Founders want investing decisions to be rational, legible and fast. Venture capital is none of those things. A great company can be wrong for a fund, a perfect pitch can arrive at the wrong moment and a polite maybe can consume months that should have gone into finding ten more investors.

In the final part of our conversation, Jamie Wood turns the questions around. We talk about what would stop me from investing in AUTONOMIC, why fund fit matters, what warm introductions really buy and why the only durable fundraising strategy is to maximize your shots on goal.

Transcript

Jamie: What would stop you from investing in Autonomic? Oh. And what would push you?

Pablos: We tend to focus on renegade tech stuff that doesn't have a home somewhere else: breakthroughs in different areas in technology that are not part of a hype cycle, don't fit in anybody else's mandate. That's the stuff I like to do because I'm good at that and almost by definition nobody else really is. For example, we mostly stay out of life sciences because lots of people specialize in that. I have a bad attitude about the FDA. It doesn't really need my help. It's not something I'd be that helpful with.

Other investors are focused on it and can be better. I might be counterproductive as an investor in some of those things. We have done some. But a lot of the time it's because it's more about the aspect of what we can do with the data and the computer stuff that I really do get than the bio part. Batteries is another example. There's a new battery technology every single day in my inbox, and every one of them has an incredible, brilliant founder and is gonna be the next amazing battery tech. One of them will be right eventually.

It's just that I would probably not be in a good position to pick the winners because there's too many, and I don't focus on it. Other people do, so let them have the batteries. I don't do those things. What I think about Autonomic: I don't really think it needs my help, because it basically is a software product. Even though I've done a bunch of that and understand a lot about it, other people specialize in it and will be more helpful to you. Even those things I was making fun of—all the SaaS metrics—other people have them tattooed on their foreheads. I don't actually know what good SaaS metrics are off the top of my head because it's irrelevant, so I don't follow those things. I think there's a better investor for you. There's nothing wrong with your company, you, the plan, or the product. I think all that's very exciting. I think everybody should do the thing they're uniquely good.

I am very adamant about that for myself. I don't wanna do the things that I think somebody else could do better. It means that I miss really good opportunities sometimes. I get all kinds of things I could invest in that are gonna be huge hits, but they're things that don't need my help, so I don't do them. We invest in other things that'll be huge hits—things where we are uniquely able. I think you're gonna be fine at raising money for this.

Jamie: Be very ruthless about crafting the story.

Pablos: You're basically doing the right thing. You're building up a company that should be a good match for venture. You just need to tell the story in a way that maps. I think you could make a case that this does need our help because it's science-oriented. But I think there's investors who are a good match. There's people who wanna invest in mental health, people focusing on mental health tech.

Maybe not a lot, but at your stage I think you'll be able to get started. I'd say for you it's early. You could raise money with a roadmap that gets you to a cash flow break even off of this first round. It's not what VCs always wanna see. We wanna see: we put a little money in, you launch the rocket, and then we're, "Holy shit, the rocket's gonna go.

Jamie: Throw in more money." They wanna see that opportunity. You wanna be able to show that it can go that way too. You wanna show the VCs, if you're raising VC money, "Hey, this is gonna be something where you can deploy more capital down the road."

Pablos: A lot of VCs are managing a lot of money. The reason they're putting money in at the early stage is they're looking for winners that they can deploy more money into, 'cause they don't wanna 10X hundreds of thousands of dollars. They wanna 10X millions of dollars.

Jamie: Wanna double down on their bets. Or 10X tens of millions dollars. You wanna be able to craft a path where that all makes sense and show that is very possible here in a pragmatic way. But still covering your ass by being able to switch to living off revenue for a while.

What would push you into investing?

Pablos: Would push you into investing? Oh, she's really going for the jugular.

Jamie: The answer isn't much different. For investors like me, I do a lot of deals, and I do them very early. Nobody will admit to it, but there is a kind of weather report to it.

Pablos: If you catch me on the right day when I feel like I have a bunch of money and a couple of other deals that I was working on are dragging along or went south, then I might just go for it. There is a kind of "squeaky wheel gets the worm."

Jamie: This is perfect. We're gonna get you on Autonomic. I'm gonna track you. I'll know when you're stressed.

Pablos: Stressing you out? My deal fell through and I don't know what to do with this.

Jamie: Wonderful.

Pablos: Genius move. Get all your investor candidates to use Autonomic.

Jamie: It's really not a bad strategy at all.

Pablos: I like that. If that works, then I'm an investor. I think that people think that raising money is a methodical process, but in a lot of cases, it's a multifactorial decision-making process. Most of those factors will always be opaque to you in the seat you're in trying to raise money. The truth is, for VCs who might cut checks for you, a bunch of those factors are opaque to them, too. They act like they're really smart, and sometimes they are.

