By Lou Sokolovskiy
Seasoned transaction advisor Wil Dublin has an uncomfortable yet essential challenge for independent sponsors navigating their first deals: stop refining your pitch and start inviting someone to break it.
It is blunt advice in a market that often rewards confidence over candor. Most independent sponsors will spend weeks polishing a deck. Far fewer will hand it to a respected peer and say: show me everything that is weak, unclear or likely to fail. But Dublin believes that is exactly where the edge is.
“It's a humbling process,” he recently told me. “You're basically saying, hey, list out all the stuff that I got wrong and list out all the problems here that make no sense why anybody would even do this, which is a very tough thing in general to do.”
That may sound simple, but it is not. In fact, it is one of the least-followed rules in business because it is “emotionally” expensive. “Some people will either run that kind of self-analysis, either fully or halfway,” Dublin noted. “But they won’t have a peer run it against them as well.”
Dublin is worth listening to because of his strong background in banking, private equity and analytics. He is the founder and managing partner of 7Alder, a strategic transaction advisory business serving lower-middle-market clients. 7Alder advises buy-side and sell-side clients on diligence, analysis, capital raising, structuring and negotiation on deals up to roughly $1 billion in enterprise value. In a nutshell, Dublin has seen firsthand how opportunities are actually evaluated, not how founders wish they were evaluated.
Numbers, skills, and relationships all matter, but Dublin argues that the most underrated layer sitting beneath all three is the discipline to pressure-test your own story. “You basically have to steel-man yourself,” he said. “Everyone needs to be honest… especially as it relates to the deal-making process and conveying a given opportunity. [Be] very clear about where the black marks are.”
What Dublin says is not just good rhetoric. It is good science. Research published in Nature Human Behaviour finds that “holding high confidence in a decision leads to a striking modulation of post-decision neural processing, such that integration of confirmatory evidence is amplified while disconfirmatory evidence processing is abolished.” Translation: the more certain we feel, the less likely we are to properly absorb the information that could save us from a mistake.
The evidence on feedback points in the same direction. A meta-analysis in PubMed Central found that performance improves most when feedback is specific, clear and frequent. Dublin’s advice mirrors that exactly. He is not calling for encouragement. He is calling for precise, uncomfortable critique that changes decisions.
The cost of avoiding that rigor is steep. McKinsey estimates that 70% to 90% of M&A deals fail to deliver expected value. The takeaway is consistent: value is lost when leaders substitute optimism for preparation.
That is why Dublin’s approach runs counter to a common habit. Too many sponsors build materials to persuade before they use them to discover. They optimize decks to impress investors instead of stress-testing them. His standard is tougher: make the opportunity not just easy to understand but also easy to challenge. A pitch should function less as marketing and more as a tool for intellectual honesty.
The pattern is well established. Strong leaders do not cling to their first draft. They operationalize dissent. Gary Klein’s well-known “premortem” approach for Harvard Business Review was built on the same principle: people are often reluctant to voice reservations during planning, and making room for those reservations improves the odds of success.
The practical takeaway is simple. Before raising capital or pursuing a deal, ask a few credible people to attack it, not to be supportive, but to expose weak assumptions, gaps and risks. Then revise until the case can withstand scrutiny. It may bruise your ego, but it’s what will keep you standing when confident amateurs have run out of explanations.
