Jason Calacanis

This Week in Startups

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.

Be sure to visit the podcast's website and support the creator: thisweekinstartups.com

Author

Jason Calacanis

Category

Technology

Podcast website

thisweekinstartups.com

Latest episode

Oct 24, 2026

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Episodes

E1 All-In with Chamath Palihapitiya & Jason Calacanis: US Response to COVID-19 & Impact on Startups, Venture Capital & Public Markets with David Friedberg 19.03.2020

0:01 Jason & Chamath intro David and check in on each other's quarantines 2:26 Has the US overreacted or underreacted so far? David & Chamath give their opinions on new directives & statistics 13:15 Thoughts on potential treatment options & policy changes 22:25 Chamath explains the circumstances of recording a podcast while the Stock Market tanks in real-time 25:03 Should the US adopt Chinese & So...

E38: "Angel" Podcast: 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 18.03.2020

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 F...

E1037: LAUNCH Accelerator Class 16 Founders of BasicBlock (payment solution for truckers), DaoCloud (lead-gen for health & wellness practitioners) & Lately (AI-powered social media writing software) reflect on their journeys through the program 17.03.2020

0:38 Jason explains the LAUNCH Accelerator 5:39 BasicBlock CEO Taylor Monks details his journey through the LAUNCH Accelerator 14:58 BasicBlock CEO Taylor Monks' biggest takeaways from the Accelerator 27:35 DaoCloud CEO Max Coleman describes his journey into the LAUNCH Accelerator 37:34 How did Max grow throughout the Accelerator? 48:36 Lately CEO Kate Bradley-Chernis describes her experience at t...

EMERGENCY POD: E0 All-In with Chamath Palihapitiya & Jason Calacanis: COVID-19 Political, Economic & Social Ramifications featuring The Production Board's David Friedberg (frmly Founder/CEO, The Climate Corporation) 15.03.2020

0:01 Jason intros Chamath and Episode 0 of All-In and they discuss their current self-quarantine 0:55 Jason intros David Friedberg 1:35 Chamath gives the inaugural (& potentially final) All-In ad read 2:17 As a Warriors owner, Chamath gives his reaction to the NBA postponing & uncoordinated actions of government & private sectors 4:37 Why was the US so slow to react on both an individual & governm...

E1036: #AskJason Special! When to join a startup to maximize equity & job security, types of companies that will thrive in an economic downturn, legendary founder & investor traits, tips for starting a podcast & more! 13.03.2020

0:01 Jason intros today's topics 2:15 George calls in and asks Jason about social media interference in the 2020 election 11:13 Joey calls in and asks Jason for some tips on starting and growing a podcast 21:05 Dan asks Jason about which health-tech startup idea to pursue 26:49 Alex calls in and asks Jason about the types companies that will thrive in an economic downturn 34:35 Karen asks Jason ab...

E37: "Angel" Podcast: 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 11.03.2020

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 busi...

E1035: SoftBank Managing Partner Jeff Housenbold on deploying the $100B Vision Fund, getting recruited by Masayoshi Son, counseling founders to manage massive capital, creating moats, reasons for shift toward profits, lessons from WeWork & more 10.03.2020

0:40 Jason intros Jeff Housenbold 2:16 What did Jeff do before joining the Vision Fund? How did he help scale eBay & Shutterfly? 4:15 How did he wind up at SoftBank? What was it like being recruited by Masayoshi Son? How did Masa pitch the Vision Fund to Jeff? 13:28 What was the timeframe for deploying the $100B Vision Fund? 18:10 How does SoftBank size their bets and how do they counsel founders...

E1034: Formlabs CEO & Co-Founder Max Lobovsky shares insights on hitting $100M in revenue as a 3D printing platform, most lucrative use cases, growing organically, best 3D printing examples in science fiction 06.03.2020

0:54 Jason intros Max Lobovsky 3:21 What is Max's business with Formlabs? What are people printing? Is it hitting scale with consumers yet? 10:52 Where does the majority of their business come from? 15:40 Is coronavirus impacting the supply-side of Formlabs? 20:16 Understanding the most lucrative use cases for 3D printing 21:58 What skill do you need to be a 3D modeler? 31:04 How did Max raise his...

E36: "Angel" Podcast: 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 04.03.2020

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 bus...

