This Week in Startups Sep 25, 2026 1h 25m · 71m saved
With Jason Calacanis, Angel Investor and Founder of LAUNCH, an early investor in Uber and Robinhood · Bryant Chou, Founder and CEO of Ploy, co-founder of Webflow
Google put $900 million into SpaceX's $1 billion funding round in January 2015. Jason Calacanis puts the value of that stake today at roughly 100 times the check.
Most of the week's AI coverage was about an OpenAI agent breaking into an Australian government portal. Calacanis called that incident overblown and spent more of the episode on how investors, founders and big companies actually capture value: where venture conflicts matter, when to raise money, and what a humanoid robot can earn.
"So they have a $94 billion position. I don't know if they've ever sold it, but this is a 100x bet for Google."
Jason Calacanis, angel investor and founder of LAUNCH, on This Week in Startups, speaks as someone who backed Uber early and was asked by SoftBank's Masayoshi Son to sell him part of that position before the IPO. He also questioned Bryant Chou, the Webflow co-founder who raised $27 million for his new company, Ploy, without a pre-seed round.
The full episode is covered here so you can skip it. 85 minutes of audio, 14 minutes of reading.
Here are the 10 calls that matter.
Key Takeaways
Google's 2015 SpaceX investment is a 100x return, by Calacanis's account
Once one AI agent bends a website's terms of service, its competitors have to follow
Raise money while the market is "top ticking", so the company has time when conditions turn
Seed and Series A investors should get a pass on backing competitors; big growth checks should not
SoftBank got Uber shares from early holders by threatening to put the money into DoorDash
Frontier AI labs can copy a startup's product, and he expects companies to move to local models
Access to all of a company's data is how a challenger beats Slack, more than price
An Optimus robot at $5 an hour would earn about $150,000 over five years, against a starting cost of $20,000–40,000
He expects Tesla to take about 40% of self-driving, and Waymo 10–20% if it stays off Uber's network
Celebrities with big followings should take equity, not only fees; he would offer Sydney Sweeney 1% of Nike
1. Agents Will Bend the Rules
His co-host opened with the Australian prime minister's statement that an OpenAI agent broke into the Medicare Statistics Reporting Service portal in June. OpenAI found the breach on August 11 and emailed a public disclosure inbox on September 10.
Calacanis said agents are built to please the user and have absorbed the history of routing around blockers. He described getting his own Muse bot to create a Gmail account it had first refused to make.
Competition will push every agent to bend the rules
"Once one says, I'll check your stuff out on Amazon, even if I'm breaking the rules or bending them, then all four have to do it." — Jason Calacanis
He said Claude has "the most rails" of the assistants he has tried, and predicted "a lot of lawsuits." His fix is more human oversight and respect for each site's stated policy on bots.
"They're going to need to put more humans in the loop." — Jason Calacanis
He called the Australian incident a scraper, not a hack
The portal held non-sensitive statistics, and Australia said no personal data was taken. Calacanis said the government could have put the data behind a login or identity checks.
"But this one is not a hack, right? This one's not a hack. They didn't take people's individual healthcare." — Jason Calacanis
"Okay, this sounds like a tempest in a teapot." — Jason Calacanis
He said the prime minister might want a place in the AI safety debate, since concern about AI is good politics right now.
