How Serial Entrepreneurs Neil and Rachel Blumenthal Keep Their Edge

One of Neil Blumenthal’s first memories of his wife, Rachel, takes place more than twenty years ago, on the quad between Ballou Hall and Goddard Chapel.

“I remember she and some folks were painting the cannon, this must’ve been during the winter,” he said. “And she had a pom-pom wool hat on.”

Rachel groaned.

“I will never live down that wool hat that I think I wore once,” she said, laughing. “That is the only thing he ever remembers.”

But if the sparks didn’t fly when Rachel (née Bravman) and Neil, both A02, met as teenagers at Tufts, it was a different story after graduation, when the pair reconnected in New York City. By the time they married in 2008, Rachel had launched her popular namesake jewelry brand, Rachel Leigh, and Neil was starting his MBA at Wharton, where he and three classmates would form the billion-dollar eyewear brand Warby Parker. Today, he’s co-CEO of the company, while she’s leading her third venture, Rockets of Awesome, a subscription service that mails curated children’s clothing to parents once a season. Rachel and Neil are also parents themselves, to eight-year-old Griffin and four-year-old Gemma.

In the dark blue living room of their spacious eighth-floor apartment in Manhattan’s Greenwich Village, the shelves are piled high with brightly colored children’s books and toys, ranging from GoldieBlox and the Spinning Machine to Star Wars Legos. Copies of Vogue and Eloise in Paris grace the gleaming white countertops in the kitchen. Near the table hangs a large painting of a panda and cub in the shape of a heart—a Rob Pruitt piece the couple acquired at a fundraiser auction for RxArt, the nonprofit that commissions and installs vibrant, playful art in children’s hospitals. Jeff Koons designed a CT scanner for the group in 2010. Neil sits on the board.
 

Neil and Rachel Blumenthal. Photo: Beth Perkins

Comfortable and stylish as it is, however, the home is a work in progress. Stray bits of painter’s tape are stuck on the walls and plastic covers sections of the floor, remnants of a year-long renovation that is finally coming to an end. Until recently, the entire family was staying at a hotel while the apartment was gutted, not that the kids seemed to mind. “Gemma sort of lived her best Eloise life,” Rachel joked. “But I think kids are just so flexible and much less shaken by change than probably adults are. And so, you know, I think it was a fun adventure and we were all ready for it to be over when it was over.”

Neil and Rachel have never been intimidated by a little chaos. After all, they’ve been building brands on the fly since the beginning. With each other’s help, they’ve managed to raise an impressive business portfolio, and in some ways, the inevitable extra demands and disruptions of raising a family at the same time have actually caused them to up their game.

***

Neil and Rachel had been in New York for about a year when a chance encounter at a party brought them back together. At the time, Neil was working as the director of VisionSpring, a nonprofit that teaches women in impoverished communities how to provide eye exams and sell affordable glasses so they can build their own businesses. The job required a lot of travel, particularly to El Salvador, India, and Bangladesh, and before he left on one of his trips, he threw himself a going-away party. It was such a success that he threw another, and another, until it became a habit.

“Neil used to throw himself a going-away party probably every three months, every time he went somewhere,” Rachel said. “And so it was like the tenth going-away party and I happened to be there. We were just chatting and were like, ‘We should hang out.’ So we started hanging out, sort of in groups of friends, and then eventually we were like, ‘Oh, maybe we like each other.’ We had dated each other’s friends all through college, so we had never really thought of each other that way.”

Their reunion happened right as Rachel was in the midst of a dramatic and, by her own account, somewhat accidental career change. She had been doing public relations and celebrity dressing for Yves Saint Laurent and designing her own accessories on the side. But when a ring she created caught the attention of the editors at Lucky, they decided to feature her as a jewelry designer. Soon the trendsetting website Daily Candy came calling.