E1033: News Roundtable! Lambda School CEO Austen Allred & General Catalyst Partner Katherine Boyle on Lambda School controversy, Techlash & late-stage journalism, Robinhood down as Dow jumps & more! 03.03.2020

0:54 Want to see what it's like to be an Angel Investor in Jason's Syndicate? DM @thesyndicate415 to read Jason's last 3 deal memos 1:37 Jason intros Austen Allred & gets his side of the recent Lambda School controversy 6:22 Jason intros Katherine Boyle & gets her take on how she would have advised Austen on PR 7:58 Explaining Lambda School in simple terms 13:10 Setting up Lambda School as a count...

E1032: News Roundtable! Robinhood Snacks' Duo Jack Kramer & Nick Martell on Coronavirus' impact on public markets, Iger out at Disney – Buy or Sell?, link-baiting Tesla crash, defining Cult Stocks & more! 27.02.2020

0:42 Jason intros Jack Kramer & Nick Martell of Robinhood Snacks 1:06 Starting Market Snacks as a side hustle after rooming together in college 13:24 What Series of Robinhood were they acquired at? 14:11 Jason's origin story meeting Vlad & investing in Robinhood 18:38 Coronavirus impact on the public market... worrisome or no big deal? 30:16 Iger steps down as Disney CEO, will this hurt them long-...

E35: "Angel" Podcast: Sarah Tavel, Partner at Benchmark shares insights on getting recruited by Peter Fenton, disrupting VC gender norms from the inside, transitioning from operator to investor & more 26.02.2020

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...

E1031: Zumper CEO & Co-Founder Anthemos Georgiades makes renting an apartment as easy as booking a hotel, shares insights on monetizing marketplaces, diversifying revenue streams to limit downside, Airbnb's effect on the rental market & more! 25.02.2020

0:44 Jason shares some thoughts on hard work 1:52 Jason intros Anthemos Georgiades and they discuss how Zumper was launched at TechCrunch 4:02 How did Anthemos wind up as a founder after working in consulting 6:45 What is Zumper's origin story? How many iterations did they go through before coming up with an MVP? 15:34 How did Zumper monetize their marketplace? 18:30 Partnering with Facebook & div...

E1030: News Roundtable! Zapier CEO Wade Foster & Early-Stage Investor Monique Woodard on Tech Journalists vs. Founders/VCs, Twitter's fake news detection, Kickstarter union, Blue Apron plummeting, Lambda School controversy & more! 22.02.2020

0:36 Jason intros Monique & Wade 8:29 Tech Journalists vs. Founders/VCs 14:48 Is link-baiting press a systemic, societal issue? 19:21 Future of Founders/VCs controlling their own voice via podcasts, email newsletters, etc. 23:59 SpaceX sending passengers into space in late 2021, early 2022 28:02 Kickstarter employees vote to Unionize 41:28 Gray New World - how lucrative is the growing elderly demo...

E34: "Angel" Podcast: George Zachary, General Partner at CRV shares insights on cancer scare shifting his focus to investing in health-tech, passing on Google at MDV, CRISPR & "designer babies", coronavirus threat, origins of Sand Hill Road & more 19.02.2020

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 19...

E1029: Basecamp Co-Founder & Author David Heinemeier Hansson (@DHH) debates Jason on reining in capitalism, benefits of state-run education & healthcare, big-tech disappointments, work-from-home paradigm shift, wealth tax & more! 18.02.2020

0:56 Jason intros David Heinemeier Hansson (@DHH) and asks about the work-from-home paradigm shift 5:28 Measuring programming success via budgets instead of estimates, quantifying creativity 9:57 Are incentive systems inherently bad? 13:01 How terrible commutes turned the tides for remote work in Silicon Valley, why do executives subject themselves to horrible working conditions? 17:59 What is the...

E1028: Laura Huang, author of "Edge: Turning Adversity into Advantage" shares insights on overcoming disadvantages to create an edge, being bitter vs. getting better, structural bias in tech & more 14.02.2020

0:41 Jason intros "Edge" Author Laura Huang 3:00 How do Harvard MBA students compare with Stanford MBA students? 7:17 Why did Laura write "Edge" at this time? 8:55 Overcoming disadvantages based on race, ethnicity & gender 14:56 Laura's experience reading her own audiobook 17:23 What does her research show about structural bias against Female entrepreneurs? 23:33 How can a founder turn adversity i...

