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 17, 2026

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Episodes

ANGEL: Canaan's Maha Ibrahim on fund sizing, distribution strategies & early VC days | E1687 28.02.2023

Maha Ibrahim of Canaan joins Molly to discuss her early days in VC (1:38), managing distributions and exiting at the right time (20:36), the clean tech bubble, being a generalist/specialist, diversity, and more (37:42). (0:00) Molly kicks off the show (1:38) Maha's first years in venture (11:18) LinkedIn Jobs - Go to https://linkedIn.com/angel and post your first job for free. (12:43) Investing in...

Neeva CEO Sridhar Ramaswamy on AI chatbots and the search revolution | E1686 27.02.2023

Neeva CEO Sridhar Ramaswamy joins Molly to talk all things search and AI chatbots, including Neeva's technology and the difficulty of building a search engine (1:41), Neeva's consumer focus and business model (20:00), and the search-to-answer revolution (41:31). (0:00) Molly kicks off the show (1:41) Neeva's Purpose (5:06) The technological underpinning of Neeva (8:00) The hurdles building Neeva (...

WallStreetBets founder on why he's suing Reddit; Andrew Hart of Hyper; and Ok Boomer | E1685 24.02.2023

The Friday variety show is back! Jason kicks it off by interviewing WallStreetBets founder Jaime Rogozinski, who's currently suing Reddit (2:08). Then, Molly is joined by Hyper CEO Andrew Hart to discuss the augmented reality market and Hyper's store-mapping technology (30:16). Producer Rachel wraps the show with content creator Humphrey Yang breaking down his creative process, what he considers v...

Sophia Amoruso on branding, raising a fund, portfolio construction & more | E1684 23.02.2023

Sophia Amoruso, Founder and GP at Trust Fund, joins Jason to discuss her angel investments (1:23), raising a fund publicly (5:54), and the creative process (12:14). Then, they discuss portfolio construction and putting past identities to bed (27:04). (0:00) Molly kicks off the show (1:23) Previous angel investing experience (5:54) Why Sophia is raising a public fund (10:45) Linode - Apply to Linod...

ANGEL: Upfront's Mark Suster on the power of alignment, setting reality, and raising capital | E1683 22.02.2023

Jason is joined by Mark Suster of Upfront Ventures to cover raising capital in the early 2000s (1:22), aligning board members (21:19), the three variables VCs need to bet on (40:51), and so much more! (0:00) Molly kicks off the show (1:22) A recap of the previous 3 market cycles (5:23) The hurdles founders will face starting a company in 2023 (6:55) Raising capital in the early 2000s (9:15) Linked...

Brain-computer interfaces and the future of neural engineering with Dr. Benjamin Rapoport | E1682 21.02.2023

Precision Neuroscience's Co-Founder and Chief Science Officer joins Molly to discuss how the brain communicates with the body (7:08) and the breakthroughs that allowed companies like Precision to exist. (12:52) Then, they discuss Precision's founding principles, the process of getting FDA approval for its neural interface, and much more. (28:55) (0:00) Molly kicks off the show (1:27) Dr. Rapoport'...

Meta's paid tier, Bing's chatbot gone wild, Stripe's $4B bill | E1681 21.02.2023

First up, J+M break down Meta taking a note from Twitter with a $12 paid tier and how it can have a material impact on revenue. (12:05) Then, they cover the problems with Bing's new chatbot (32:13) before wrapping on Stripe potentially missing its window (46:14) and Meta copying a Telegram feature! (1:00:30) (0:00) J+M tee up today's topics! (2:22) Proper PTO operating standards, what's in store f...

US crypto crackdown with Vinny Lingham & Sunny Madra + OK Boomer | E1680 17.02.2023

Vinny and Sunny join Jason and Molly for another crypto roundtable discussing the federal government's crackdown on crypto. (1:39) They define what staking is (10:13), and Jason addresses his Twitter Exchange with Coinbase founder and CEO Brian Armstrong. (32:20) Then Producer Rachel is joined by Prince Ghosh of Factored Quality for another edition of Ok Boomer. (1:06:45) (0:00) Molly kicks off th...

