The Gang Has a Mid-Life Crisis

Tech leaders’ psychology and mid‑life crisis

• Many see current tech moguls as insecure, addicted to validation, and unable to “stop” despite extreme wealth; their internal crises get projected onto the rest of society.
• Others argue insecurity and pathological competitiveness have always fueled outsized achievement; mid‑life crisis just replaces hope with dread.
• Some think absurd wealth and constant deference warp personalities: like dictators, they get no real pushback, can’t form genuine friendships, and are trapped in status games (yachts, jets, social circuits).
• A counterpoint: only a few celebrity “wealth-addicts” behave this way; most tech leaders still quietly build businesses.

DEI, nostalgia, and blame

• Several commenters find the DEI framing loose: article name‑drops DEI, then barely connects it to the rest.
• One interpretation: older moguls idealize their “glory days,” including the 90s monoculture, and misattribute success to demographics rather than privilege and economic stability; DEI becomes a scapegoat.
• Others argue owners oppose DEI because it constrains hiring power, not because of mid‑life angst.
• There is also open hostility to DEI from some: framed as a movement of entitlement and zero‑sum redistribution.

Privilege, safety nets, and the “garage” myth

• The “no garages in the trailer park” line resonated: a garage implies a house, supportive parents, time, and often connections and seed capital.
• Long subthreads argue that:
  • Many people share that starting point and never become billionaires (so effort and talent matter), yet
  • Safety nets, family wealth, and the assumption that one “belongs” massively change one’s ability to take risk.
• Analogies used: coin‑flipping or at‑bats where rich founders get unlimited attempts; poorer people may never even get to the carnival or onto the field.
• Some push back that land and basic security are still attainable with sacrifice; others note land speculation and housing crises have raised the bar.

Is the software frontier “over”?

• One camp agrees with the article: early internet problems (OS, browsers, search) were huge and tractable by small teams; now key frontiers are saturated, regulated, or require deep domain expertise and larger, multidisciplinary groups.
• Others strongly disagree: software is slow, buggy, enshittified, and dominated by rent‑seekers; there’s enormous room to build better tools and systems, especially outside attention‑driven consumer apps.
• Several note that monopolies, network effects, and investor pressure for growth—not a lack of ideas—make it hard for “better” products to win.

Unicorns, illegality, and regulation

• Uber, Airbnb, and similar post‑2008 giants are described as:
  • Naive “How hard can it be?” software applied to deeply complex social/legal domains, backed by massive VC burn; and
  • “Regulatory entrepreneurship” that exploited or ignored laws (taxis, hotels, taxes), plus took on huge real‑world “bullshit” (assaults, property damage).
• Some argue that, legality aside, they significantly improved user experience over stagnant incumbents, breaking out of local minima; others emphasize that most founders cannot afford to take that kind of legal/regulatory risk.

Attention economy, culture, and article reception

• A few blame the distraction economy: enormous tech talent is spent on capturing attention, while builders themselves lose the 5–10 pm “side‑project” hours that used to produce breakthroughs.
• Others reflect on coding as play and art rather than competition, contrasting that with moguls’ desperate attempts to relive youthful glory.
• The essay itself gets mixed reviews: some call it sharp and relatable; others see it as bitter psychoanalysis, sloppy with examples (especially around DEI and including non‑moguls) and more focused on personalities than systems or ideas.