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Jason Calacanis
Cofounder All-in Podcast & Founder of LAUNCH, All-In Podcast

Jason Calacanis's Investing Philosophy in 3 Rules

📅 Jun 15, 2026 This Week in Startups Clips 5 MIN 19804 VIEWS 19 SEGMENTS · 2 SPEAKERS
Thanks to our partners IM8 health. Start feeling like your best self every day. Go to IM8health.com/twist and use the code TWiST to get a free welcome kit, five free travel sachets, and 10% off your order. 📺  Watch the full episode here:    • SpaceX IPO Day: What Wall St. and the medi...   After watching Elon build SpaceX and Tesla from near-death, Jason has some insights. In this TWiST highlight, he boils his entire investing philosophy down to three rules… Back the team and the vision, not the hype. Dollar-cost average into companies you believe in (buy a little at a time, consistently,...
Jason Calacanis 0:00 ↗
Which bucket do I put it into? When it's Elon Musk, you put it into like three or four buckets. Short, medium, long, and fantastical.
Co-Host 0:07 ↗
Right.
Jason Calacanis 0:07 ↗
And that's just his gift. He is able to pursue multiple of those visions at the same time like Steve Jobs. Very few entrepreneurs are able to pursue this kind of vision concurrently. That's his gift.
Co-Host 0:22 ↗
Right.
Jason Calacanis 0:22 ↗
That's his gift. He's able to keep three or four business lines in his brain at once. And I've sat with him while he does meetings. He's got a meeting about the nuances of, you know, the X, formerly known as Twitter, business and how it's structured, how the functionality works on a very granular basis, and then he's able to task switch and talk to the people about the latest Starlink constellation. Then he's able to task switch to long-term. 'Hey, show me the designs of the solar arrays for the data centers in space.'
Co-Host 0:57 ↗
Yeah, we saw this at All-In Summit. He was talking and he would go on this really long tangent about robotic hands and, 'Oh, we're redesigning Optimus's hands so they are more like human hands,' and then he would jump right into, 'Oh, we're going to put these solar panels in space and that's how we're going to power the data center.' He's, it's — you're right. He could just jump between like 18 different fantastical ideas and lock in on each one.
Jason Calacanis 1:22 ↗
When you're all in on your business, no pun intended, pun intended, whatever you like, you know, you are able to do those simultaneously.
Co-Host 1:31 ↗
Right.
Jason Calacanis 1:33 ↗
Things in their brain like that. That's why I advise them. And I'll have many founders say, 'Hey, Elon runs two businesses. So why can't I?' And I'm like, 'Cuz you're not Elon.'

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APA

Calacanis, J. (2026, June 15). Jason Calacanis's Investing Philosophy in 3 Rules [Interview transcript]. This Week in Startups Clips. CEOInterviews.AI. https://ceointerviews.ai/interview/987189/

MLA

Jason Calacanis. "Jason Calacanis's Investing Philosophy in 3 Rules." This Week in Startups Clips, 15 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/987189/.

BibTeX
@misc{calacanis2026_987189,
  author       = {Jason Calacanis},
  title        = {Jason Calacanis's Investing Philosophy in 3 Rules},
  howpublished = {Interview transcript, This Week in Startups Clips. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/987189/},
  note         = {Speaker-attributed transcript with timestamps}
}