At the stage that you're at in the seed stage round, these people can't spend six months on due diligence. They don't have the time to do that. They just have to see more green flags than red flags. You wanna stack the deck in your favor there.

Jamie: My job is just to get more shots on net.

Pablos: I think shots on goal is a really important way to think about it because people say, "Do your research, look up an investor, make sure you match their thesis." But the truth is, you look on every VC website.

Jamie: It's all the same.

I wonder if they know that. They all lie. Y'all sound the same. You didn't know.

Pablos: They all sound the same. They all lie and say that, "We do early—"

Jamie: Stage investing.

Pablos: "Wanna be the first check," and they're not doing that. Almost none of them actually will do that. They just wanna be entertained, and they wanna see these things early so they can brag to their golfing buddies.

Jamie: How smart they are. I don't—

Pablos: —think there's a lot that you can learn meaningfully from what's online about venture firms. If you found some that say they wanna invest in mental health, that would be a good one. Human performance is a huge area right now. Casting it as that might make more sense. Say, "Look, we're performance enhancing." There's a lot of interest in that in different ways, and you'll find investors who map to that. You wanna prioritize them. But by and large, you just gotta plan to pitch a lot. Other founders might say something different; other investors might say something different. I do think getting good intros helps. I see a lot of stuff that comes in cold. Most of it's clearly not a match for us. I talk to founders that are introduced by people I know. Even if I think it's not a match, I'll try to make time to talk to those founders, see if I have any insights for them. Sometimes they win me over.

One I might do. I don't wanna do it, but I like it a lot better than I thought I would. These things are fluid. There is no enlightened or efficient algorithm for fundraising from your position.

Jamie: I'm so in agreement with you because there's all this content and blogs, and everybody wants to tell you how to fundraise. Ultimately it's a numbers game. Finding the pattern recognition: "Interesting. I talked to these five people across different investment theses"—air quotes right now—and 8% of what they're saying aligns each time, so maybe I need to look into that. Your industry in the VC world is a very interesting beast.

It used to be more interesting. I think now it's very systematized.

Pablos: The truth is the majority of venture firms are just gonna follow. Their entire thesis, which is not posted on their website—their actual thesis—is: we go golfing with our old frat buddies who work at Sequoia. That's their thesis. We look for secondaries in SpaceX. That's our thesis. They won't say thesis, but that's basically all they do. Probably three quarters or 80% of VCs are irrelevant. It doesn't mean they won't take the call, look at the deck, and go through the motions. But you won't know. That's why I say: just go pitch five or 10.

Jamie: It's sad. The value I got is that you become better; you become more honed in. I will say one thing in terms of you and your ability to provide insight: you do have a very unique way of looking—from a founder perspective, from a creator, a disruptor, and an investor.

Pablos: Suffer through all of it at one stage or another, for better or worse. I try to be really candid, which sometimes backfires. But I think not everybody can do that, and some of the people who could don't want to. I try to be really helpful to founders—especially the deep tech founders. Your top fundraising strategy probably should just be to tell people that you have Geraldine—fucking boss.

Jamie: It was the one thing that perked your ears.

That's true. You were like, "Oh, she's on your team? I'll invest."

Pablos: I did say that. We'll see how that goes.

Jamie: We'll see how it goes. Who knows? Maybe I'll be the one that grows on you.

Pablos: I can string you out through due diligence for a year.

Jamie: You'll be talking to other people: "I really don't wanna invest in this."

Pablos: But they do have Geraldine.

Jamie: This was awesome.

Pablos: We can wrap this up. Thanks. That's fun. I think people will really like it.

Jamie: I hope so. I think it's being able to have a candid conversation around where you're at.

Pablos: It's one of the things I want to do that I haven't gotten to do on the podcast: have candid conversations with founders. A lot of founders, I really don't wanna put them in the position of being exposed to critique on the podcast, but you seem to handle it really well.

Jamie: Actually, it's pretty special. I was thinking: the question, "What would stop you from investing?" You can be a lot harsher than you are right now. You can just be, "I think it's bullshit. It's not only not in my thesis," but whatever it may be. It's important.

Pablos: Even if I had gone that way, it would've been a good thing for you to endure. But I want other founders to also be willing to come on the podcast. I don't want this to be the last episode. I'm not pulling any punches. I would've told you, and I think there is real potential there.

Jamie: Exciting. I appreciate that. That's saying something coming from somebody who's had such a vast career in this industry.

Pablos: It's a lot of weird stuff.

Jamie: You're a unique weirdo. We'll leave it there.

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Recorded on January 16, 2025