

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

Aug 10, 2022 • 1h 25min
VC market overview, Vision Fund impact, Amazon's core businesses & more with Acquired | E1530
Acquired's Ben Gilbert and David Rosenthal join the show to discuss how they think about public market investments (1:43), VC token sales (27:25), a VC market overview (45:40), the Vision Fund's impact on Silicon Valley (1:00:33), and Amazon's core pillars! (1:13:21)
(0:00) Jason intros today's guests and topics: Crossover Pod with Acquired!
(1:43) Private markets overview, Jay Trading, Ben's investment thesis for TSMC and Shopify
(13:44) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist
(14:52) Jason makes two live Jay Trades, better solutions for employee stock options
(26:14) Dell - Apply for Dell for Startups and get an additional 10% off Dell Latitude products at https://dell.com/twist
(27:25) Crypto regulation, VC token sales
(39:33) Zapier - Try for free today at https://zapier.com/TWIST
(41:02) The burden of going public, final ideas on digital asset regulation
(45:40) Major takeaways from PitchBook's Q2 US VC Monitor: exit value collapse, deal volume down, seed not impacted as much, signs of life in the early-stage
(1:00:33) Reflecting on Masa's precarious position and the impact that SoftBank's Vision Fund has had on the VC industry
(1:13:21) Ranking the most impressive pillars of Amazon's business: AWS, Prime, marketplace, advertising

Aug 9, 2022 • 1h 14min
SoftBank's Vision Fund loses $21B+, DTC brands struggle + NutriSense CEO Alex Skryl | E1529
Jason breaks down SoftBank's Vision Fund losing $21B+ last quarter and reflects on how founders should approach raising capital from megafunds. (2:11) Then, Jason reflects on lessons learned from the tough DTC space (27:05) and gives a quick Jay Trading update! (36:17). To wrap, NutriSense CEO Alex Skryl joins J+M to break down the benefits of continuous glucose monitoring! (47:37)
(0:00) Jason tees up today's solo news + founder interview!
(2:11) Jason breaks down SoftBank's Vision Fund losing ~$21B+ last quarter and analyzes some clips from Masayoshi Son's investor presentation
(11:31) Microsoft for Startups Hub - Apply in 5 minutes, no funding required, sign up at http://aka.ms/thisweekinstartups
(12:54) Jason disagrees with Masa's new strategy and direction and explains how founders should approach raising capital by megafunds like the Vision Fund and differences between how Uber and WeWork deployed SoftBank capital
(22:46) Assure - To get 20% off your first Special Purpose Vehicle (SPV) visit https://Assure.co/twist
(24:06) Reviewing the biggest hits and misses from Vision Fund I
(27:05) Lessons learned from DTC shutdowns, how VCs deploy capital in a downturn
(34:45) Prometheus - Go to Prometheusalts.com or download it on the App Store and use the access code TWIST to sign up
(36:17) Jay Trading update: $DIS, $AMZN, $WBD, $SFIX
(47:37) Nutrisense CEO Alex Skryl joins to talk glucose monitoring benefits, biohacking, and more!

Aug 7, 2022 • 1h 3min
Why some VCs won't invest in first-time founders + $369B carve-out for climate/energy | E1528
First up on VC Sunday School, J+M cover the stigma around investing in first-time founders: Is it a myth? What are the pros and cons? What really matters when evaluating a founder? (3:01) Then, Molly interviews Jay Koh of The Lightsmith Group to break down the Inflation Reduction Act's $369B climate/energy allocation. (29:08)
(0:00) Jason and Molly tee up today's segments!
(3:01) why is there a bias against investing in first-time founders?
(15:04) OpenPhone - Get an extra 20% off any plan for your first 6 months at https://openphone.com/twist
(16:21) Most important factors to startup success
(21:42 Jason and Molly tee up Molly's climate interview which is focused on the Inflation Reduction Act's $369B climate/energy carve-out
(27:53) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups
(29:08) Jay Koh of The Lightsmith Group joins to break down the $369B earmarked for climate/energy in the Inflation Reduction Act
(36:39) Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist
(37:58) What will the $369B do for the climate VC industry?
(48:48) What will this investment do for America's standing as a global climate tech leader?

