Many founding teams pursue opportunities for clout and status first, problem/customer/opportunity second. What’s high status in tech is ephemeral. Problems and customers are not.

Ramp keeps finding itself in the right place at the right time because the company is built to be in the right place at the right time, executing against a mission that will never go out of style with a structure and team that allows it to take advantage of new ways to fulfill it.

The secret most don’t want to know about running a successful business … it’s mostly about accountability It’s not sexy It’s not packageable as an info product It’s not a quick fix It’s not automateable … but it’s the truth

We have machines now that we can basically talk to like humans. It’s a remarkable testament to the human capacity to adjust that this seems normal, that we’ve become inured to the pace of progress.

What I learned from reading “Situational Awareness” is that the next generation of privilege-blind Silicon Valley investors are even more out of touch than expected. It’s really sad and feels like a cosmic joke that the world’s most affluent class of people who legitimately have the resources to change the world for the better are living and thinki... See more

The Silicon Valley small business, the SV-SB, is a hybrid of sorts — it intertwines small business values and discipline with big tech know-how and ambition.

• Founding teams may look like that of a “traditional” Silicon Valley startup. They’re native to Silicon Valley ethos, skills, and playbooks. But , beneath the surface, they’re different. You m

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You want to build a competitive advantage that will endure over time. You don’t want to build a competitive advantage that is fleeting or that will get commoditized. Some awards, for example, may have been impressive early on, but as they have expanded significantly they’ve become more diluted and thus no longer as impressive. You want to have skil... See more

I’ve started to think about the idea of the trophy job — a job that people covet for its status more than its substance.