Wales v. Calacanis

🎥 Jan 09, 2008 📺 TechCrunch ⏱ 4m 👁 2219 views

Jimmy Wales and Jason Calacanis discuss their startups at DLD in Munich - Jan 2008.

About Jason Calacanis

Jason Calacanis, co-host of the All-In podcast and founder of LAUNCH, has been active on his podcast and at events discussing investment strategy, the technology industry, and political dynamics. In October 2024, he outlined his investing philosophy, emphasizing backing a team's vision over hype and dollar-cost averaging into companies one believes in. He described Elon Musk as having a gift for pursuing multiple visions concurrently and argued that criticism of valuation hand-wringing stems from an inability to tolerate ambiguity across multiple business lines. In mid-2026, Calacanis moderated the All-In Liquidity Summit in Napa Valley, describing it as an event for the "top 0.1%" of the podcast's audience, with 550 capital allocators representing $7 trillion in capital present. He stated that the event was part of a broader community-building effort and that his philosophy for events is that attendees return if they make a great contact, have a great experience, or learn something. Calacanis has also commented on the current tech boom, which he attributed to AI, noting that companies like xAI, OpenAI, and Anthropic are going public. He described seeing "a Cambrian explosion in startups" and said he personally invests in roughly 100 new companies per year through his fund LAUNCH and a program called Founder University. In a May 2026 appearance on the Bulwark Podcast, Calacanis discussed why some in Silicon Valley have been reluctant to criticize President Trump, arguing that access to the administration to shape policy is preferable to not having one's phone calls returned. He also described former President Trump's handling of Iran as "an unmitigated disaster" and said he believed it would "kill his presidency." Additionally, Calacanis has been publicly critical of Mark Zuckerberg, stating that the Meta CEO has "damaged the reputation of the industry" by repeatedly prioritizing self-interest over what Calacanis described as the right thing for humanity, including in matters of privacy and content moderation.

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Transcript (7 segments)

✨ AI-enhanced transcript with speaker attribution

Jason Calacanis0:00

Well, for me, the thing that we need more of is transparency research. I think this is going to help us get to a new level of quality research as well. But for the last several years, I think we've hit a bit of a plateau. It's pretty good, but it has a lot of problems. You can still find plenty of searches in Google where there'll be similar examples that he showed. And for me, a big part of what I'm all about is open source software, transparency, openness. This is something that has benefited us across the entire internet. Most of the software that really runs the internet—Apache, PHP—all of us are using the same thing.

The thing is, what I don't understand is why, if you know, this room is not the typical demographic for which your products must appeal, right? So if the average user is still enormously excited about what they can essentially newly accomplish with Google and other search engines, and Google's market share is growing, it suggests there's tremendous satisfaction. There's not yearning for an alternative by any evidence in terms of the general consumer culture.

That's actually not correct. There's a study that came out... and that's up from 50% last year. So, I think people do have a problem with some results, but I think they're hinting at a bigger problem, which is in order to make something that is worth building, worth switching, it has to be a magnitude better than the current solution. And Google's pretty fantastic. So, if you're going to beat Google or Yahoo, you're going to have to be two, three, four times better. You can't be 15% better.

Is that your aim, to do something better? I think we're already five or ten times better for the pages we do. And so we don't have to compete for the whole long tail. We can be fantastic with the most common searches. And if you type in a general word like flat panel or TV or Paris, the less words you use on Google or Yahoo or Ask, the worse the result is. Actually, in our service, it's the opposite because more care is given to those by humans. So you know, it's a fallacy to think that you have to beat Google to compete in this space. Most people use three or four search engines a month. And so while people want to make it a 'Jason is taking on Google' story, it's a little ridiculous. And Google only has 60-65% market share. You know, Microsoft had 98% market share in desktop software. So if you want to talk about monopoly, that's correct in Microsoft's case, absolutely not correct in Google's. And Google is only a couple years old. When they came into the space, they had 0%. And so we're coming in with zero, but I don't see why each of us can't say 5 or 10%. And each percentage point of search on a market basis is worth one to two billion. So if we usually have one or two percent of search, we've got extremely large businesses.

I mean, when you address that explicitly, do you think you're going to draw significant numbers of users away from Google, Yahoo, and Microsoft?

Uh, yeah, I mean, I definitely think we can. My mind is a little bit different from Jason's though on the point of what it takes to beat Google. You know, he's speaking in loose numbers, 5% better. I don't... it's a loose way of speaking. But what I see is that right now we have a situation where the search result quality coming from Google, from Yahoo, from Ask are all very, very similar. MSN is still much worse in my opinion, but those three and actually some of the lesser-known competitors are all generating industry-standard quality search. But we're no longer in the era that we were in when Google first came out, where Google was this massive quantity ahead. So if we have all the major search engines generating similar quality results, they're actually competing on brand, not competing on technology.

That was exactly you. I think that's my taking a highly technological approach as well. If you ignore the brand advantage of just the name Google, the habituation of the consumer—that is a whole factor that...