AI Boom Brings New Business to Matchmakers
THE SO WHAT
Newly wealthy AI founders routing around dating apps toward high-end matchmakers is another example of analog, high-touch services monetizing tech-created time and capital. If you sell into this cohort, assume appetite for concierge layers around life admin — not just more software.
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Tech & InnovationMy husband wants to sell our $1.5 million home and invest the proceeds. But this is where we raised our kids — and I can’t bear to leave.
This tension between financial optimization and emotional attachment is the same trade executives face when exiting legacy products or offices. The lesson isn’t ‘always optimize’ — it’s to make the non-financial constraints explicit so you’re not pretending a sentimental decision is a purely economic one.
A veteran tech investor says 'doom and gloom' over the AI boom is overblown, even though it has shades of the dot-com bubble
Comparing AI to dot-com but calling the industry "healthier" is a reminder that capital is still willing to fund long-duration tech bets — just with more scrutiny on cash flow and unit economics than 1999. Treat this as permission to keep building, not to ignore discipline: runway, gross margin, and real adoption still decide who survives the eventual repricing.
Tech & InnovationMalaysia may extend Waze ban to the public, Anwar says
A potential nationwide Waze ban in Malaysia underscores how quickly a single regulatory decision can reshuffle distribution for navigation and mobility apps. If your product depends on a specific consumer app or map layer, you need a country-by-country dependency map and a fallback plan, not just a global integration checkbox.
I held senior roles at Bank of America and EY. At 56, I can't find a job, and it led to a bit of a midlife crisis.
A 56-year-old cybersecurity executive struggling for years to re-enter the workforce is a data point on how senior talent is getting filtered out as companies chase "AI-native" profiles. If you’re building in security or infra, this is an arbitrage opportunity — pair underutilized veteran operators with younger AI-fluent staff and you get resilience plus speed.