Smash Company Splash Image

August 17th, 2018

In Business

1 Comment

How to deal with a psychopath

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:

Monday, November 2nd, 2015

I woke up and got ready for work. Still at my apartment, I checked our team communications. I saw that Milburn (a member of the Board Of Directors, and possibly the secret founder of the company) had sent me a short email:

“Why did you send those emails over the weekend? Please call me as soon as you get to the office.”

I was surprised. Did he really want to start the week with another argument? And why did he have to take issue with those emails, when they were the epitome of common sense?

In an attempt to give him one last chance to think about what he was doing, I replied:

“I send email all the time. Do we now have a policy that says I cannot communicate with my coworkers? That is unusual.”

Who was this guy? Was he secretly the CEO? If so, why weren’t they honest about that? Why were we still being told that John, our 22 year old leader, was the CEO?

I went to the office. I settled in and checked GitHub, and I pulled all the latest code that anyone had committed. A few minutes later, Hwan showed up. I was excited to see him. I had not seen him since October 16, and he had not been to New York since June. We started to talk about what we should accomplish while he was in New York.

Then John came over. He was on the phone with Milburn. I heard John say, “Yes, he’s here. I’ll tell him to call you.”

I found a private corner of the incubator and gave Milburn a call. “Good morning, Milburn. What can I do for you?”

He skipped salutations altogether: “I asked you to call me. Why didn’t you call me?” He sounded sad and angry simultaneously.

“I just got to work, and Hwan got here from DC. We simply stopped for a chat.”

“I asked you to call me. It’s a simple request. Just a phone call.”

A long pause.

“Yes, sir, but I just got to work, and Hwan got here at the same time.”

“It’s a simple request! Basic politeness. I wrote you an email, I made a request, and you ignored the request. I had to call John, and John had to pressure you to pick up the phone.”

“I was aware that we would be speaking soon. We have a conference call coming up, don’t we?”

“I made a very simple request, and you deliberately decided to ignore it. Basic human decency should have been enough for you to honor that request, but I guess you don’t believe in basic human decency. And you decided not to call.”

He paused. I said nothing. After a long silence, he continued:

“You decided not to call. That is not nice. It’s rude, it’s disrespectful, and I’m hurt. As a human being, as someone with feelings, I am hurt, and I would like an apology.”

He sounded like he was going to cry. The note of self-pity surprised me.

My friends and I have sometimes discussed the right-wing television personality Glenn Beck and his tendency to cry on television. Is Beck truly overwhelmed with emotion as frequently as it seems, or is it all just an act? The best explanation I had ever heard, from a friend of mine who is a professional actress, was that a great actor fully experiences the emotions they’re portraying—so it’s possible that Beck is both playing a character and also genuinely feeling his emotional raptures. I think something similar must be true of Milburn. On the one hand, it seems naive to think that he really felt such strong emotions over my failure to call him, but on the other hand, his emoting seemed entirely sincere.

This was the third time I was having a conversation with him. The first time was the previous Wednesday, which was bad, and then we also had a rough time on Friday. And yet, for 6 months before that, John and Sital and Gregory and myself had been making steady progress, in relative peace. And we were on schedule, at least according to the estimates I’d given in August. But from Milburn’s point of view, we were running late. I had a suspicion that he had promised investors that we’d already be making money.

I tried to be factual: “I received an email from you stating that you would like to talk, but we have a meeting scheduled at 11 AM and so—”

“I told you to call me!”

“—I knew we were going to talk.”

“I told you to call me! Don’t send a bullshit email! Pick up the phone if I tell you to pick up the phone!”

The innocent often believe that salespeople aim to be nice all the time, but this is based on encounters with retail-level salespeople who have to work with customers who they don’t know. And when the type of retail is known for narrow profits, then the salespeople don’t have time to get to know the customers — because the game is all about volume. If you go to buy lipstick, the salespeople will often be nice, because they don’t have much leverage over you. But if you go back to the same store repeatedly, a good salesperson will learn your weaknesses. Maybe you are worried about your thinning hair. Maybe you are worried about your weight. Maybe you have lines around your eyes. Every weakness is a potential sale.

If the obvious forms of manipulation fail to work, then a great salesperson will get nasty. Okay, reject their advice, don’t take care of yourself. That’s fine. Let yourself go, look like a wreck. Why care that your children will be embarrassed when their friends see you? Why care that your husband will lust after other women? You’ll be a terrible mother and partner, but hey, I guess it’s okay to be selfish, right?

Every industry has certain euphemisms for the least savory aspects of its business. In sales, there is the secretly ugly phrase, “goal-oriented.” That sounds pleasant, doesn’t it? If I point at a woman and I say, “That entrepreneur is goal-oriented,” then you probably think I am complimenting her. But if I point at her and say, “That entrepreneur is a lying, manipulative, soulless psychopath who brutally exploits labor from the eleven-year-olds she employs in her sweatshops in Indonesia,” then you probably think I am insulting her, unless you are a libertarian. And yet both statements mean about the same thing: that she is someone who is willing to do whatever is necessary to ensure the success of her business.

When I read about Milburn online, I’d seen testimonials from his colleagues in which he was often described as a goal-oriented salesperson. That probably meant that he was a master of manipulating other people’s emotions. He knew all the tricks: praise, shame, laughter, anger, promises, guilt, threats.

Whether his use of these tools was conscious or unconscious is, of course, unknowable. But it doesn’t matter much. A lifetime as a sales professional left him with an arsenal of psychological ploys that had become second nature to him.

In this current situation, he surely knew that once a person apologizes, the apology sets a precedent for the conversation, and the person who apologizes tends to continue to apologize. But that much is Psychology 101, and I was aware of the trap. For this reason, I avoided apologizing.

“I was confused by the email that you sent. It sounded like you wanted to talk about the fact that I sent emails to my—”

“You are wasting the time of your coworkers, when they are trying to stay focused on getting the next release out. Does that interest you at all? Do you want us to get the next release out?”

Shame and guilt. There he was, skillfully wielding those tools from his sales-tactics tool belt.

“Milburn, I have been working very long hours to try to get the next release out.”

“The time you spent writing those emails is time you could have spent debugging your software. But I guess that doesn’t interest you, does it?” Effectively, he was saying that I was no longer allowed to communicate with my coworkers regarding any issue except for a small set of issues that he would arbitrarily define. That wouldn’t make sense if he wanted me to maximize my effectiveness as an experienced programmer, but it would make a lot of sense if he simply wanted me to stop putting so many of my opinions into written form. Assuming it was his idea, and his alone, to use our “brilliantly creative data scientist of incredible genius” as a trap for unwary investors, then my emails would be quite a revelation to the rest of the Board Of Directors and to any disgruntled investors.

A line such as, “But I guess that doesn’t interest you, does it?” is never meant in a literal sense; it is always thrown out there to show that the speaker has the power to throw it out there. The previous Tuesday he had praised me for working long hours and shamed Hwan for not working as late as I did, yet now he wanted to suggest that I was lazy and didn’t want to work.

“Who am I to you, right now?” he asked.

“You are Milburn Jennings, a member of the Celolot Board Of Directors.”

“Yes, that’s right, but who else am I?”

For the life of me, I could not imagine what he wanted me to say. Did he want to hear something stupid like, “We are teammates!” or “You are my friend!”? At a stretch, I could imagine he wanted to hear something like, “You are an investor in Celolot,” but I did not actually know if he was an investor or just a board member, so I couldn’t say that.

“Who else are you?” I wondered aloud.

“Yes, who am I to you?”

“Uh, I’m not sure what you are looking for.”


I was unable to hide my surprise. “Oh?”

“And do you know why I am the leader of the tech team?”

I said nothing.

“Do you know why I am the leader of the tech team?”

Again I said nothing.


In court, lawyers typically follow the rule, “Do not ask any question unless you already know the answer.” I knew to adopt that rule in an adversarial situation such as this. That meant censoring the first few responses that came into my head. I wanted to ask, “How do you define failure?” but that would have been like handing him a sledgehammer and inviting him to take his best shot.

I filtered out any questions and instead stuck to firm counter-assertions.

“This project is on time,” I insisted.

“You could’ve done something great.” He almost sounded sad. “You could’ve come in here and been a real leader. You could’ve shown the world what you were made of. But you decided to do nothing. You decided you’d rather sit around and complain. You didn’t lead this team. You don’t know how to lead. Admit it. I want to hear you say it. Admit that you failed.”

“We have built some very impressive technology. This is a service that has to deal—”


“—with massively concurrent real-world communications going between multiple points, from the iPhone to our servers, though our NLP—”


“—engine, sometimes back to the iPhone and other times to Salesforce. And we have built a working demo—”


“—in a remarkably short amount of time.”

He was silent for a moment after I finished. I looked around the incubator and watched all the other people, at all the other startups, working hard on their projects. I wasn’t sure what Milburn was waiting for. I wasn’t sure what he expected me to say.

I took out my iPhone and I started texting Natalie. I sent her bits of what Milburn had said to me. (It was the text messages and emails to Natalie that allowed me to later reconstruct this dialogue.)

A very long moment passed in silence. He was waiting for me to speak, and I was waiting for him to speak. Actually, I was waiting for him to hang up so I could go and get some actual work done.

“You can’t do it, can you?” he finally asked.

I stayed silent.

“You can’t do it, can you?” he repeated.

I stayed silent some more.

“You can’t admit that you failed. Because that hurts, and you don’t like to feel hurt, do you?”

This was a guy who was almost crying a few minutes ago because I didn’t give him a phone call. It was quite an accusation for him to now throw at me. Another very long silence followed. He was hoping that I would talk into the silence. That’s the kind of mistake that John always made. I also used to make that mistake; I suppose we all do when we are young. It’s an easy trick whereby those who are good at verbal combat can get their opponent to sabotage themselves: create an awkward silence and then see if the other person feels compelled to say something.

He let out a long sigh.

“So where are we right now? Where is the software? What more needs to happen?”

“We are stuck at the point where we call the NLP ‘model’ that Sital has built, so I assume there is some problem in Sital’s code.”

A long silence passed.

“You like to blame others, don’t you?” he asked. “Does that make you feel good, when you blame other people? I’ve heard you blame Sital, I’ve heard you blame Hwan, I’ve heard you blame Gregory, but you know who you never blame? You never blame yourself. I’ve never heard you say one bad thing about yourself. And yet every single time you blame Sital or Hwan or Gregory, in the end, when we find the real problem, it always turns out to be you. All of our problems go back to you, but you never take responsibility for what you’ve done.”

Several things occurred to me at once:

First, I could repeat these words, verbatim, about Milburn himself, and the statement would be true. Certainly, if the Board Of Directors felt we were running late, the root problem was Milburn’s decision to proceed with the Big Pivot back in July.

Second, it would be a mistake to treat any of what he said as rational.

Third, the only accusation I’d ever thrown at Hwan or Gregory was that they were relentlessly talented. Their excellence was noteworthy. My serious criticisms had been confined to Sital’s programming and John’s managing.

Fourth, it would be a mistake to respond as if we were having a good faith conversation, eagerly trying to discover the real facts of the situation or discussing the interesting ideas that could make Celolot better. The conversation had become a pure power struggle.

“We have added debugging statements to every function in the system,” I tried to explain, “and the code runs until we call Sital’s model. That strongly indicates that there is a problem in that model.”

“Why didn’t you foresee this problem and put in some guards against it?”

“We have made huge progress making this code more and more stable. We are on track to meet our deadline this week.”

“Can you guarantee that the project will be complete on Friday? Every bug is fixed? We can put this in the hands of a customer on Friday, and you guarantee it?”

