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I once killed a $125M deal by being “too honest” (twitter.com/apartovi)
289 points by akh 3 months ago | hide | past | favorite | 133 comments



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 subjective opinions: “They’re team is better than us.”

3) You appear to be lacking confidence by buying into this subjective thought that another team could be “better than” yours.

4) You don’t lead with the important information, about why you think they’re better: Are they more efficient? More experienced? More creative? More careful?

5) Your passion and attention is placed on the future rather than the present and the more important task that I’m paying you for which is integrating your business into our ecosystem.

The list probably goes on, but the phrase “They’re team is better than ours” raises a lot of red flags IMO.

Looks like it ended well in the end as they sold for 2x to Microsoft just 6mo later. A great example of “failing up”, which happens to a lot of successful entrepreneurs.


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.


Or it could just be a drunk person running their mouth and a nervous exec getting spooked. No need to overanalyze every word of conversation to look for red flags.


Well if the speaker is drunk, then its exactly excusable is it? Seems like I would rather take the parent comments point than wave it away as poor communication skills on the part of the listener, or intoxication of the speaker.


Most clever people I know are self deprecating. Treating a sentence like that at face value is bizarre - it says more about the listener's people skills.


> 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"


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


> You appear to be lacking confidence by buying into this subjective thought that another team could be “better than” yours.

I feel personally attacked !!


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.


Exactly. It is basic Business 101 with Yahoo. It wasn't about "too honest". ( What a nice way he is trying to spin it ). But that is Ok. We were all once young, naive and vigorous.

But that was the Yahoo era. He then repeat the same mistake with Steve? And Apple has a history of not paying much for M&A. It was really well known even in 2008. And $300M for P.A Semi was considered a very big deal back then.


> 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.


It’s kind of the same mistake? Talking when he should have stopped talking.


I’m not sure he bombed the Steve Jobs discussion. Throwing out a higher number you believe in is not destroying the deal, that’s just Jobs being a dick. His “i can’t trust you” is pure bullshit and nothing but a negotiating tactic.

Now a better approach would be to ignore Steve and negotiate with the deal team (and let them argue with Steve).

But the outcome could have been the exact same.


From his recounting of it, he literally killed the deal.

Steve had said "yes" and said Eddy Cue would take it from there, and was preparing to leave the meeting. Then Ali decided it would be good to start negotiating price right then and there.

Steve might have really been offended by Ali bluffing the sale price he could command. Or he could have been offended that this guy was such an obvious amateur.


Steve said yes and Eddy will take it from here is not 'a deal' yet


Of course.

It's interesting, though, how the CEO managed to present successfully to Steve without crumbling (no mean feat!) and still didn't have the sense to understand that Steve himself would not be negotiating the deal, just giving final signoff. A bizarrely rookie move.

Just based on these two anecdotes, I get the impression this guy simply does not have a feel for the etiquette of these negotiations.


> Throwing out a higher number you believe in is not destroying the deal, that’s just Jobs being a dick.

From the thread the difference was when he followed up his "I think we're worth $150M" with a corrected "I know we're worth $150M".

Jobs probably balked at the "I know" part because he knew Apple was one of less than 5 companies that had tons of extra cash in a financial crisis (2008) and had the strategic alignment to make the acquisition.

Plus Jobs undoubtedly already had internal estimates for cloning the company.

I don't think Jobs was being a dick, I think Jobs was just defining a strong negotiating point by telling this young entrepreneur that he sets the market price for acquisitions, not the startup. Sometimes aggression is a good negotiating tactic.

They apparently continued to negotiate after that, so it wasn't like it killed the deal.

Thinking you're worth 3x what your investors and your target acquirer thinks you're worth is what kills the deal.


I think we're saying the same thing. They were both negotiating, maybe Steve was being a bit more strategic.

But if he honestly felt the company was worth $150M and Steve thought it wasn't willing to pay more than $50M, then the deal never would have happened regardless what's was said.


Yeah that’s a very good point, I didn’t think about it that way. Even two life-long friends couldn’t have made a deal under those conditions.


He bombed - he should have stopped once he had the Yes from Steve.

Negotiation can happen later.


The elephant in the room of this thread is that Steve was a Goliath of negotiation. He had his own reality distortion field and he should, and was, considered an aggressive player. You don't overplay your hands to aggressive bigshots like Steve.


Just to be clear, he was also offered $285 million 6 months later from Microsoft, so whatever he's doing seems to have worked out pretty well for him.

