This Week in Startups Jason Calacanis
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- Technology
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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.
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Mastering Venture Capital and Founder Strategies with Rory O’Driscoll and Mark Suster
This Week in Startups is brought to you by…
Northwest Registered Agent. Start your business fast and secure with Northwest Registered Agent! In just 10 clicks and 10 minutes, set up your entire business identity—name, address, mail service, phone, email, website, and domain. Everything You Need to Launch Your Business in Minutes! For just $39 plus state fees, Northwest will handle your complete business identity. visit https://www.northwestregisteredagent.com/twist
Wistia - The all-in-one video platform for business, with tools that help you create, manage, and measure the impact of your videos. Try Wistia for free at https://www.wistia.com/startups1
HiddenLayer - Generative AI is revolutionizing industries. HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Helping you generate more – by enabling seamless & secure Generative AI. Visit https://www.HiddenLayer.com/TWiST to learn more.
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Todays show:
Rory O’Driscoll joins guest host Mark Suster to discuss: advice for founders with traction but not yet booming (2:33), thirty years of internet cycles and their impact on venture capital (13:25), the approach to big-picture thinking vs. immediate traction and strategizing exits (36:58), and more!
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Timestamps:
(0:00) Rory O’Driscoll joins guest host Mark Suster.
(2:33) Rory’s advice for founders with traction but not yet booming.
(9:09) Aligning incentives between founders and venture; reminding CEOs to be "selfish.”
(10:23) Northwest Registered Agent - For just $39 plus state fees, Northwest will handle your complete business identity. Visit https://www.northwestregisteredagent.com/twist today.
(13:25) Reflections on thirty years of internet cycles and their impact on venture capital.
(18:25) Debating AI: Does it favor the incumbents?
(20:07) Wistia - Try Wistia for free at https://www.wistia.com/startups
(21:35) What Rory and Scale Venture looks for when investing in AI.
(26:20) How OpenAI has changed the landscape
(29:18) HiddenLayer - HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://www.HiddenLayer.com/TWiST to learn more.
(30:30) Debating “faux-mentum” vs. long-term sustainability in investments.
(34:34) Balancing deep passion and business savvy when evaluating founders.
(36:58) Rory’s approach to big-picture thinking vs. immediate traction and strategizing exits
(44:02) The importance of picking vs. price discipline.
(1:00:58) Advice for founders dealing with “busted cap tables.”
(1:08:07) Rory’s advice for his younger self.
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Check out Scale Venture Partners: https://www.scalevp.com/
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Follow Rory:
X: https://x.com/rodriscoll
LinkedIn: https://www.linkedin.com/in/roryodriscoll/
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Follow Mark:
X: https://twitter.com/msuster
LinkedIn: https://www.linkedin.com/in/marksuster/
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Thank you to our partners:
(10:23) Northwest Registered Agent - For just $39 plus state fees, Northwest will handle your complete business identity. Visit https://www.northwestregisteredagent.com/twist today.
(20:07) Wistia - Try Wistia for free at https://www.wistia.com/startups
(29:18) HiddenLayer - ****HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://www.HiddenLayer.com/TWiST to learn more.
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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Check out Jason’s suite of newsletters: https://substack.com/@calacanis
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Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast -
TWIST News: xAI's massive $6B raise, the startups building our drone future & TWIST500 | E1957
This Week in Startups is brought to you by…
LinkedIn Ads. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to http://www.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 http://www.vanta.com/twist
DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist.
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Todays show:
Jason and Alex discuss xAI raising $6B (2:07), the TWiST500 (30:11), the startups building our drone future (39:55), North Korean tech talent taking American remote tech jobs (55:50), and more!
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Timestamps:
(0:00) Jason and Alex kick off the show
(2:07) xAI raised $6B series B
(10:03) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(11:30) The evolution of smartphone adoption over time
(19:08) Global Internet users from 2005-2023
(26:06) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist
(26:57) The control over silicon and Apple’s move switch from Intel
(30:11) TWiST500 announcement
(38:24) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist
(39:55) Armed robot dogs, drone warfare, and the startups building our drone future
(55:50) North Korean nationals taking American remote tech jobs
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Links and articles from show:
https://x.ai/blog/series-b
https://www.twz.com/sea/rifle-armed-robot-dogs-now-being-tested-by-marine-special-operatorshttps://news.crunchbase.com/ai/defense-military-ai-tech-startups-vc-funding-anduril-shield-ai/?utm_source=cb_daily&utm_medium=email&utm_campaign=20230703
https://www.axios.com/2024/05/21/north-korea-it-workers-us-hiring
https://www.cnbc.com/2024/01/24/north-korea-crypto-hacking-activity-soars-to-record-high-in-2023-new-report-shows.html
https://www.statista.com/statistics/273018/number-of-internet-users-worldwide
https://www.axios.com/2024/05/26/china-robot-gun-dog-military-cambodia
https://www.allencontrolsystems.com
https://www.youtube.com/watch?v=YMnkqY98Cyo
https://www.youtube.com/watch?v=8igjcW39T4k
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm/
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Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thank you to our partners:
(10:03) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(26:06) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist
(38:24) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast -
AI investments, VC ecosystem geography, and VC hypocrisy | E1956
This Week in Startups is brought to you by…
Squarespace. Turn your idea into a new website! Go to http://www.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.