“I don’t want to speak to—”


“—how much Hwan or Sital still need to do, or how—”


“—many hours Gregory feels he can work this week.”


“It is not a yes or no question!”


“It is not a yes or no question!”


“It is not a yes or no question! I cannot take responsibility for Hwan or Sital or Gregory!”


“Why have more than one programmer if I can write all the code myself? Why did you even hire Hwan or Gregory or Sital if you thought I could get this project done by myself?”


“If I am the lead developer at Celolot, then why are we ignoring the estimate I gave in August? That was accurate, and we are on schedule.”

“Oh, I see. I get it. You don’t want to be lead developer any more, is that it? Too much responsibility? Is that it? When the going gets tough, Lawrence goes home. Is that it? Well, I just looked at your LinkedIn profile. Do you know what it says there? IT SAYS YOU ARE LEAD DEVELOPER AT CELOLOT!”

“What about John’s responsibilities? If I am the lead developer, then—”


“—why can’t I get rid of Sital and why can’t I get someone better—”


“—as a replacement? And why can’t I get Gregory hired full-time?”


I wasn’t even sure what that meant, and it’s possible that Milburn didn’t know either. Milburn was very, very good at this kind of verbal combat, and he had clearly learned long ago that he could win a fight like this by getting the advantage and keeping it. And a person doesn’t need to make sense in order to keep the advantage; sometimes it’s enough to simply shout loudly until the other person backs down.

To the extent that he had any kind of rational point, he seemed to imply that, because I was the most experienced person on the tech team, I should take on the responsibilities of being CTO. But for the first four months I’d been at Celolot, I was told that Dennis was the CTO, and then later that turned out to be a lie. I also recalled that when John had encouraged the rest of the team to pick titles, he said we could pick any title for ourselves besides CTO. If they had wanted me to be CTO, then they would have needed to pay me more, and I would have demanded complete honesty and direct access to the Board Of Directors.

Much later, I thought about what he had said: “I just went and looked at your LinkedIn page …” That is a truly revealing remark. Before I had called him, he knew he was going to need some ammunition to use against me, so he had checked out my LinkedIn page in the hopes of finding something. He had probably also checked out my blog and my other online sites. That says a lot about how he operates. Although he seems to engage in sudden bouts of rage, he actually plans his attacks carefully, just as any good salesperson carefully plans each sales call. His actions are probably deliberate, even though he tries to create the illusion that his emotions are spontaneous.

And of course, we never talked about the idea that the so-called CEO should take responsibility for anything. Was there, at this moment, an unspoken awareness that John was secretly Milburn’s assistant, and John had been given the title of CEO just for fun, because Milburn did not need another credential on his resume? In a startup with just three programmers and one CEO, four people in total, the CEO would normally take some responsibility for the progress of the tech team.

“No one ever told you September,” Milburn barked.

“Pardon?” I had not idea what he was referring to. Perhaps when I said “Spring” in my email over the weekend?

“No one ever told you September.”

“I’m … I’m honestly not sure what you mean,” I replied.

“In your bullshit email,” Milburn retorted. “‘Stable and feature complete.’ No one ever told you September. No one ever said that to you.” For the life of me, I could not imagine what he meant.

“September?” I had not said September, I had said “Spring.” I thought we would be done with our initial list of features by the Spring of 2016.

“Don’t you parse my words!” Sudden anger again. Perhaps he realized he’d made a mistake. “Don’t try to derail this conversation again!

Milburn truly had a genius for the strategic use of anger. If he sensed the risk of losing control of the conversation, he would indulge in another outburst. If I were to ever switch over to the Dark Side, I would want to study with him. His techniques were fundamentally dishonest and manipulative, but that is probably what made him so good at sales. And his tactics were probably an effective way to drive a sales team, but I sincerely believed that such tactics were the wrong way to run a software development team. Especially when doing something cutting-edge original, like we were doing, I think open and honest communications were extremely important. (I have worked with many companies where the sales team was both friendly and successful. One does not need to use abusive tactics to have success in sales. Indeed, the sales manager who relies on abuse is typically more interested in aggrandizing their own success, rather than the success of the company they work for.)

