Hacker News Board Hacker News, browsed like a classic message board
Live data from Hacker News

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

twitter.com

Post reply on HN
Print view View original

121–130 of 137 posts

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

#121

Post by raydev »

rexreed wrote: post #87
FinanceAnon wrote: post #8

Is this the same guy who recently posted about trying to bluff Steve Jobs, getting called out on it and losing a deal? I wonder how many more stories like these he has lol Edit: found the link for those interested https://news.ycombinator.com/item?id=28826437

Yup I was about to post, it's the same guy. You'd think he'd learn his lesson about keeping his mouth shut. Not speaking sometimes is as strategic as speaking. Not sure what impact he wants these tweet threads to have, but if all you know from him are those tweet threads, it doesn't paint a very positive light. I'd like to replace TL;DR with TT;DR: Tweet Thread, Didn't Read.

> Not sure what impact he wants these tweet threads to have

They're notable stories and helpful to others who might make the same mistakes.

I'm more concerned that you are bothered by his honesty about past mistakes.

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

#122

Post by 533474 »

awb wrote: post #71

Another moral to this story that I haven’t seen mentioned yet: Don’t give unsolicited advice. Not only was this advice to buy a different company not asked for, it was presented in a vague way: “They’re better than us”. If I was the CEO of Yahoo on the receiving end of that, I’d be thinking a few things: 1) You don’t know my business well enough to be giving me unsolicited advice. 2) You’re passionate about subjectiv…

We don't know exactly how that conversation unfolded. Anyhow, they were lucky at the end

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

#123

Post by raydev »

buescher wrote: post #90

Am I the only one who reads these stories (others have linked to his Steve Jobs story - he was, um, not honest enough for Steve Jobs) as "I almost got acqui-hired twice by names you'd recognize but flunked the job interview both times" rather than as dashing tales of dealmaking derring-do?

Why do you think your initial reading isn't his intent?

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

#124

Post by raydev »

novaleaf wrote: post #84
awb wrote: post #71

Another moral to this story that I haven’t seen mentioned yet: Don’t give unsolicited advice. Not only was this advice to buy a different company not asked for, it was presented in a vague way: “They’re better than us”. If I was the CEO of Yahoo on the receiving end of that, I’d be thinking a few things: 1) You don’t know my business well enough to be giving me unsolicited advice. 2) You’re passionate about subjectiv…

I don't think the introspection need be so nuanced. The instinctual "Why are you shit talking yourself? What did you just let slip that I don't know?!?" Is just as valid a red flag.

> The instinctual "Why are you shit talking yourself? What did you just let slip that I don't know?!?"

I'm not understanding your instinct here. My first thought would be "this guy I trust enough to spend 100m is super confident about another team too, even better to keep him around for further insights"

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

#125

Post by solarmist »

admissionsguy wrote: post #44
brk wrote: post #7

In sales there is a term "know when to stop selling", this story is kind of a variant of that. If you have acceptable terms worked out, stop "selling", stop trying to show or add more value to the deal. Close the deal you have, and then work on any new or additional things.

It’s something I’ve been always struggling to accept. Be it sales, academic debates, court cases, or just dinner table conversations. Why does the outcome depend on the timing and specific choice of words used? Isn’t it a proof or irrationality of it all? Shouldn’t the outcome converge to the "best" one (optimal, true) the longer the process takes?

This argument ignores the context of the conversation.

The goal is rarely (almost never?) to find an optimal solution (if that's even possible).

Also why would you assume outcomes would converge? That is not a given in most situations.

You’ve never gotten tired of a conversation with someone that didn’t know when to stop? If so then you are exceptional in you're curiosity. I am a very curious person, but I have plenty of topics that are like nails on a chalk board to me.

Plus, every conversation burns energy, and at some point, people will get tired or bored or both, so continuing indefinitely does not rationally lead to better outcomes. Continuing past that point will lead to worse and worse conclusions.

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

#126

Post by solarmist »

solarmist wrote: post #125
admissionsguy wrote: post #44

Earlier quoted context omitted.

It’s something I’ve been always struggling to accept. Be it sales, academic debates, court cases, or just dinner table conversations. Why does the outcome depend on the timing and specific choice of words used? Isn’t it a proof or irrationality of it all? Shouldn’t the outcome converge to the "best" one (optimal, true) the longer the process takes?

This argument ignores the context of the conversation. The goal is rarely (almost never?) to find an optimal solution (if that's even possible). Also why would you assume outcomes would converge? That is not a given in most situations. You’ve never gotten tired of a conversation with someone that didn’t know when to stop? If so then you are exceptional in you're curiosity. I am a very curious person, but I have plent…

A good analogy is making pancakes or biscuit batter. You have to stop far earlier than I'm comfortable with, or the outcome is ruined.

This is because there are tons of (nearly) invisible processes going on, and you need to trust the recipe that people have come up with for getting good results.

And trying to understand every input and process could quickly become an entire career for any of these topics.

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

#127

Post by khazhoux »

tarsinge wrote: post #67
gumby wrote: post #16

Earlier quoted context omitted.

That’s not the takeaway. One of the classic rules of selling is “shut up and leave as soon as you have the order.” It’s not just literal sales call. If your meeting is to get the signed contract, run out the door once it’s in your hand. Don’t push for the P.O. in that moment. If you have a call with a prospect to set up a meeting, you’ve got that scheduled hang up and prepare for the in person meeting. Etc etc.

Also applicable to interviews. > run out the door once it’s in your hand Resisting the urge to add something at the door is crucial, more than one good meeting was ruined there (at least for me).

You mean the candidate (or hiring manager) said something that turned you off, or you said something?

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

#128

Post by khazhoux »

darkerside wrote: post #13

I know pop culture references don't always go over well here, but this reminds me of the Kanye situation at the VMAs. He was likely drunk and attention-seeking, but he was also probably completely incensed when he saw Beyonce fail to win Best Music Video for "Single Ladies". He saw such a misunderstanding of a clearly superior talent and effort that resulted in a qualitatively better result, and he couldn't help but…

That was just Kanye being Kanye though.

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

#129

Post by khazhoux »

jiveturkey wrote: post #108

ouch. I want to bask in the schadenfreude and the superiority complex over this noob, but I cannot. The way he relates the story is deceptively endearing. I like this guy and would work for him, even knowing that he so deftly killed his own companies in the past. I mean, taking him at his letter. It is all a lie though.

Your comment was the fastest roller-coaster I've ever ridden.

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

#130

Post by gumby »

khazhoux wrote: post #127
tarsinge wrote: post #67

Earlier quoted context omitted.

Also applicable to interviews. > run out the door once it’s in your hand Resisting the urge to add something at the door is crucial, more than one good meeting was ruined there (at least for me).

You mean the candidate (or hiring manager) said something that turned you off, or you said something?

If they like you, stop talking. It’s unlikely that you could say anything to like you more, but you could say something to change their mind the other way.
Post reply on HN