annual team plan 20:59 Bolt vs. Stripe VC Twitter beef continued 30:07 Vanta - Get get $1,000 off automating your SOC 2 at https://vanta.com/twist 31:27 The best jokes from Bolt & Stripe 37:40 Neil Young petitioned Spotify to remove his music over Joe Rogan's COVID conversations 43:16 Is Spotify a publisher or a platform? 1:04:39 Scratchpad, a slick Salesforce front-end raises $33M 1:06:23 Request for new types of startups: beautiful interfaces for giant crappy products

    FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

    1 hr 23 min
  • TikTok vs. YouTube, Bolt CEO calls Stripe & YC "Mob Bosses," Culdesac, Anduril wins $1B contract | E1369

    In this all news show Jason and Molly talk about Jason's strategy for meeting with founders (1:48) and we talk about monetization for creators on TikTok and how payouts compare to YouTube (6:48). Then we look at the post where Bolt Founder Ryan Breslow accused Stripe and YC of being Silicon Valley mob bosses (31:41). Our startup of the day is Culdesac, which is building a walkable community in Arizona (45:42). To wrap, we cover Anduril's $1B Department of Defense contract for counter-drone tech, their largest contract to date (58:55).

    00:00 Jason and Molly intro the all news show 01:48 Jason's strategy during founder meetings 06:48 Why creators aren't happy with payouts from the TikTok creator fund 10:10 Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST 11:55 How creator earnings compare between TikTok and YouTube 20:43 Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist 21:52 Jason's hot take on TikTok 24:00 How creators can take advantage of platforms 30:30 Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist 31:41 How Bolt's Founder accused Stripe and YC of being Silicon Valley mob bosses. 45:42 Startup of the day - Culdesac 53:13 Anduril's $1B Dept of Defense Contract for counter-drone tech

    FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

    59 min
  • TikTok vs. YouTube, Bolt CEO calls Stripe & YC “Mob Bosses,” Culdesac, Anduril wins $1B contract | E1369
    In this all news show Jason and Molly talk about Jason's strategy for meeting with founders (1:48) and we talk about monetization for creators on TikTok and how payouts compare to YouTube (6:48). Then we look at the post where Bolt Founder Ryan Breslow accused Stripe and YC of being Silicon Valley mob bosses (31:41). Our startup of the day is Culdesac, which is building a walkable community in Arizona (45:42). To wrap, we cover Anduril’s $1B Department of Defense contract for counter-drone tech, their largest contract to date (58:55).
    59 min
  • Comparing 2022 to the Dot-Com bubble + Activist investor challenges Peloton leadership | E1368

    Due to the volatility in the market, Jason and Molly review the fundamentals of Block, Zoom, Netflix, Coinbase, and AirBnB and compare this correction with the Dot-com crash (2:11). They discuss investing in a downturn, the difference between private and public investors, speculative businesses vs. strong fundamentals and more! To wrap, we cover activist investor Blackwells Capital calling for the Peloton Board to terminate CEO John Foley and consider a sale (57:10).


    (00:00) Jason and Molly intro the show (02:11) Breaking down the fundamentals of Block (09:57) Marketerhire - Get $500 off your first hire at https://MarketerHire.com/twist (11:28) The difference between private and public investors (12:18) Breaking down Zoom & Netflix (20:20) Superside - Go to https://superside.com/twist to get $3000 or more in credits when you sign up for an annual subscription (21:38) Breaking down Coinbase and AirBnB (32:38) FanDuel Sportsbook - Sign up with promo code TWIST to place a special $1000 risk-free bet at https://fanduel.com (34:24) Breaking down AirBnB (38:12) Is crypto really an uncorrelated asset? Fundamentals vs. speculation (46:46) Comparing this correction with the Dot-com crash (51:43 )Are we at peak SPAC? (57:10) Blackwells Capital calling for the Peloton Board to terminate CEO John Foley and consider a sale

    FOLLOW Molly: https://twitter.com/mollywood FOLLOW Jason: https://linktr.ee/calacanis

    1 hr 7 min
  • Sunday VC School: how investors work together + Prime Movers Lab’s Ramez Naam | E1367
    First, Jason teaches Sunday VC School: how investors work together (01:54). In this segment you will learn.

    1. How collaboration varies across investing stages.
    2. How lead investors are determined and what their responsibilities are.
    3. The strategies you can use to win deals (Jason explains the pitch he gives to founders with options).
    4. The warning signs to watch for when working with other investors.
    5. Tactics founders can use for lower-friction fundraising.

    Then, Molly chats with Ramez Naam from Prime Movers Lab in a This Week in Climate Startups segment (35:10). They discuss the declining costs of renewable energy, making the choice between advancing existing technologies and inventing new ones, how science fiction can make you a better investor and more.
    1 hr

About This Week in Startups

From the publisher's feed

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.

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