Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, ...
Databricks' Record Raise, TikTok goes to the Supreme Court, and all about the Grammarly-Coda Deal | E2063
This Week in Startups is brought to you by…
Coda. Coda empowers your startup by bringing words, tables, and teams together. Strategize, plan, and track goals effectively with all your valuable data in one place. Go to https://www.coda.io/twist to get started for FREE and get 6 free months of the Team plan.
Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
Gusto. Gusto is easy online payroll, benefits, and HR built for modern small businesses. Get three months free when you run your first payroll at https://www.gusto.com/twist
*
Todays show:
Alex and Jason discuss Databricks’ record raise, TikTok’s big day at the Supreme Court, Shishir Mehrotra on the Coda-Grammarly merger, and more.
*
Timestamps:
(0:00) Jason and Alex kick off the show
(3:38) Insights on Databricks' private fundraise and venture capital trends
(8:37) Predictions on unlimited free energy, water, and food
(9:41) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist
(14:25) The declining costs of cloud computing
(17:12) Evaluating growth rate for startup valuations
(19:46) Competitive landscape: Databricks vs. Snowflake
(20:48) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
22:07 The strategic importance of selecting the right customers
26:34 Venture capital communication and the ghosting phenomenon
28:43 TikTok's ongoing legal challenges
(31:25) Gusto - Get three months free when you run your first payroll at http://gusto.com/twist
(32:33) Shashir Mehrotra on the Coda-Grammarly merger
(37:16) Vision and applications of the Coda-Grammarly partnership
(42:35) Future of AI agents and Grammarly's role
(45:13) SaaS industry dynamics and AI's role in upselling
(49:10) The impact of AI on job automation and workforce productivity
(54:40) Team sizes and AI-driven productivity debate
(57:18) The future interaction with AI agents
(1:00:40) Efficiency gains from combining Grammarly and Coda
(1:02:02) The role of ChatGPT and AI in social media
(1:03:46) Tailoring AI tools for business needs
(1:06:26) Lessons from mergers and acquisitions in the tech sector
(1:08:08) Strategic acquisitions and their importance in the tech industry
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Follow Shishir:
X: https://x.com/shishirmehrotra
LinkedIn: https://www.linkedin.com/in/shishirmehrotra
*
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:
(9:41) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist
(20:48) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(31:25) Gusto - Get three months free when you run your first payroll at http://gusto.com/twist
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
--------
1:09:36
Sora Disappoints, ChatGPT Pro Tested, Inference Time Reasoning & More with Sunny Madra | E2062
Timestamps:
(0:00) Jason and Sunny kick off the show
(1:26) Discussing Groq's recent developments and Middle East tech inspiration
(3:51) Global business challenges and Jason's 2025 announcements
(7:53) Gemini app demo and ChatGPT 4 comparison
(9:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(11:24) Evaluating ChatGPT 4.0 Pro limitations and robo-taxi fleet costs
(12:46) Differences between ChatGPT models and future improvements
(19:57) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(20:58) LLM focus shift and robo taxi cost model experimentation
(23:01) Importance of prompt engineering in AI tools adoption
(25:31) Workplace AI adoption challenges and generational tech differences
(27:22) New productivity hacks and Gemini app's growth
(30:27) Zendesk - Get six months free at https://www.zendesk.com/twist
(34:06) Startup support programs and Google Gemini's research capabilities
(37:08) AI model performance evaluation and simplification
(45:02) Meta's Llama 3.370b launch and AI industry impact
(46:37) Infrastructure costs, competitive landscape, and AI-generated content evolution
(55:44) Trust and bias in language models, news analysis startup ideas
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Mentioned on the show:
Check out Sora here: https://sora.com/
Check out Kling here: https://klingai.com/
Check out Groq: https://groq.com/
*
Follow Sunny:
X: https://x.com/sundeep
LinkedIn: https://www.linkedin.com/in/sundeepm
*
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Thank you to our partners:
(9:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(19:57) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(30:27) Zendesk - Get six months free at https://www.zendesk.com/twist
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
--------
1:02:05
Silicon Valley Clones and Jersey Drones: Decoding the Signals with Nicole Wischoff | E2061
This Week in Startups is brought to you by…
Ramp. The corporate card and spend management software designed to help you save time and money. Get $250 when you join Ramp today at https://www.ramp.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
Digital Ocean. Whether you’re just getting started with AI, or seeing your project take off, DigitalOcean is the cloud platform that lets you focus on what matters: building killer apps. Right now get up to $100k in free credits at https://www.do.co/twist. Terms and conditions apply.
*
Timestamps:
(0:00) Jason and Alex kick off the show
(3:03) Government reactions to drone sightings
(4:02) Theories and politicians' reactions to the drones
(9:21) Ramp. Get $250 when you join Ramp today at https://www.ramp.com/twist.
(10:48) Official statements on drone sightings
(13:34) Speculation on drones' radiation detection capabilities
(15:20) TikTok insights and Swiss startup Arctis Radiation Detectors
(20:21) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist
(21:52) Personal reactions and media aspects of drone sightings
(26:12) Startups in drone detection and geopolitical implications
(30:36) DigitalOcean. DigitalOcean is the cloud platform you need to turn your AI project into a rocket ship. Right now, approved listeners can get up to $100,000 in free credits to try us out. Visit https://www.do.co/twist - get started and view terms and conditions.
