Investor Stories 470: Passing on Uber, Perplexity, and Fintech's Breakout Winners — The Stories Behind the Misses (Orthlieb, Callaghan, Byunn)

**SPEAKER_1** (0:00)
Today's episode of TFR is brought to you by.Tech Domains. I review thousands of startup decks each year, and small branding decisions signal how founders think. That's why more startups are choosing.Tech. It's simple, modern, and clearly communicates what you build. Go secure your.Tech domain today.

**SPEAKER_2** (0:25)
Welcome to the podcast about Venture Capital, where investors and founders alike can learn how VCs make decisions and reach conviction. Your host is Nick Moran, and this is The Full Ratchet.

**SPEAKER_1** (0:41)
Welcome back to TFR. On today's special segment, we asked guests to discuss their anti-portfolio, a startup investment that they passed on. Here's the segment called Why I Passed. On today's special segment, we have Ben Orthlieb from Blue Moon.

**Nick Moran** (1:02)
Can you tell us a story about a startup that you passed on, your anti-portfolio?

**Ben Orthlieb** (1:06)
The biggest one in the anti-portfolio is Perplexity. We met them the week that they were doing the raise. See? The 90 million raise. And it's a question of price discipline. So we passed on price, and partially because we didn't really have time to go deep into personality. Now, at the time, maybe it's a rationalization. It was very early in the LLMs, and there was this whole talk about, are they commodity? But it still is far and away the biggest anti-portfolio company, which, by the way, if we had invested alongside Merck or our portfolio, would be borderline legendary at this point.

**Nick Moran** (1:53)
On today's special segment, we have Jon Callaghan of True. Tell us about your anti-portfolio startup that you pass on.

**Jon Callaghan** (2:01)
There's so many. Look, if you're doing this job right, I don't worry. Well, of course I worry. Of course I wish I funded the ones that I will tell you about one in a second, so I'll get there. But I worry about what we don't see. And if we're seeing something, and for some reason we pass, that on us, I wish we didn't pass on the mega mega winners, the one I'm gonna tell you about stings. But we saw it, and there was a reason why we passed, and I can have peace with that. Okay, so Uber.

**Eric Byunn** (2:31)
Oh, I know.

**Jon Callaghan** (2:33)
Seed Round. I used the product. I'd heard about it. I actually read a blog post about how amazing it was. This was when Garrett...
So actually, I think there was a little before that, when we heard about it from Garrett, because we knew him, we loved him. And our conversation was like, okay, great, this is cool, we want to do it. Do you want to be CEO? And he's like, oh, no, no, there's no CEO. By the way, my decision was wrong. We should have seed funded that company. Obviously, the data is there. But one of our things is that we need to have we need to have a leader. Like we need to have the the person who's really going to kind of be a part of this whole journey with us. Right. And there was none at the time. This is before Travis showed up. And so when I look back at that, of course, it's like, wow, that would have been life changing for everyone. By the way, I ended up there through another way. We ended up having a piece of Uber early, through another pathway, through the portfolio and things. And it worked out very well. But that was hard. And I think it's still to this day, one of our things that we need to have a protagonist. We need to have a visionary leader leading the charge. And at that point, it was a project and it was a pretty cool one. But there was no leader. So anyway, that's the truth. And there's many others. And like I said, I worry about what we're not seeing. That keeps me up at night.

**SPEAKER_1** (4:03)
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