Perhaps his tolerance, and aptitude for risk-taking, which seems crazy to us (talking carelessly right before deal has been formalized) is also what lead him to success in the first place.


The mistake was he tried negotiating with Jobs himself lol. I dunno, getting 50m in Apple stock would have been fine if the buyout had to be 50m. The deal would have been way more than 3x by now. Bravado at work here. Yes, this man has the same problem I suffer from (not in selling myself, I’m pretty good about shutting the fuck up in that regard), but in general, this gentleman suffers from ‘can not shut the fuck up’. I can commiserate.


Exactly ! Now carving out a new career talking a lot about how he got in trouble by talking too much.


Yeah now he's starting to give me pinky and the brain vibes, like always getting so close and then fucking up ;o


He did manage to sell his company later to Microsoft for twice the price, so in this case, Pinky finally won.


Ah nice


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?


Because nobody knows the optimal, true outcome. That outcome probably doesn't exist, and even if it does, it's impossible to know with the limited information available.

Practically every significant real-world interaction involves judgment calls, heuristics, and personal feelings. They feed in to you taking your best guess based on your limited information.

So adding more time to the process doesn't always make it better. You may learn, for example, that the person seems untrustworthy. "Selling past the close" implies that the person doesn't understand the situation, and is pursuing more contact for some reason other than your own best interest. The disconnect suggests that you may not understand what's going on, and it may be in your best interest to break off a deal that may not be what you think it is.

Humans do practically everything on the basis of very incomplete information. They use timing and word choice, among many other things, to try to close that gap.

This is a very important lesson. This isn't a case of humans failing to be logical. It's a case of incomplete information, and if you treat it as if it were a complete-information game, you're going to lose. That's illogical.

If it were a job that we could send computers to, we would. We can't, because we can't define the job well enough for the computers to do it. And this is a lesson for all programmers as well: most of our job is not talking to the computers, but talking to the humans to figure out what they actually want. If they could have said it in complete and logical terms, they'd have written the programs themselves.


The techie in me, paying attention to technology, thought exactly precisely that way for 20 years.

But it is in itself an irrational thought, focusing on some ideal platonic "what should be" which is eminently not observable anywhere in the real world. NONE of us are hyper-rational creatures of pure logic. Myself too, holding that thought of "shouldn't we converge on strictly logical optimal resolution", were in fact influenced by emotion, timing, personalities, circumstance, and other carp going on in my life. As was everybody else.

Now, though I'm not in sales, I'm in people management role, and I've learned quickly that timing and choice matters. It matters in sales, but it also matters in architecture, requirements gathering, solution design, project planning, everything. No matter how technical or sales your role, you eventually HAVE to deal with people, they need to agree/approve/confirm, and people ARE people. If you have a goal in mind, it is only rational for you to take into account the personalities involved and realities of the process, and be aware of timing and emotions and words.

Note - This is what I say now; I'm still struggling to implement it fully myself - the decades of sciencey-techy are still strong in me :D


Is the optimal outcome really the same as the one that would result from the most complete presentation of the facts?

If you're buying an appliance, and you already agreed, and then the salesperson gives you additional info, you might change your mind ("oh, I thought the failure rate was 0.1%, you said it's 1%") even if in reality this may be a perfectly good enough appliance for you and a good sale for the seller. Optimal would probably be getting the sale done - even if that depends on untrue assumptions in your head not being challenged. Not getting the sale done means your back at square one, depending on what else you want to be doing with your time, that's not good.

When interacting with another party you have a mental model you build to try to figure out what they're thinking, but it's very incomplete. Adding information can change your mind, and even not necessarily in a "true" way - imagine you're on a date, it's going well, both parties want to hook up... and then they say something that makes you think maybe their political views are offensive to you. You might be making a wrong assumption based on what they said. Or they might just disagree with you that much. But you're probably not going to have as much fun tonight anymore! You may have a more "true" outcome but is that what you wanted?


Yes, of course it's irrational. People are not machinelike optimizers of information accuracy. If that's your mental model of people, you're going to have a bad time.


The explanation is perfectly rational.

Once the buyer has been convinced, his worldview is dependent upon a number of assumptions he's made by extrapolating limited information. He makes a number of those assumptions on the basis of trusting the seller. If that trust wavers, the assumptions crumble and the worldview collapses.

The buyer's trust in the seller is fragile because the buyer doesn't really know the seller. His image of the seller is based on an internal model that the seller has triggered by being similar on a few heuristic markers.

The buyer jumps to the conclusion that the seller is that good guy he's been waiting for, on the strength of a few matching signals.

But the more the seller says after that point to demonstrate defining characteristics of his knowledge, personality, or character, the more he risks varying from the buyer's internal model. Less is more, because by increasing the number of points of comparison, the more the seller risks spoiling the match.


There's a nobel prize awarded in 02 for the guys who figured out that people are irrational


In a universe without inherent meaning, define best, optimal, and true.

We all choose paths forward with uncertainty both about what is desirable and about how each path might get us there. The perceived trustworthiness of the people pitching each path factors into that decision, precisely because of the uncertainty involved.

Calling people "rational" or "irrational" doesn't make sense if there isn't an end goal to measure us against.


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.


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.


Because the timing IS information. Why was a piece of information stated up front, or last, or in the fine print, or released to the public on friday at 5pm, etc.

We're not evaluating an arbitrary collection of facts, we're evaluating a flow (ie time varient) of information from a source of unknown trusthworthyness and as such we are looking for more information than just taking everything stated at face value.


At an old job we had techs (me) and sales. Management threw both at each team and you can guess the result of that.

During work event we all took a personality test and the tech were scored "yellow" and we tech "green" in other words we were different. Pretty much people in technical jobs have an aptitude for technical and sales for selling.

So reading what you wrote I can see the salesman just doing what is his nature. It's the same for a technician we don't turn it off it's a personality trait than a job or a skill we have.


I've heard it as "don't sell what has been sold."


This makes sense. It's disappointing that you're doing your best to sell your value, but instead, you got your chances ruined.


> "know when to stop selling"

I disagree. Stop over-selling, maybe, but at the end of a sale, there's a buyers remorse window. And you need to make sure you're communicating with the "buyer" and strengthening their resolve so they don't get cold feet. This applies with selling, hiring (esp after the candidate signs), etc.

A good way to do this is to make sure to remind them of why they bought in the first place.


Buyers remorse is real, but usually less so in B2B sales.

In most B2B sales that I have been involved in, you can summarize it down to a certain amount of budget, and a set of needs. If you can fill the needs within the budget, it's an easy sale and there is no buyers remorse. This is an oversimplification, but I think in many cases buyers remorse is rooted in the buyers realization that making a particular purchasing decision is going to reduce their overall cash reserves, and thus eliminate other potential decisions. The way most corporate budgets works is more of a "use it or lose it" scenario, where the buyers have more incentive to make actual purchases.

In regards to your last sentence, yes, nothing wrong with reinforcing the decisions that led to the purchase decision. But that is much different than introducing new factors (eg: we should buy this other company too) or altering your buyers perception (this other company or product is even better than what you agreed to purchase).


I know we're on a forum associated with a startup accelerator, but something just rubs me wrong on these waxing poetic startup stories. It's like these people live in their own little world, where companies and little "ideas" and massive sums of money are just pawns in some game that ultimately doesn't matter. It's a sort of entrepreneurial aggrandizement, and there's a lot of unnecessary adulation and cult of personality.

There was some reply there that was basically "I lost tens or even hundreds of millions of dollars because of a dumb decision too but I have no regrets". Seriously? That's immediate retirement money for me, my immediate family, and then enough left over to pursue pet projects, volunteer work, and non-profit(s). This guy in the posted Tweet made an idiotic decision that killed an opportunity for himself and his employees, and he seems okay with that and even fond of the decision. Kind of weird to me.


Ha, I noticed this part in the twitter thread:

> Yahoo offered $125 million

> As a financially-insecure immigrant, I knew this deal would change my life.

I enjoyed how he specifically qualified that this was a lot of money for a "financially-insecure immigrant." Um... no. This is a lot of money for 99.999% of human beings on the planet.

A good read though.


Another interpretation is "[because] I was a financially-insecure immigrant, I knew this deal would change my life [by clearly achieving the financial security I had been constantly worrying about and seeking to get][and therefore I was nervous that the deal might not happen]". It's not that the amount of money was larger for him than other people, but that having $125m/n founders was so clearly financially secure.


Sure, I suppose it could have meant "Because I had no financial security, I would have agreed to any large amount of money."

