Podcast Summary: Uncapped #39 | Daniele Perito from depthfirst

Podcast: Uncapped with Jack Altman
Host: Jack Altman (Alt Capital)
Guest: Daniele Perito, Co-founder of depthfirst (ex-Fair, Cash App/Square)
Date: January 14, 2026

Episode Overview

This episode features a deep-dive discussion with Daniele Perito, co-founder of the AI security startup depthfirst, and previously a founding team member at both Fair and Cash App (Square). The conversation explores company building in rapidly shifting AI and security landscapes, drawing on Daniele’s extensive experience in operationally intensive businesses, marketplace platforms, and advanced security systems. The episode is rich with insight on product-market fit, the evolution of security alongside AI, and the future of AI-driven defense mechanisms.

Key Discussion Points & Insights

1. The Shift in Security Threats: From One Bear to a Thousand AI Bears

• Timestamps: 00:00, 27:22
• Daniele opens and closes with a memorable security metaphor: “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. ... With AI, you can think about the fact that there isn’t just going to be one bear, there's going to be a thousand AI bears.”
• Quote [00:00 & 27:22]: "We're really trying to secure the whole software from AI bears, really." (Daniele Perito)

2. Founding Fair: Contrarian Thinking, Product-Market Fit, and Operational Rigor

Inspiration & Early Experiments

• Fair was a contrarian bet—few believed in the growth potential of brick-and-mortar retail. The founding insight was to take discovery risk off retailers by allowing “try before you buy” on net terms, enabled by technology.
• Quote [01:00]: “From Square we knew that taking risk on behalf of your customers was always a good way to create value.” (Daniele Perito)

Finding Product-Market Fit

• Pre-product-market fit journey was "meandering"—various models like consignment and points programs were tested. A key turning point was rapidly prototyping try-before-you-buy and witnessing instant customer resonance at a trade show.
  • Quote [02:18]: “I think we need to go with, like, try before you buy...The day after he went in front of customers, they immediately got it. And that's when we knew we had something.” (Daniele Perito)

Operational Complexity & Truth-Seeking

• Marketplace business requires intellectual rigor, constant A/B testing, and balancing intuition with data. Small changes can ripple unpredictably across a marketplace.
• "Seeking the truth" became a core operational value, as the business demanded agility and epistemic modesty.
  • Quote [07:28]: “Operating Fair has given me a healthy amount of epistemic modesty and humbleness.” (Daniele Perito)

Product-Market Fit Realization & Evangelization

• Even after achieving clear product-market fit, convincing candidates and investors took years. The true addressable market (TAM) proved elusive at first.
• Quote [09:20]: "For the first two or three years we were trying to estimate the size of the Fair market in a thousand different ways...It took really like two or three years for us to be like, okay, this is a gigantic market and we have a place in it." (Daniele Perito)

3. Building in the AI Era: A Faster, Higher-Stakes Landscape

Comparison to Previous Startup Environments

• Unlike nine years ago (when Fair was founded), the AI landscape is volatile, with foundational assumptions shifting every few months. Unpredictability and urgency are heightened as both risk and potential rewards increase drastically.
  • Quote [10:57]: “Right now, the assumption is that everything is about to change every three months…The stakes are higher and everything is just so intense all the time.” (Daniele Perito)

Team Behaviors & Mindset

• The need to pursue opportunity aggressively and expect continuous change is now central to founding and operating startups in this sector.

4. Early Cash App Days: Individual Impact Mindset

Founder's Empowerment and Security Challenge

• Daniele recounted moving from academia to industry, feeling initial imposter syndrome, but soon adopted a mindset: "There has to be a way for me to 2x the value of this entire business." This self-fulfilling belief led him to own challenging security and fraud problems at Square, directly contributing to Cash App's survival and growth.
  • Quote [12:18]: “If you knew that success was guaranteed, what would you do to achieve that success?” (Daniele Perito)
• His security and risk interventions reduced fraud losses by 80%, helping Cash App emerge as a $10B+ business.

5. Founding depthfirst: AI for Security as a Mission

Motivation and Mission

• The mission: “Without much better computer security, we do not get to play the AI safety and control game.” Secure software forms the substrate through which all AI safety efforts are mediated.
  • Quote [16:38]: "If I can create a business that is both commercially successful, but it's aligned with admission of making the whole software more secure, then maybe I can create a flywheel there." (Daniele Perito)

Long-Term Vision

• depthfirst aims to create an "AI security engineer"—a system that, like a team of security researchers, constantly maps and probes a company’s code and infrastructure.
  • Quote [18:31]: "What we're building is an AI security engineer…going through your organization…and they're saying, hey, there is a code bug here that allows someone to log in as someone else." (Daniele Perito)

6. The Evolving Security Landscape with AI

Emerging Security Dynamics

• AI fundamentally changes the penetration vs defense equation, enabling intelligent adversaries to probe for vulnerabilities with superhuman speed.
• Despite new threats, defenders maintain some advantages—most notably access to far more context about their own systems versus attackers, who “fly blind.”
  • Quote [21:40]: “Perfect security is not achievable...In software, it's similar. There is no perfect vault…But with the technology we're building at depthfirst, we can tilt the scales in favor of defenders.” (Daniele Perito)