Aug 6, 2022 • 1h 18min
$COIN partners with $BLK, $AMZN acquires iRobot for $1.7B, Jay Trading update + OK Boomer | E1527
Solo Jason news day! First up, Jason breaks down Coinbase's performance as a public company and its recent partnership with BlackRock (2:18), then he covers Amazon acquiring Roomba-maker iRobot (18:08), before wrapping the news with a Jay Trading update. (24:53) Producer Rachel wraps the show by interviewing Minted's Marcus Milione for OK Boomer! (52:35)
(0:00) Jason intros today's topics!
(2:18) Jason analyzes $COIN's performance as a public company and its volatile price fluctuations
(14:52) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(15:59) BlackRock partnering with Coinbase to manage its institutional crypto trading business
(18:08) $AMZN acquires Roomba-maker iRobot for $1.7B
(23:38) Helpware - Go to https://helpware.com/TWIST to get $1000 off your first invoice
(24:53) Jason debuts jaytrading.com and gives his reasons for doing it
(30:58) $WBD down ~17% after a bad earnings report
(36:53) Bubbles - Get unlimited screen and video recordings for free at https://usebubbles.com/twist
(38:10) Jason tells a quick story about meeting Bill Clinton & talks to Producer Rachel about her first year of interviews on OK Boomer
(52:35) Rachel interviews Marcus Milione on brand building, monetizing a passion, and more

Aug 5, 2022 • 1h 13min
$WBD shakeup, streaming earnings, Locket raises $12.5M, Lina Khan/FTC sues Meta | E1526
Lon Harris joins the show to break down the chaotic shakeup going on at Warners Bros. Discovery, what's happening with HBO Max, potential new roadmaps for the DCEU, and more. (2:46) Then, J+M break down a new intimate social app called Locket raising $12.5M (44:02) and Lina Khan taking action against Meta. (51:39)
(0:00) J+M intro today's topics!
(2:46) Lon Harris joins to break down what is going on at Warner Bros. Discovery
(14:05) Grammarly - Sign up for a free and get 20% Grammarly Premium at https://grammarly.com/TWIST
(15:22) Is streaming subscription revenue a viable business compared to big box office hauls? Is $WBD making a terrible move re: creative relationships?
(24:26) Indochino - Get $50 off any purchase of $399 or more by using code TWIST at checkout https://www.indochino.com
(25:48) Discovery vs. HBO branding, Roku/Paramount Plus subscriber counts
(38:11) Microsoft for Startups Founders Hub - Apply in 5 minutes, no funding required, sign up at https://aka.ms/thisweekinstartups
(39:34) Lon's crypto queen series update
(44:02) Social app Locket raised a $12.5M early-stage round of funding
(51:39) Lina Khan sues Meta over a ~$400M VR acquisition and tries to change the antitrust precedent

Aug 4, 2022 • 1h 6min
YC reduces S22 batch by 40%, $HOOD RIF, $MSTR CEO change, $ABNB earnings + Blueprint Part 4 | E1525
BIG show! First up, our co-hosts break down why YC cut its summer cohort size by 40% (2:13), Robinhood letting go 23% of its employees (12:40), Michael Saylor out as MicroStrategy CEO (32:09), and Airbnb earnings. (42:07) Then, Jason is back with another edition of The Blueprint, where he covers the benefits of having a bias for action! (48:52)
(0:00) Jason and Molly intro today's topics!
(2:13) Y Combinator cuts its Summer 2022 batch size by 40%: what does this mean for the early-stage market?
(11:35) iTrust Capital - Visit https://itrust.capital/twist to create your Crypto IRA today
(12:40) Robinhood terminates 23% of employees: RIF vs layoff vs furlough explanation
(27:42) Brave - Download today at https://brave.com/twist to browse faster, search privately and so much more
(29:02) Jason gives a Jay Trading recap and lays out his reasons for doing it
(32:09) Michael Saylor steps down as MicroStrategy CEO
(39:14) Visa - Learn more about Visa’s online Small Business Hub at Visa.com/smallbusinesshub
(40:10) Jason's predictions for MicroStrategy's direction
(42:07) $ABNB earnings, comparing $ABNB and $UBER p/s, $COIN and $HOOD p/s
(48:52) The Blueprint Part 4: The Benefits of Having a Bias for Action
(54:12) How bias for action relates to other cognitive biases
(1:02:50) How founders can have a bias for action: Product velocity

Aug 3, 2022 • 1h 22min
$UBER & $PINS Q2 earnings + customer-centric primary care with The Lanby's Chloe Harrouche | E1524
J+M break down Uber and Pinterest's Q2 earnings (2:42), and Jason makes a Jay Trade live on air (18:51). Then, The Lanby CEO Chloe Harrouche joins to break down approaching primary care from a customer-centric perspective. (49:40)
(0:00) Jason and Molly tee up today's show! Big news day + a great early-stage founder interview
(2:42) $UBER Q2 earnings: doubled revenue y/y, FCF positive, rides business is back to pre-pandemic levels
(13:12) Vanta - Get $1,000 off automating your SOC 2 at https://vanta.com/twist
(14:24) Does Airbnb have similar pricing controls as Uber?
(18:51) Jason does a LIVE Jay Trade and explains his investment thesis! ***NOT investment advice
(27:28) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST
(28:45) $PINS Q2, Should public CEOs be able to retain super-voting shares?
(38:01) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist
(39:08) Jason proposes a perfect merger target for Pinterest
(45:44) Jason and Molly tee up the interview with The Lanby CEO Chloe Harrouche
(49:40) Chloe breaks down approaching healthcare from a customer-centric POV, pricing model, unit economics, and more
(1:06:09) Onboarding doctors, scaling the business, opaque pricing in healthcare

