I say this as someone who knows Marc. I’m not in his inner circle, but I got to know him years ago when I sold one of my companies to Salesforce. I knew him then as a shrewd, long-term thinker who understood how to weigh costs and benefits. Yes, Salesforce depends in part on federal contracts, and the Trump administration is known for rewarding loyalty and punishing dissent. From that angle, calling for federal involvement might look like pragmatic self-preservation — a CEO making nice with power to protect his shareholders.
But that narrow lens misses a much bigger picture. I learned a term from Goldman Sachs called “Lookback Risk” — the certainty that a decision that feels “necessary” in the moment will be repriced by history. A short-term hedge becomes a long-term liability once norms and memories reset.
That’s the risk Benioff is taking, along with Elon Musk, Marc Andreessen, and others who are wagering that this administration and its strong-man instincts will outlast the next three years. They’re measuring value in billions, and right now, appeasement feels like a safe way to protect that value.
It isn’t.
The instinct to hedge against uncertainty is a familiar one in business. But when leaders start hedging against democracy itself, they’re trading away the very asset that made their success possible. Markets may reward that in the short term; in the long term, they won’t — and history won’t, either.
Any student of American history knows that our politics have not historically been permanent; rather, they swing like a pendulum. Just look at how incumbent presidents — including President Trump — traditionally do in the midterms. What endures are the soil conditions — the freedoms and institutions that allow creativity and risk-taking to flourish. To his credit, Benioff spent years investing in that soil, giving millions to improve San Francisco’s civic health.
But calling for military deployment against your own city — a measure we expect from Beijing or Moscow, not Market Street — jeopardizes the very ground that built your company. There’s a reason we don’t see thriving entrepreneurship in countries defined by federal overreach: it chokes innovation at the root.
I’ve lived in the same San Francisco zip code for 28 years. I’ve seen dot-com booms and busts, fires and rebirths. Before my wife and I got married, I made one thing clear: the only way I’m leaving San Francisco is in a box.
What makes this place special isn’t its balance sheets — it’s its belief in openness, creativity, and civic care. Those are the qualities that built the modern tech economy, and they’ll be the ones that save it if our leaders have the courage to remember where their success really came from.
The real lookback risk isn’t crime stats or conference optics. It’s that a man who built a fortune on San Francisco’s openness might one day be remembered for betting against it.
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