Founder Secondaries and Questionable Loans

This Week In Startups is made possible by:

Vanta - https://www.vanta.com/twist

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Today’s show: 

Domestic robots have never been hotter… so why is iRobot in so much trouble?!

On TWiST, we’re investigating the recent troubles facing the automated vacuum robot, Roomba. We’ve all seen these little discs sweeping up our friends’ floors… but now the company behind them is running out of cash.

What happened to iRobot, and would things have turned out differently if they had been sold to Amazon back in 2022?

PLUS why Jason thinks you should spend your disposable income on investing… Is Alex still a journalist, and what does that actually mean for his portfolio?… Are founders and investors too cautious when it comes to signaling risk?… Why did all those internal Pipe documents leak online?… And MUCH MORE!

Timestamps:

(00:00) Why Jason loves Incentivizing New Ventures and Economic Strength Through Capital Formation!

(09:48) Jason warns “no one is coming to help you with your job loss”; you’re on your own!

(10:21) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(13:05) Why Jason thinks laid-off HR folks should be starting their own “micro-funds"

(14:13) Does Alex consider himself a journalist? Is it unethical for him to invest in companies? (Let’s get INTO IT.)

(16:02) You can’t become complacent when you’re in the lead!

(20:03) Why you should use disposable “entertainment” income on investing

(22:32) Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(23:36) $9B in new funds?! What is Lightspeed up to?

(26:10) Is everyone too cautious about “signaling risk”?

(28:39) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(31:21) How does Jason think those Pipe documents leaked? And WHY?

(38:15) The critical importance of diversification

(39:35) iRobot went BANKRUPT! Who killed the Roomba?

(44:47) Are there ANY potential deals that would bother Jason? It’s all about market share.

(48:18) HuggingFace is moving major Reachy Minis! How open source turns everything upside down.

(53:22) How Polymarket will decide when/if the AI bubble “bursts.”

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Follow Lon:

X: https://x.com/lons

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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:

(10:21) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(22:32)  Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

(28:39) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

Great TWIST interviews: 

Will Guidara

https://youtu.be/pvJa2pzuXWQ

Eoghan McCabe

https://youtu.be/9dHN4YFkgv4

Steve Huffman

https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424

Brian Chesky

https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112

Bob Moesta

https://youtu.be/y2UMzSqX94Q

Aaron Levie

https://podcasts.apple.com/ca/podcast/box-ceo-aaron-levie-breaks-down-box-ai-and-generative/id315114957?i=1000612384545

Sophia Amoruso

https://podcasts.apple.com/ca/podcast/sophia-amoruso-on-branding-raising-a-fund-portfolio/id315114957?i=1000601352978

Reid Hoffman

https://podcasts.apple.com/ca/podcast/reid-hoffman-on-ais-crescendo-moment-regulation-and/id315114957?i=1000612548498

Frank Slootman

https://podcasts.apple.com/ca/podcast/snowflake-ceo-frank-slootman-on-moving-the-needle-win/id315114957?i=1000602560622