

This Week in Startups
Jason Calacanis
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.
Episodes
Mentioned books

Feb 2, 2022 • 1h 1min
Playstation's $3.2B Bungie acquisition, Metafy gaming tutoring, Shopify CEO joins Coinbase Board of Directors | E1375
Another big news drop in the gaming space! Jason and Molly discuss Sony is acquiring Bungie for $3.6B (2:36). We break down what this means for Sony, Bungie’s crazy history, and if other big tech giants should look for M&A targets in gaming. Then, we talk about our startup of the day called Metafy which allows pro gamers to do 1-on-1 teaching, online for hourly rates (29:38). Finally we wrap with Shopify CEO Tobi Lütke joining Coinbase’s board (48:33).
(00:00) Jason & Molly tee up the topics, Sony's big acquisition, Metafy
(02:36) Sony is acquiring Bungie for $3.6B & Bungie history
(10:41) Boast - Get your R&D tax credits without the hassle at https://boast.ai/twist
(11:58) Other big tech giants should look for M&A targets in gaming
(19:46) OpenPhone - Get an extra 20% off any plan for your first 6 months at https://openphone.com/twist
(21:27) Current console pricing and Big Tech competition
(29:38) Startup of the day - Metafy is company where pro gamers to do 1-on-1 teaching online for hourly rates
(32:07) RealGoodFoods - Go to https://realgoodfoods.com and use code TWIST for $15 off!
(33:39) Breaking down Metafy's raise and investment terms
(42:11) Jason explains how Blayze is another example of pro-coaching for athletic training
(48:33) Shopify CEO Tobi Lutke joining Coinbase’s board
(01:10:11) Learn what's going on at TWIST
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 1, 2022 • 1h 23min
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).
(0:00) Jason and Molly tee up today’s topics: Bolt CEO steps down after another spicy thread, Rogan “apologizes” for COVID misinformation
(2:11) Bolt CEO Ryan Breslow stepped down as CEO to executive chair: was it really his decision?
(7:07) Jason and Molly break down Breslow’s thread on YC not being worth it for founders
(15:43) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(17:00) Breslow’s YC thread cont.: breaking down Breslow’s five beliefs about YC
(27:53) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist
(29:11) YC scaling fundraising and opening access to venture capital to more groups of founders; Breslow’s advice on building a network and fundraising
(36:03) Marlow - Get 15% off your individual or team memberships at https://getmarlow.com/twist.
(37:18) YC alumni have started a blockchain-based DAO called Orange DAO to invest in crypto startups
(44:32) Joe Rogan’s “apology” video and Spotify’s new COVID disclaimer: Molly nails the prediction, has Spotify done a bad job of content moderation so far?
(53:42) Breaking down Joe Rogan’s explanology (explanation/apology) piece by piece
(1:13:17) Jason breaks down the math of Spotify acquiring Joe Rogan for ~$100M and Howard Stern’s similar deal with Sirius XM
Ryan's Thread: https://twitter.com/theryanking/status/1487500943511932941
Joe Rogan's Video: https://www.instagram.com/p/CZYQ_nDJi6G/
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Jan 30, 2022 • 60min
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

Jan 29, 2022 • 1h 2min
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

Jan 28, 2022 • 1h 11min
$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

Jan 27, 2022 • 1h 23min
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

Jan 26, 2022 • 59min
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

Jan 25, 2022 • 1h 7min
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

Jan 23, 2022 • 59min
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.:
How collaboration varies across investing stages.
How lead investors are determined and what their responsibilities are.
The strategies you can use to win deals (Jason explains the pitch he gives to founders with options).
The warning signs to watch for when working with other investors.
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.
(00:00) Jason and Molly introduce the show
(01:54) Sunday VC School - how investors work together
(06:53) How collaboration varies across investing stages
(08:43) Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist
(09:49) Why seeing other late stage investors be passive in a deal is a warning sign
(11:20) How raising from more investors can be actually be easier than raising from a few
(15:44) Lead investor responsibilities
(20:09) Fellow - Sign up and get $1000 in credits at https://fellow.app/twist
(21:38) How VCs can win over founders
(26:44) Do VCs get offended by what order they get into a startup?
(29:16) Will investors still invest if the founder picked another VCs term sheet?
(31:33) Molly and Jason introduce the next segment
(33:25) Revelo - Get 20% off the first 3 months by mentioning TWIST at https://revelo.io/twist
(35:10) This Week in Climate Startups - Ramez Naam
(37:55) Advancing existing technologies vs. inventing new ones
(42:19) Early stage climate investing
(46:43) The declining costs of renewable energy
(52:52) Confronting climate tech skeptics
(57:06) How writing science fiction impacts Ramez's investing
Check out Prime Movers Lab: https://www.primemoverslab.com/
FOLLOW Ramez: https://twitter.com/ramez
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Jan 23, 2022 • 1h 30min
Apple AR headset scoops with Mark Gurman + Campbell Baron: Gen Z startup content creator | E1366
First, Jason and Molly chat with on the top Apple reporters, Bloomberg's Mark Gurman, about Apple's AR headset (2:02). They talk about Apple's strategy, timeline, competitive strengths and more. Then our Producer Rachel chats with Campbell Baron, a 19-year old who sold his TikTok to Workweek, a new startup-focused media company (1:00:25). Campbell created business content and accumulated millions of views before he turned 18! In the interim, the producers Jason & Molly have a chat about what they are working on, lessons from their early careers and more (35:25).
00:00 Jason & Molly introduce the show
02:02 Bloomberg News' Mark Gurman joins to discuss Apple's headset
06:37 Will Apple enter AR at the expense of iPhone sales?
11:48 Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist
12:58 The next major platform battle
17:37 Expected initial target market for an Apple headset & design cues
21:41 Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout!
23:11 Expected screen resolution and other features
26:37 Forecasting who will be in the lead in 10 years
33:39 OpenPhone - Get an extra 20% off any plan for your first 6 months at https://openphone.com/twist
35:25 Fun banter with Jason, Molly & the This Week in Startups producers
1:00:25 Producer Rachel introduces Campbell Baron
1:08:48 How Campbell sold his TikTok account
1:17:31 Building in public vs. private
1:24:52 Gen Z's way of networking
FOLLOW Mark: https://twitter.com/campbelljbaron
FOLLOW Campbell: https://twitter.com/campbelljbaron
FOLLOW Rachel: https://twitter.com/_rachelbraun
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood


