Uncapped #39 | Daniele Perito from depthfirst

January 14, 2026

AI Summary

5 min read

🎙️ The Voices & The Context

The Format: Casual interview-style podcast chat between host and guest, blending storytelling, startup lessons, and tech deep dives.
The Key Players:
- Guest: Daniele Perito – Co-founder of FAIR (retail marketplace), founding security team at Cash App/Square, now founder/exec chairman of Depth First (AI-powered security firm). Interesting for his serial founder track record in high-stakes ops and shift to AI security.
- Host: Unnamed (likely Lattice investor/founder), draws parallels to own experiences, keeps convo flowing with probing questions.
The Vibe: Educational yet energetic – optimistic about AI, laced with humor (bear attacks!), reflective on startup grit. Fun "water cooler" energy from war stories and bold predictions.

🗝️ Key Themes & Topics

The episode traces Perito's journey from retail marketplaces to AI security, emphasizing rigor, experimentation, and AI's disruptive potential. Main topics: FAIR's scrappy origins and ops intensity; Cash App fraud battles; Depth First's mission against AI-fueled threats; building companies in volatile times.

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What you'll learn

1 (00:00) **🎙️ Introduction: Daniele Perito**
2 (00:40) **Founding FAIR**
3 (02:10) **FAIR Product-Market Fit Journey**
4 (04:30) **Operating FAIR as a Marketplace**
5 (09:00) **Post-PMF Growth at FAIR**
6 (12:00) **Time at Square/Cash App**
7 (16:20) **Launching Depth First**

+ Full timestamped outline available in the app

Show Notes

Daniele Perito is Co-founder and Executive Chairman of depthfirst, an AI-native security platform that understands your code, business logic, and infrastructure to find real vulnerabilities, slash false positives, and give developers actionable fixes in their workflow.

Daniele is also Co-founder and Board Member of Faire, where he previously served as Chief Data Officer and helped build the company’s data, risk, and analytics foundations from the early days to a multi-billion dollar valuation. Before co-founding Faire, Daniele worked at Square and was on the founding team of Cash App, where he focused on security, fraud, and risk systems supporting products used by millions of merchants and consumers.

We covered:

Inception stories from Faire and Cash App
The ultimate truth seeking machine
Building superhuman attackers with AI
Who wins over time: attackers vs defenders
Why security feels like its own world

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Timestamps:

(0:00) Intro

(0:40) The founding Faire insight

(4:34) Operational rigor of marketplace businesses

(10:39) Starting a company now vs in 2017

(12:01) The inception story of Cash App

(16:22) depthfirst’s mission

(18:08) AI security landscape

(26:10) Security is a fantasy world

(31:15) Building superhuman attackers for defense

(38:27) Roles of humans and AI in security

(39:14) Platform vs pipeline businesses

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