Shouldn’t schedule estimates come from the tech team? There were really only two ways of interpreting our current situation:

One, Milburn was our real CEO and John was merely his assistant. If Milburn was our CEO, it was appropriate that he was generating our completion estimates and which tasks we needed to do. But in this scenario, we were a startup of just five people and yet we had gone almost six months without a single conversation between the CEO and the tech team.

Two, John was our real CEO. Milburn was merely a member of the Board Of Directors. In this scenario, we had daily conversations with our CEO, which was appropriate, but our Board Of Directors, which should be merely advisory, was scheduling our deadlines, generating our estimates and even deciding which tasks we should put into PivotalTracker.

No matter which way we interpret this situation, something fundamentally irrational was happening.

I could imagine why Milburn might be in trouble with the other board members. Did he really think that because he wrote some Visual Basic code 15 years ago he was competent to estimate a cutting-edge NLP project in 2015? If so, this was perhaps an example of the Dunning-Kruger Effect, where someone with little knowledge of a subject doesn’t realize how much they don’t know and therefore assumes they are highly competent.

“I think the Spring of 2016 is a reasonable estimate for being feature complete and reliable,” I offered.

“You will never say that again,” Milburn snapped. “Do you hear me? You will never say that again. You have done everything in your power to demoralize this team. You have done everything in your power to distract them from the mission. You have done everything in your power to sabotage this project. I’m sick of it. I am sick of your bullshit. I am sick of your sabotage. You will never say that again, do you understand?”

I might have argued that is was his unrealistic deadlines that were demoralizing the team. Instead, I spread the blame over the whole board: “Fear is being communicated to the team by the Board Of Directors.”

Milburn did not take that well, either. “The board simply wants you to meet a deadline for once! You feel fear because we need you to live up to one of your deadlines?”

“We are on track to meet my estimated deadlines.”

“Your estimates are bullshit! You keep telling John, ‘I’ll be done tomorrow,’ and you never are!”

“Honest communication might clear up some of the confusion.”


“Why were we not consulted about the change of direction in July?“


I was amazed by that and my voice expressed my surprise: “There was no change in direction back on July 28th?”


“My tricks?”


“Why were we told some ridiculous story about Griffin and Dennis—”


“—and John? Why tell us that they went to a Salesforce convention and magically found—”


“—some investors who were willing to write a check on the spot? Why not tell us the truth?”


I wondered if his instincts told him to pre-emptively throw accusations at me before I could throw them at him.

A fascinating aspect of this whole conversation was that he never threatened to fire me. All of these threats and accusations were his way of motivating me to work harder. With almost scientific precision, he had moved through many of the same kinds of tactics that might have sucked a potential customer into committing to a purchase:

• First, he tried to get me to apologize for hurting his feelings, knowing that if I apologized for anything, then I would have to apologize for everything.

• Then, he tried to shame me by insinuating that I was slowing down my coworkers. “You are wasting the time of your coworkers, when they are trying to stay focused on getting the next release out.”

• Next he attacked my masculinity: “ARE YOU MAN ENOUGH TO ADMIT YOU FAILED?” Many men, especially younger men, might retort with something akin to, “Dammit, even if I have to work ninety hours a week, we are going to succeed!”

• That didn’t work, so he switched tactics and tried to make me feel selfish and petty because I had offered an honest assessment of Sital: “You like to blame others, don’t you?”

• None of that worked, so then he tried to get me to commit to something that he could use against me later, and when I didn’t rise to the bait, he tried to pressure me into conceding that something was black and white, when it wasn’t: “IT’S A YES OR NO QUESTION!”

• At that point I tried to raise the issue that John also needed to take some responsibility for the progress of the company, at which point Milburn had tried to get me to take on a CTOs level of responsibility: “ONCE YOU RING THAT BELL YOU CAN’T UNRING IT!”

