What Captaining At Manhattanville Taught Me About Advising Founders

The thing about captaining a college team is that almost none of the work that matters happens in the games. The games are where the work shows. The work itself happens in the practices nobody watches, in the locker-room conversations after a bad performance, in the off-season conditioning when nobody is grading you, and in the quiet management of two or three teammates whose readiness will swing the next four games. The captain who only shows up for the games is the captain whose team underperforms when it matters.

I think about this a lot in the work I do now. I run an advisory firm that works with lower-middle-market founders through the preparation window before a sale and into the transaction itself. The structural pattern in the work is the same as the structural pattern in captaining at Manhattanville. The transaction itself is the game. Everybody sees it. Everybody scores it. Almost none of the actual work that determines the outcome happens during it. The outcome is mostly set in the preparation window that comes before, in the quiet operating cycles that nobody outside the company is watching.

We published a working paper on the pattern in April (DOI 10.2139/ssrn.6515478). The finding is that the gap between LOI value and close value in the population studied is forecastable months before LOI. The forecast comes from observable characteristics of the business in the preparation window eight to twelve months before the marketing process opens. The compression that founders experience at the closing table is almost never a closing-table phenomenon. It is a preparation-window phenomenon, surfaced at the closing table.

The parallel to team sports is direct. Teams that win in the final quarter are mostly teams whose conditioning, judgment, and depth were built in the off-season and the early-season practices. Teams that fall apart in the final quarter are mostly teams that tried to compensate in-game for preparation work that was never done. A captain who understands this allocates attention to the parts of the team's calendar nobody is grading, because that is where the games are actually being won and lost.

A few of the captaining habits I picked up at Manhattanville that show up almost daily in the advisory work.

One. The captain's job is to see the gaps between what the coaching staff is telling the team and what the team actually needs to hear. The coaching staff manages the big arc. The captain manages the day-to-day translation of that arc into what the team is going to do at practice on Tuesday. In advisory work, the bankers and the lawyers manage the big arc of the transaction. The advisor's job in the preparation window is the day-to-day translation. What is the operating team going to do this quarter that closes the structural gap that would otherwise produce compression at LOI.

Two. The captain who is mostly visible in good moments is the captain the team doesn't trust in bad moments. The captain who absorbs the bad moments calmly is the captain who can ask the team to do hard work later. In advisory work, the advisor whose presence is mostly visible when the news is good is the advisor founders eventually stop calling. The advisor who is the same person in the hard quarters as in the good ones is the advisor founders bring back for the next transaction and refer to the people they care about most.

Three. The captain's most important relationships are with the two or three teammates whose readiness will swing the season. Not the stars. Not the ones who are guaranteed to perform. The ones whose performance is variable and whose preparation can be moved. In advisory work, the most important relationships in the preparation window are with the operating leaders below the founder whose readiness will swing the transaction. The COO. The CFO. The head of sales. The buyer's diligence team is going to read those leaders' readiness as a major input into the underwriting model. The advisor who recognizes this allocates time to those leaders accordingly.

Four. The captain who reads the calendar and notices when the team is over-trained or under-rested is more valuable than the captain who only reads the playbook. In advisory work, the founder is the team that can be over-trained or under-rested in the preparation window. The founder who is grinding through quarter after quarter of preparation work without a real reset is the founder who arrives at LOI not at peak form but past it. The advisor whose calendar discipline includes the founder's calendar discipline is the advisor whose founders close strong.

Five. The captain whose team loved playing for him is not the captain who managed the most yardage or the most points. It is the captain whose teammates felt that their preparation was being honored. In advisory work, the founders who refer the most business afterward are not the founders whose deal closed at the highest absolute number. They are the founders whose preparation was honored, and who arrived at the close calm rather than wrecked.

The Valiants jersey hangs in my office. The reason it hangs there is not nostalgia. It is the reminder that the actual work is upstream of the game. That has held in every professional context since.