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A Newsletter for Deal Pros
“What makes a decision great is not that it has a great outcome. A great decision is the result of a good process, and that process must include an attempt to accurately represent our own state of knowledge. That state of knowledge, in turn, is some variation of 'I’m not sure.'"
- Annie Duke
The Crux
Finding Insights in Contradictions – Why Diligence Should Lean into Inconsistencies
A PE firm under LOI on a curated talent marketplace had every signal pointing the same direction—strong momentum, repeat business, glowing customer feedback—except one. The company's NPS was mediocre, and the investment committee couldn't square it. Rather than write it off as an outlier, they chased the contradiction down. The answer reshaped how they understood the entire market—and where post-close growth would actually come from. Read more
Origin Stories
Palantir: The Half-Life of Igor
By 2000, PayPal was losing as much as $10 million a year to fraud. The fix Peter Thiel and Max Levchin built—pairing an AI algorithm with human analysts—was named "Igor," after the Russian fraudster who had plagued them most. Repurposed after eBay bought PayPal for $1.5 billion, that same hybrid model became one of the most dominant technology companies of ...
Risk & Return
From Tribe to TAM–The Challenges of Scaling Niche Brands
Henry Ford won over racers before there was a car market. Nike's founders were running people first. There's a recurring pattern in great businesses: they start inside a niche too small, too weird, or too fringe to read as a market—until they aren't. The danger for buyers is that the same quirks driving low CAC and premium pricing can look ...
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The Art of Asking Good Questions
Time, Trust, & Attention
On one deal, a junior associate kept typing with their mic open while the target's CEO was speaking—click-click-click. It took four requests to get them to mute, and the quality of every answer dropped for the next ten minutes. The best diligence questions rarely fail because they aren't sharp enough. They fail because nobody is spending the three scarcest resources ...
Recommendations & Reviews
Team of Teams
How did a smaller, low-tech adversary stay a step ahead of the world's most formidable military? General Stanley McChrystal's answer became a blueprint for any organization where information moves too slowly to matter. For deal teams built as rigid top-down hierarchies, Team of Teams makes an uncomfortable case: the distance between what you know and when you act is exactly ...
Writing Well in M&A
Writing as Investment Thinking
M&A gets filed under quantitative work—models, trackers, data rooms, endless rows of numbers. But look at how careers are actually spent: CIMs, IC memos, QofE reports, LOIs, board updates. Almost none of it is taught, and that's a problem, because writing in M&A isn't administrative work—it's analytical work. A weak sentence usually reveals a weak idea. This first installment of ...
Habits That Create Value
Be Curious and Develop Pattern Recognition
The average major leaguer hits .250. Ted Williams hit .344 over a nineteen-year career—not by swinging harder, but by reading patterns no one else could see. Warren Buffett devoted part of a Berkshire shareholder letter to the approach. When information is abundant, context is the scarce asset, and pattern recognition is how the best investors build it. Read more
I Wish I Had Known
I Wished I Had Known: David Keys
Three decades leading healthcare investment banking teams, and David Keys says two things kept him engaged: a lot of coffee, and relentless curiosity. He shares how aiming that curiosity at clients' legal teams and R&W underwriters taught him the purchase agreement better than any framework could—and why the best advisors treat every rep as a learning opportunity. Read more