• Since I hadn’t backed down, he switched tactics again, and focused on limiting what I was allowed to have any say over: “No one ever told you September.”

• Finally he attacked my maturity, to imply that I had no authority to offer opinions about co-workers: “YOU’RE A FRIGHTENED LITTLE BOY!”

His tirade could be considered a master class in sales tactics, except those tactics were too obvious. The audience is not supposed to see how a magician performs their tricks. When I first read about him online, I assumed Milburn combined penetrating emotional insights with the expressive range of a great actor. But that was not what I had run into today. He really had just a handful of gambits, and he leaned on them too heavily, like a chef who tries to hide their mistakes by using a lot of salt.

By this point we had been talking for so long that it was time for the meeting with the entire team. We had to end our call.


The above is an excerpt from my book How To Destroy A Tech Startup In Three Easy Steps


Check out my book:


March 21, 2019 10:38 pm

From Adam Trepanier on Object Oriented Programming is an expensive disaster which must end

"Thank you for this post. This sums up what I have been feeling for years now with OOP in such a great way. I..."

March 13, 2019 1:58 pm

From ball on Facebook activated my dormant account and it won't let me deactivate it

"Same shit here. I regret ever making a spraybook account..."

February 20, 2019 10:41 am

From Just An Observer on Don't waste your life on Twitter

"A couple of my favorite bloggers started doing twitter. Instead of permanent additions to knowledge, there is..."

February 20, 2019 3:24 am

From Brennan on Did sleep paralysis start the Salem Witch Trials?

"If you have occasional sleep paralysis, you can take steps at home to control this disorder. Start by making s..."

February 19, 2019 11:09 am

From Ryan Earp on Why I prefer dynamic-typing over static-typing: the speed of adapting to change

"If static typing lead to greater programmer productivity (via a reduction in bugs) then corporate Americ..."

February 3, 2019 2:32 pm

From ruurd on Argument about attraction and sexuality and trans

"wait wait wut? what's the liberals doing here?..."

January 18, 2019 10:22 am

From Justin McGuire on When will the era of CyberPunk end?

"The reason cyberpunk doesn't die is because it all came true. From Noah Smith on twitter: "The cool thing a..."

December 16, 2018 9:06 am

From lawrence on Yair Lapid: What does it say about us that Israel has become the only democracy in the world in which Jews don’t have freedom of religion?

"Cat Mara, thank you for catching that. I've fixed it now. (The URL was a "v" by mistake. Looks like I was tryi..."

December 12, 2018 7:50 pm

From lawrence on Object Oriented Programming is an expensive disaster which must end

"Jussi Nurminen, thank you for writing. I believe you are correct, in the sense that Python 2.x had all the bas..."

December 12, 2018 5:13 am

From Jussi Nurminen on Object Oriented Programming is an expensive disaster which must end

"Hello! I've lately became a bit more suspicious of OO designs (including my own), so I read your original 2014..."

December 4, 2018 9:22 am

From lawrence on Docker is the dangerous gamble which we will regret

"GK, thank you for writing, but I don't understand what you mean when you write: "However, at that point you..."

December 4, 2018 7:14 am

From GK on Docker is the dangerous gamble which we will regret

"A development VM is a fine choice, provided that it comes with tools that make it just as easy to run commands..."

November 30, 2018 7:04 pm

From lawrence on Docker is the dangerous gamble which we will regret

"GK, thank you for writing. About this part: "That thing is writing portable shell scripts. The moment you n..."

November 30, 2018 1:41 pm

From GK on Docker is the dangerous gamble which we will regret

"The fat binaries article was nice, but full blown fat binaries are not really necessary. Whats needed is that ..."


August 18, 2018
4:59 am

By Cat Mara

One of my favorite passages in the book. Like a lot of people in tech, I’m pretty introverted & would do almost anything to steer my way out of the conflict you describe. I imagine this guy’s techniques worked all too well for him in the past

Leave a Reply

Your email address will not be published. Required fields are marked *


You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>