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 https://www.openphone.com/twist
Lemon.io. Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
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Todays show:
David Weisburd hosts Jaime Matus, Michael Eisenberg, and Jason Calacanis to discuss AI investments and the potential washout of overfunded startups (4:11). They also touch on VC hypocrisy (38:47), and the role of geography in the VC ecosystem (54:53).
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Timestamps:
(0:00) David Weisburd intros Jaime Matus, Michael Eisenberg, and Jason Calacanis
(4:11) Pitchbook data summarizing the total amount of capital invested in AI
(12:12) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(16:33) Predicting a washout of overfunded AI startups and sky high valuations
(25:30) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(26:57) Discussing Michael Eisenberg's career and investment experiences
(37:22) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(38:47) Discussion on Greg Isenberg's tweet about VC hypocrisy
(54:53) Fundraising rankings by ecosystem
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Follow Jaime:
X: https://x.com/JaimeMatusVC
LinkedIn: https://www.linkedin.com/in/jaime-matus
Check out: https://www.invariantes.com
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Follow Michael:
X: https://x.com/mikeeisenberg
LinkedIn: https://www.linkedin.com/in/mieisenberg
Check out: https://aleph.vc
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Follow David:
X: https://twitter.com/DWeisburd
LinkedIn: https://www.linkedin.com/in/dweisburd
Check out: https://10xcapital.com
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Follow Jason:
X: https://twitter.com/jason
Instagram: https://www.instagram.com/jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thank you to our partners:
(12:12) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(25:30) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(37:22) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
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Check out the Launch Accelerator: https://launchaccelerator.co
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Check out Founder University: https://www.founder.university
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast -
Glue: The New Slack Killer with David Sacks and Evan Owen | E1955
In this episode, David Sacks and Evan Owen of Glue join Jason to demo their new “slack killer” product (4:38), explain the role of AI within Glue (14:14), discuss building products with remote vs in-person teams (36:47), and more!
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Timestamps:
(0:00) David Sacks and Evan Owen join Jason to show us newly launched Glue.
(2:42) David Sacks answers, “Why build another product?”.
(4:38) Evan jumps into a demo of Glue.
(9:37) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(12:15) Popular data sources users are incorporating into Glue.
(14:14) Digging deeper on the AI of Glue and when it will be able to be proactive in its participation.
(19:42) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(21:07) Glue’s strategy on converting users from tools like slack in this competitive landscape.
(27:18) Glue’s approach to pricing.
(30:16) Dot Tech Domains - Don’t miss our “Jam with JCal” contest. To apply and get more details go to https://jamwithjcal.tech/
(31:45) Training models and the heated subject of privacy and security.
(34:12) How building a company now, fourteen years after Yammer, has been different for Sacks.
(36:47) Diving into the topic of building products with remote vs in-person teams.
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Check out Glue: https://gluegroups.com/
Glue on X: https://x.com/GlueAI
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Follow David:
X: https://x.com/DavidSacks
LinkedIn: https://www.linkedin.com/in/davidoliversacks/
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Follow Evan:
X: https://x.com/kainosnoema
LinkedIn: https://www.linkedin.com/in/evanaowen/
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Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thank you to our partners:
(9:37) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(19:42) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(30:16) Dot Tech Domains - Don’t miss our “Jam with JCal” contest. To apply and get more details go to https://jamwithjcal.tech/
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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast -
$NVDA's earnings, media economics in the AI era, Farcaster's mega crypto round, and more! | E1954
This Week in Startups is brought to you by…
Zendesk - The best customer experiences are built with Zendesk. Qualifying startups can join their Startup program and get Zendesk products free, for six months! Visit http://www.zendesk.com/twist today to get started.
Mercury - Mercury is the fintech startups use for banking* and all their financial workflows.
Paying bills, staying in control of company spend, and closing the books doesn't need to be so complex — that's why Mercury powers it all from the one thing every business needs: the bank account. Join 200K startups who use Mercury to operate at their best 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.