Instead, I read it as a rather amusing statement of "Because I struggled financially, I would truly appreciate $125 million dollars." Lol, no -- anyone who isn't born filthy rich, would appreciate that kind of money.

But overall it was a fun story to read. The above just struck me as an unconscious almost-defense, to justify the huge piles of money founders can get in silicon valley.


Sometimes there are people who really are temporarily embarrassed (hundred-)millionaires.


He has enough money for him and his children to retire comfortably. _Now_ he doesn't need to regret it. In 1998 he probably regretted it a lot when he realized what happened.


Integrity matters. Even if he hadn't gotten a big offer later on, he could still walk away with that.

Yes, you can argue that he could have just kept his mouth shut and still honestly taken the Yahoo deal, but he said what he thought was right and gave Yahoo some good judgement about pg's team.

I recently interviewed with a number of firms, and the ones that give off the best impression are the ones who ask to integrity at some point in the process. Hopefully this won't turn into the next "what's your greatest weakness" of interview questions. But firms doing the same thing in the same industry can often have a very different feel to them, and this is one of those things that might change your impression.


Sometimes this type of integrity is just being too honest as he said. Is like telling your customer there is a better restaurant down the road with cheaper prices, go there.


How do you have integrity when you throw your own engineers under the bus?


Integrity is about telling the truth (as you see it), not about doing stuff for the benefit of "your own".

In fact the latter can lead to exactly the opposite of integrity.


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.


Integrity involves placing our duties to others in the proper order.

Sometimes that means doing stuff to benefit "your own." sometimes that means blowing the whistle on something. It really depends on the context.


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.


Someone devoted to his own interests lacks charity, but not integrity. And yes, being whole and undivided is also in reference to the moral quality, not just structural integrity.


>Someone devoted to his own interests lacks charity, but not integrity.

Well, I wasn't talking about some hermit fully devoted to his own self without impact on others.

I was talking about someone pursing his own interests ahead of everything else - who would e.g. lie if it benefits him, steel, backstab, and so on.

This man might be an "whole and undivided" jerk, but he lacks integrity - that is, an actual good moral character.

So, "whole and undivided" is not what people mean when they say "this person has integrity". They mean that he is a "man of his word", has honor, is not two-faced, and so on.


I am not going to argue with you. There is a lengthy discussion of the breadth of the word in the Wikipedia article. It does not mean what you think it means. https://en.m.wikipedia.org/wiki/Integrity

There's a saying: you can lead a horse to water, but you cannot make him drink. I can provide you the resources to show you the meaning of the word, but I'm not going to waste my time in any further back-and-forth. Have a good day.


That's honesty, not integrity.


You'd be surprised.

Dictionary to the rescue: "Integrity: 1. the quality of being honest and having strong moral principles."


Your response is (intentionally?) incomplete. Talking about integrity...

https://www.merriam-webster.com/dictionary/integrity

Definition of integrity

1 : firm adherence to a code of especially moral or artistic values : INCORRUPTIBILITY

2 : an unimpaired condition : SOUNDNESS

3 : the quality or state of being complete or undivided : COMPLETENESS


My response is about integrity as it pertains to the discussion - as a property of a person.

Note that (2) and (3) are not about people.

We don't say that someone who is not impaired (in "an unimpaired condition") has "integrity". We call them able and other things.

We don't say that someone who is "complete or undivided" has integrity either (we use the term "complete" for humans, but there it means something like satisfied or fulfilled).

(2) and (3) are not about integrity as in "X has integrity". It's about integrity as a property of things, in usages like "structural integrity", "mechanical Integrity" (the same sense used when we talk about "integrals" and so on).

And you made it sound like I did something nefarious. Talking about integrity (1).


> Note that (2) and (3) are not about people.

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

> (2) and (3) are not about integrity as in "X has integrity"

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

> And you made it sound like I did something nefarious.

You did. In a discussion about whether a word's meaning was narrow or broad, you argued it was narrow by citing its definition -- but left out every part of its definition that didn't align with your argument.


Yeah, exactly, honestly is just a part of it. He failed hard on the other part by saying his own team was worse then some other team. Integrity is standing up for the people you lead, it falls under the moral principles part.


If you always standup for the team you lead, then where is the moral principles and honesty? My (fill in the blanks) is always right means you have no integrity.

Integrity is having a set of moral principles and evaluating against them honestly. You will see your beauty, warts and all.


I think you could consider looking out of the people under you as mouths to feed as moral.

