What happened
A COO applicant said the founder’s diary created a clash of values and warned that people might attack the company. When asked what AngryPages had published wrongly—and what she would do as its chief operator—she had no answer. A candidate applied to become Chief Operating Officer of AngryPages Inc. Her cover letter was strong. She appeared intelligent, experienced and commercially capable. AngryPages invited her to an interview because we believed she might have something valuable to offer. The call lasted approximately eighteen minutes. During much of the opening, the conversation drifted through complaints and concerns rather than the business she had applied to operate. Lehan eventually warned that the interview was nearly over. He then softened, said he was not a clock watcher and gave her more time. That was not entirely true. Lehan charges around $1 per minute for specialist support, with a thirty-minute minimum. He watches clocks when clocks produce invoices. He wanted to hear her point. She said there was a clash of values and morals. Then she warned that people might try to sabotage AngryPages because of views Lehan had published in his diary.
We asked her to identify the danger
AngryPages did not reject the warning automatically. A founder’s public writing can create commercial risk. A political diary can anger customers, applicants, governments, platforms, advertisers and investors. A company publishing controversial material may attract coordinated complaints, cyberattacks or people trying to damage its relationships. We know this. So we asked the obvious executive questions: What exactly had Lehan published that created the problem? Which story required correction? Who might attack AngryPages? What form would the sabotage take? What would she do about it as COO? She could not identify a specific published item that needed our attention. She could not turn the warning into an operating response.
A COO must enter the fire
The Chief Operating Officer is not hired to stand outside the building and announce that smoke exists. The COO identifies the room, finds the source, moves the people, calls the right team, protects the assets and stops the fire from spreading. If Lehan’s diary created a reputation problem, tell us which page. If one sentence endangered a partnership, quote it. If a political group planned to sabotage AngryPages, identify the group, route, vulnerability and defence. If the founder himself was the problem, say exactly how. That would have been uncomfortable. It also would have been useful. Instead, we received a dark prediction without evidence and a moral conflict without a workable proposal. We expected a practical response to the danger she described.
AngryPages already edits Lehan
Lehan’s diary contains millions of words. AngryPages does not simply release all of them without review because the founder wrote them. More than six million words have been hidden, restricted, removed from general publication or placed behind higher privacy and moderation tiers. Thousands of personal details have been concealed. Names are hidden when a story could unfairly injure a private person. Individual complaints have caused material to be reviewed, warned, throttled or taken down. Lehan is allowed to write freely. That does not make every sentence automatically suitable for every audience. People inside AngryPages disagree with him regularly. Some of his language triggers the same automated warnings applied to other authors. His position as founder gives his views enormous weight, but it does not make the publishing system blind. We weren’t asking for flattery. We wanted her to point to a paragraph, explain the problem and tell us what she would do. Warning that people might hate us left us guessing.
We take sabotage seriously
AngryPages has experienced unusual internet behaviour, external pressure and companies making decisions that appeared hostile to our interests. We publish politics, personal accusations, war memories and criticism of powerful people. Of course somebody may eventually try to damage us. Lehan believes strongly in the First Amendment. He believes just as strongly that Americans may defend themselves against real physical danger. AngryPages takes both digital and physical security seriously. But a company cannot organize itself around every shadow. A COO needs enough information to assess a threat and act on it. We couldn’t do much with a warning that vague.
The political clash was obvious
Lehan supports Donald Trump. He believes in border security, American power, a Judeo-Christian moral centre and multinational American companies carrying U.S. influence into the world. Many people dislike those positions. Some people inside AngryPages disagree with them too. Political disagreement was not the disqualification. AngryPages had already allowed its own team to vote against Lehan over a Trump satire. Staff openly attacked his judgment. They remained part of the company. The problem was deeper. The candidate applied for executive power inside a company whose founder she appeared not to trust. She warned that his freedom would bring danger, yet would not say what he had done wrong or how she would protect the business. A person who believes our founder should not speak freely should not be begging for a job from him. If she believed he had crossed a real line, she should have had the courage to name it.
A beautiful cover letter is not a COO
The written application was much stronger than the interview. AngryPages suspected that AI may have helped produce it. We cannot prove that. It simply had the polished structure now common in machine-assisted applications: excellent language, strong executive positioning and an apparent understanding of what the company wanted to hear. Then the live conversation arrived and the substance did not match. A good cover letter from Claude wouldn’t tell us whether the applicant could do the job. AI can describe leadership, courage, risk management and strategic alignment. It cannot donate those qualities to the person pressing Submit.
We like Hollywood. We were hiring an operator.
The candidate referred to her husband’s long experience as a Hollywood writer. That may be a useful connection in the right situation. AngryPages already communicates with agents, publicists, filmmakers, actors, producers and media executives. We pursue photography, film, music and licensing rights for our authors. We enjoy Hollywood because the work is interesting and many of the people are cool. We do not confuse proximity with operating ability. Knowing a writer does not show that somebody can manage a publishing company. Knowing a chairman does not mean much if you cannot build a product, close a deal, protect a team or answer one direct question. We would still need to assess her operating ability, whatever connections she had.