(32:23) American Security Drone Act of 2023 and government coordination
(39:01) Nicole Wischoff joins Alex and Jason.
(40:28) Startup pitches and trend discussions
(46:14) Investment strategies and AI's impact on startups
(51:10) Market dynamics in various industries
(52:09) Fundraising strategies and venture capital insights
(57:56) Closing thoughts with Nicole Wischoff
(58:05) Venture capital performance metrics
(1:00:39) Challenges for large venture funds
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Mentioned on the show:
Check out Wischoff Ventures: https://www.wischoff.com/
Robin Radar Systems: https://www.robinradar.com/
Arktis Radiation Detectors: https://www.arktis-detectors.com/
ApolloShield: https://www.apolloshield.com/
John Ferguson’s full post: https://www.instagram.com/thegardenstate/reel/DDnmN8oRw3T/
American Security Drone Act Of 2023: https://smartpay.gsa.gov/resources/american-security-drone-act/#:~:text=On December 22%2C 2023%2C the,Fiscal Year 2024
(NDAA)
*
Follow Nicole:
X: https://x.com/NWischoff
LinkedIn: https://www.linkedin.com/in/nicholewischoff
*
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:
(9:21) Ramp. Get $250 when you join Ramp today at https://www.ramp.com/twist.
(20:21) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist
(30:36) DigitalOcean. DigitalOcean is the cloud platform you need to turn your AI project into a rocket ship. Right now, approved listeners can get up to $100,000 in free credits to try us out. Visit https://www.do.co/twist - get started and view terms and conditions.
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
--------
1:02:12
Cyera's Hypergrowth, Cake's Cap Table Push, and ServiceTitan's Stellar IPO | E2060
This Week in Startups is brought to you by…
LinkedIn Jobs. A business is only as strong as its people, and every hire matters. Go to https://www.linkedin.com/twist to post your first job for free. Terms and conditions apply.
Washington Post. Stay informed with trusted journalism from The Washington Post.
Right now, TWiST listeners can subscribe for just 50 cents per week for your first year at
https://www.washingtonpost.com/twist
Beehiiv. Power your newsletters with AI tools, referral programs, and ad network features—all in one platform. Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist
*
Todays show:
Alex Wilhelm kicks off the show with Cyera’s Yotam Segev to dive into the state of enterprise data security. They discuss Cyera’s impressive feat of raising $300 million just quarters after its previous mega-round and explore the company's recent nine-figure acquisition of Trail Security. Next, Alex unpacks ServiceTitan's successful IPO and Broadcom's milestone achievement of reaching a $1 trillion market cap. To close, Cake Equity’s Kim Hansen joins the conversation to share insights into his company’s growth strategy and how it’s thriving in a highly competitive market.
*
Timestamps:
(0:00) Alex kicks off the show
(2:12) Cyera’s Yotam Seveg joins the show
(10:05) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(11:34) Evolution from information security to cybersecurity and automated data categorization
(20:44) Cyera's acquisition strategy and impact on the company
(28:00) Washington Post - TWiST listeners can subscribe for just 50 cents per week for your first year at https://www.washingtonpost.com/twist
(29:10) AI's impact on data security and competition in the cybersecurity market
(34:19) ServiceTitan IPO, market reaction, and implications for the industry
(37:34) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist
(39:05) Tech companies reaching significant market caps and IPO performances
(47:17) Texas attorney general's lawsuit against tech companies over data practices
(48:21) Cake Equity’s Kim Hansen joins the show
(49:02) Cake Equity's mission, platform, and cap table management software demo
(54:29) Cake Equity's user interface, employee engagement, and expansion plans
(58:22) Automation in onboarding and international growth challenges for Cake Equity
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Mentioned on the show:
https://www.cyera.io
https://www.cakeequity.com
*
Follow Yotam:
LinkedIn: https://www.linkedin.com/in/yotam-segev
*
Follow Kim:
X: https://x.com/KimHansenYeah
LinkedIn: https://www.linkedin.com/in/kimhansencake
*
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:
(10:05) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(28:00) Washington Post - TWiST listeners can subscribe for just 50 cents per week for your first year at https://www.washingtonpost.com/twist
(37:34) Beehiiv - Get 30 days free and 20% off your first 3 months at https://www.beehiiv.com/twist
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
--------
1:09:38
The Top 6 Startup Finance FAQ’s | Startup Finance Basics w/ Kruze's Scott Orn
Todays show:
In the latest edition of Startup Finance Basics, Jason sits down with Scott Orn from Kruze Consulting to answer the
six most important founder/startup questions around finance, accounting, and taxes.
*
Timestamps:
(0:00) Kruze COO, Scott Orn, joins Jason to dive into Finance Basics FAQs.
(1:05) How can I avoid paying payroll tax as a startup founder?
(6:54) How do you shut down a startup?
(11:33) Why do I owe Delaware $50,000 in franchise taxes?
(12:58) I’ve got my first customer lined up! How do I get paid?
(16:26) Can I tell VCs that implementation revenue is ARR?
(19:59) Should I raise venture debt when I raise my Series A?
*
Check out Kruze: https://kruzeconsulting.com
Check out more Finance Basics here: THISWEEKINSTARTUPS.COM/basics
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Follow Scott:
LinkedIn: https://www.linkedin.com/in/scottorn
X: https://twitter.com/scottorn
*
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
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.