


15 Oct 2026 · 4m · 4 chapters
VC “anti-portfolio” stories—startup investments the guests passed on—and the “rules of thumb” that led to costly misses.
Vivek Vadia (Superset; recently investing; focuses on inference engineering and open-weight/open-inference models). Ross Fubini and Manish Patel (XYZ Venture Capital; share early-career misses). Micah Rosenbloom (Founder Collective; met Hugging Face founder Clem; concerned about chatbot behavior with kids).
Vadia says he didn’t invest early because he was new to investing; he would have loved seed/angel exposure to Base10/Fireworks-like companies. Fubini/Patel cite “don’t invest in sexting/gray-zone usage” and “don’t invest in tools companies” as misguided heuristics. Rosenbloom claims he was spooked by a kids chatbot’s potential outputs, despite a later pivot.
Snapchat, Canva, Hugging Face.
Written by AI. May contain mistakes.
Introducing the segment where guests discuss startups they passed on.
“anti-portfolio, a startup investment that they passed on.”
Vivek Vadia shares his experiences passing on key startups.
“Ross and Manish, tell us a story about a startup you passed on, your anti-portfolio.”
Ross and Manish discuss their regrets over Snapchat and Canva.
“So two really, really big misses in my career.”
Micah shares his thoughts on passing on Hugging Face.
“On today's special segment, we have Micah Rosenblum, MP at Founder Collective.”

Get the gist, explore an idea or ask about something said.
On The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Vivek Vaidya: This episode is brought to you by Ramp, the spend management platform we use here at TFR. They're offering listeners$150 just to take a demo. We've never had an offer quite like this. Claim your$150 before this offer is gone at our partner link, ramp.com slash partners slash TFR. Now on to the episode.
0:23Manish Patel: 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.
0:39Vivek Vaidya: Welcome back to TFR. On today's special segment, we ask guests to discuss their anti-portfolio, a startup investment that they passed on. Here's the segment called Why I Pass.
0:56Vivek Vaidya: On today's special segment, we have Vivek Vadia of Superset. Vivek, tell us a story about a startup that you passed on, your anti-portfolio.
1:06Nick Moran: I haven't passed on too many startups because I just started investing very, very, very, very recently as part of Superset. And as I told you, we don't look at that many companies ourselves, but I love hard systems engineering problems. And I've spent the last three to six months going deep on inference engineering, this whole point about open weight, open inference models. I would have loved to have been a seed investor, angel investor, whatever, in like a base 10 or a fireworks or any of these companies.
1:34Vivek Vaidya: Love it.
1:39Vivek Vaidya: On today's special segment, we have Ross Fabini and Manish Patel of XYZ Venture Capital. Ross and Manish, tell us a story about a startup you passed on, your anti-portfolio.
1:50Ross Fubini: I got a good one. Canva and Snapchat. Both were like sad, sad stories where I saw them early in my career. Snapchat, Evan actually was in the design program where I teach at Stanford. The advice was don't, I took a lot of venture advice from people that were older, wiser, gray-haired. And the advice was like, oh, you should not invest in that company because it's about sexting. And I was like, but the usage is amazing. And I was like, you don't understand. And it was just a little bit of that, like too much of the rule of thumb, like, oh, that seems like gray zone. Don't touch it, actually. But it was this joyous experience for these young people, not about sexting, but engagement.
2:26Ross Fubini: Canva, don't invest in tools companies was what I was told. And I was like, this is an amazing company as a design tool. I was like, I love this thing. Melanie, the founder, is incredible. Many of my good friends, Cable Desai and Wesley Chan, did that early deal. But I was just like, this is an amazing product. Nope. Don't invest in tools companies. So two really, really big misses in my career.
3:11Vivek Vaidya: As our preferred partner, they're offering listeners$150 just to take a demo. No need to sign up. Head to ramp.com slash partners slash TFR to claim your$150 before the offer expires. Now back to the interview. On today's special segment, we have Micah Rosenblum, MP at Founder Collective. Micah, can you tell us a story about a startup you passed on, your anti-portfolio?
3:37Micah Rosenbloom: There are so many, it's hard to do. But right now, the present one is hugging face because when Clem came to see me, you know, by the way, we knew the Betaworks guys pretty well. They had been doing these camps. And I think it was Matt Hartman and John Borthwick. And I think I met Clem a few times. And my kids were little. He was working on a chatbot for kids. I think it was teenagers. And I was a little bit, like, spooked about what it could, you know, like, what is this thing going to say to kids? especially my kids or anybody. And, you know, I, it was the beginning of this chat bot client era that, again, started as a toy.
4:16Micah Rosenbloom: I didn't totally get it. I will defend myself because it was a pretty big pivot from where they started. But they definitely saw something. And so, boy, right now that one hurts.
4:31Vivek Vaidya: That will conclude this installment of Investor Stories. If you're enjoying the program and would like to see it continue, take a moment and leave a five-star review in iTunes. Okay, that will wrap things up for today. Until next time, over-prepare, choose carefully, and invest confidently. Thanks for joining me.
5:08photo page
On this special segment of The Full Ratchet, the following Investors are featured:
Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.
The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area.
We're proud to partner with Ramp, the modern finance automation platform. Book a demo and get $150—no strings attached.
Want to keep up to date with The Full Ratchet? Follow us on social. You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter.







