Weaponizing deal structure, the safe asset illusion, and AI models

THE CARRY

1. Cross-Podcast Themes

Weaponizing Deal Structure to Expose Seller Fiction

A seller suddenly locks the data room right after you sign the LOI. Jeremy Segal sees this as the ultimate test of deal discipline. On M&A Science, Segal explains how Progress codified an Orange Flags system during the MarkLogic deal when access to the target team evaporated. By structuring their M&A process with mandatory CEO-level escalation triggers, buyers effectively weaponize their deal structure to expose seller fiction, forcing them to demand transparency or walk away rather than blindly hoping for the best. Watch full episode

When it comes to venture capital, David Weisburd argues on How I Invest that structuring your access is critical to avoiding adverse selection. He limits risk by only partnering with high-conviction emerging managers or investing when a top-quartile fund is making its first investment. By rigidly structuring how he accesses deals, he effectively weeds out the fiction of weak assets and relies on the true conviction of top-tier cap table members. Watch full episode

The Illusion of the Safe Asset: Why Coasting on Past Returns Fails

The illusion of safety plagues public market investors chasing impenetrable businesses. On Capital Allocators, Pat Dorsey warns that blindly hunting for the widest moat possible can actively stunt your company's growth. Network effects eventually saturate, and if a company lacks an obvious reinvestment runway to plow profits back into high-return internal projects, that massive moat just traps idle cash. Watch full episode

The illusion of safety also traps private software companies clinging to the irrational valuations of 2021. Jeremy Segal explains on M&A Science that sellers often expect past market conditions to dictate current deals. Because interest rates have risen, coasting on those historical multiples fails to attract disciplined buyers like Progress. Public acquirers ground their targets in current market realities, meaning private firms must abandon their outdated valuation expectations or miss out entirely.

The End of the Spreadsheet Grind: Shifting from Manual Labor to Access

The days of junior associates functioning as expensive data-entry clerks are over. Caroline Phipps predicts on the Private Equity Funcast that within a year, AI agents will handle the vast majority of CRM logging. Tarun Amasa envisions these professionals transforming into orchestrators, acting like "train conductors" who manage intelligent agents rather than manually grinding through status updates. Watch full episode

When the manual grunt work disappears, the only remaining differentiator is your access to information. David Weisburd argues on How I Invest that the true eighth wonder of the world is the compounding of brand and access to information. He leans on the well-worn statistic that the large majority of wealthy families lose their fortune by the third generation because they fail to pass down institutional knowledge and networks. Once AI handles the spreadsheets, it's your early network choices and your ability to secure exclusive insights that become the primary drivers of long-term success.

2. Best Of the Week

• Capital Allocators: Pat Dorsey warns that Warren Buffett's famous “any idiot could run it”▶ 17:01 rule has pushed investors to ignore critical leadership flaws, shifting his own weighting to place heavy emphasis on management humility.
• How I Invest: David Weisburd advises aspiring top performers to humble themselves and work directly for the most competent person in their desired field, arguing that daily proximity to mastery is the ultimate predictor of career excellence.
• M&A Science: Jeremy Segal outbids PE firms for software targets by shifting high-cost engineering operations to Progress's existing global centers of excellence, driving down the effective EBITDA multiple post-close.
• Private Equity Funcast: Tarun Amasa had a rude awakening in high school regarding the limitations of spreadsheets, noting that while developer tools evolved rapidly, core financial platforms like Excel remained visually and functionally unchanged for 30 years.

3. Most Quotable

"Einstein famously said compound interest was the eighth wonder of the world. But he was wrong."

David Weisburd on How I Invest · July 12, 2026. A stark reminder that accumulating capital means nothing without the compounding returns of brand and access.

"I would bet in a year associates and analysts at PE funds are doing a lot less manual logging in the CRM. I would bet that most logging in the CRM is going to be automated by agents."

Caroline Phipps on Private Equity Funcast · July 12, 2026. A bold timeline for the death of junior-level data entry.

"We’re a financially disciplined buyer. We’re not just going to go buy assets at 10, 15, 20 times revenue multiples. That’s just not in our DNA."

Jeremy Segal on M&A Science · July 12, 2026. The strategic buyer's answer to the frothy software valuations left over from 2021.

Bottom Line: Deal structures and exclusive access are replacing brute-force valuations as the sharpest tools in a buyer's arsenal, while AI quietly prepares to rewrite the operational daily grind.