Dreaming Bigger
Alumna and POPSUGAR founder Lisa Sugar pivots to funding—to power the future of commerce.
Story // By Caite Hamilton
There’s a paragraph in “Power Your Happy,” Lisa Sugar’s 2016 self-actualization book, where the author confesses, “I don’t believe in having a five-year plan.”
It seems a bit incredible, given that Sugar, B.A. ’98, is the founder of the mega-popular (as in, audience-of-100-million kind of popular) women’s pop culture, lifestyle and beauty website POPSUGAR. It’s difficult to achieve that level of success simply by following your whims—but that’s exactly what Sugar has done her whole career. In 2020, she followed a new one and launched VC firm Sugar Capital with her husband, Brian, and together, they’re taking the same energy that grew a happy little blog into a $300 million media empire and using it to reshape American commerce.
To hear her tell it, Lisa and Brian were just two kids who fell in love their first week at GW—she was drawn to his confidence, he admired her FIFA soccer chops on Sega Genesis—and have been finding new ways to achieve success (in whatever form that might take) ever since. They subscribe to a “just-do-it” philosophy. “We never hesitate to act on promising ideas or expand into new businesses we believe in,” she writes in the book. For his part, Brian left GW after his third year to establish an internet service provider, which led to e-commerce work with major brands like J. Crew, Kmart and Martha Stewart. Sugar’s path was slightly more serpentine, seizing any opportunity and landing in the advertising world early on—first in New York City with Young & Rubicam and eventually Showtime, and later in San Francisco, where the couple is still based, with Goodby Silverstein & Partners. But her heart was in entertainment, and, on the side, she’d write up recommendations and email them to friends to satisfy her creative itch.
She wanted to be writing. Sugar always felt the most academically capable in her English classes, and early encouragement from teachers in high school (where she turned in a paper with the title “I Don’t Know Yet!” handwritten at the top, an early sign of her informal, approachable style) and college (where she wrote a paper comparing an episode of “The Simpsons” to Goethe’s “Faust”) helped her turn the talent into a true passion. But her work at Goodby didn’t afford a lot of opportunity to use her gift, so in the fall of 2005, at the urging of Om Malik, a friend of the couple and an up-and-coming media titan himself, Sugar started writing a blog.
While these days it’s not unusual to open Instagram and see everyone from big-time influencers to your aunt Cathy hawking their favorite products, back in 2005, blogs like POPSUGAR—that is, friendly, first-person journal-type writing that provided recs on everything from what to watch to what to wear—were just starting to take off. Print media had yet to figure out online content integration, and sites like blog network Gawker and gossipy TMZ had taken over the web, giving rise to a certain brand of celeb-obsessed muckraker.
POPSUGAR had a different voice, one that approached the same kind of stories but from a place of curiosity rather than voyeurism, empathy rather than spite. Sugar’s job at the ad agency gave her access to early releases of magazines and TV shows, and her reviews and recommendations provided the basis for the website’s content for the next 18 years (and counting).
“I started practicing this daily exercise of writing, whether it was a fun article that I read or a show,” Sugar says. “I wasn’t even telling people about it because I felt like people didn't know what blogs were. They weren’t going to understand.”
Sugar’s tone resonated with the readers she did share the blog with, and eventually with bigwigs at movie studios and media companies. She took an almost compulsive approach to content creation, writing early in the morning, on workday breaks—even getting back in front of her laptop just days after the couple’s first daughter, Katie, was born. The hard work paid off: Within its first 11 months, POPSUGAR’s audience had grown to an unprecedented 1 million readers, necessitating a move to a bigger server and prompting Brian to join the company full time to help grow it into a full-fledged business. The rapid growth also drew the attention of venture capital firms like Sequoia Capital, which gave the company a $5 million investment that allowed them to hire more writers, take on bigger stories and expand their content.
“We envisioned reimagining the newsstand,” Sugar says. “Looking at health and wellness, looking at fashion and beauty, looking at parenting—all these categories of different magazines that you would go buy and just put it all in one place.”
From there, they acquired ShopStyle, an e-commerce site, and enabled readers to click and purchase the items POPSUGAR was recommending, directly from the site. They expanded to video, producing everything from live feeds of the Oscars red carpet to exercise content. The site launched a successful subscription box, licensed clothing lines and hosted a weekend-long festival with celebrity speakers, shopping booths and group workouts. By the time Sugar handed over the day-to-day duties at her eponymous media company (following its sale to media conglomerate Group Nine in 2019 and merger with Vox in 2022), the company had grown from a party of two to a staff of more than 500 employees across the globe—and it was time for Sugar’s next move.
“We love to power the brands and the tools and the technology—all the stuff on the backend that a lot of people don't see—to make brands grow and thrive and become successful.”
Lisa Sugar
Brian launched Sugar Capital in September 2020 with an initial fund of $16 million, which the company deployed to just over 30 founders. Sugar, who came on board after POPSUGAR landed at Vox, says they have a leg up over other investor competition because they can take what they’ve learned as founders themselves and apply the experience to up-and-comers in the consumer and commerce tech fields.
“I do think that the fact that we were founders of our own company—that we spent many years building in a variety of different ways—is something that appeals to a lot of founders when they talk to us,” Sugar says. “It’s definitely not a traditional VC trajectory for a lot of our founders. They’re meeting with VCs that have a lot of money and are great visionaries as well, but they don’t necessarily have that founder background and history.”
Sugar joined the firm for the sophomore fundraise, and together she, Brian and two other Sugar Capital founding partners—Will Hawthorne, a former executive director at JP Morgan, and Krista Moatz, a POPSUGAR co-founder—acquired $33 million, which, Sugar says, they’ll deploy into early-stage companies shaping the way we as consumers buy, sell and do business. (Sugar Capital also reserves about 20 percent of the budget for consumer brands.)
“We love to power the brands and the tools and the technology—all the stuff on the back end that a lot of people don’t see—to make brands grow and thrive and become successful,” Sugar says. In other words, they go after what’s called the “picks and shovels,” like Reflex, a staffing solution that allows associates to float between retail jobs where they’re needed, or Violet, a universal checkout system that enables users to buy products directly in any platform, from social media to text messages.
The Sugars have a knack for disrupting the industry. Remember, Sugar eschews the idea of a traditional five-year plan, so their success comes less from planning ahead than looking ahead. It’s a skill she and Brian honed while growing POPSUGAR—the site was at the forefront when it came to utilizing SEO data analysis, video content and e-commerce, among other things—and it’s that same innovation that powers the Sugars’ interest in emerging brands.
“Brian, one hundred percent, is fueled by what is next to be disrupted and how we can solve for that,” Sugar says. “I remember him telling my parents way back when we first met that no one’s going to have phones attached to walls anymore—everyone’s going to have one in their back pocket. He’s always had that vision toward what’s next.”
Unlike POPSUGAR, which emphasized spotting and responding to trends in real time, Sugar Capital allows Sugar to get in on the what’s next even earlier and invest in the emerging players that could change the game over the next three, five and 10 years.
One such company, Exponent Beauty, attracted the investors as a beauty industry disruptor. A line of skincare that protects anti-aging ingredients for peak clinical potency (“Today’s skincare contains active ingredients that degrade rapidly once exposed to air, light, water,” says the company’s founder, Liz Whitman), Exponent received pre-seed money from Sugar Capital in February 2020 that allowed the company to ready its line of products for manufacturing, as well as to launch the brand on exponentbeauty.com. Sugar Capital was there at each step.
“While I work with the whole team on various business decisions, I rely on Lisa, in particular, when it comes to product development, assortment strategy and retail targets,” says Whitman. “Lisa is certainly enthusiastic and supportive but, importantly, very thoughtful with a kind way of providing useful suggestions for improvements or new approaches, which I very much appreciate.” Whitman echoes what Sugar believes is the investors’ superpower: “Our founders appreciate that we can see where they’re coming from and relate on a much different level than just people with wallets.”
It’s not entirely altruistic—as business owners, the Sugars obviously focus on companies and brands they believe will be financially viable. But, from the beginning, Sugar has done things a little differently, with an approachable voice and a unique point of view. This still comes through, everywhere from emails—she often leaves punctuation off the ends of sentences and peppers in emoticons to communicate a friendlier tone—to the Sugar Capital branding, which boasts a logo reminiscent of pop art and subs in Memojis for headshots on the company bio page. It’s a more youthful modus operandi than some of their competitors, and signals that their eye is trained on the next generation—of commerce, of consumer needs, even of their own three daughters, who have grown up watching their parents build a business and, lately, fund others’ growing businesses, too.
“[Our daughters] are seeing that there are always new chapters and seeing us, as their parents, helping other people achieve dreams that we had when we created POPSUGAR,” Sugar says. “That’s something that’s pretty cool for them.” And it’s pretty cool for Sugar, too. With her trendspotting blogging days behind her, she’s open to the possibilities.
“In the VC space,” she says, “I’m seeing more of the future.”
Photos courtesy of Lisa Sugar