Narcissistic Sugar Daddy CEO’s “Can’t Buy Me Love” Lament

Lester Golden
Dec 22, 2020 · 18 min read
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His money couldn’t buy him this:

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But he’s really just trafficking with a dating face:

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His Real Lament: the Persistent Power of the Weak

This story expands on my comment about Jessica Chou’s Refinery29 interview with a rich software CEO about his Sugar Daddy dating story:

So how did you end up on Seeking Arrangement? I started using the site because I thought it was the only way to meet women who have not been tainted by life….I thought, maybe I should start to pursue younger women. But then it became clear to me that conventional dating wasn’t going to work. I wasn’t meeting younger women in the bars I went to, and when you go on a site like Bumble, you’re aren’t going to find many women on there who are open to dating a 50-year-old guy. So I found Seeking Arrangement.”

I got lots of claps and comments when I wrote that Mr. Sugar Daddy’s interview, if authentic, perfectly illustrated the narcissistic sociopathy of wealth that assumes absolutely every object of our tech-bro CEO’s desire can and should be buyable. So I decided to further analyze what this case signifies and why my comment struck a chord.

Mr. tech-bro CEO ignores a single and fundamental moral symmetry: you get what you give. The magic in mating happens not when you’re in control, but when you trust the other enough to surrender it. But our anonymous tech Ubermensch wants the magical emotional high from discovering, youthful, innocent feminine energy that gives life, while giving nothing of himself but money in return. But offering only what he has in abundance to the point of excess equals giving nothing. Our tech bro CEO fails to comprehend that to give nothing means to get nothing, thinking he can get what he desires from the other box, while turning its switches on and off at his convenience:

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Image for post Tech bro CEO sees these switches’ lived experience as“tainted by life”.

It’s the sociopathy of wealth and asymmetry of power that keeps tech-bro locked up in his single switch onanistic echo chamber and leaves him completely clueless about the wholly transactional motives of the sugar baby he dubs “mercenary”, “the most dangerous person I ever met”, who briefly moves in with him. He’s clueless about his counterparty, who merely applies the same principles to her business that he applies to his:

For True Tech-Bro Nookie Narrative…..

Listen to the Counterparty: the Sugar Baby

This guide to sugar dating by an experienced sugar baby, could have enlightened him:

“Some relationships are PPM, or “pay per meet” — in those arrangements, the sugar daddy gives the sugar baby a specified amount per date. In another type of relationship, sugar daddies give an “allowance” on a set schedule, like monthly or biweekly, either in cash or through a payment app like Venmo. Many relationships start out PPM, as it’s less risky for the sugar daddy than setting up an allowance right away. “Experience daddies” are the ones who don’t pay sugar babies in money — just gifts like fine dining, hotel stays, and glamorous vacations. A “Splenda daddy” is a sugar daddy with a cheaper budget. And a “salt daddy” is just a jerk, especially if they’re faking generosity just to get into your pants. And though the term’s a bit crass, sugar babies have to be wary of what the community calls a “pump and dump” — the common occurrence of a false sugar daddy not providing any allowance or PPM, getting intimate with a sugar baby, and ghosting. To avoid falling victim to one of these, you should never initiate any intimacy with a sugar daddy unless you’ve already received your sugar.” (

He would have known that, for his sugar baby, getting real is not part of the deal:

If you’re considering sugar dating solely for the money, it will be much more stressful, since it’ll become a second job….It’s common practice to adopt a sugar identity separate from your real-life identity. My online profile uses a generic name, and I do not disclose my real identity — even after I meet my sugar daddy in person, in some cases….” (Business Insider, August 29, 2019)

Symptoms of Suicidal Sociopathic Capitalism: Capitalists Who Don’t Get What Sustains Capitalism

Our love-lorn tech-bro’s case also shows how, left unregulated, capitalism commodifies everything it touches and saws off the tree branch upon which it sits (Hobsbawm, 1991). The market’s commodification by default corrodes the pre-capitalist social reflexes and reciprocity that permit societies to function and, literally, reproduce themselves. Tech-bro’s SeekingArrangement experience proves philosopher Michael Sandel’s point that markets are far from morally neutral and that their commodification poisons the parts of life they should not touch:

“”The most fateful change that unfolded in the last three decades was not an increase in greed. It was the expansion of markets, and of market values, into spheres of life where they don’t belong….(it’s) unambiguously clear that markets have a moral impact on the goods that are traded in them.” (

The greed is good libertarian conception of capitalism, and its utility maximization school of economics, have used spurious claims of moral neutrality to deform our discourse about the software is eating the world economy these tech titans now dominate. Our Sugar Daddy CEO has no doubt better applied the principles of reciprocity in relationships to managing his software team than he has in his private life. His business would fail if he didn’t.

