Deal Feelings

Author: Jared Hecht (co-founder of GroupMe and Fundera), on his blog Ride It to the Sky URL: https://jared.xyz/deal-feelings How it reached the wiki: Will Manidis quoted Hecht’s own re-share and called it “one of the best blog posts ever written and i send it to people 100 times a year” ([[this is one of the [2]… (tweet)]], Oct 26, 2026). One-line: The stretch between signing an LOI and closing an acquisition is among the most emotionally turbulent in a founder’s life; compress it, choose counsel and board advisors carefully, keep the circle small, and expect to learn who your people are.

Key claims

• Time kills all deals — a lesson from Emil Michael: compress the time between term sheet and close, both because deals fall apart and to limit “the mental anguish the process imposes on yourself and the team.”
• The honeymoon ends at signing. Before the LOI both sides are in love with the shared vision; after it, incentives conflict (seller wants the LOI terms realized, buyer wants to mitigate risk), and tiny points — “esoteric indemnity clauses that protect against .001% catastrophic scenarios” — feel insurmountable.
• Choose your battles with the counterparty CEO, because escalating everything erodes goodwill.
• Counsel matters most in M&A. Good versus bad lawyers can make or break a deal: “Reference the living hell out of whomever you select.”
• Weigh board advice by experience. For some board members it’s their first exit; for others it’s a rounding error. Their advice will conflict; figure out whose actually holds credence.
• Corp dev quality varies. A junior or first-time corp dev lead optimizes for looking like they got a good deal, not for the working relationship you’ll need after close.
• Teammates are the biggest source of feeling. Keep the circle small (also from Emil Michael); acquisitions are something employees didn’t choose, and reactions run “from absolute euphoria to people lawyering up.” David Weiden: every team gets the jitters at the final yard line.

Notable quotes

“Then you sign a term sheet and everything changes on a dime.”

“It becomes difficult to differentiate between what is subjectively desirable versus what is objectively important.”

“Morale takes a long time to build, and it can take a day to evaporate.”

“I’ve been both blown away by selflessness and astounded by selfishness. It’s an experience that illuminates who you want to work with forever.”

“You learn (and feel) a lot at the finish line.”

How it connects

• 88% of VC-Backed Founders Got $0 (Discourse) — the same week’s argument about what founders actually walk away with at exit.
• Will Manidis — who keeps recommending it.