Aug 2, 2022 • 1h 25min
TikTok takes on Spotify, startup advice + US housing market w/ Redfin & Divvy Homes CEOs | E1523
First up, Jason and Molly cover TikTok's recent patents that indicate it might be going after Spotify (2:23). Then, the duo breaks down a recent WSJ report about VCs giving conflicting advice to founders. (18:05) After the news, J+M are joined by Redfin CEO Glenn Kelman and Divvy Homes CEO Adena Hefets for an in-depth break down of the current US housing market. (33:36)
WSJ article: https://www.wsj.com/articles/silicon-valley-lurches-between-deep-cuts-and-bold-spending-11659268801
(0:00) Jason and Molly tee up today's topics and guests!
(2:23) TikTok might be going after Spotify's music streaming business with "TikTok Music"
(16:45) Policygenius - Go to https://policygenius.com to get a free life insurance quote
(18:04) Jason and Molly break down a WSJ report about conflicting advice that VCs are giving to founders re: approaching the current downturn; Jason debuts his "Cash vs. Profitability Matrix"
(32:04) Notion - Get $250 off by using code TWIST at https://notion.so
(33:36) Redfin CEO Glenn Kelman and Divvy Homes CEO Adena Hefets join and break down their businesses before getting into how a 2022 housing downturn might be different from 2008
(41:36) Prometheus - Go to Prometheusalts.com or download it on the App Store and use the access code TWIST to sign up
(43:09) Institutional buyers' impact on housing supply, pandemic migration impact on local inflation, new construction outlook
(1:08:36) Rental market outlook, commercial real estate's grim projections

Jul 31, 2022 • 53min
How VC diligence works at different stages + Fion's Sudarshan Sridharan on wildfire tech | E1522
First up on the Sunday show, Jason breaks down the different levels of diligence at different company stages for VC Sunday School (2:02). Then, Fion Technologies CEO Sudarshan Sridharan joins to talk helping firefighters fight wildfires with mapping technology. (21:31)
(0:00) Jason tees up today's Sunday edition of This Week in Startups!
(2:02) Molly recaps her first half year of investing, then asks Jason about diligence at different stages of investing in different verticals
(10:23) UserTesting - Get real human insights from customers, try for free today at https://usertesting.com/twist
(11:40) Jason on great investments coming out of "prepared minds", the importance of testing and trying
(19:57) OpenPhone - Get an extra 20% off any plan for your first 6 months at https://openphone.com/twist
(21:31) Molly welcomes Fion Technologies CEO Sudarshan Sridharan to discuss helping wildfire fighting with software and his founding story
(32:36) Brave - Download today at https://brave.com/twist to browse faster, search privately and so much more
(33:56) Sudarshan explains how the Fion app helps firefighters, its pricing model, and more
(41:06) The state of wildfires in the US, why Sudarshan is building Fion

Jul 30, 2022 • 1h 9min
$AMZN & $AAPL earnings, $META investors losing faith, Jay Trading + OK Boomer with Nate O'Brien | E1521
Jason is BACK and he's ready to Jay Trade! Jason and Molly wrap up big tech earnings week with a major deep dive on $AMZN's impressive quarter (1:53), $AAPL's slowing revenue growth/growing subscriber base (26:04), and the lack of faith in $META's big bet. (31:44) Producer Rachel wraps the show with another great edition of OK Boomer, featuring popular YouTube and investor Nate O'Brien! (40:18)
(0:00) Jason is BACK for a huge news day!
(1:53) $AMZN Q2 was highlighted by two insane business segments: AWS and advertising
(18:20) iTrust Capital - Visit https://itrust.capital/twist to create your Crypto IRA today
(19:24) Continued breakdown of $AMZN's Q2: Amazon Prime and retail; Jason makes another Jay Trade and gives his investment thesis for $AMZN
(24:43) MicroAcquire - Sell your business with no fees at https://try.microacquire.com/twist
(26:04) $AAPL earnings: slowing growth, but still putting up huge numbers, Apple's 800M+ paid subscribers
(31:44) Antitrust action against Meta, Jason gives his take on Meta's all-in bet on the metaverse
(39:01) Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist
(40:18) OK Boomer: Investor & YouTuber Nate O'Brien joins to talk growing his YouTube to 1M+ subscribers, his journey to investing, and more


