This Week in Startups

This Week In Startups is made possible by:

Deel - deel.com/twist
LinkedIn - linkedIn.com/twist
Northwest Registered Agent - northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twist
Today’s show:

Anthropic stabbed Cursor in the back. Then SpaceX swooped in with $60 billion. Today, TWiST connects the dots on the biggest deal in AI since the Microsoft-OpenAI partnership, and why it's a warning sign for every startup building on top of a frontier model. Jason is joined by Bling Capital’s Ben Ling, Banana Capital’s Turner Novak, and co-host Alex to go deep on the future of coding models, the current golden age of venture liquidity, OpenAI’s financials, and the ‘Four Ds’ of venture investing. The show closes with a tribute to Josh Baer, the founder of Capital Factory.

Guest Links:

Ben Ling https://x.com/bling0?lang=en
Bling Capital https://www.blingcap.com/
Turner Novak https://x.com/TurnerNovak
Banana Capital https://www.bananacapital.vc/
Show Links:
Hanover Park https://www.hanoverpark.com/
SpaceX buys Cursor https://www.cnbc.com/2026/06/16/spacex-spcx-cursor-acquisition-ipo.html
Cursor Composer 2.5 https://cursor.com/blog/composer-2-5
OpenAI financials source https://www.wheresyoured.at/exclusive-openai-financials/
AMD’s new deskside data center https://www.amd.com/en/products/processors/desktops/ryzen/ryzen-ai-halo.html
Perplexity Model Council https://www.perplexity.ai/hub/blog/introducing-model-council

Timestamps:

0:00 Guest introductions
1:15 Guest introductions
2:43 SpaceX acquires Cursor for $60B
6:13 The golden era of M&A
9:13 Northwest Registered Agent: Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist
12:04 Cursor's negative gross margins & the compute problem
13:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
15:04 Rolling your own model: When does it make sense?
19:35 LinkedIn: Thanks to our partners at LinkedIn! Post your job for free at https://linkedIn.com/twist then promote it to get access to LinkedIn Jobs' new AI assistant.
22:53 The "headless product" thesis
28:31 Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.
34:22 OpenAI financials leaked: $13B revenue, $38.5B net loss
40:13 Where does AI value accumulate?
45:34 Portfolio Spotlight: Hanover Park
48:37 Seed stage graduation rates have fallen from 50% to 25%
54:59 The four Ds of venture: Deal flow, Decisions, Doubling down, Distributions
1:06:36 How to find 'undiscovered gems'
1:30:59 Snap Specs AR glasses: $2,195, and a bit chunky
1:39:29 Tribute to Joshua Baer, Capital Factory's founder

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 Lon:
X: https://x.com/lons
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
Check out all our partner offers: https://partners.launch.co/
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

This Week In Startups is made possible by:

Every.io - visit every.io
Sentry.io - sentry.io/twist
Vanta - vanta.com/twist

Today’s show:
The next SpaceX won't be building rockets; it'll build the first hotel on the Moon. Today on TWiST, GRU Space founder Skyler Chan brings a brick made from lunar soil into the studio and lays out a plan to manufacture on the Moon as early as next year. We get into the science, the business model, and the regulatory land-grab ahead!
Then, the US government forces Anthropic to pull Fable 5 and Mythos 5. Jason and Lon unpack what it means when a single AI model can vanish overnight, and the US government's emergency order.
Stick around for the winner (or winners?!) of the $5,000 AI podcast-companion bounty!

Timestamps:
0:00 Knicks playoff run, San Antonio & Texas BBQ (Black's vs. Terry Black's)
8:23 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
9:52 Guest intro: Skyler Chan, GRU Space — and the lunar-soil brick
10:29 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io
12:14 Why the next SpaceX builds habitats, not rockets
15:18 NASA's $20B moon-base signal & the TRL contracting path
16:13 Business model: from construction contractor to owning lunar land
18:06 Building the hotel robotically + $1M refundable deposits
20:00 Sentry - Your team should be focused on shipping features — not chasing down bugs. New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
31:09 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
39:28 News: US government blocks Anthropic's Fable 5 & Mythos 5
41:34 The politics: Hegseth, Sacks, Jassy & the "conspiracy" angle
1:09:39 Why no single model dependency is safe (multi-model harnesses)
1:18:47 Bounty results: MySidecast wins $3,000
1:19:07 Honorable mentions: Couchverse (Lemon Slice) & Convalenz
1:29:44 Next bounty: the Annotated app
🔗 Links & Resources Mentioned:
Guest & company
Skyler Chan: Founder, GRU Space → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-space
GRU Space (Galactic Resource Utilization): YC startup building lunar-regolith bricks and a robotic Moon hotel → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-space
GRU Space lunar hotel bookings → https://payloadspace.com/gru-space-opens-bookings-for-planned-lunar-hotel/