ANGEL: Insight's Deven Parekh on venture tourists, cleaning cap tables & winning investments | E1679 15.02.2023

Deven Parekh of Insight Partners joins Jason to discuss navigating markets during the dot com era and the pandemic. (1:50) Then they discuss "venture tourists" and cleaning up cap tables before wrapping up with a look back at some of Deven's winning investments. (20:04) (0:00) Jason kicks off the show (1:50) Experiencing the dot com burst (10:14) LinkedIn Jobs - Go to https://linkedIn.com/angel an...

Bing dodges $100B bullet & IVP's Tom Loverro on the looming startup collapse | E1678 14.02.2023

Molly is joined by Rachel as they discuss the news that some companies are selling data about their mental health patients. (1:33) Then they discuss how Bing's AI chatbot was presenting false information during its reveal last week. (11:57) To wrap, Tom Loverro joins Jason to talk about his viral tweet thread about a "mass extinction event coming for early & mid-stage companies". (24:36) (0:00) Mo...

ChatGPT's alter ego and moderating AI-generated content | E1677 13.02.2023

Molly and Jason kick off the show catching up after the weekend, discussing the Super Bowl and the spy balloons that the US airforce has shot down. (1:30) Then they have a very interesting conversation about bypassing ChatGPT's guardrails and content moderation. (23:29) (0:00) M+J kick off the show (1:30) Super Bowl 57 (8:33) LinkedIn Jobs - Post your first job for free at https://linkedin.com/twi...

ANGEL: Surviving a down market, early VC stories & more with four-cycle investor Geoff Yang | E1676 11.02.2023

Four-cycle investor and Redpoint Ventures Co-Founder Geoff Yang joins to discuss his early years in VC (1:45), what it takes for a founder to survive in a down market (11:47), what makes CEOs like Frank Slootman and David Zaslav stand out, and more! (43:35) (0:00) Jason kicks off the show (1:45) Geoff Yang's experience cracking into VC (10:26) LinkedIn Jobs - Go to https://linkedIn.com/angel and p...

Airbnb Co-Founder Joe Gebbia on early "a-ha" moments, elite design + his new startup Samara | E1675 08.02.2023

Joe Gebbia joins Jason to discuss the early days of Airbnb, gaining traction, persevering through the "no's," and functional design. (2:09) They also discuss gaining customer trust and Airbnb's incredible COVID turnaround. (21:17) Joe wraps the show by breaking down his new venture, Samara. (45:05) (0:00) Jason kicks off the show (2:09) Airbnb's first sign of traction (9:05) Vanta - Get $1000 off...

Google announces Bard, Adam Neumann's business plan, Blue Collar tech's moment | E1674 07.02.2023

Molly and Jason discuss Google's announcing plans to roll out its ChatGPT competitor, called Bard, in the coming weeks. (1:10) Then, they discuss Adam Neumann's explanation of Flow's business before wrapping up with a SOTD, Jobber. (18:59) (0:00) M+J kick off the show (1:10) Breaking down Google's announcement of Bard (9:29) Coda - Startups can get $1000 credit by visiting https://coda.io/twist (1...

The AI arms race escalates: Google's $300M bet, Neeva's paid search engine + So Syncd CEO | E1673 06.02.2023

Molly breaks down Google's $300M investment in Anthropic and how this deal compares to Microsoft's investment in OpenAI. (2:00) Then, she dives deep into a former Google executive's paid search engine and ShiftMed raising $200M to solve the nursing shortage. She wraps the show with an interview featuring the CEO of dating app So Syncd, Jessica Alderson. (13:44) (0:00) Molly kicks off the show (2:0...

Google, Amazon & Apple earnings + OK Boomer with Slush CEO | E1672 03.02.2023

Molly is off for the day, so Producer Rachel joins Jason to break down Google, Amazon, and Apple's latest earnings report. (1:29) Then LA26 graduate Perrin Davidson, CEO of EATERCLUB, joins Molly. (46:05) Lastly, we end the week with another edition of Ok Boomer, where Rachel interviews Eerika Savolainen, the CEO of Slush. (1:02:16) (0:00) Jason and Rachel kick off the show! (1:29) Google earnings...

Meta's massive comeback, FED's latest hike, GPT-4 rumors + Spotify earnings with Lon Harris | E1671 02.02.2023

Jason and Molly kick off the show by discussing Meta's Q4 earnings and the news that the Fed is raising rates by only 25 basis points (3:06), which leads to a discussion on unemployment, automation, and generative AI updates. (11:24) Then, Lon Harris joins to discuss Oscar nominations, Spotify earnings, "peak podcasting," and more. (37:51) (0:00) M+J kick off the show (3:06) Meta Earnings (7:56) T...