“They said, ‘We want to feature your website. What’s the domain?’” Rachel remembered. “And I was like, ‘Uh, I’m in a meeting, I have to call you back.’ Because I didn’t have a website. I barely even knew what that was. I had no business other than making some jewelry on my coffee table. So I called a guy that I hadn’t seen since I was thirteen, who I heard did websites, and he threw together a landing page with a photo and an email address, and that was my website. Then after the Daily Candy post about my pieces hit, there was this onslaught of buyers and editors and customers that wanted this brand that really didn’t exist.”

That was Rachel at twenty-three—quick-thinking, adaptable, and already fundamentally capable. And it was not long before she got the push she needed to become a business leader. It came from Neil. “I just remember this really pivotal moment where Neil and I were early into dating and he came over to my apartment and we were having this conversation,” she said. “He was like, ‘You’ve got to do this. You’ve got to build this business. This could be something really big.’ And you know, I thought he was crazy. But he really encouraged me to jump off the grid and take the risk. So I ended up leaving my job and setting up shop in my living room. I figured I’d go back in six months.”

Instead, Rachel Leigh exploded into a brand available from five hundred retailers worldwide. The vintage-inspired pieces became a fixture in fashion magazines, eventually landing on Oprah’s coveted O List. Meanwhile, Neil went on working at VisionSpring, and eventually, after he’d been there for five years, he was ready for a change himself. Hoping to parlay his nonprofit background into new opportunities, he enrolled in the MBA program at the University of Pennsylvania’s Wharton School in the fall of 2008. He and Rachel had just got married on the beach on Cape Cod that summer.

At Wharton, Neil befriended three fellow MBA candidates: Dave Gilboa, Andrew Hunt, and Jeff Raider. The four men had bounced around different industries, so they each had a unique perspective on the startup world. But they all wore glasses, which meant they agreed on one thing: eyewear was way too expensive. Wouldn’t it be cheaper, and easier, if you could just buy it online?

As they developed their eyewear ecommerce concept in their Philadelphia apartments, Neil and his cofounders leaned on their individual strengths. One of Neil’s was his half decade at VisionSpring, which had taught him how glasses get made. But he had another key strength as well, in Rachel.

“I was coming from the nonprofit social enterprise world, and my three cofounders had worked in management, consulting, and finance,” he said. “So Rachel was the one that had fashion industry experience. She was our go-to in terms of how to navigate the fashion world, because glasses, yes, they’re a health product, but they are also fashion accessories.”

Warby Parker launched in February 2010 to enviable early press, thanks in large part to Rachel’s PR advice. Vogue praised its “revolutionary price point,” while GQ called it “the Netflix of eyewear.” Readers took notice. Within three weeks, the company hit its first-year sales targets. Within four, it sold out of its top fifteen styles. Demand was so great that two days after the Warby Parker team started filling orders, they had so little product left that they had to temporarily suspend their home try-on program, which allows customers to choose five pairs of glasses to test out at home for free.

And as Neil and his cofounders scrambled to restock their inventory, they were also trying to satisfy consumers who were clamoring to see the product right away, without having to wait for glasses to come in the mail. “People started calling up saying, ‘Hey, we hear you’re in Philadelphia. Can we come into your office to try on some glasses?’” Neil recalled. “And we said, ‘Yeah, we’re not working out of an office, but you can come to our apartment.’ So we literally, using the furniture that Rachel had purchased, set up a table, put the glasses on there, moved this vintage mirror that we had, and set up a small sort of store in our quote ‘office,’ which was our apartment.”

The four cofounders continued to make do with improvised office space after they graduated from Wharton and moved back to New York City. “While we were searching for a proper office of our own, we were working at Rachel’s,” Neil said. “We would invite customers to come in and they would get really confused because here they were walking into a jewelry company looking for glasses.”

But Warby Parker wouldn’t stay in that office for long, and neither would Rachel. In 2011, she licensed Rachel Leigh to GlamHouse, closing the book on her first entrepreneurial effort. That same year, she gave birth to Griffin, who had helped inspire her next venture while still in the womb.