HiddenLayer - Generative AI is revolutionizing industries. HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Helping you generate more – by enabling seamless & secure Generative AI. Visit https://HiddenLayer.com/TWiST
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Timestamps:
(0:00) Jason and Alex kick off the show
(1:50) Nvidia earnings for First Quarter Fiscal 2025
(12:53) Zendesk - Get six months free at http://www.zendesk.com/twist
(14:32) Continuing discussion on Nvidia's earnings
(22:39) News Corp and OpenAI strike ‘multi year global partnership’
(29:21) Mercury - Join 200K startups who use Mercury to operate at their best at http://mercury.com
(30:51) Apple News+ is driving big numbers for The Daily Beast
(39:03) HiddenLayer - HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://HiddenLayer.com/TWiST to learn more.
(40:14) Wearable AI startup Humane is exploring a sale
(50:56) Windows Recall
(1:08:45) Farcaster raises $150M: Is crypto making a comeback?
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Links and articles from show:
https://nvidianews.nvidia.com/news/nvidia-announces-financial-results-for-first-quarter-fiscal-2025
https://techcrunch.com/2024/05/21/farcaster-a-crypto-based-social-network-raised-150m-with-just-80k-daily-users/
https://gizmodo.com/humane-ai-pin-selling-billion-1851493143
https://www.semafor.com/article/05/19/2024/as-clicks-dry-up-for-news-sites-could-apples-news-app-be-a-lifeline
https://www.wsj.com/business/media/openai-news-corp-strike-deal-23f186ba?mod=latest_headlines
https://s201.q4cdn.com/141608511/files/doc_financials/2025/Rev_by_Mkt_Qtrly_Trend_Q125.pdf
https://x.com/dsiroker/status/1792956339515273537
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm/
*
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Thank you to our partners:
(12:53) Zendesk - Get six months free at http://www.zendesk.com/twist
(29:21) Mercury - Join 200K startups who use Mercury to operate at their best at http://mercury.com
(39:03) HiddenLayer - HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://HiddenLayer.com/TWiST to learn more.
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast -
OpenAI drama, billion-dollar exits, and founder salaries with new co-host Alex Wilhelm | E1953
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 http://www.vanta.com/twist
LinkedIn Ads - To redeem a $100 LinkedIn ad credit and launch your first campaign, go to http://www.linkedin.com/thisweekinstartups
Equinix - The Equinix Startup program offers a hybrid infrastructure solution for startups, including up to $100K in credits and personalized consultations and guidance from the Equinix team. Go to https://www.equinixstartups.com to apply today.
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Timestamps:
(0:00) Alex Wilhelm joins Jason to dive into this week’s news.
(1:17) Announcing new co-host on TWiST Alex Wilhelm of TechCrunch fame!
(3:03) Alex breaks down what’s on the docket for today!
(4:16) The OpenAI equity issue.
(10:38) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist
(12:39) OpenAI’s ChatGPT 4o.
(15:33) Why ChatGPT is better than Siri.
(17:50) OpenAI’s net revenue in the wake of last week’s announcements.
(20:04) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(22:06) Comparing the needs of consumers vs enterprise for ChatGPT.
(24:17) OpenAI has pulled “Sky” one of the voices for the new ChatGPT 4o due to it sounding like Scarlett Johansson
(28:48) Equinix - Join the Equinix Startup Program for up to $100K in credits and much more at https://deploy.equinix.com/startups
(30:01) Alex’s favorite topic around how much founders paying themselves.
(38:46) A billion-dollar deal in cybersecurity.
(45:43) Breaking news Scar Jo!
(56:24) What’s going on with crypto-venture capital.
(58:02) A look at “decentralized twitter” called Farcaster.
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Links from episode:
OpenAI Equity link: https://www.businessinsider.com/sam-altman-openai-nda-clause-vested-equity-ilya-sutskever-2024-5
OpenAI revenue growth https://techcrunch.com/2024/05/20/chatgpts-mobile-app-revenue-saw-biggest-spike-yet-following-gpt-4o-launch/
Founder salary report: https://pilot.com/founder-salary-report-2024
CyberArk-Venafi deal: https://techcrunch.com/2024/05/20/cyberark-snaps-up-venafi-for-1-54b-to-ramp-up-in-machine-to-machine-security/
Crypto VC rising: https://www.reuters.com/technology/venture-capital-funding-crypto-rises-24-bln-pitchbook-says-2024-05-20/
Check out Farcaster: https://www.farcaster.xyz/
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm/
*
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Thank you to our partners:
(10:38) Vanta - Get $1000 off your SOC 2 at http://www.vanta.com/twist
(20:04) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(28:48) Equinix - Join the Equinix Startup Program for up to $100K in credits and much more at https://deploy.equinix.com/startups
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast