This Week in Startups

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 and post your first job for free. (11:36) Comparing Web 3.0 and the dot com era + navigating the markets during the pandemic (18:40) Cast.ai - Get a free cloud cost audit with a personal consultation at https://cast.ai/twist (20:04) Venture Tourists (29:30) Unfavorable preference stacks (37:07) Acquire.com - Sign up for FREE at https://try.acquire.com/twist (38:32) Cleaning a cap table (47:57) Looking back at Deven’s investments FOLLOW Deven: https://twitter.com/djparekh FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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) Molly and Rachel kick off the show (1:33) America’s mental health data is being sold (10:28) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST (11:57) Bing dodges $100B bullet (20:23) House of Macadamias - Get 20% off at https://houseofmacadamias.com/twist by using code TWIST20 (21:51) Molly and Rachel’s AI predictions (24:36) IVP’s Tom Loverro joins Jason (39:32) Fitbod - Get 25% off at https://fitbod.me/twist (40:42) Tom’s prescriptions for founders FOLLOW Tom: https://twitter.com/tomloverro FOLLOW Rachel: https://twitter.com/_rachelbraun FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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/twist (9:58) UFOs in American airspace (22:26) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist (23:29) ChatGPT’s alter ego DAN + content filter transparency (37:17) Revelo - Get 20% off the first 3 months by mentioning TWIST at https://revelo.com/twist (38:44) Programming LLMs and neural networks FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 post your first job for free. (11:47) Surviving and thriving in a down market (22:35) First Republic Bank - Discover what a long-term financial relationship can do for you. Visit https://firstrepublic.com today to learn more. (23:29) Being flexible and understanding risk as an entrepreneur (30:00) Accomplishing the most with the least (34:05) ProsperStack - Take 10% off your subscription by mentioning TWIST at https://prosperstack.com/twist (35:17) Geoff’s favorite investments (43:35) Working with David Zaslav (50:57) What’s next for Geoff + Generative AI FOLLOW Geoff: https://twitter.com/geoff_yang FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 your SOC 2 at https://vanta.com/twist (10:04) Persevering through the “no’s,” and functional design (19:48) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST (21:17) Gaining customer trust (30:46) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (32:17) Airbnb’s incredible COVID turnaround (45:05) Joe’s new startup Samara Check out: https://www.samara.com/backyard FOLLOW Joe: https://twitter.com/jgebbia FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 (11:00) Neeva’s approach to search (17:33) Linode - Apply to Linode's Rise program for up to six figures in discounts at https://linode.com/twist (18:59) An update on Adam Neumann’s Flow (36:31) Meowtel - Save $25 on your first booking with code TWIST25 at https://meowtel.com/ (37:53) SOTD: Jobber raises $100M (46:17) Microsoft officially announces the integration of ChatGPT into Bing FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 (2:00) Google invests $300M in Anthropic (12:15) LinkedIn Marketing - Get a $100 LinkedIn ad credit at https://linkedin.com/thisweekinstartups (13:44) Neeva’s new approach to search (21:33) Acquire.com - Sign up for FREE at https://try.acquire.com/twist (22:58) AI’s data problem (28:27) ShiftMed raises $200M (33:18) LMNT - Get a free sample pack with any purchase at https://drinklmnt.com/twist (34:45) Seed/Series A Interview: Jessica Alderson, CEO of So Syncd FOLLOW Jessica: https://twitter.com/jesssalderson FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 (11:19) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups (12:44) Amazon earnings (23:28) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (24:30) Apple earnings (33:36) Fitbod - Get 25% off at https://fitbod.me/twist (34:36) The US jobs report (46:05) LA26 Founder: Perrin Davidson of EATERCLUB (1:02:16) OK Boomer with Eerika Savolainen, the CEO of Slush FOLLOW Perrin: https://twitter.com/LAeats FOLLOW Eerika: https://twitter.com/EerikaSav FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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) The Fed raises rates by 25bps (9:57) House of Macadamias - Get 20% off at https://houseofmacadamias.com/twist by using code TWIST20 (11:24) Unemployment and Automation (21:59) Microsoft for Startups Founders Hub - Apply in 5 minutes for six figures in discounts at http://aka.ms/thisweekinstartups (23:30) ChatGPT hits 100M MAUs + Google’s Apprentice Bard (36:46) Anyplace - Get $250 off your booking with the code TWIST250 at https://www.anyplace.com/twist (37:51) Oscar Nominations with Lon Harris (44:06) Spotify earnings (55:35) The Last of Us is another hit for HBO (1:00:58) James Gunn reveals chapter one of the DC Universe FOLLOW Lon: https://twitter.com/lons FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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 reaction to the downturn (11:33) LinkedIn Jobs - Go to https://linkedIn.com/angel and post your first job for free (12:58) Rick’s memory of the Dot Com bubble (19:39) Advice for founders in a downturn (22:27) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist (23:29) How CAC and LTV have changed (26:30) The emotional state of Founders and keeping them focused (35:09) Term sheets in the Dot Com era and today (40:06) Letterhead - get 50% off their first year at tryletterhead.com/twist (41:21) Different forms of exits + Key attributes in founders FOLLOW Rick: https://twitter.com/rick FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood