Sam Altman holding no shares in OpenAI is unprecedented for a CEO of his stature. This seemingly disadvantageous position paradoxically grants him more power by making him immune to accusations of purely financial motives, separating his leadership from personal capitalist gain.
A16z's strategy is likened to the Soviet Red Army: overwhelming the battlefield with sheer numbers. Their massive fund and broad platform create a "wall of news" and allow them to march capital forward relentlessly. This illustrates the venture capital maxim that "quantity has a quality all its own."
Despite public drama, OpenAI's restructuring settled based on each party's leverage. Microsoft got a 10x return, the foundation was massively capitalized, and employees gained liquidity. This pragmatic outcome, which clears the path for an IPO, proves that calculated deal-making ultimately prevails over controversy.
An analysis of 547 Series B deals reveals two-thirds return less than 2x. This data demonstrates that a "spray and pray" strategy fails at this stage. The cost of misses is too high, and being even slightly worse than average in your picks will result in a failed fund. Discipline and picking are paramount.
Merco's explosive growth and $10B valuation are less about its standalone business and more a direct proxy for the AI CapEx boom. With massive customer concentration among foundation models, its success is a high-leverage bet that AI giants will continue their massive spending on training for the next 3-5 years.
Mega-funds can justify paying "stupid prices" at the seed stage because they aren't underwriting a seed-stage return. Instead, they are buying an option on the next, much larger round where they'll deploy real capital. This allows them to outbid smaller funds who need to generate returns from the initial investment itself.
Ultra-late-stage companies like Ramp and Stripe represent a new category: "private as public." They could be public but choose not to be. Investors should expect returns similar to mid-cap public stocks (e.g., 30-40% YoY), not the 2-3x multiples of traditional venture rounds. The asset class is different, so the return profile must be too.
When a company like Synthesia gets a $3B offer, founder and VC incentives decouple. For a founder with 10% equity, the lifestyle difference between a $300M exit and a potential $1B future exit is minimal. For a VC, that same 3.3x growth can mean the difference between a decent and a great fund return, making them far more willing to gamble.
When a founder faces a major acquisition offer, the pivotal question isn't just about valuation, but temperament. A board member should ask, "Are you built to be a public company CEO?" The intense stress and public scrutiny aren't for everyone. Pushing a founder who isn't an "IPO guy" to reject an offer can be a disastrous long-term decision.