I recently turned 26, and, to celebrate, I took a weekend trip to Sequoia National Park with my mom. We both work a lot—she as a doctor in rural Vermont, and I as the CEO of a startup—so it’d been a few years since we’d spent any time together one-­on-­one, and we were looking forward to the trip. Plus, as she only half-joked, if she was visiting she could make sure I took the weekend off.

It was a five hour drive from San Francisco to the park, and we spent most of it talking about my company, Twice. Twice is a marketplace for upscale women’s fashion, and we’d raised our Series B from Andreessen Horowitz about six months before. Now, though, we were waist deep in all the usual—so I’m told—challenges that come with scaling your organization and customer base at breakneck pace. Still, as I talked through all the different projects we had underway, it started to sound like a lot, even to me.

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