Nick Hanauer, the first non-family investor in Amazon, has said the fundamental driver of the teamwork that capitalism depends on is not greed and self-interest, but reciprocity ( Adam Smith, in his Theory of Moral Sentiments, recognized reciprocity and social empathy as essential for markets to function. But this is the Smith work that mainstream economists and free market fundamentalists conveniently forget about.

Mr. Sugar Daddy CEO’s whines about “women tainted by life”, showing how prescient this subtitle of Arlie Hochschild’s 1997 book, The Time Bind was: When Work Becomes Home and Home Becomes Work. Our tech-bro CEO has inverted life as it should be by investing unconditional love in his business and applying business principles to his love life ( The mystery is how he ever expected to saw off love’s tree branch of altruistic sentiment and still remain above ground. Thinking he could get away with pursuing real love while acting as a transactional accessory to human trafficking is standard move fast and break things tech-bro hubris.

Financializing Tinder: SeekingArrangement

This inversion of values, a secular version of the religious right’s prosperity gospel, returns mating to its pre-modern, pre-romantic state: a status-driven alliance of convenience, but without parental supervision. The story of SeekingArrangement’s founder Brandon Wade shows how turning mating into a business deal was the ultimate Revenge of the Nerds by removing all feminine emotional intelligence and choice to seal the deal. SA’s founder and our Sugar Daddy CEO are the anti-Bumble, deploying a financialized tech fix for their frustration at female choice in mating ( Here’s sugar dating’s digitization story, straight from SeekingArrangement’s founder who said “love is a concept invented by poor people” (

How’d you get into this business? I got into it because I was dateless, and I was shy and I was just completely awkward….And my mother had always told me when I was growing up to channel all my sexual frustration into my books because when you get older and have money to be generous with, the girls will flock to you. When I graduated I was making six figures, and I still had that problem so I created this website because normal dating sites weren’t working for me.

Did this one work for you? Oh, yeah! I was actually one of first members. In a normal site I used to have to compete with guys with triceps and biceps and great-looking bodies. The online dating process is such a visual process. Seeking Arrangement is different: This is where you’re going to meet Google executives and Facebook executives. And girls know that. This is where you’re going to find really wealthy guys to date, and that turned the tables immediately. Suddenly the guy who is writing hundreds of emails hoping to get one response is getting his inbox flooded.

Are technology executives a large part of your clientele? It is for San Francisco. We did a study where we looked at every single city based on what career people are in. Every city is different, and in Silicon Valley obviously it’s technology executives and when we looked in New York, it was all Wall Street people. The average sugar daddy is a 40-year-old male, who makes more than $250,000. The average sugar baby is around 27. At the beginning of the site around 50 percent of the sugar daddies were married, but that’s since dropped to 30 percent. More single men are coming to the site to find love.

Actually Wade and his company are nothing more than sugar-coated pimps, a soft, tech titan fix for incel male anger at having to accommodate and adapt to female choice, individuality and romantic narrative in mating. In essence, SA has financialized Tinder’s hook up culture and exponentially increased its asymmetry of power. It’s the mating subset of turbocapitalism’s sociopathy of wealth, with platform tech working as a trojan horse for human trafficking:

“In 2018, a young female member of the Coalition Against Trafficking in Women (CATW), which campaigns to end the global sex trade, attended a sugar industry event undercover. Hosted by Let’s Talk Sugar, a blog in partnership with SeekingArrangement, the event aimed to recruit sugar babies onto the site.. In the tips and Q&A portion of the (sugar dating industry) event, Brook Ulrich, the SA representative, announced, “These guys are rich and they don’t have enough time to craft an eloquent message … they want to get to the point … they want to press a button to say, ‘I am interested, are you interested?’ ” She referred to sharing private photos as a “game,” and recommended a little “reveal” in private photos. Ulrich told the young women they “shouldn’t be embarrassed or ashamed” to have an older man paying for her expenses. In response to a woman who asked about potential dangers and safety, Ulrich said that women signing up for SA should assume that all the men on the site have “baggage,” and the women should be cautious about who they meet. (

Just listen to some of the sugar-babies’ experiences to properly answer the question, “what’s love got to do with it?”:

It’s advice that Cheryl, who feels she “lost everything” when she was forced to run away from her abusive sugar daddy, finally understands. “I would tell any woman planning on doing it: ‘Don’t even think about it!’ It is prostitution, but it is even worse in some ways, because the john doesn’t walk away after having sex. He sticks around to take your life from you and make it his.” (”

“Judy learned about SeekingArrangement from her friend at work. “I was earning £5 [$7] an hour in a coffee bar and could not even pay my rent, let alone go out and have fun. I signed up and was immediately inundated with requests to meet, from nice looking men. Initially, Judy says she met some “quite nice” men, and was taken for meals and, after sex, was paid between $260 to $650. “It felt like very high-class prostitution, but prostitution nevertheless,” Judy says. For that amount of money there was, of course, a catch. “I was juggling three daddies at once, and I had to be available to see them when they called. It was like that initial payment ‘bought’ me, and they kind of owned me after that.” (

And the slavemaster complains that the slaves are “tainted by life”. More variations of sociopathic high net worth hubris in other contexts and their sources:

Sociopathic Wealth: Big Money, Short Fuse

The Financial Times just published a piece on why billionaires make pathologically litigious neighbors about trivial stuff like trees that block a view and other superficial idiocy; plutocrats killing canaries with cannon fire: “From blaring music to blocking beaches, the super wealthy are bad at sharing with others”. Some of these guys invented the sharing economy, but apply it to everyone but themselves:

“I wouldn’t want an angry billionaire with a short fuse living next to me,” his (Bond King Bill Gross) neighbour Mark Towfiq was told. The inevitable quarrel, with accusations of harassment, came to court this week. Upset by Mr Towfiq’s complaints about a $1m glass sculpture on his property, Mr Gross blared loud music over the fence, including mariachi tracks and the theme song to the 1960s US sitcom, Gilligan’s Island. “Peace on all fronts or we’ll just have nightly concerts, big boy,” 76-year-old Mr Gross allegedly texted.” (

This case, and our anonymous sugar daddy CEO, are not sampling error. The spat between neighbors with six or seven spare zeroes of their net worth to burn in legal fees would be funny if it weren’t so symptomatic of how American society has been feudalized by extreme inequality (US Gini coefficient measure of inequality in 1968: .36, now: .48,

And Bill Gross’ self-aware confession doesn’t presage behavioral change by masters of the universe who “thrive on beating others”:

“Battles between neighbours over noise and obstructive vegetation are quite common, but the wealthy take them to extremes. Why are billionaires so prone to falling out with the people next door? I can think of three reasons. First, they thrive on beating others. Mr Gross once remarked that “my desire is to win, and win forever”, and his self-diagnosis in a Lunch with the FT interview last year was not far off the warning given to Mr Towfiq. Mr Gross said that undiagnosed Asperger’s had made him “a singular, dominating, angry, quiet, introverted person”. (ibid)

At the age of 76, Gross has had ample time to acquire self-knowledge, though, apparently, his impulse control skills are still a work in progress.

Why Rich People Are So Mean (Wired, 9/26/2019)

Tech-bro CEO’s confessional shows how difficult it is to compartmentalize his “desire to win and win forever” and “thrive on beating others” from his dating and love life, the one game where that talent is uselessly dysfunctional.

SeekingArrangement and other sugar dating sites, by financializing Tinder’s degradation of female bargaining power in mating, aggravate the sociopathy of wealth examined by Wired in “Why Rich People Are So Mean: call it Rich Asshole Syndrome — the tendency to distance yourself from people with whom you have a large wealth differential.” This study of narcissistic, corrosive workaholism begins with Gary Rivlin’s 2007 NY Times profile of an overworked Silicon Valley millionaire:

“Hal Steger, lived with his wife in a million-dollar house overlooking the Pacific Ocean. Their net worth was about $3.5 million. Assuming a reasonable return of 5 percent, Steger and his wife were positioned to cash out, invest their capital, and glide through the rest of their lives on a passive income of around $175,000 per year after glorious year. Instead, Rivlin wrote, “Most mornings, [Steger] can be found at his desk by 7. He typically works 12 hours a day and logs an extra 10 hours over the weekend.” Steger, 51 at the time, was aware of the irony (sort of): “I know people looking in from the outside will ask why someone like me keeps working so hard,” he told Rivlin. “But a few million doesn’t go as far as it used to.” Steger was presumably referring to the corrosive effects of inflation on the currency, but he appeared to be unaware of how wealth was affecting his own psyche. “Silicon Valley is thick with those who might be called working-class millionaires,” wrote Rivlin, “nose-to-the-grindstone people like Mr. Steger who, much to their surprise, are still working as hard as ever even as they find themselves among the fortunate few. But many such accomplished and ambitious members of the digital elite still do not think of themselves as particularly fortunate, in part because they are surrounded by people with more wealth — often a lot more.” (Wired, 5/7/2020, Christopher Ryan)

So tech-bro CEO can blame our ever rising Gini coefficient (from .36 to .48 since 1968) and a workaholic version of the hedonic treadmill for the gulf between him and his dates and resorting to SeekingArrangement. He just assumes without stating so that his money and social rank buy him the right to impose his single switch workaholic life on any woman he allows into his life. His unstated assumption: adaptation is a one-way, not two-way street.