🎙️ About the Guest:
Skyler Chan is the founder of GRU Space (Galactic Resource Utilization), a Y Combinator–backed startup developing a payload factory that manufactures bricks from lunar regolith to build the first robotic hotel on the Moon.
Follow GRU Space → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-space
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 Lon:
X: https://x.com/lons
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
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

This Week In Startups is made possible by:
Plaud https://Plaud.ai/twist
Pilot https://pilot.com/twist
Agree https://agree.com
IM8 Health https://IM8health.com/twist

After watching Elon build out his rocket (and AI) company over the past 20 years, Jason celebrates the SpaceX IPO on a new TWiST. He explains why some investments are evaluated based on earnings and current numbers, while other stocks are bets on expensive visions for the future, and why SpaceX why likely pay off across multiple time horizons.
PLUS Polsia solo founder Ben Cera is back with guidance for founders on creating a “Purple Cow”: a unique experience that makes their brand memorable.

Guest:
Ben Cera on X: https://x.com/Bencera
Polsia: https://polsia.com/
Polsia on X: https://x.com/polsia
Ben on TWiST E2256 (Feb 2026): https://www.youtube.com/watch?v=QCce8e02Isw

Relevant Links:
SpaceX: https://www.spacex.com/
SPCX on Yahoo Finance: https://finance.yahoo.com/quote/SPCX/
Starlink: https://www.starlink.com/
Planet Labs: https://www.planet.com/
Palantir: https://www.palantir.com/
Valor Equity Partners: https://www.valorep.com/
Seth Godin’s “Purple Cow” on Amazon: https://www.amazon.com/Purple-Cow-New-Transform-Remarkable/dp/1591843170
Uber Ice Cream stunt article: https://finance.yahoo.com/news/ubers-brilliant-marketing-stunt-hail-195946535.html
Hillsborough Flintstones House article: https://www.sfgate.com/travel/article/The-Flintstone-House-is-now-for-rent-on-Airbnb-10420107.php
“19 Hours Inside the Airbnb X-Mansion” article: https://www.theringer.com/2024/05/29/pop-culture/x-mansion-airbnb-x-men-icons-experience
Was The Pepsi Challenge based on LIES? https://www.historyoasis.com/post/the-pepsi-challenge
CloudKitchens: https://cloudkitchens.com/
Cluely: https://cluely.com/

Timestamps:

0:00 SpaceX IPO details
2:12 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
7:21 The voting vs. weighing investment framework
9:41 Pilot: Focus on your product, let Pilot handle your bookkeeping. Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses. Head to https://pilot.com/twist and get $1,200 off your first year.
19:53 Agree - Stop chasing invoices at https://agree.com and tell them Jason sent you to get 50% off for life!
22:25 The media's SpaceX criticisms and "hot takes"
23:54 Ben Cera of Polsia is back
26:53 Why Jason says no to a free tier
29:10 IM8 Health: Start feeling like your best self every day. Go to https://IM8health.com/twist and use the code TWiST to get a free welcome kit, five free travel sachets, and 10% off your order.
34:27 The wisdom of Seth Godin's "Purple Cow"
50:37 The "Pepsi Challenge" model
1:05:45 Lon got a dog, Jason got routers
1:10:37 The YouTuber to movie theater pipeline
1:15:20 Jason's new favorite travel bag
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 Lon:
X: https://x.com/lons
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
Check out all our partner offers: https://partners.launch.co/
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

This Week In Startups is made possible by:

NetSuite - Netsuite.com/TWiST
Deel - Deel.com/TWiST
Squarespace - Squarespace.com/TWiST

Two days before SpaceX launches the largest IPO in history at a flat $135/share, our VC roundtable drops a scorcher: The top 1% of seed deals might actually be underpriced. Plus: the "Sequoia scam" dual-tranche controversy, tokens-for-equity deals, and whether Claude Fable 5 is a true step function.
Tomasz Tunguz (Theory Ventures), Michael Downing (Castalia Capital), and Paige Doherty (Behind Genius Ventures) join Alex to go deep on Seed investing, startup economics, AI spend, and the impact of smarter AI on the founder journey.

