This Week in Startups

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Today’s show:
*There are $100 trillion in global assets sitting on top of what Hanover Park co-founder/CEO Chris Hladczuk calls “human duct tape”: armies of accountants in offices patching together work from various legacy tools (QuickBooks, Excel) that are holding funds’ own data hostage. Can all of this be replaced with AI? Find out how their startup went from overseeing $1B to $20B in assets in just 15 months.
PLUS, we flash back to March 2020, when Jason and Figma co-founder/CEO Dylan Field broke down the design tool’s initial go-to-market strategy, made some WILDLY inaccurate COVID predictions, and considered anxiety about “SaaS burnout” years before the category went full apocalyptic.
Guests:
Chris Hladczuk on X: https://x.com/chrishlad
Hanover Park: https://www.hanoverpark.com/
Dylan Field: https://x.com/zoink
Figma: https://www.figma.com/

Relevant Links:

Turner Novak on X: https://x.com/TurnerNovak
Banana Capital: https://www.bananacapital.vc/
Emergence Capital: https://www.emcap.com/
Lux Capital: https://www.luxcapital.com/
Susa Ventures: https://susaventures.com/
Bill.com: https://www.bill.com/
METR: https://metr.org/
Granola AI note taker: https://www.granola.ai/
Vanta: https://www.vanta.com/
Foo Camp on YouTube: https://www.youtube.com/c/foocamp
TechCrunch Mahalo coverage: https://techcrunch.com/2014/01/27/inside-mobile-news-launch/

Timestamps:

0:00 Hanover Park & the fund admin problem
3:32 Why funds outsource instead of building
5:44 Why fund accounting is so complex
10:38 The "one-click migration" goal
10:48 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
13:51 Context vs. intelligence gaps
16:11 No PMs, No Designers
20:46 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
23:18 This is a $100T opportunity
25:36 Flashback w/ Dylan Field of Figma
29:15 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
31:22 Pre-AI enterprise security worries
36:30 SaaS overload and SaaS burnout
37:30 The evolution of Figma pricing
42:38 The rise and fall of Mahalo dot com
51:38 The work-from-home revolution begins
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X: https://x.com/lons
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LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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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
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Substack: https://twistartups.substack.com

This Week In Startups is made possible by:

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Today’s show:
Forget the triple-triple-double-double-double; the new bar for startups hoping to raise venture capital has reached the stratosphere, though our venture panel is worried that startups are focusing too much on today’s problems that may not become companies tomorrow. During a lively VC roundtable, Cowboy’s Aileen Lee, Floodgate’s Mike Maples, and Lerer Hippeau’s Ben Lerer joined Alex to dig into exiting pre-AI startups, rising valuations, token spend, why they are keeping their funds small, and whether the government just tripped OpenAI and Anthropic!

Guest Links:
Aileen Lee https://x.com/aileenlee
Cowboy VC https://cowboy.vc
Mike Maples https://x.com/m2jr
Floodgate https://www.floodgate.com
Bene Lerer https://www.linkedin.com/in/benjlerer
Lere Hippeau https://www.lererhippeau.com

Timestamps:
0:00 Aileen Lee, Mike Maples, and Ben Lerer join the show
5:13 Venture liquidity returns: what SpaceX/Stripe distributions mean for LPs
9:13 Bending Spoons prices IPO at $29/share, roughly $18.4B valuation
10:31 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life!
12:09 "Companies get bought, not sold" — Ben on taking first offers seriously
17:41 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!
19:34 Mutiny's burn-the-boats AI pivot with Jaleh Rezaei
20:19 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://www.northwestregisteredagent.com/twist
22:15 Mike's KeepSafe story: the "rule of 70" and profit-first companies
25:12 The new growth bar: 5x, 4x replaces triple-triple-double-double
28:55 Fund size is your strategy: why Floodgate and Lerer Hippeau stay small
30:11 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://www.claconnect.com/withyou
37:39 The $100M Series A: Starcloud, General Intuition, Scale Cognition, Scout AI
40:35 King-making rounds and why mega-seeds destroy optionality
54:11 Open-weight models: the GLM-5.2 moment and going model-agnostic
55:30 Why fine-tuning open models is a treadmill, with Cursor/Kimi as an example
1:03:28 Grading the Trump administration on Mythos and Fable
1:06:33 Rising anti-AI sentiment, the wealth gap, and lessons from social media
1:11:43 Raising kids in the post-intelligence era
1:12:35 Where to find the panel and what each firm is investing in

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Follow Lon:
X: https://x.com/lons
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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
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Substack: https://twistartups.substack.com

This Week In Startups is made possible by:
Plaud
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Shopify
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Today’s show:
*It’s another All Star Summer, as we welcome back some of our favorite guests from throughout “This Week in Startups” history.

Chamath Palihapitiya’s development platform 8090 just raised $135 million, and he’s using it to go after a $4 trillion market: the software maintenance, migration, and middleware spending that’s currently “pure waste” for enterprises.

Find out why the All-In Podcast bestie says every company should use AI to build custom software the way that Google, Facebook, and Meta already do, then go inside Software Factory, the “system on a chip” organizational model, and why Chamath believes AI will allow every human on Earth to start their own company.

Guest:

Chamath on X: https://x.com/chamath
8090: https://www.8090.ai/
Learn With Me on Substack: https://chamath.substack.com/p/learn-with-me
Drink With Me: https://www.drinkwithme.com/age-verify.html
All-In Podcast: https://allin.com/
Social Capital: https://www.socialcapital.com/

Relevant Links:

8090 Series A announcement: https://x.com/chamath/status/2071571183665881515
Salesforce Ventures: https://salesforceventures.com/
Craft Ventures: https://www.craftventures.com/
The Production Board: https://www.tpb.co/
WNDR: https://www.wndr.vc/
LAUNCH: https://www.launch.co
Coatue Management: https://www.coatue.com/
Jack Dorsey: “From Hierarchy to Intelligence”: https://block.xyz/inside/from-hierarchy-to-intelligence
Thomas Keller’s The French Laundry: https://thomaskeller.com/tfl/

Timestamps:
0:00 It's TWiST All-Star Summer!
0:44 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!
3:21 Chamath's origin story
7:54 Tom Sawyer entrepreneurship
11:29 Shopify - Turn those What If's into sales with the ecommerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist
16:25 The $5 trillion software market
21:06 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist
25:00 Building "a co-founder for every human"
31:51 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
35:00 How product development lost its way
45:00 Regulated industries are the beachhead
50:00 Raising the $135M Series A
55:00 8090's "System on a Chip" model
1:04:44 What to tell your kids about AI

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
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Follow Lon:
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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

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This Week In Startups is made possible by:
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Today’s show:
F1 teams spend up to a third of their budgets on aerodynamics, often utilizing wind tunnels to simulate what happens on the track.
But Lyall Davenport of SKN Systems created a sensor-embedded tape that sticks directly to race cars as they drive around the real world, generating 420M data points per hour. And it comes in at roughly 95% less cost than running a full simulator.
Hear about how Lyall’s background in racing helped him develop the concept, plans to expand from motorsports to drones and defense, and his experiences going through Jason’s various programs.
PLUS OpenAI’s new models are so good, you can’t use them. Why Apple’s Vision Pro chief defected to OpenAI (and why their laptops and devices are getting more expensive). A look at the world’s most annoying data center in Sterling, Virginia. And Jason remembers iconic and influential tech journalist Om Malik.

Guest:

Lyall Davenport: https://x.com/Lyalldavenport
SKN Systems: https://www.skn.systems/

Timestamps:
0:00 How SKN uses tape to generate aerodynamic data
4:04 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!
6:17 How SKN uses tape to generate aerodynamic data
9:55 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
17:20 F1 teams are worth HOW MUCH?
19:42 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
20:35 Future markets beyond motorsports
30:03 DigitalOcean - Want to see what building on a true AI-native platform looks like? Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today — and cut your AI workload costs by up to 50%.
32:45 GPT-5.6 is banned for now
43:46 Vision Pro chief makes for the exit
51:24 Apple raises their prices
56:05 The data center you're allowed to hate
1:06:04 Zuck's new prediction market app
1:08:42 RIP Om Malik (1966-2026)
1:19:50 Streaming and camera recommendations
1:28:06 All about eFoiling

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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
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This Week In Startups is made possible by:

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Northwest Registered Agent - northwestregisteredagent.com/twist
LinkedIn - linkedIn.com/twist

Today’s show:

Jason sits down with Brynn Putnam, CEO and founder of Board, to learn more about her company’s tabletop gaming console. The pair talks about how to raise capital for yet-to-launch hardware projects, the screen-time debate, and how Board is approaching building or buying IP for its family-friendly games. Next, Alex got Heremus’s AJ Piplica on the horn to chat hypersonic, autonomous jets. The startup’s technology bridges the gap between rockets and airplanes, and may represent the future of warfare, yes, but also fast freight!

Guest Links:

Brynn Putnam https://x.com/BrynnPutnam
Board https://board.fun/
Board Series A announcement https://techcrunch.com/2026/06/02/board-the-new-game-startup-from-mirror-founder-brynn-putnam-raises-20m-has-already-sold-thousands/
Mirror https://www.lululemonstudio.com/
AJ Piplica https://x.com/AJ_Piplica
Heremus https://www.hermeus.com/
Heremus Series C announcement https://www.prnewswire.com/news-releases/hermeus-reaches-1-billion-valuation-with-350-million-raise-to-build-todays-fastest-aircraft-for-the-american-warfighter-302735273.html

Timestamps:

0:00 Board's Brynn Putnam joins the show
2:54 Board's proprietary AI software stack
6:43 Why Board manufactures in Mexico (not China)
9:21 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.
9:42 How to raise a Seed round for hardware without a finished product
15:26 Brynn's daughter and the mermaid example
17:09 Can Board limit screen time fears?
18:47 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
22:54 Selling the first 10,000 units
28:38 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.
29:42 Why Board is steering away from simple ports toward native IP experiences
35:32 Hermeus's AJ Piplica joins the show
35:32 What is Dark Horse?
43:48 Commercial applications: Cargo, organs, flowers, and trans-Atlantic in 90 minutes
47:47 Commercial applications: Cargo, organs, flowers, and trans-Atlantic in 90 minutes
57:00 Dark Horse range and the "reusable first stage" analogy
58:42 Dark Horse range and the "reusable first stage" analogy
1:02:42 $350M Series C led by Khosla; total funding now exceeds $500M
1:03:39 The SpaceX model: get customers to fund your R&D
1:07:47 Closing: the American Dynamism pitch

Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
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Follow Lon:
X: https://x.com/lons
Follow Alex:
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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:
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Instagram: https://www.instagram.com/thisweekinstartups
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Substack: https://twistartups.substack.com