It's impossible to calculate the moral implications of the entire world for every decision you make, but taking care of your own is a pretty easy start.


>I think you could consider looking out of the people under you as mouths to feed as moral.

That's a quality a mafia boss might also have (taking care of its own team/employees/famiglia). Doesn't mean they have integrity (heck, it's not even moral - not every quality that results to the good of some people is moral).


I guess that depends on what you consider morals? Local or Universal.


Telling the truth isn't throwing anyone under the bus. If "they" are better than "us", that's the truth. Personally, I'd have bought the guy's company just because that's the right sort of engineer I want. Having said that, he wasn't under any obligation to tell Jerry anything.


He compared engineers he's worked with to engineers he hasn't worked with (Viaweb) and said they were better. How did he know they were better? Is he just better at assessing engineering talent than the rest of us?

You're assuming he knew they were better. Based on all of us (esp. here) not trusting technical interviews to determine engineer quality, I suspect he did not know they were better and was simply trying an off-the-cuff comparison to get Yahoo to acquire both of the companies.

What he really gave was an opinion. It wasn't truth.


Dude he didn’t literally mean they were better. He gave a sincere compliment to Viaweb (an exaggerated one) as a compelling counterpoint to shift the other’s view.

I dunno, the Yahoo guy seemed a little sociopathic for doing this. Reminds me of when Paul McCartney told Michael Jackson he wanted to buy The Beetles catalog, only to have MJ go ahead and buy it instead. Douchey to say the least.


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

>“They are hands down better than us."

Uh, I'm pretty sure he meant what he said, with the second being a solid assertion. He didn't dance around it, he literally meant they were better.


Makes you wonder if behind the scenes, someone at Microsoft checked with someone at Yahoo and heard the story, and then Microsoft did the deal.


If that were true, they wouldn't have paid more than Yahoo offered.


I read it as they sold later (amount of time unspecified), so presumably they continued to grow before the Microsoft offer.


> Integrity matters

Citation needed :-)


> As a financially-insecure immigrant, I knew this deal would change my life.

What is it with this guy and his desire for a hero narrative? First he took credit for the Like button, now this... His cousin Dara is totally insufferable in his lackluster position as CEO of Uber, but at least he’s honest about their very privileged upbringing.

Is this a prelude to a political career or something?


> What is it with this guy and his desire for a hero narrative?

LOL, that's practically every SV CEO. They all want us to believe that a) they were the underdog, and b) they were the hero in their own story.

What I can never tell is which ones are doing it deliberately as part of a PR strategy and which ones simply lack the perspective to realize they're doing it at all.


Porque no los dos, as they say.


As a financially-insecure immigrant, that line actually helped me understand his mindset, and did not come across in any way as a "hero narrative".


Nitter.net link. Here's the link that should have been submitted to HN assuming not all HN users have/want Twitter accounts: https://nitter.net/apartovi/status/1449856639331340289


Or use the privacyredirect addon ;)


Ok, my take away: if I ever want to merge my team with another team, I'll avoid "but that team is better than us"

(not that I'll ever be in that situation in the foreseeable future anyway)

(pg's answer in this thread: "Whoah, I had no idea about any of this till now...")


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?


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.


Sorry for the poor wording, I mean I said something.


“X is better than Y” is subjective, so kind of a silly position to debate in the first place.

It would be interesting for me to know what he meant by “better”. More efficient? More prestigious? More collaborative? More visionary?


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."


That hurt to read. I'm expecting to be in a position where I could meaningfully influence any acquisition or merger (let alone a 125 million USD one), but knowing when to shut your mouth is a valuable skill to have in many situations.

I'll try to keep this in mind whenever I realize that I'm overexcited (which I tend to be).


*not expecting to be


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!


*6 months

> The lessons proved helpful 6 months later when Microsoft offered $265M for LinkExchange.


Oops! Could swear that I typed "six". At least "months" was properly plural.


failing forward


Blabbering your opinion when you should shut up has nothing to do with "honesty".


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 say something, and ended up putting his foot in his mouth.


As the Tamarians say, “Kanye when the single ladies fell.”


A big difference being that in your case Kanye had no specific stake either way. The parallel would be if Taylor Swift would've said: Beyonce's video is better, and the VMAs would've said: actually you're right, please hand back the award.


That was just Kanye being Kanye though.