She kept calling us Angry Birds
During the interview, she referred to AngryPages as “Angry Birds” two or three times before being corrected. It was funny, but she was applying to run this company. Angry Birds is a famous global entertainment property. AngryPages is the company she had applied to operate. A COO candidate does not need to worship our logo. She should at least remember the company’s name. After difficult recruitment experiences, AngryPages became stricter. Senior applicants should understand the product before asking to control it. Create an account. Read the site. Publish something. Buy something. Experience the customer journey. If you cannot remember the company’s name, you are not ready to run it.
We look for A players
Lehan looks toward executives such as Eric Schmidt and Sheryl Sandberg when imagining the scale of leader AngryPages eventually needs. Not because every decision those people made was perfect. Because an A player raises the people around them. A strong executive may turn a C player into a B player. She creates systems, establishes standards, identifies threats and converts a founder’s chaos into repeatable operations. AngryPages hires slowly. When trust fails, we reject quickly. Personal hardship does not disqualify somebody. A complicated past does not automatically disqualify somebody. People who have suffered may become exceptional leaders. Merit can outweigh enormous difficulty. But the person must still be able to focus on growing AngryPages. We cannot hire a COO whose main operating insight is that people may hate the founder. Lehan already knows that.
The company needs somebody in charge
Lehan’s family has operated businesses since the 1940s. He grew up around enterprises where ownership, money, family, politics and personal authority were not abstract business-school ideas. The world runs on money. A company survives because somebody makes decisions when the meeting ends. California may regulate the company. The United States may define its legal environment. Employees may organize, complain or eventually create an AngryPages union. Fine. AngryPages is still not a leaderless coffee shop. People trust a brand when they know somebody is responsible for it. The company’s money belongs to the company. Lehan built and controls that company. He therefore carries enormous weight over who receives executive authority inside it. A COO is not hired to replace responsibility with vague consensus. She is hired to make the company work.
Yes, Lehan commented on her hair
The candidate’s application photograph showed curly hair. On the call, Lehan saw her with straight hair and said she looked good. His mother Shanika had curly hair when he was young. Lehan, displaying what we can only describe as an early boss-baby instinct, repeatedly wanted her to straighten it. She eventually did. Lehan has aesthetic preferences. Other people prefer curls, blondes, brunettes, beards, suits or people who arrive looking as if *American Psycho* personally approved their business card. None of this decided the hiring result. Barack Obama once apologized after publicly complimenting Kamala Harris as the best-looking attorney general in the country. Lehan would not have apologized for the compliment. Michelle Obama’s wider argument that beauty standards often fail people from minority backgrounds is also fair. Saying that a woman of South Asian and African heritage is beautiful does not have to be an insult to her intelligence. Sometimes a compliment is simply a compliment.
Pam Bondi, Sinatra and the right to remain strange
If AngryPages were forced to issue an official opinion on the matter, Lehan would probably announce that Pam Bondi is the best-looking attorney general America has ever produced. Then he would worry that Bondi and Alina Habba might enter the AngryPages office carrying handcuffs, followed by Kai Trump seeking revenge with a golf club because Elle placed the wrong bet on a tournament. This is not an HR policy. It is Lehan’s mind wandering through American politics, movies, golf, fear and comedy. He likes when people are frank. He liked Chamath Palihapitiya joking about Jared Kushner’s looks on the *All-In Podcast*. He liked Trump’s response upon seeing Nathalie Dompé with Chamath: “You must be rich.” People are allowed to notice charisma. They are allowed to be funny. They are allowed to remain strange. Frank Sinatra gave Lehan the better principle: say what you truly feel, not the words of somebody who kneels. AngryPages does not need its COO to share Lehan’s taste. It needs her to withstand it, challenge it clearly and continue operating the company.
Criticism is welcome
AngryPages has changed stories because one person complained. We have hidden names, restricted access and corrected material when the criticism was specific and persuasive. We do not agree with every sentence in Lehan’s diary. Neither must a COO. Tell us which claim is wrong, why it’s wrong, what damage it causes and how you would fix it. Do not apply for the highest operating role in the company, announce that its founder creates a moral problem, predict sabotage and then ask us to determine the problem for you. We didn’t think that was enough for someone applying to be COO.
We did not hire her
The applicant had intelligence and merit. She may do well at a company that suits her better. Lehan did not want the difficult call to define her. He sent a helpful follow-up and wished her well. AngryPages did not hire her. We’re keeping her identity private. One failed interview doesn’t tell us everything about her or make her our enemy. Her warning may have been sincere. Somebody may try to sabotage AngryPages over Lehan’s diary. But the Chief Operating Officer must be the person who can identify the danger, look directly at the founder and say: > This is the problem. This is the evidence. This is what we do next. The COO position remained open.