***

The lightbulb appeared over Rachel’s head as she struggled to figure out what to buy for her first baby’s arrival: she would create one-stop online shopping for overwhelmed parents. A new website would provide curated picks from a trusted community of parents who had tried every stroller and diaper imaginable. There would also be an ecommerce platform for purchasing the recommended products. This concept became Cricket’s Circle, which got up and running in 2014.

In 2016, Rachel built on her experience with Cricket’s Circle to establish her current company, Rockets of Awesome. Promising “clothes your kids will actually wear,” it mails a personalized box of clothing and accessories to subscribers every three months. When parents sign up, they take a personality quiz that helps determine whether their kid might prefer, for instance, a striped hoodie or a star-spangled skirt. Based on their answers, the company sends them their first box of duds. They keep what they like and return the rest, and the Rockets of Awesome algorithm takes those choices into account when it comes time to send the next box. The process repeats itself continually, allowing the algorithm to make smarter and more sophisticated recommendations.

The earliest Rockets adopters were naturally Griffin and Gemma. Both can be seen modeling the merchandise on the company website. “I think it’s fun for them,” Rachel said. “As much as we can, we try to involve them. They’ve been fairly connected to what we’re doing, and we always want to make it really relatable for them.”

They may be making it too relatable. Neil and Rachel were both flabbergasted when Griffin offered his unprompted explanation of their supply chains, a topic they’ve never exactly discussed around the dinner table. The budding business leader has also started 3D printing his own iPhone cases, and doing market research on the competition.

“He asked us, ‘How much does your iPhone case cost?’” Neil recalled. “And we said, ‘Uh, like forty dollars.’ He was blown away, rightfully so, that an iPhone case is that expensive. So he said, ‘Okay, well, I’m gonna 3D print iPhone cases and sell them for ten dollars, and I’ll be the Warby Parker of iPhone cases.’ We thought that was pretty funny.”

Griffin is probably still a few years away from disrupting the iPhone case market, but clearly, the Blumenthals’ entrepreneurial spirit is contagious. It shows no sign of drying up, either: Rachel and Neil, drawing strength from the mutual support that has always marked their relationship, continue to generate great business ideas and pursue them zealously. Rachel has been testing out brick-and-mortar locations for Rockets of Awesome and finding ways to make them attractive to kids—the recent pop-up in Manhattan included a ball pit and a rainbow swing. At Warby Parker, Neil is experimenting with applications in telemedicine, such as the prescription-check app, which lets customers conduct a vision test at home and transmit the results to a local ophthalmologist. And his commitment to social entrepreneurship is unflagging; the company has provided more than five million pairs of glasses to those in need across fifty countries, an achievement for which Tufts’ Jonathan M. Tisch College of Civic Life named him its 2019 Corporate Citizen Fellow.

For Neil and Rachel, the demands that come with two companies and two kids actually work to their advantage. The chaos forces them to adapt in the moment, compromising and solving problems creatively in real time. While their entrepreneurial careers allow for some flexibility, they also disrupt routines. “Sometimes set schedules don’t work as effectively for us in terms of ‘hey, on X, Y, and Z date, you take Griffin and Gemma to school,’” Neil said. “So we’re constantly juggling.”

But it’s not all juggling. Gemma and Griffin also encourage their busy parents to recharge. Some of their preferred activities include skiing—usually at Mount Snow in Vermont with Neil’s parents—and skating. Rachel, who figure skated competitively as a teen, has passed that love down to Gemma, who’s started lessons of her own.

Interestingly, parenthood has not only opened Rachel’s eyes to whole new markets but also sharpened the focus of both Blumenthals. “Parents tend to be the most efficient and effective employees and leaders because you have to make sure that every single minute that you’re at work is going toward the most critical drivers of the business,” she said. “Because you don’t have the time to be there all night. If you’re going to leave your kids, you want to be doing something that you’re incredibly passionate about. And for us, that passion has certainly come through at home. Our kids really understand what we’re doing and why we’re doing it.”