Is this art or Kanye West? Snark intended


From pg:

“Whoah, I had no idea about any of this till now...”

https://mobile.twitter.com/paulg/status/1449861338390466561


I'm very curious what narrative he had on what he did right to land this deal and if that changed with this new information.


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?


I think it’s pretty plain that he’s cuing up the stories - which I’ve enjoyed by the way, he’s a good raconteur - as “what I learned about negotiation that day” rather than “how I didn't get hired”. The pivotal moments in his stories may not have actually been what kept the deal from going through - he alludes to this in the yahoo story, even, but discounts it.


Tdlr; he was "too honest" because he literally told the buyer that there was a similar company with better engineers - essentially that there was another company which could do the same exact thing much better. So they bought the other company instead.

Were the engineers objectively "better" than yours, or was there still something your company offered that the other did not? If the other company was essentially better, than you're lucky Yahoo didn't realize and you got that deal in the first place.


I am sorry he lost the money, but this quote:

> My intentions were good, if naive. I helped both Yahoo and Viaweb. Business isn’t just about winning; it’s about helping others.

Tells me that he's a decent chap.

I mentioned in another post, that today's culture doesn't reward "decent chaps."

In my own case, I don't care. I do my best to be a "decent chap," even though I'll never get rich that way.

I'm clean-shaven, and it's important to be able to look myself in the eye every morning, or I'd cut myself to ribbons.


Twitter web UI is not loading tweets for me past the 18th message. Is anyone else facing this or knows how to read the rest?

Edit: https://threadreaderapp.com/thread/1449858706750033921.html


They've seemingly done some a/b on me so that many times it requires me to log in/sign up.

Also looking at you reddit, "this thread can be read in the app". Thank the kings and queens for 3rd party viewers (using Slide).


I wonder how many A/B tests take into account the people who get so pissed off that they immediately leave the platform.

(This is how I stopped using YouTube)


I don’t even see his mistake as being “too honest”, it’s more like he was just being petty. If someone thinks a company sucks but you think it’s great, is it really worth arguing to change their opinion, especially with such an inflammatory statement?


Yeah, the guy doubted himself and his own team even after they landed that deal, and as a result lost the deal? If I was on his team I would be pissed.


This wasn’t integrity - just bad sales technique. He had some knowledge that was potentially of value to Yahoo, but instead of seeing if Yahoo was interested in buying that knowledge, he just gave it to them for free.


"When you're young, the temptation is maybe to think, 'More is more.' But a lot of the time less is more."

-- Daniel Ricciardo


Why is everyone so sure Yahoo would not have reneged on the deal anyway? If they were ready to renege the way they did, which is extremely ruthless, what makes you all think Yahoo would divulge they were doing due diligence on Viaweb with an existing floating offer already in place for LinkExchange? Maybe another company was out for Viaweb, Yahoo secures LinkExchange, but continues to try for Viaweb, totally ready to drop LinkExchange if Viaweb comes through.

Look at what the company did (renege an offer) and you will understand what they were also doing behind the scenes.

A little bit of a hot take, but I don’t think $125 mil goes out the window because someone said something over drinks (especially something as benign as an exaggerated flattering compliment).

I often give similar compliments when others undermine someone I know well, but respect me. I always say ‘look, that person is a better person than me’, all I’m trying to convey is if ‘if you respect me, know that I respect them, so take that into consideration’. I don’t literally mean they are a better person, that’s not for me, or for you to judge, so let me flip this notion on its head for all of us.


An off-color comment over drinks has tanked many, MANY deals.


No kidding. If I was giddy to buy out a company and their CEO told me there's another company that is much better than them and also looking to get acquired and insist their people are better when I push back on it, I'd be extremely cautious about going forward as planned.

It may not be that the other company really is that good, but if the CEO is so comfortable underselling their own team, that suggests the company is not as attractive as initially thought. Especially in a space where hype is the norm.


“To lose one parent, Mr. Worthing, may be regarded as a misfortune; to lose both looks like carelessness.”


If he didn’t make that momentous blunder, YC may never have happened…


> I wasn’t allowed to respond to him, and I wasn’t allowed to tell him why.

This is ridiculous. I can hardly believe such requirements are legally allowed to exist.


To whoever has downvoted: what if the person you were forbidden to respond to, the other company executive, was yor mother or your best friend?


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.


I admire him for his honesty and not letting greed and ambition get in the way of being a decent person.


There are many reasons why Yahoo may have called off the deal. I doubt it was this one single comment.


Alcohol damages more than our brains.




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