
The Future of AI Software Security | Ep. 39
Daniele Perito (guest), Jack Altman (host)
In this episode of Uncapped with Jack Altman, featuring Daniele Perito and Jack Altman, The Future of AI Software Security | Ep. 39 explores aI-driven security and building Depthfirst to defend software ecosystems Daniele Perito (co-founder of Faire, early Cash App leader) explains how marketplace businesses demand operational rigor, truth-seeking through experimentation, and comfort with uncertainty—especially before true product-market fit.
AI-driven security and building Depthfirst to defend software ecosystems
Daniele Perito (co-founder of Faire, early Cash App leader) explains how marketplace businesses demand operational rigor, truth-seeking through experimentation, and comfort with uncertainty—especially before true product-market fit.
He contrasts starting companies in 2017 versus today’s AI era, describing faster-moving “shifting ground,” higher stakes, and more frequent strategic resets.
Perito lays out Depthfirst’s thesis: AI will dramatically lower the cost of attacking software (“a thousand AI bears”), forcing a step-change in defensive capabilities.
Depthfirst aims to unify fragmented security tooling into an always-on AI security engineer that understands context, reduces false positives, verifies assumptions, and eventually uses reinforcement learning to build “superhuman attackers” for defensive testing.
Key Takeaways
Product-market fit can flip from ambiguous to obvious overnight.
Faire’s breakthrough came when they reframed their offer as “try before you buy” (net terms + returns). ...
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Marketplace businesses force epistemic humility and tighter rigor.
Because small changes can ripple through a recursive supply/demand system, Faire relied heavily on data analysis, A/B testing, and risk modeling—while still needing intuition to avoid purely incremental decisions.
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TAM estimates are often unknowable early; treat them as directional.
Perito describes spending years triangulating Faire’s true market size. ...
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The AI era changes founder psychology: constant re-evaluation is required.
Unlike 2017’s relatively stable assumptions, Perito argues today’s environment shifts every few months—market structure, product capabilities, and competition can all change quickly, increasing both paranoia and potential upside.
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A single person can create outsized impact by targeting the biggest constraint.
At Square/Cash App, Perito focused on the highest-leverage risk: fraud losses. ...
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AI will increase attack frequency by driving the cost of attacking down.
Security is inherently “relative,” like bank vaults—perfect defense is impossible, and enforcement online is weak. ...
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Defense can still win by using context and continuous verification.
Perito claims defenders retain an advantage because they can analyze their own full systems deeply, while attackers often “fly blind. ...
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Notable Quotes
“There isn't just going to be one bear, there's gonna be a thousand AI bears.”
— Daniele Perito
“The market is an incredible truth seeking machine for the type of questions that it can investigate.”
— Daniele Perito
“Individually, in a company of a few hundred people, there has to be a way for me to x the value of this entire business.”
— Daniele Perito
“Without much better computer security, we do not get to play the AI safety and control game.”
— Daniele Perito
“I'm always about making three 90% confidence decisions every week rather than one 99% confidence decision every quarter.”
— Daniele Perito
Questions Answered in This Episode
On Faire: What specific metrics or customer behaviors convinced you “try before you buy” was the real PMF unlock, versus just a good feature?
Daniele Perito (co-founder of Faire, early Cash App leader) explains how marketplace businesses demand operational rigor, truth-seeking through experimentation, and comfort with uncertainty—especially before true product-market fit.
Get the full analysis with uListen AI
On marketplace rigor: Can you share an example of a small A/B test change that produced an unexpected second- or third-order negative effect?
He contrasts starting companies in 2017 versus today’s AI era, describing faster-moving “shifting ground,” higher stakes, and more frequent strategic resets.
Get the full analysis with uListen AI
On AI security: What types of vulnerabilities are realistically “too deep” for legacy scanners but now reachable with LLM reasoning—and what’s a concrete example pattern?
Perito lays out Depthfirst’s thesis: AI will dramatically lower the cost of attacking software (“a thousand AI bears”), forcing a step-change in defensive capabilities.
Get the full analysis with uListen AI
On measurement: If security is “hard to know what you’re buying,” what objective evaluation methodology should CISOs use to compare AI-native vendors?
Depthfirst aims to unify fragmented security tooling into an always-on AI security engineer that understands context, reduces false positives, verifies assumptions, and eventually uses reinforcement learning to build “superhuman attackers” for defensive testing.
Get the full analysis with uListen AI
On false positives: How does Depthfirst decide what assumptions to surface to customers, and how do you prevent assumption lists from becoming noisy or overwhelming?
Get the full analysis with uListen AI
Transcript Preview
There is this saying in, uh, uh, security circles that in order to survive a bear attack, you don't need to outrun the bear, but you need to outrun the person running next to you. That's the way that the business has been operating for a very long time. But with AI, you can think about the fact that there isn't just going to be one bear, there's gonna be a thousand AI bears.
That's terrible.
[chuckles] Like, so we're really trying to secure the world's software from AI bears, really. [upbeat music]
Today, I'm here with Daniele Perito, who co-founded Faire. Before that, you were a founding team member at Cash App at Square, and you also ran data and security there. And then most recently, you've now become the founder of Depthfirst, which is an awesome AI security company. Really excited to be doing this, uh, podcast with you today.
Thank you for having me.
I want to start by learning about Faire and sort of like, what your experience was like there, but maybe if you could take us back to sort of the founding insight or what sort of led to the creation of the company.
I would say that Faire was probably a little bit of a contrarian bet. Uh, people at the time didn't think that brick-and-mortar retail was this place where there was gonna be a lot of growth, like Faire proved. But, uh, at the time, Max, Marcelo, and I were talking about ideas on companies to start together with Geoff Golitzen as well, and, uh, Max was introducing a high-end umbrella from the-- from New Zealand to the US market. He was seeing, uh... That was a side gig. You know, he was working at Square, but he had a little bit of a side gig, and he, he was seeing how getting sales on Amazon was extremely hard. Getting into a Nordstrom or a Walmart was also extremely hard, and working with the hundreds of thousands or millions of retailers was just impossible because there were, like, many, many regional sales reps and things like that.
Mm.
So we thought that there had to be a better way, and then from Square, we knew that sort of taking risk on behalf of your customers w- it was always a good way to create value because, you know, Square is in the risk management business, in a sense, and we had learned that there. So we decided to give retailers the ability to order and not have to pay for sixty days and be able to return anything that they don't like. So... And taking the discovery risk off of their balance sheet, and then not even asking brands to offer that value prop, but us sort of trying to use technology to offer that value prop. So that was a big insight-
Yeah
... in starting Faire.
Did it go sort of the way you expected from the beginning? Like, how linear was it from, like, that concept to just, like, the company, you know, taking off and going the way that it ended up going?
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