ANGEL: FirstMark's Rick Heitzmann on shaking off the bull run, "shock absorbers," and more | E1670 02.02.2023

Jason is joined by FirstMark Capital's Rick Heitzmann, who started his investment career in 1999. They discuss "sobering up" after the 14-year bull run (1:55), Airbnb's response to the downturn (7:38), how senior leaders must act as shock absorbers for their founders (26:30), and more! (0:00) Jason kicks off the show (1:55) Rick's experience of the "Speculative Asset Bubble" (7:38) Airbnb's reacti...

Instagram co-founders team up for new startup + Magic Spoon's Gabi Lewis | E1669 01.02.2023

Jason and Molly kick off the show with a quick third-rail story about Area 51. (1:56) They then cover Instagram co-founders Mike Krieger and Kevin Systrom's new startup, Artifact. (10:44) Finally, Gabi Lewis of Magic Spoon joins Molly for an awesome interview about their latest raise, launching in big box stores and more. (41:56) (0:00) Molly Kicks off the show (1:56) Conspiracy Theories with Moll...

Anthropic seeking $5B valuation, OpenAI hires 1000 contractors, Mr. Beast's latest video | E1668 30.01.2023

Jason and Molly kick off the week with a generative ai update! (5:00) Then, they cover Mr. Beast's latest video and "stunt culture" (35:21), some more third-rail topics (49:40), and Billy McFarland being back in the news! (59:50) (0:00) M+J kick off the show (2:10) Apply to Founder University 2-Day Workshop at https://intensive.founder.university/ (5:00) Anthropic raises at a $5B valuation (9:31)...

MSG's facial recognition software, BuzzFeed's deal with Meta, The Creator Economy and more | E1667 27.01.2023

Please take our 90-second audience survey for a chance to win a $50 amazon gift card at www.thisweekinstartups.com/survey Molly and Jason chop it up about New York Attorney General Letitia James probing into MSG's alleged use of facial recognition to identify and target specific patrons (1:46). This segues into a great discussion about Meta's $10M deal with BuzzFeed and The Creator Economy as a wh...

Macro picture, Bitcoin's bull/bear case, DCG controversy & more | E1666 27.01.2023

Please take our 90-second audience survey for a chance to win a $50 amazon gift card at www.thisweekinstartups.com/survey Vinny and Sunny are back for our first crypto-roundtable of 2023. Vinny breaks down the macroeconomic variables affecting Bitcoin's price (1:39), plus they all predict whether Bitcoin will hit $30K or $16 first (11:43) (This is not financial advice). They delve into the ongoing...

ANGEL: Venrock's Bryan Roberts on 25 years in VC, hitting wins early, avoiding bad habits | E1665 25.01.2023

Please take our audience survey!: https://launchevents.typeform.com/to/K5RhKaEH Jason sits down with Bryan Roberts of Venrock for another episode of Angel Season 7! They discuss Bryan's first bets (2:22) and his perception of the dot com bubble. (14:38) The two also dive into topics like creating optionality as a startup (21:24), bad habits in VC (28:49) and Theranos. (36:18) To wrap the show, Bry...

DOJ sues Google over ad practices, Ticketmaster takes the stand + LA26 founders | E1664 24.01.2023

Please take our audience survey!: https://launchevents.typeform.com/to/K5RhKaEH Molly goes solo today to cover the DOJ joining eight states to file an anti-trust lawsuit against Google (2:04) before covering Ticketmaster taking the stand in a Senate hearing today. (15:37) Producer Rachel then joins to discuss the latest on user-friendly ticket competitors. (23:07) Then, Molly is joined by two diff...

Employee reactions to Google layoffs, Microsoft & OpenAI codify deal + NVIDIA's new feature | E1663 23.01.2023

Join Molly and Jason as they react to TikToks posted by former Google employees who have recently been let go. They discuss why Google is letting people go despite their massive profits (8:54). They also explore Open AI and Microsoft's codified partnership (38:39) and the report from the WSJ that activist investor Elliot Management has invested billions into Salesforce (45:06). To end the show, we...

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