Ashley Quinto Powell once swore she’d never be her own boss again.

At 24, she’d started an online jewelry company, though online shopping hadn’t yet become popular and, as she puts it, she “knew nothing” about retail, tech or merchandising.

“I can’t even imagine the amount of hubris it takes to think, ‘Yes, I will absolutely be successful at this.’ Looking back it’s so ridiculous, but at the time, I was really hopeful,” Quinto Powell said. “I lost my shirt, so from that point, I said, ‘I’m never going to work for myself again.’”

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