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  1. Private Equity FunCast
  2. Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)
Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast · Aug 26, 2026

Tech due diligence in the AI era demands scrutiny. Experts discuss separating hype from value, building a defensible AI story, and new metrics.

Use the Wayback Machine to See if a Company's 'AI Story' Precedes ChatGPT

Many companies now claim to be AI-native. A check on the Wayback Machine can reveal when they started using AI terminology. If it is only after ChatGPT's launch, their claims warrant deeper scrutiny as they might be narrative-driven rather than core to the business, a key diligence check.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

Prove Your 'Game-Changing' AI with One Chart, Not a Complex Narrative

During M&A, don't rely on key personnel to explain your AI advantage. Instead, create a separate document presenting the 'game-changer' with a single, compelling chart. Provide the raw backup data to prove the chart is not hallucinated, ensuring a cohesive and trustworthy story that stands on its own.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI-Written Code Can Take 10 Days Longer to Approve Than Human Code

CEOs expect AI to massively increase feature output, but data from tools like Jellyfish shows AI-generated code often requires much longer review cycles. This can slow a team's overall momentum despite the high volume of code produced, creating a disconnect between executive expectation and engineering reality.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

Your Old Support Tickets Are a Goldmine for Proprietary AI Training Data

Many businesses overlook their most valuable existing data assets. Years of unstructured data, like support tickets detailing integration issues and customer problems, are invaluable for training specialized AI models. This 'boring' data can become a key source of competitive advantage when activated with an LLM.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI Cost Conversation Rapidly Shifted from 'SaaSpocalypse' to 'Token Economics'

A few months ago, the fear was AI replacing SaaS businesses. Now, the pressing issue is managing massive AI bills. This has elevated 'token economics'—optimizing costs by using different models for different tasks (model routing)—from an advanced technique to a non-negotiable, table-stakes practice for any serious AI implementation.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI Has Created a 'Toddler with a Handgun' CTO Archetype

AI tools empower non-technical CTOs—those who primarily manage vendor contracts—to believe they can direct engineering. They push for rapid feature development without understanding engineering fundamentals like test coverage, creating massive technical debt. This is akin to giving a toddler a handgun.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI Coding Tools Can Cause 'Cognitive Atrophy' in Engineering Teams

Over-reliance on AI for coding can lead to engineers simply approving auto-generated code without deep understanding. This 'cognitive atrophy' erodes fundamental skills, creating significant long-term risk for the organization as nobody is truly responsible for the codebase's integrity or logic.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI Makes Previously Unsellable Legacy Tech Companies Viable Acquisition Targets

Companies with outdated codebases were often too risky to acquire due to modernization costs. AI-powered code translation tools now make it feasible to refactor legacy systems into modern languages relatively quickly, opening up a new category of M&A and roll-up targets that were previously untouchable.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

Top AI Teams Use Pods of Product, Design, and Engineering in Shared AI Sessions

High-performing teams are creating small 'pods' with a product manager (business context), a designer (UI/UX), and an engineer (technical execution) who work together in shared AI coding sessions. This collaborative model ensures features are viable, usable, and well-built from the start, breaking down traditional silos.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI Lets Product Managers 'Detox' from Scope Creep via Cheap Prototypes

AI prototyping allows product managers to build out every feature of an idea cheaply. This process of externalizing the full scope often reveals which features are unnecessary. This rapid iteration helps them 'detox' from initial over-scoping and arrive at the core value proposition before involving engineering.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

A Company's 'Business Scars' Are Its Most Defensible AI Training Data

The most valuable AI assets are not models, but proprietary data from years of solving domain-specific problems. This 'scar tissue'—like knowledge from undocumented APIs or complex integrations—is painful to acquire and impossible for competitors to replicate quickly, creating a durable competitive moat.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago

AI-Generated Code Without Human Oversight Creates Existential Security Risks

Companies are pushing for more AI-generated code to cut costs, but this code is often not fully understood by engineers. This creates significant security vulnerabilities that advanced AI models will inevitably exploit, potentially destroying smaller companies that fail to maintain a strong security posture and rigorous engineering standards.

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.) thumbnail

Can You Still Trust Tech Due Diligence? (w/ Jason Gill & Kirby Montgomery, Code & Co.)

Private Equity FunCast·a month ago