This Week in Startups

This Week in Startups is brought to you by… LinkedIn Marketing. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to linkedin.com/thisweekinstartups Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at vanta.com/twist CLA. Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at CLAconnect.com/tech * Today’s show: Bill Gurley and Sunny Madra join Jason to discuss open-source AI vs. proprietary AI (1:12), friends and foes of open-source AI (5:42), and strategic choices companies make between open and closed approaches (9:48). Then, Sunny demos more AI tools (22:45), and much more! * Time stamps: (0:00) Sunny Madra joins Jason (1:12) Bill Gurley joins to break down open-source vs. proprietary AI (5:42) Friends and foes of open-source AI (8:17) LinkedIn Marketing - Get a $100 LinkedIn ad credit at https://linkedin.com/thisweekinstartups (9:48) Strategic choices companies make between open and closed approaches (21:37) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (22:45) Sunny demos LLaVA: Large Language and Vision Assistant (29:56) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech (31:00) Sunny breaks down parameter models (38:56) Companies manufacturing their own chips (42:26) Sunny demos Mistral AI (46:56) Jason and Sunny demo Meta AI on WhatsApp (50:44) FTX and the SBF trial * Follow Bill: https://twitter.com/bgurley Follow Sunny: https://twitter.com/sundeep * Check out LLaVA: https://llava-vl.github.io/ Check out Mistral: https://huggingface.co/spaces/Open-Orca/Mistral-7B-OpenOrca?utm_source=substack&utm_medium=email * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… House of Macadamias is the next big health trend! Get a free month's supply of Macadamia Milk with any order at https://houseofmacadamias.com/twist by using code TWIST20! Roots. Invest in the only real estate investment trust that creates wealth for you and its residents at https://investwithroots.com/TWIST Embroker. The Embroker Startup Insurance Program helps startups secure the most important types of insurance at a lower cost and with less hassle. Save up to 20% off of traditional insurance today at Embroker.com/twist. While you’re there, get an extra 10% off using offer code TWIST. * Today’s show: Jason breaks down the SBF trial (11:47), the peak of the crypto hype (19:15), and takes a few live questions (42:26)! * Time stamps: (0:00) Jason kicks off the show (1:42) Michael Lewis’ book and FTX’s downfall (10:18) House of Macadamias - Get a free month's supply of Macadamia Milk with any order at https://houseofmacadamias.com/twist by using code TWIST20! (11:47) SBF’s trial and the prosecutor's argument (15:42) The reasons people flipped on SBF (19:15) Crypto hype, wash trading, and the reason for regulations (23:31) Roots - Head to https://investwithroots.com/TWIST to sign up and start investing today! (25:05) The defense's argument (28:49) How investors look at SBF and the importance of governance in a startup (33:57) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist (35:12) Witnesses and Jason's verdict prediction (42:26) Questions from live audience! * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… Embroker. The Embroker Startup Insurance Program helps startups secure the most important types of insurance at a lower cost and with less hassle. Save up to 20% off of traditional insurance today at Embroker.com/twist. While you’re there, get an extra 10% off using offer code TWIST. With Mercury Raise, startup founders no longer have to navigate roadblocks alone. Visit mercury.com/raise to get access to a network, connections, and advice. Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. NetSuite. Once your business gets to a certain size the cracks start to emerge.  Things you used to do in a day take a week. You deserve a customized solution - and that's NetSuite. Learn more when you download NetSuite’s popular KPI Checklist - absolutely free, at NetSuite.com/twist. * Today’s show: Jason breaks down Amazon’s Anthropic deal and the state of AI mega-rounds (5:29), Flexport’s growing pains through the lens of founding CEO vs. hired gun (24:58), and DoorDash’s new stealthy “Dine Out” feature (44:52). * Time stamps: (0:00) Jason kicks off the show (2:42) Recap of Anthropic's big week (5:29) Amazon’s Anthropic deal and the state of AI mega-rounds (7:35) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist (9:04) Two major details in Amazon’s Anthropic deal (18:57) Strategic investors and Anthropic’s corporate structure (23:32) Mercury Raise - Visit http://mercury.com/raise to get access to a network, connections, and advice (24:58) Flexport’s growing pains through the lens of founding CEO vs. hired gun (35:17) Why Dave Clark being fired “for cause” instead of being allowed to resign matters (38:20) NetSuite - Download your free KPI Checklist at http://netsuite.com/twist (39:45) Flexport's offer to Clark (44:52) DoorDash’s new stealthy “Dine Out!” feature * Reuters article: https://www.reuters.com/markets/deals/amazon-steps-up-ai-race-with-up-4-billion-deal-invest-anthropic-2023-09-25/ The Information article: https://www.theinformation.com/articles/openai-rival-anthropic-in-talks-to-raise-2-billion-from-google-others-as-ai-arms-race-accelerates CNBC article: https://www.cnbc.com/2023/10/02/the-inside-story-of-dave-clarks-tumultuous-last-days-at-flexport.html * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… Roots. Invest in the only real estate investment trust that creates wealth for you and its residents at https://investwithroots.com/TWIST Squarespace. Turn your idea into a new website! Go to https://Squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. LinkSquares. Life for in-house legal just got a whole lot easier. From contract creation to execution and more, LinkSquares is the go-to for all your legal needs. Learn more at https://linksquares.com/twist * Today’s show: Kayak CEO Steve Hafner joins Jason to discuss the current landscape of the travel industry (1:56), its economic dynamics (17:40), emerging trends in hospitality (41:08), and much more! * Time stamps: (0:00) Kayak CEO Steve Hafner joins Jason (1:56) The state of the travel industry today and the adoption of AI (10:50) Roots - Head to https://investwithroots.com/TWIST to sign up and start investing today! (12:15) Navigating shifts in UI and building bulletproof features for at-scale companies (15:32) Kayak's response to the impact of Covid-19 on the industry (17:40) The economics of the travel industry (28:14) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/twist (29:36) OpenTable, diner ratings, and the advent of QR code ordering (34:29) The drive behind OpenTable's revenue stream and product adoption (39:54) LinkSquares - The go-to for all your legal needs; learn more at https://linksquares.com/twist (41:08) Hospitality trends in hotels (50:02) The impact of AI gains on Kayak’s operations * Follow Steve: https://twitter.com/shafner * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://vanta.com/twist LinkedIn Jobs. A business is only as strong as its people, and every hire matters. Go to https://LinkedIn.com/TWIST to post your first job for free. Terms and conditions apply. Fitbod. Tired of doing the same workouts at the gym? Fitbod will build you personalized workouts that help you progress with every set. Get 25% off your subscription or try out the app for FREE when you sign up now at [https://fitbod.me/TWIST.](http://fitbod.me/TWIST.) * Today’s show: Sunny joins Jason for more demos! Microsoft’s Windows 11 Copilot (2:42), ChatGPT’s multimodal features (28:37), and Meta’s new AI chatbots (1:04:34) are all covered!! * Time stamps: (0:00) Sunny Madra joins Jason (2:42) Sunny demos Windows 11 Copilot preview (9:48) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (10:55) Windows 11 Copilot to desktop interaction and areas needing improvement (15:06) Consequences of recording desktop interactions for AI and the final grade for Windows 11 Copilot (27:17) LinkedIn Jobs - Post your first job for free at https://linkedin.com/twist (28:37) Sunny demos ChatGPT’s multimodal features (36:32) Fitbod - Get 25% off at https://fitbod.me/twist (38:01) Job destruction and AI’s effects on the workplace (43:57) The utilization of multiple AI agents (46:05) ChatGPT’s voice chat feature (52:24) Personalization and the path to AGI (1:02:09) Common Crawl and use of web crawl data (1:04:34) Meta’s new AI chatbots * Follow Sunny: https://twitter.com/sundeep Check out Definitive Intelligence: https://www.definitive.io/ * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… Supergut is the only nutrition brand clinically-proven to improve digestion, balance blood sugar, sustain energy, and manage weight. Save 25% on their delicious shakes, bars, and prebiotic mix at https://Supergut.com with code TWIST. Catalog. Stop wasting time and money with expensive design firms and unreliable freelancers! Get fast, 3-day turnarounds for a flat monthly fee with Catalog! Get $1200 off right now at https://trycatalog.com/twist Codecademy. Build the future you want to see with Codecademy. Codecademy Pro helps you learn everything you’ll need to shape what comes next in the tech space. Try it free for 14 days. Visit https://codecademy.com/TWiST * Today's show: Jason kicks off the show by discussing the reported talks between OpenAI, Jony Ive, and Masayoshi Son to build the "iPhone of AI” (1:17), and the FTC’s antitrust lawsuit against Amazon (9:45). Then, Roam Around CEO Shie Gabbai joins Jason to discuss the journey of doing a travel startup in the AI space (20:53), and much more! * Time stamps: (0:00) Jason kicks off the show (1:17) OpenAI in advanced talks with Jony Ive and Masayoshi Son, aiming to Raise $1 Billion for the "iPhone of AI” (8:13) Supergut - Get 25% off with code TWIST at https://supergut.com (9:45) The FTC and 17 states have brought an antitrust lawsuit against Amazon and Lina Khan's agenda (13:48) Quick recap of Lina Khan’s results so far as FTC chair and the tactics used in the Amazon lawsuit (19:24) Catalog - Get $1200 off right now at https://trycatalog.com/twist (20:53) Roam Around CEO Shie Gabbai joins Jason (23:51) Shie demos Roam Around and explains the driving idea behind the app (27:23) The emergence of multimodal LLMs and other technological advancements (31:46) Business model, additional product features, and the path ahead (37:01) Codecademy - Try Codecademy Pro FREE for 14 days at http://codecademy.com/TWiST (38:21) The B2B side of AI and the travel industry's tension with Google * Follow Shie: https://twitter.com/Shie_eth Check out Roam Around: https://www.roamaround.io * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at openphone.com/twist .Tech Domains has a new program called startups.tech, where you can get your startup featured on This Week in Startups. Go to startups.tech/jason to find out how! Mercury. 