Guest Links:

Tomasz Tunguz: https://x.com/ttunguz
Theory Ventures: https://theoryvc.com/
Michael Downing: https://www.linkedin.com/in/michaeldowning/
Castalia Capital: https://castalia.capital/
Paige Doherty: https://x.com/paigefinnn
Behind Genius Ventures: https://www.behindgeniusventures.com
Show Links:
Anthropic’s IPO announcement: https://www.anthropic.com/news/confidential-draft-s1-sec
OpenAI’s IPO announcement: https://openai.com/index/openai-submits-confidential-s-1/
Bending Spoons F-1 filing: https://www.sec.gov/Archives/edgar/data/2004711/000110465926071170/tm2613674-7_f1.htm
SpaceX IPO filing: https://www.sec.gov/Archives/edgar/data/1181412/000162828026040364/spaceexplorationtechnologib.htm
Brendan Foody’s post on Sequoia: https://x.com/BrendanFoody/status/2063470286515683759
Claude Fable 5: https://www.anthropic.com/news/claude-fable-5-mythos-5
OpenRouter data on Chinese models: https://openrouter.ai/rankings?view=day
Saronic: https://www.saronic.com/
MotherDuck: https://motherduck.com/
Nox Metals: https://noxmetals.co/

Timestamps:

0:00 Tomasz Tunguz, Michael Downing & Paige Doherty join
2:07 The SpaceX IPO and the IPO window
4:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
6:30 The new bar: 10x growth (not 3x) to raise a great Series A
8:46 Net-new AI budgets
9:46 Squarespace: Turn your idea into a beautiful website! Go to https://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.
11:09 How some founders are outgrowing venture capital
11:44 The power pendulum swings back to founders
12:46 SpaceX vs. OpenAI vs. Anthropic: Which IPO is most enticing?
19:53 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.
26:07 Tokens-for-equity, GPU-hours-for-equity & the financialization of compute
28:35 Founders airing VC dirty laundry (napping VCs included)
29:56 Netsuite - The business landscape is very chaotic right now. That's why you need NetSuite, by Oracle. Get the free business guide Demystifying AI at https://Netsuite.com/TWiST
36:38 Claude Fable 5 first impressions: pricing, benchmarks & orchestration
45:42 Where value accrues: application layer vs. models vs. private data
1:00:06 Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?!
1:01:25 Portfolio spotlights: Saronic, MotherDuck, and Nox Metals

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 Lon:
X: https://x.com/lons
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
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

The AI Tutor That Makes Kids Actually Think | E2298

This Week In Startups is made possible by:

Northwest Registered Agent https://northwestregisteredagent.com/twist

LinkedIn Jobs https://LinkedIn.com/twist

Shopify https://shopify.com/twist

Plaud https://Plaud.ai/twist

Today’s show:

*Schools teach kids to memorize formulas. AI helps them skip thinking entirely. Brilliant founder Sue Khim joins TWiST to tell us how her new AI tutor, Koji, uses the Socratic Method to help students solve complex problems on their own. Find out why she says “People aren’t anti-AI. They’re anti-being replaced and anti-slop.”
PLUS Jason’s take on the VC horror stories going around X… and his own anecdote about the tenacity and passion of legendary investor John Doerr.

Guest:

Sue Khim on X: https://x.com/suekhim
Brilliant: https://brilliant.org/
Viral Koji launch video: https://x.com/suekhim/status/2060378988606878147

Relevant Links:

Viral Greg Isenberg post about VCs: https://x.com/gregisenberg/status/2061794787825479818
Travis Kalanick’s story: https://x.com/travisk/status/2062224472426365045
Matthew Prince’s stories: https://x.com/eastdakota/status/2062860530360959273
John Doerr on X: https://x.com/johndoerr
Roelof Botha on X: https://x.com/roelofbotha
Michael Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/
Mohr Davidow Ventures: https://mdv.com/
Jason’s book “Angel: How to Invest in Technology Startups”: https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700

Timestamps:

0:00 Sue Khim's Alltuition origin story
1:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
4:10 Brilliant: from launch to product market pull
10:46 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist
15:08 Pricing against tutors, not apps
19:25 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist
21:22 Koji demo
24:11 Keeping Brilliant local while expanding
30:22 Shopify - Turn those What Ifs into sales with the e-commerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist
40:10 Every founder has a VC horror story
44:33 John Doerr went the extra mile to hear JCal's pitch
52:55 The LAUNCH investment strategy
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 Lon:
X: https://x.com/lons
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
Check out all our partner offers: https://partners.launch.co/
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