To Know the Truth, Talk to Their Servants

Though not rich, I know this world, having scrounged a few crumbs off plutocrats’ tables in advertising and real estate. I spent 20 years in the yachting industry dealing with guys like this and got to know the type very, very well. The crews on the yachts and private jets know all too well how these man-children assume that money buys them the inalienable right to be narcissistic, selfish, spoiled and infantile beyond measure. ( Click the link to digress to the gory, gossipy details. Read below for my experience of this toxic man-child social competition arms race.

And Who’s Got the Biggest…..

When staying at a hotelier friend’s house in the Caribbean we saw a 40 meter superyacht offshore one day replaced by a 50 meter the next. My friend explained that the owner of the 40 meter moved his boat to the other side of the island because he didn’t want to be the second biggest boat in the bay. This is the true measure of the personality type we have put in charge of our financial and economic systems, and, for four years, the White House.

Our software CEO never asks a simple five word question: am I what she needs? Narcissists never ask questions that require listening to an answer they might not wish to hear. He gives away the game with his inability to resist the narcissistic urge to display superiority: “I’m 50 years old but I probably look 38. I’m incredibly fit, I work out all the time, and I have the mentality of someone in their 20s because I just love to have fun. I jump out of planes, you know? I’m just one of those guys.” Our second president, John Adams, coined a fitting aphorism for this kind of narcissist: “the human appetite for superiority is without limit.”

And I get it. The male ego can be an insecure and bulimic beast that requires constant feeding. I’m a 65 year old with an insatiable ego who loves beating young guys on the basketball court. But I have the good sense to confine my adolescent id and fantasies to the basketball court instead of subjecting my mate to them. So ask yourself how much longer a 50 year old will wait before figuring out the proper trough from which to feed his adolescent id. The answer: the higher up the food chain in our winners take all socioeconomic order you are, the longer you are likely to remain clueless about your errant ego feeding and prey to the sociopathy of wealth.

Who Gets Socialism? Not the Crash Test Dummies in Our PTSD-Gofundme Economy

This capitalism as plutocrats’ ego-driven competitive game will take us nowhere stable and secure. American turbo capitalism is a crash prone asset bubble-blowing system in which the percentage of the people riding as crash test dummies without seat belts and absorbing the system’s volatility is always rising in a spiral of increasing bets of heads I win, tails you lose. Some of the crash test dummies have begun to figure out there’s plenty of socialism to go around; it’s just a question of who gets access to it. Big Banks get bailouts, Big Pharma gets federally-funded university research for free, Big Tech got the internet royalty-free from DARPA (the Defense Advanced Research Projects Agency) and, until this week, a free pass on antitrust enforcement, Big Insurance and MLB get antitrust exemptions, Big Sports gets the welfare of subsidized stadiums built by taxpayer money, Big Oil and Gas get climate-wrecking fossil fuel subsidies and Big Agribusiness and Big Food get industrial food system socialism that feeds you the addictive high carb and hormoned meat diet that makes you chronically sick, which guarantees you’ll need Big Pharma’s drugs to cure the avoidable chronic conditions Big Agribusiness and Big Food gave you while taking away your ACA insurance during a pandemic.

Then the same people who voted to cut Big Banks/Pharma/Insurance/ Sports/Oil/Gas/Ag/Food’s corporate taxes use their donor class money — protected speech according to Citizens United — to scare you with:

Bernie’s and the Squad’s “SOCIALISM!”,

A phony war on Christmas

BLM rioters will invade your picket fence suburbs

The Socialists will take away your hamburgers, guns and churches.

They’re coming in caravans to rape your daughters and only our Mexico-financed wall (by way of raiding military base maintenance funds) can stop them.

They’re coming for your bathrooms.

And it’s socialism so radical it would fit right into…..Angela Merkel’s Christian Democratic platform in Germany.

Symbiosis: Punch-down Tribalism and Meritocracy

Our winners take all tournament economy drives its losers to use the cheap emotional compensation of xenophobic nationalism or racial tribalism to punch down. But this punch-down MAGA political tribalism is merely the flip side of the meritocratic individualism doctrine that legitimizes our monopolistic tech titan oligarchy (recently certified by FTC antitrust action against Facebook and Google, the price-fixing Standard Oils of the 21st century).

Of course, our lovelorn tech-bro CEO is certainly not at fault for all of this. And his tech-bro style of male entitlement is certainly less vulgar than that of the grab ’em by the pussy pornstar payoff Goodfellah Archie Bunker in the White House (Born in Queens near Trump’s house, I know this type well). But he is certainly an integral part of a system built on the lie that people like him built their businesses all by themselves in a perfectly fair meritocracy, and that anyone who objects is just waging envy and class warfare. Yes, there is class warfare. But, as Warren Buffett said, his class is winning.

And this tech-bro CEO’s sugar-coated trafficking by sugar dating is symptomatic of this widening asymmetry of power, of which the gender component is only one part. He then has the breathtaking chutzpah to whine about not getting the love he was promised on a site whose founder said “love is a concept invented by poor people.”

It’s the System, Not Its Individuals

Ignore the personal and personality differences between charitable, emotionally intelligent billionaires like MacArthur, Pew, Buffett and Gates and clueless narcissists like Breitbart owner, libertarian hedgie billionaire Robert Mercer and the Nazi trivializer Steve Schwarzman, who said raising the tax rate on his carried interest was like Hitler’s invasion of Poland. Pay attention to what the misunderstood crybaby Leon Cooperman really said when he teared up on CNBC (

“For months now, Leon Cooperman has been very upset. He has complained that Bernie Sanders “doesn’t have a clue” that “capitalism works.” He is so agitated by Elizabeth Warren that he sent the senator a letter in which he complained that she treated him like “an ungrateful child” because she suggested that he pay more taxes….“I don’t need Elizabeth Warren telling me that I’m a deadbeat and that billionaires are deadbeats. The vilification of billionaires makes no sense to me,” he added. The world is a better place, he said, “because of Bill Gates, Michael Bloomberg, David Rubenstein, Bernie Marcus, Ken Langone.” (

Cooperman settled insider trading charges for $4.9 million with NY, the financial equivalent of a parking ticket for him (or a sugar-dating binge by our tech-bro):

“When it comes to crime, wealth is a magic eraser. Cooperman does not have to cry in his prison cell over the unpaid court fines that sent him there. No one will Tase Leon Cooperman. He is just crying over taxes.” (

The core of our software CEO’s love-lorn lament: he can’t understand why his magic money eraser didn’t work in the dating and mating market. Perhaps if your net worth has only seven instead of nine zeroes, you get no magic eraser to turn your sugar baby’s control box switches on and off as you please.

As an angel investor I’d never touch a founder with his unreflective and megalomaniacal temperament. If he’s incapable of listening to the women he dates, he won’t listen to his investors. Even if he makes us money, we wouldn’t enjoy the process of nurturing the investment, which is half the point in early stage investing.

There’s a long history of the system’s serfs enthralled by tear-jerking stories of the unhappy rich to keep the serfs from wandering off the estate, whether in Brazilian and Mexican telenovelas or American soap operas. If you fall for them, you’re looking behind the wrong curtain for the real wizard.

The inescapable conclusion from our love-lorn tech-bro’s lament: capitalism’s built-in systemic default is to commodify everything it touches, even to the point of sawing off the tree branch of love upon which human reproduction itself rests. To stop this default requires a political choice, as Harvard philsopher Michael Sandel makes clear:

“The question of markets is really a question about how we want to live together. Do we want a society where everything is up for sale? Or are there certain moral and civic goods that markets do not honour and money cannot buy?”” (

You can buy the tech-bro CEO’s transactional love life, or have the real thing; have a commodified market society, or protect the best things in life from the market. Choose.

An Idea (by Ingenious Piece)

Everything Begins With An Idea

Lester Golden

Written by

From Latvia I write to share learning from life in 6 languages in 5 countries & seeing fascism die in Portugal & Spain in 1974 and 1976.

An Idea (by Ingenious Piece)

No Matter What People Tell You, Words And Ideas Can Change The World.

Lester Golden

Written by

From Latvia I write to share learning from life in 6 languages in 5 countries & seeing fascism die in Portugal & Spain in 1974 and 1976.

An Idea (by Ingenious Piece)

No Matter What People Tell You, Words And Ideas Can Change The World.

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