E33: "Angel" Podcast: Dan Rose, Chairman at Coatue Management is leading a $700M early-stage fund, shares insights on working with Bezos & Zuckerberg during pivotal years at Amazon & Facebook, 100+ angel investments, standout founder traits & more 12.02.2020

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...

E1027: Orreco CEO & Founder Dr. Brian Moore built a platform that optimizes performance of elite athletes, shares cutting-edge benefits of blood sampling, biomarkers, inflammation reduction, glucose monitoring & more! 11.02.2020

0:46 Jason intros Dr. Brian Moore 3:39 What does Orreco do and how do they help elite athletes? 4:46 Do they sample blood? 6:33 What teams do they work with? 7:50 What is a bio-marker? 9:05 Why has inflammation monitoring become so popular? 15:01 Brian demos the Orreco app 22:56 What are the top reasons for elite athletes to use Orreco? 28:06 How did Brian get into this business? 30:34 How does bl...

E1026: Cocoon Co-Founders Sachin Monga & Alex Cornell are building an intimate app to connect close circles, share insights on key standout features, raising money as a messaging app, breeding trust via strong domain names, ideal customers & more 07.02.2020

0:57 Jason intros Alex & Sachin 4:46 When and why did they start Cocoon? 6:40 Why did Facebook keep changing their developer tools platform? 9:22 What is the vision for Cocoon and who is it made for? 14:58 How did they get the cocoon.com domain name and why do strong domain names breed trust? 16:57 What are they doing with customer data and how will they monetize? 20:20 Cocoon demo and Alex takes...

E32: "Angel" podcast: Season 4 Premiere! Sarah Cannon, Partner at Index Ventures, shares insights on investing in the future of work, underrated emerging startup markets, going from the Obama Administration to Venture Capital, increasing upward mobili 05.02.2020

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...

E1025: #StartupTuneup @ Founder.University Part 2!: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on AI driving assistance, sleep-aid wearables, marijuana, B2B food analytics & more! 04.02.2020

1:07 Megan pitches Moment AI (facial recognition software that helps drivers) 3:19 Juan pitches DreamOn (wearable and app that help you fall asleep and sleep better) 5:38 Elissa pitches Fumé (marijuana products) 7:46 Feedback & questions for Cohort 3 19:54 Rankings for Cohort 3 23:38 Stewart pitches EVOLUTIONS (marketplace for financial fitness) 25:34 Nadia pitches Keybee (marketplace for short-te...

E1024: #StartupTuneup @ Founder.University: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on merging communication networks, athlete performance tracking, DTC women's clothing, smart tabletop gaming systems & more! 04.02.2020

1:31 Bryan pitches Project OWL (smart communications platform) 3:46 Erin pitches Nude Barre (DTC eco-friendly hosiery) 6:02 Mike pitches STACT (Athlete performance tracking) 8:05 Feedback & questions for Cohort 1 16:53 Rankings for Cohort 1 19:53 Jonathan pitches Move38 (smart tabletop gaming) 22:04 Brandon pitches ReplyBuy (text messaging support for sports, entertainment & higher education) 24:2...

E1023: News Roundtable! Machine Zone CEO Kristen Dumont & The Register's Iain Thomson on Bezos phone hack, Tesla valuation skyrocketing, DJ Elon, Coronavirus, Barstool Sports funding, unions, proposed Uber/DoorDash merger & more! 01.02.2020

0:48 Jason intros Iain Thomson & Kristen Dumont 1:58 Iain on the grim state of his WeWork office 4:34 Bezos phone hack, Saudi interference 15:12 DJ Elon plays Jason out of the break 16:45 $TSLA vs. $TSLAQ, Elon haters & more 23:07 Airborne Tesla in LA 27:30 Coronavirus effects on business, are China's numbers legit? 35:27 How regulated are food markets in China? 47:46 Iain's thoughts on Brexit 50:...

E1022: One Drop CEO & Founder Jeff Dachis helps people with diabetes manage & improve their blood-sugar levels, shares insights on making data actionable, recent strategic partnership with Bayer, issues with US healthcare & potential life-expansion 28.01.2020

0:47 Jason intros One Drop CEO Jeff Dachis 2:37 What was Jeff's original vision with One Drop? How has it evolved over time? 5:39 How did One Drop go from collecting data to making it actionable? 8:09 How important was getting the One Drop retail products into Apple stores? 9:46 Raising money as a hardware healthcare product 15:23 How did the Bayer partnership come about? 17:57 Have any major drug...

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