90% of startups fail. Just 10 out of every 100 make it. Mercury exists to close that gap — helping companies succeed with banking and credit cards engineered for the startup journey. Join over 100,000 companies banking with Mercury at ⁠http://mercury.com⁠ Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. * Today’s show: Kelly Schricker joins Jason to kick off another startup pitch competition featuring four companies from Founder University Cohorts 5 and 6! * Time stamps: (0:00) Jason and Kelly kick off another startup pitch competition! (6:52) Why founding teams have an advantage over solo founders (11:47) OpenPhone - Get 20% off your first six months at https://openphone.com/twist (13:18) Founder University's program, and crafting the best pitch for your company (22:24) .Tech Domains - Apply to get your startup featured on This Week in Startups at https://startups.tech/jason (23:38) Jason Kappes pitches Newcomer Games (25:58) Jason’s feedback for Newcomer Games (32:24) Mercury - Join 100K+ startups banking with Mercury at http://mercury.com (33:36) Matthew Majcher pitches Scrumly (35:43) Jason’s feedback for Scrumly (40:41) Jared Rosen pitches HomeScore (42:59) Jason’s feedback for HomeScore (52:21) Phoenix Do pitches Fitted (54:26) Jason’s feedback for Fitted (1:08:49) Kelly and Jason review the four companies and their pitches (1:16:16) Jason picks his winning startup! * Check out Newcomer Games: https://newcomergames.com Check out Scrumly: https://www.scrumly.ai Check out HomeScore: https://homescore.co Check out Fitted: https://www.fittedcollective.com * Follow Kelly: https://twitter.com/KSchricks * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Plaid CEO Zach Perret discusses the canceled merger with Visa, Plaid's origin story, growing a community within your early customer base, Plaid's involvement with crypto companies, the importance of insurance for startups, building personal connections, increasing competition in the fintech industry, and the future of fintech and digital payment systems.

This Week in Startups is brought to you by… CLA. Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://CLAconnect.com/tech Codecademy. Build the future you want to see with Codecademy. Codecademy Pro helps you learn everything you’ll need to shape what comes next in the tech space. Try it free for 14 days. Visit https://Codecademy.com/TWiST LinkSquares. Life for in-house legal just got a whole lot easier. From contract creation to execution and more, LinkSquares is the go-to for all your legal needs. Learn more at https://linksquares.com/twist * Today’s show: Grammarly CEO Rahul Roy-Chowdhury joins Jason to discuss his journey to CEO (15:28), Grammarly’s product features (26:20), AI integrations (32:28), and much more! * Time stamps: (0:00) Grammarly CEO Rahul Roy-Chowdhury joins Jason (4:19) Rahul's start in tech and his time on the Google Chrome team. (8:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech (10:24) The Chrome team and Chrome OS (15:28) Journey to Grammarly CEO (19:29) Exploring applications and platforms for Grammarly (25:05) LinkSquares - The go-to for all your legal needs, learn more at https://linksquares.com/twist (26:20) The product roadmap and what draws people into Grammarly (35:04) Grammarly's business and enterprise offerings (37:32) Codecademy - Try Codecademy Pro FREE for 14 days at http://codecademy.com/TWiST (38:53) Product Features: Knowledge Share and Grammarly Goals (42:28) The addition of Grammarly Go and the LLM powering it (47:12) Controversial product features (54:17) When to use the native desktop application and extensions (57:13) Future integration of AI and the path ahead * Follow Rahul: https://twitter.com/rahulrc * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by… LinkedIn Marketing. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to linkedin.com/thisweekinstartups Squarespace. Turn your idea into a new website! Go to Squarespace.com/TWIST for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. Roots. Invest in the only real estate investment trust that creates wealth for you and its residents at https://investwithroots.com/TWIST * Today’s show: Sunny Madra joins Jason to discuss Google's recently launched Bard Extensions (2:27), demo AI tools (49:02), and much more! * Time stamps: (0:00) Sunny Madra joins Jason (2:27) Demo of recently released Google Bard Extensions (7:51) LinkedIn Marketing - Get a $100 LinkedIn ad credit at https://linkedin.com/thisweekinstartups (9:23) Demo of Google Bard Extensions continued (Google Maps) (20:07) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/twist (21:30) Demo of Google Bar Extensions (Gmail and YouTube) (33:58) Roots - Head to https://investwithroots.com/TWIST to sign up and start investing today! (35:23) Jason and Sunny grade and share opinions on Google Bard Extensions (41:24) Microsoft Copilot (43:01) YouTube Create, YouTube’s editing app for mobile creators (49:02) Jason demos VENDOR (52:21) Sunny demos SEC Insights * Check out Google Bard Extensions: https://www.bard.google.com Check out yc.v.inc: https://www.yc.v.inc Check out Microsoft Copilot: https://blogs.microsoft.com/blog/2023/09/21/announcing-microsoft-copilot-your-everyday-ai-companion/ Check Out YouTube Create: https://blog.youtube/news-and-events/made-on-youtube-2023/ Check out SEC Insights: https://www.secinsights.ai/ * Follow Sunny: https://twitter.com/sundeep Check out Definitive Intelligence: https://www.definitive.io/about * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast