When Amy Errett decided to leave her job in venture capital to start Madison Reed, an online business selling hair-coloring kits for home use, a few of her colleagues were skeptical.
"They're like, 'Is this just another e-commerce thing in some crazy market that nobody cares about?'" Ms. Errett said.
Home hair color didn't sound sexy, and women's products tend to be a hard sell among the male-dominated venture capital ranks. Also, Ms. Errett was embarking upon a rarefied career path. It is not unusual for entrepreneurs to trade in the hustle and grind of the start-up world for the stability of venture capital jobs — but most don't do the reverse.
"Very, very few people go from being a V.C. back to being an entrepreneur," said Jeff Crowe, a managing partner of Norwest Venture Partners.
As a former entrepreneur, Ms. Errett knew what she was getting into. Earlier in her career, she had founded the online market research firm Spectrem Group, had run a $200 million business for E-Trade, and had served as chief executive of the lesbian-focused travel company Olivia.
"It wasn't like I had visions of, 'Oh, this is going to be magical because it's not hard,'" she said of her idea to start Madison Reed. "Running a company or starting a company, it's really hard."
Thoughts of a return to entrepreneurship began to percolate several years into Ms. Errett's tenure as a venture capitalist, so she began looking for business ideas. Around the same time, she grew concerned about the harsh hair-coloring chemicals her wife, Clare, was handling during twice-monthly touch-ups.
At dinner parties in their home, she began asking her guests the awkward question, "Hey, do you dye your hair?" And, "Do you know what's in your hair color?"
The answer to the second question was invariably no. And even though the emotional stakes can be high with hair-color expenditures — a botched dye job is more likely to provoke tears than, say, an unsightly pair of shoes — many of her respondents weren't quite sure what brand they were using.
"If you ask a woman what hair color she uses, she'll be like, 'I don't know, I go to my stylist,'" Ms. Errett said. "Or, if she buys it off the shelf, and you ask which box she buys, she's like: 'I'm not sure. I think it's L'Oréal, or maybe it's Clairol.'"