DoorDash is America's fastest-growing brand, driven not by its expected young user base, but by senior citizens. This exposes a significant blind spot in the tech industry, which often overlooks the massive wealth and needs of the baby boomer demographic, representing a major untapped market opportunity.

The most lucrative exit for a startup is often not an IPO, but an M&A deal within an oligopolistic industry. When 3-4 major players exist, they can be forced into an irrational bidding war driven by the fear of a competitor acquiring the asset, leading to outcomes that are even better than going public.

The typical 'buy and hold forever' strategy is riskier than perceived because the median lifespan of a public company is just a decade. This high corporate mortality rate, driven by M&A and failure, underscores the need for investors to regularly reassess holdings rather than assume longevity.

Investors often invent compelling secular narratives—like a permanent housing shortage or "Zoomers don't drink"—to justify recent price movements. In reality, these stories are frequently post-hoc rationalizations for normal cyclical fluctuations. The narrative typically follows the price, not the other way around, leading to flawed trend extrapolation.

A major driver of today's housing scarcity is that homeowners, particularly Boomers, who refinanced into sub-3% mortgages have no financial incentive to ever sell. This seemingly positive economic condition has had the negative side effect of locking vast amounts of housing inventory in place, worsening the supply crisis.

The American housing market is increasingly inaccessible to younger generations. The median age of a homebuyer has hit a record high of 59, the same age one can access retirement funds. Even the median first-time buyer is now 40, indicating a systemic affordability crisis.

The career arcs of venture and buyout investors differ starkly. VCs rely on networks relevant to young founders, leading some to retire by 45 as connections become stale. In contrast, buyout investing is an apprenticeship business where age and experience are increasingly valued.

Banks started in the 80s and 90s are led by founders nearing retirement. With no new generation of talent eager to run small, three-branch banks, these institutions are increasingly looking for an exit. This succession problem is a primary driver of M&A activity in the sector.

Callaway is selling Topgolf for $1B after paying $2.5B four years ago. This loss highlights that businesses booming due to unique pandemic conditions may not sustain that growth, creating significant risk for acquirers who buy at the peak.