The False Security-Productivity Dichotomy

• Daniele argues the apparent tradeoff between productivity and security is being rendered obsolete by AI-driven, real-time code review and vulnerability detection.
  • Quote [24:47]: "This is a false dichotomy at this point…we will be able to achieve security with productivity as well." (Daniele Perito)

7. Why Security Is a Unique Market

Market Complexity & Information Challenges

• Security software is challenging to buy and sell: “Neither the buyer nor the seller really know what's going on.” Security problems often depend on context and often require deep, manual verification.
  • Quote [28:26]: “Security is such a different market just because of how hard it is for both buyers and sellers to know what they're buying and what they're selling.” (Daniele Perito)

AI’s Promise in Verification & Transparency

• depthfirst’s product aims to increase trust by showing the assumptions and reasoning behind every finding, allowing customers to verify issues step by step.

8. Technology & Tactics at depthfirst

Founding Team and Technical Focus

• The founding team combines expertise from Databricks, DeepMind, and high-level security ops. Infrastructure and deep AI research blend to create a system where LLMs can autonomously spin up secure sandboxes, execute code, and reason about complex vulnerabilities. Reinforcement learning helps agents go deeper and connect multistep exploits.
  • Quote [31:23]: “Fundamentally, I believe that reinforcement learning plus large language models will allow us to sort of create a superhuman hacker for defensive purposes.” (Daniele Perito)

Learning and Collaboration

• While customer data is never shared, lessons are generalized by training on similar open-source issues. The AI is designed to serve as a collaborator for human security engineers—augmenting their abilities, not replacing them (yet).

Product Vision

• Ideal outcome: customers can “install depthfirst” and have an always-on, context-aware, superhuman security agent that learns organizational specifics and drastically shrinks vulnerability windows.

9. Comparing Company Building: Fair vs. depthfirst

Platform vs Pipeline Businesses

• Marketplace (platform) businesses, like Fair, require tight coordination due to feedback loops and cross-side effects. Conversely, pipeline (product-focused) businesses allow more experimentation and “letting flowers bloom.”
  • Quote [39:50]: “In a platform business...you need to keep a tighter grip...because there is always going to be second and third order things that might happen. In a pipeline business...there is a little bit more of letting a thousand flowers bloom.” (Daniele Perito)

Decision Making: Emphasizing Intuition and Speed

• Daniele encourages founders to analyze ~30 real data points deeply—forming intuition from specifics over big data/averages. He prefers making frequent, high-confidence decisions quickly (three 90% confidence choices per week vs. one 99% per quarter).
  • Quote [45:09]: “I'm always about making three 90% confidence decisions every week rather than one 99% confidence decision every quarter.” (Daniele Perito)

Notable Quotes & Memorable Moments

• Opening/Closing Bear Metaphor [00:00; 27:22]:
  “With AI, you can think about the fact that there isn’t just going to be one bear, there's going to be a thousand AI bears.”

• On Product-Market Fit [04:00]:
  “You try to convince yourself, I think we have product market...And then you actually say, oh yeah, we've product market before. And this is actually what it is.” (Daniele Perito)

• On Security Market Complexity [28:26]:
  “Security is such a different market just because of how hard it is for both buyers and sellers to know what they're buying and what they're selling.” (Daniele Perito)

• On Technological Ambition [31:23]:
  “I believe that reinforcement learning plus large language models will allow us to sort of create a superhuman hacker for defensive purposes.” (Daniele Perito)

• On Decision Making [45:09]:
  “I'm always about making three 90% confidence decisions every week rather than one 99% confidence decision every quarter.” (Daniele Perito)

Timestamps for Key Segments

• Opening security metaphor: 00:00
• Founding Fair and product discovery: 00:49 – 03:50
• Marketplace operational rigor & product-market fit: 04:45 – 10:33
• Shifting from Fair to AI startup landscape: 10:39 – 11:47
• Cash App & maximizing impact: 12:01 – 16:23
• depthfirst mission & security landscape: 16:38 – 20:35
• AI’s role in defense/attack dynamics: 21:13 – 25:23
• Security as its own market: 28:08 – 31:15
• depthfirst technical approach/team: 31:23 – 34:54
• Product vision/learning/collaboration: 34:54 – 39:00
• Pipeline vs. platform company-building: 39:14 – 45:09
• Final thoughts on speed/intuition in decision-making: 45:09

Conclusion

For listeners fascinated by building resilient, innovative companies in the AI and security domains, this episode is a profound masterclass. Daniele Perito shares hard-won tactical wisdom, candidly explores the complexity and excitement of the modern security landscape, and articulates a bold vision for AI’s role in rebalancing the perennial attacker-defender contest. Through stories, analogies, and practical advice, he offers a roadmap for founders and security leaders navigating what might soon be a world with a thousand AI bears.