Is AI Killing Software? & Talking to Your Kids About Greek Life

Answering Tim’s question about his 18-year-old son joining a Florida State fraternity, Scott describes his own UCLA experience: he rushed at 17, moved into the fraternity house with three other men, later became president of the Interfraternity Council, and credits the fraternity with helping him graduate. He says fraternities and other groups shrink a university of 20,000 students into a community, much like cultural societies, dance clubs, or choirs. He cites data suggesting members are more likely to graduate, earn better grades, and remain involved after college, while acknowledging serious problems, including alcohol abuse and a study finding fraternity men twice as likely to perpetrate sexual violence.

Scott recalls seeing “deaths of despair” and “deaths of drunkenness” while serving on the fraternity council. A student fell from a balcony at an SAE rush party; a council officer reportedly hanged himself after a marriage proposal was rejected; and a friend took a jet ski out at night while intoxicated and was found eight days later. He says he heard less about sexual assault, but that may mean cases were handled privately or suppressed. He also recounts a pledge-pinning party where students drank bottles of Andre Pink Champagne: one nearly unconscious pledge was initially going to be left to sleep, until another member insisted on taking him to the emergency room, where doctors said he was breathing only six times per minute.

Scott’s first practical message is that young people should understand that their bodies may not yet tolerate alcohol and should stop drinking, switch to water, and say they do not feel well, even if peers are pressuring them. He says his sons have gradually learned social drinking, partly because they were exposed to alcohol in England, where drinking can begin earlier but, in his view, often develops more slowly. By contrast, he drank little in high school and arrived at college without knowing his limits; during his second week he became drunk, fainted, hit a wall, and needed two stitches, generating an awkward $320 bill to his financially careful father.

After discussing the Cornell incident with his son, Scott asks him to imagine that a sister were in the same situation and consider how he would want the men around her to behave. He also asks him to picture his future self five or ten years later—with a job, partner, children, and professional standing—and whether that person would approve of his current conduct. Scott recommends that people be sober or nearly sober the first time they are physically intimate, because intoxication increases the risks of misunderstanding, unprotected sex, and regret. He personally describes sex involving multiple men and one woman, as well as choking, as violence, while acknowledging that consenting adults retain the legal right to make their own choices.

Scott repeatedly qualifies his advice by saying he is not a parenting expert and is still making mistakes, but he urges fathers to talk directly with their sons about fraternity culture, alcohol, sex, empathy, and limits. He recommends bringing up difficult events even if children roll their eyes or pretend not to listen, and says he speaks with his sons every day. In his view, debates over Cornell’s administration or prosecutors miss a more basic intervention: if society wants better men and fewer incidents like this, more fathers need to be present and engaged in their sons’ lives.

Responding to a question about stocks, private equity, real estate, and bonds, Scott repeats the maxim that people get wealthy through concentration and stay wealthy through diversification. Entrepreneurs, technology workers, financiers, and employees with valuable options generally have to concentrate early because they lack capital and are building one business or career. Once someone has an asset base—he suggests roughly six figures or more—they should seek distinct cash flows that are not highly correlated. He cites Ray Dalio’s approach at Bridgewater: find about 12 good investments with different sources of risk and return. He warns that an S&P 500 fund is not fully diversified because about 40% of the index is concentrated in its ten largest stocks.

Scott says his greatest wealth-creation mistake was believing individual performance could overcome market dynamics. He has been rich three times and lost wealth twice: first in the dot-com collapse because he was concentrated in technology and his startups, and again in 2008 after rebuilding for seven years while remaining heavily invested in tech. He now tries not to hold more than 3% of assets in one stock, though he owns substantial real estate spread across regions and uses limited leverage. He calls leverage the way smart people go broke: an over-borrowed Florida condo could lose half its value and force a sale before recovering. He recommends diversification across asset classes and geography, including low-cost Asian and European index funds, even if it reduces upside.

Scott explains the SaaSpocalypse thesis through three mechanisms: AI agents may replace software used by human employees; companies may need fewer paid “seats”; and coding agents may make building internal alternatives cheap enough to pressure vendors at renewal. Yet Stripe’s index of 72,000 SaaS businesses showed year-over-year growth above 30% at or above 2023 levels, while a software ETF rose 17% in the third quarter, Salesforce gained 46%, and Workday 55%. He says the market’s real concern is terminal value: investors no longer assume software is permanently embedded in workflows. Salesforce still offers relationships, training, security, debugging, and accountability, and Scott says his own company would keep using it even if a replacement were free.

OpenAI’s Dots agents reportedly operate across more than 4,000 applications and are being piloted for procurement, invoices, customer support, and contracts. Scott says OpenAI’s enterprise revenue reportedly reached $70 billion and Anthropic’s annualized revenue about $65 billion, while Salesforce’s Agentforce reached $1.5 billion in annual recurring revenue, up 240% year over year. Jefferies found information technology services and systems integrators most exposed to budget cuts, followed by IT service-management and CRM software; cybersecurity was rated least exposed. Intuit is the clearest S&P casualty, down about 55% despite 14% revenue growth. Scott predicts AI-enabled firms may sell completed services—such as tax preparation or compliance—instead of merely selling software, much as AI-enabled radiologists can perform more scans, lower prices, and ultimately expand demand.

Scott initially says he assumes little from the Trump administration can be trusted, then distinguishes political interference from the Bureau of Labor Statistics’ underlying processes. Trump fired Commissioner Erica McEntarfer in August 2025 after accusing her of bias without evidence, nominated an inexperienced conservative, and withdrew that nomination after bipartisan backlash; the Senate later confirmed career BLS economist Brett Matsumoto, praised by former commissioners. Economist Justin Wolfers says career staff, two separate employment surveys, outside checks, state unemployment records, and private payroll data make deliberate falsification difficult. However, response rates fell from 66% in 2016 to 35% last December, funding declined more than 22% after inflation between 2010 and 2025, and BLS later overcounted job growth by about 860,000 jobs. Scott’s conclusion is mixed: the numbers remain hard to tamper with, but underfunding and low responses make them less reliable.