This Week in Startups Jason Calacanis

This Week in Startups is brought to you by…

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Today’s show:
Jason kicks off the show discussing the reported talks  between OpenAI, Jony Ive, and Masayoshi Son to build the "iPhone of AI” (1:17), and the 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!

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Time stamps:

(00:00) 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

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Follow Shie: https://twitter.com/Shie_eth
Check out Roam Around: https://www.roamaround.io
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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

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Follow Jason:

Twitter: https://twitter.com/jason

Instagram: https://www.instagram.com/jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by…

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.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

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Today’s show:

Kelly Schricker joins Jason to kick off another startup pitch competition featuring four companies from Founder University Cohorts 5 and 6!

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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!

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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

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Follow Kelly: https://twitter.com/KSchricks

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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

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Follow Jason:

Twitter: https://twitter.com/jason

Instagram: https://www.instagram.com/jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by…

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Today’s show:

Plaid CEO Zach Perret joins Jason to break down the behind-the-scenes details of Plaid’s canceled merger with Visa (1:21), Plaid’s origin story (16:44), tactics on growing a community within your early customer base (27:36), and more!

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FOLLOW Zach: https://twitter.com/zachperret

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Time stamps:

(0:00) Jason welcomes Plaid CEO Zach Perret!

(1:21) Plaid's canceled Visa merger, coming out the other side of a canceled acquisition stronger

(11:30) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist

(12:36) Zach breaks down Plaid's product and business

(16:44) Plaid's origin story

(26:08) Embroker - Use code TWIST to get an extra 10% off insurance at https://embroker.com/twist

(27:36) Tactics for growing a community within your customer base

(35:24) Competition, specifically from financial giants

(38:58) Fount - Get $500 off an executive health coach at https://fount.bio/twist

(40:28) FedNow, CBDCs, and the next evolution of payment rails

(50:13) Silicon Valley Bank implosion from Plaid's POV

(53:17) Surviving 2022, and the future of fintech in 2023 and beyond

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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

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Follow Jason:

Twitter: https://twitter.com/jason

Instagram: https://www.instagram.com/jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

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

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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!

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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

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Follow Rahul: https://twitter.com/rahulrc

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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

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Follow Jason:

Twitter: https://twitter.com/jason

Instagram: https://www.instagram.com/jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by…

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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!

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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

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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/

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Follow Sunny: https://twitter.com/sundeep

Check out Definitive Intelligence: https://www.definitive.io/about

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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

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Follow Jason:

Twitter: https://twitter.com/jason

Instagram: https://www.instagram.com/jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

This Week in Startups is brought to you by…

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Today’s show:

Jason goes live to break down Cisco acquiring Splunk and what this means for the broader M&A market (3:56), the latest IPO trends (13:50), WaPo tactics against Dave Portnoy (16:14), and questions asked by the live audience (23:52)!

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Time stamps:

(0:00) Jason kicks off the show!

(3:56) Cisco acquires Splunk for $28B

(7:07) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups

(8:36) Instacart’s IPO and why CPG is a major advertising category

(13:50) IPO trends and what that means for the startup market

(16:14) WaPo tactics against Dave Portnoy

(22:26) Masterworks - Skip the waitlist to invest in fine art using at https://Masterworks.com/twist

(23:52) Questions from live audience: "Do VCs ever go back to previous business trends or does everyone focus exclusively on the it-thing like AI today?”

(26:05) "How do startups outside Silicon Valley access VC funding, or do you just have to make the journey there?”

(27:10) "Heard you say you believe we still have six months of this down market. What makes you arrive at this prediction...?”

(30:57) "Since you invest in so many companies each year, how do you find alpha and separate these startups from each other?”

(33:49) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com

(34:49) Why is Jason doing the cloud kitchen incubator?

(38:19) "Do you believe there should be guardrails on AI or as little regulation as possible to help spur innovation?”

(40:40) " Which areas do you recommend founders to cut burn that impacts growth released?”

(42:24) "Interest is forbidden in Islam, but I really want to invest or create an investment group without interest. Is this possible?”

(44:14) "How do you advise founders to solve disagreements internally?”

(45:39) "What is a book that you've read recently that you would highly recommend?”

(45:56) "Do you think the UK is underperforming when it comes to unicorns and big impact on startups?”

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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

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast