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A Newsletter for Deal Pros
“People want guidance, not rhetoric. They need to know what the plan of action is, and how it will be implemented. They want to be given responsibility to help solve the problem and authority to act on it.”
- Howard Schultz
The Crux
Avoid Compounding Bad Investments by Misattributing Failure
Losing money on a deal is painful but finite. Misidentifying why it failed—and writing off an entire sector because of it—keeps costing you long after the loss is booked. One senior partner's emotional scar from a bad PEO investment killed a deal his own team never got to finish evaluating. The company went on to reward three or four subsequent PE owners with strong returns before being acquired by a strategic buyer. Read more
Risk & Return
Equity Risk vs. Debt Risk
A CEO spent four years fighting to turn his business around—and when he finally did, his lender told him to find a new bank. What he learned the hard way is that debt investors are paid to avoid volatility, not endure it. Once your debt starts behaving like equity, expect to pay for it. Read more
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The Art of Asking Good Questions
Double-Barreled Questions
In diligence, a poorly constructed question doesn't just get a bad answer—it gets a misleading one. Double-barreled questions ask about two things at once, which lets respondents agree with the convenient part and ignore the rest. Here's how to spot them and why it matters. Read more
Recommendations & Reviews
Boom
Recommendations & Reviews Boom Not all bubbles are created equal—some fund promises that never find a business model, while others bankroll the infrastructure that real innovators build on for decades. Boom by Bryne Hobart and Tobias Huber gives investors a framework for telling the difference before the bill comes due. Read more
The Fundamentals
Cash-Free, Debt-Free
A broker once told his client that "Cash-Free" meant the buyer gets to keep the cash—and it cost the seller over $800k at closing. Four words that appear on nearly every private M&A deal, and they're widely misunderstood. Here's what they actually mean and why it matters. Read more
Habits That Create Value
The Power of Habits
Careers aren't built on a handful of big moments—they're built on what you do every single day. The small behaviors you repeat quietly compound over time, widening the gap between average and exceptional long before it's visible. Watch the video. Read more
I Wish I Had Known
I Wish I Had Known: Molly Twigg
A decade at EY gives you a lot of reps—and a lot of perspective. Molly Twigg reflects on managing offshore teams, navigating uncooperative management, and the career advice she wishes she'd had earlier: your job isn't your identity, and knowing that actually makes you better at it. Read more
