Dreamers and Doers: Making It Big As An Outsider

What does it take to go from outsider to major player? In “Dreamers and Doers” FastCo. Works and Dark Horse Wine present stories of those successful entrepreneurs who have overcome seemingly impossible odds. Here, Ellevest’s Sallie Krawcheck and rewardStyle’s Amber Venz Box share how they built remarkable companies when everyone thought they didn’t have a shot.

Dreamers and Doers: Making It Big As An Outsider
Amber Venz Box, co-founder and president, rewardStyle and with Sallie Krawcheck, CEO & co-founder, Ellevest

Gather a group of industry leaders in fashion and finance, and it’s soon clear that Amber Venz Box and Sallie Krawcheck are the ultimate dark horses among industry luminaries. The two epitomized the term “outsiders” in hypercompetitive fields where industry contacts and proximity to major industry centers like New York City can make or break careers.


Dallas-based Box tapped a lifelong obsession with fashion and accessories to build rewardStyle, a novel ecommerce platform that enables bloggers and influencers the world over to monetize their fashion expertise. Her seven-year-old startup has tallied more than $2 billion since its inception in 2011. Krawcheck, a Charleston, South Carolina native and college journalism major, built a legendary 20-year Wall Street career. She rose from junior banker to arguably the highest-ranking woman on the Street before the 2016 launch of her popular personal finance and investment platform for women, Ellevest.

While the specifics of their career journeys, obstacles, and industries differ, Box and Krawcheck share a great deal: a similar sense of fearlessness, ingenuity, and gritty determination.

Fashioning an Unlikely Success Story

Growing up in Texas, Box was obsessed with fashion from a young age. As a fifth grader, she knitted and sold scarves to her classmates—she even got kicked out of math class once because her enterprising ways were deemed a distraction. “I was knitting in the back row,” she says. “I was holding the bag underneath the desk and then literally vending these scarves to people.”

In high school, Box turned to jewelry making, creating and selling knockoffs of luxury necklaces and earrings. Later, in college, she started her own fashion blog to highlight her work as a personal shopper. She garnered attention but was still frozen out by snooty fashion editors and retail buyers.

With the help of her now-husband, Baxter, she turned her site into a platform that allowed her to make a commission whenever people bought her recommendations. That led to the creation of rewardStyle, which she then offered to other bloggers to monetize their work.

One of the first indications that Box was onto something big came when she was 23. A representative from leading fashion merchant Shopbop contacted her about working together. She walked downstairs and told her father the news.


“I didn’t realize that I was completely broken out in hives, because I was so nervous. I had never negotiated with someone in my life, and here I was trying to convince these guys that they needed to work with our business, and negotiate a commission rate and all of these things.”

Related: More Dreamers and Doers: Damian Kulash and Alli Webb
Related: More Dreamers and Doers: Justin Woolverton and Devin Dawson

Over several years, and with little fanfare, she amassed a social media fashion empire—more than 25,000 influencers worldwide and 4,000 retailers on her platform—that was largely overlooked by fashion’s traditional tastemakers. “It’s a successful company, so there’s a level of respect from people across the industry,” Box says. “But I didn’t network it, I wasn’t born into it. The fashion industry did not want influencers to win, and they especially didn’t want to give a piece to me because I was a ringleader of all of it.”

Being the Bull

At the University of North Carolina at Chapel Hill, Krawcheck started out wanting to be a journalist, a field where her dogged determination would have a meaningful impact on the world. But the paltry economics of journalism were no match for finance. She moved to New York and found herself fighting for respect in the ranks of mostly male analysts at Smith Barney.

“I was two days into my job, and I was sitting at my desk and smelled cigar smoke. This big huge guy who seemed super old at the time—I think he was all of 33—comes up behind me and looks me up and down in a way that you would be arrested for today and goes, ‘What kind of effing discount maternity wear is that?'” she recalls.

It didn’t take her long to distinguish herself, though. Krawcheck’s first research report was on subprime lender American General, and it immediately raised the hackles of the entrenched investment world. “It was a negative piece titled Whoa Nelly,” she says. “They were trying to expand, but it became clear to me that this business was going downhill fast. And I published it, the company got mad at me, but dammit if in January their reported earnings were even worse than I expected.”


That report helped her become the number-one analyst in her first year on the job. It was an unprecedented achievement.

Krawcheck’s career was taking off, but she was haunted by “what if, what now” insecurities. The night the top ranking came out, she says, “My husband came by, and we were walking down Fifth Avenue, and he wanted to buy me a gift to celebrate. And I remember being on the verge of tears. I was having so much fun with the fight, and now that I’ve made it, what do I do now?” she recalls.

Again and again, she found her fight, often against the Wall Street status quo. At a who’s who of companies—Sanford C. Bernstein & Co., Smith Barney, Citigroup, Merrill Lynch, Bank of America—she found ways to have an impact as few women had. “One of the things I’ve figured out early on is I may not be smarter than everybody else, but I’m not dumber than everybody else,” Krawcheck says. “I’m not scared of risk. I’m not scared of failing. I’ve been fired twice on the front page of The Wall Street Journal. And I simply refuse to go away.”

Related Video: More with Sallie Krawcheck and Amber Venz Box

Overcoming the Obstacles

Both Box and Krawcheck routinely encountered roadblocks that could have derailed their ambitious goals. Even as rewardStyle was attracting a growing audience and top social media influencers, members of the notoriously exclusive fashion industry dismissed Box. And Krawcheck butted heads with dismissive male coworkers in finance before outperforming them, rocketing from being the top-ranked analyst to the executive ranks. Sometimes, the founders had to dig deep to come up with the fortitude to keep going and figure out the best ways to move toward their goals.

“There were days I would just get this pit in my stomach where I thought, This just isn’t gonna work. It’s too hard, it’s too—what we’re trying to do is too sophisticated. We’re too far out on the edge. It’s just not gonna work,” she says. “And I always stepped back, and thought to myself, I may not be smarter than anyone else, but I can outwork everybody else.”


Box was inspired after seeing an interview with a company founder who was dealing with a crop of copycats. “He was asked, ‘What do you think about this XYZ company that just popped up and says they do what you do?’ And this founder said, ‘They have no soul, so they will not win.’ And it’s true, as people see your success, they then want to jump into this industry, but they don’t get it. They don’t have what we have, the real-life experience of knowing what customers need,” she says. The combination of vision and work ethic helped each keep going, even when it was tough or when they had to find a new path to get to where they wanted to go.

“I think about all the times I tried to work in the industry and was declined. That would be the story. But we don’t need the industry’s permission anymore,” Box says.

“Society makes us think you have one path,” Krawcheck says. Having a drive to succeed means finding a way to make your vision work, one way or another.

Ultimately, that drive is perhaps what these entrepreneurs share the most. You can trace it between a dorm room in North Carolina and a teenager’s bedroom in Dallas. It can be found in a bold Wall Street report as well as an emerging fashion blog. And, now, it’s evident in both Ellevest and rewardStyle, two startups in different industries led by successful women. It’s the very drive that led these dark-horse founders to overcome new obstacles and seek out new opportunities—a drive that never stops.


This story was created for and commissioned by Dark Horse Wine.

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