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Deborah Benton was on the pre-IPO team at eToys, ran a $100 million P&L at Teleflora, was COO of ShoeDazzle and then president and COO of Nasty Gal. In 2020 she co-founded Willow Growth Partners with Amanda Schutzbank. Willow was the first investor in Coterie, which Mammoth Brands agreed to buy in October 2025. It also backed Goodles, which Barilla bought this year. She told me both deals returned the fund.

We talked about raising for the exit you can actually get. The Practical Edge is the margin she checks before anything else.

If you are a founder doing $1 million to $40 million in sales and thinking about raising, reach out to us at Cutting Horse. Whether you want an investor or just advice from people who have been in your seat, we are glad to talk.

Let's get into it.

Start From the Exit and Work Back

The Advantage · Mike Wystrach × Deborah Benton · 53 min

Deborah and I had never met before this conversation. We have a lot of the same background. We both ran consumer companies and then moved to the investing side, and she got there first.

At ShoeDazzle she raised from Lightspeed, Polaris and Andreessen. At Nasty Gal it was Index, at what she called "a ridiculous multiple of revenue." The investors priced both companies like tech because they sold online. Deborah sees online as a channel, and the economics of a shoe or a dress do not change because the order came through a website.

She told the Nasty Gal story straight. The company got an offer from a retailer at a price she thought was amazing. It was flat to what they had raised two years earlier. The investors who came in at the high number would have had to tell their own investors that the money sat flat for two years. Those funds, she said, are built to swing for the fences.

Her advice to her younger self is to look at how consumer brands actually exit and plan the raise backward from there. Past a billion, she said, "the air gets very thin." A $300 million acquisition is "beautiful if it's been capitalized correctly."

At Willow she walks founders through that plan before the check. Her rounds are usually $3 million to $5 million, into brands doing $2 million to $5 million over the trailing 12 months. She wants one more round after hers, somewhere between $8 million and $20 million, and then she wants every investor to do well at a $300 million sale. "It doesn't mean we have to exit, but it buys us optionality."

I learned this one with Petfolk. I was a second-time founder, and money came easier, so valuations came easier. Looking back, we could have raised about $20 million less and done fewer dumb things with it. I treat a raise as an obligation now. You do not walk out of a bank celebrating a loan, and a round works the same way.