I once killed a $125M deal by being “too honest”

Not exactly. Having integrity means being whole, united, and indivisible. That certainly can involve telling the truth, but it's much broader than that. Someone who leads a double life, even if they don't make any commitments about their private behavior and even if they don't lie about it, lacks integrity.

Integrity means the opposite of being two-faced.

In this case, OP's behavior lacked integrity, even though it was likely honest. Although he was at the Yang meeting as a representative of LinkExchange, he advocated in favor of Viaweb. The forcefulness with which he argued ("your guys are wrong") definitely crossed the line into advocacy, not just an off-hand honest opinion. This set up a conflict within himself (his feelings toward Viaweb vs. his own interests and duties to his partners) as well as a conflict within the LinkExchange team.

https://insighttimer.com/consciousleadershipgroup/guided-med...

https://www.commonsensemedia.org/character-strengths-and-lif...

"the standards of integrity involves regarding internal consistency as a virtue, and suggests that parties holding within themselves apparently conflicting values should account for the discrepancy or alter their beliefs."

https://en.wikipedia.org/wiki/Integrity

>Not exactly. Having integrity means being whole, united, and indivisible.

Not just any kind of whole. Somebody "whole, united, and indivisible" devoted to his own interests for example, doesn't have integrity (even if he's open about it and e.g. is equally and wholy bad to everybody).

Let's stick to the dictionary: "1. the quality of being honest and having strong moral principles."

The "whole, united, etc" thing is "integrity" in objects (e.g. as in "structural integrity". Not integrity as the moral quality in people.

>Consciously or unconsciously, he was trying to serve three masters: his current company, Yahoo!, and PG's company. That kind of conflict of interest is inconsistent with integrity.

It's the opposite. That kind of conflict of interest is what you want to test someone's integrity.

Someone more strategic or someone which places tactic over integrity would have stayed silent (and neither lose nor verify their integrity). Someone without integrity would have lied against PG's company to promote their own.

Great story (& from the same guy with the Steve Jobs story ~last week).

Immediately calls to mind two phrases of advice I've found very useful over the years related to sales and deal making.

"Quit drilling - you struck oil", as in don't try to keep selling once your counterparty agrees - you can only cause harm at that point (and even if there are more great things to discover, no harm if they get happier after the deal closes.)

And, one of the the most frequently applicable ones in life (& once seen l, it's amazing to see how much unhappiness comes from not heeding it):

"The deal's not done until the check clears."

Lost a $125M deal, but gained a $265M one months later. It may have hurt originally, but sounds like things eventually ended up better than expected!

I wonder how many times there were pep-talks with the LinkExchange engineering team about how everyone was great.

Idk, maybe the twitter OP told their engineering team they were worse than Viaweb every day via automated, department-wide emails.