The Most Important Entrepreneurs of the Past Decade
Selecting the most significant entrepreneurs of the past decade is a bit like picking best-of-show at a dog competition. So many great choices, but decisions differ based on one’s preferences for workers or herders or hounds. Fame is a superficial metric that, too often this decade, has segued into infamy. Who wants to read an article celebrating Elizabeth Holmes, Harvey Weinstein, and Martin Shkreli? Fast growth, large scale, and financial success matter. But listing unicorn founders is a snore.
Instead, we considered traits like audacity, innovation, disruption, and social responsibility. We also called out several entrepreneurs whose work has influenced and supported other founders. This list–which is in no particular order–could have been 10 times as long and still left off many amazing people. 2020 marks a new decade. Let’s see who rises to the top.
In 2012, when SpaceX became the first private company to send a rocket to the International Space Station and Tesla finally delivered its heralded electric Model S sedan, Musk appeared to have supplanted Steve Jobs in his hold on the public’s imagination. Behold! This is what an entrepreneur looks like. The personification of audacity, Musk took big dreams and squared them. SpaceX wouldn’t just ferry people to Mars–he would use it to colonize the planet. He didn’t build simple factories, but rather behemoths of scale and sustainability dubbed “gigafactories.” (One going up in Sparks, Nevada, will be the largest building by footprint in the world.) Motivated by a wager, Musk developed the world’s biggest lithium ion battery to power South Australia’s energy grid–and he did it in 100 days. The Hyperloop–Musk’s plan to shoot passengers in capsules through low-pressure tubes traveling at airplane speed–is a vision for transportation worthy of our finest futurist writers, even if it does sound like Senator Ted Stevens’s infamous description of the internet.
Lately, missteps and erratic behavior have tarnished the entrepreneur’s previously Ayn Rand-worthy image. But if anyone doubts Musk’s stature in the zeitgeist, just consider that in 2015, The Simpsons devoted an entire episode to him. Jobs only ever merited a secondary plot line.
Emily Heyward, JB Osborne, and Simon Endres
Founders are good at explaining what their companies do, but not always what they are. That’s where Red Antler comes in. The agency is arguably the nation’s most sought-after and respected brand-builder, crafting clients’ identities virtually from scratch: logos, packaging, industrial design, advertising, digital experiences, and even naming. Venture capitalists point their portfolio companies in Red Antler’s direction; and many of the decade’s starriest direct-to-consumer brands were born in its Brooklyn offices. Heyward, Osborne, and Endres were behind Casper’s positioning as a lifestyle brand for the well-rested, which helped drive that startup’s early success. The team also gave Brandless its signature generics-reimagined labeling system. And Allbirds owes virtually its entire brand identity to Red Antler, including its name, its comfort-meets-curiosity messaging, and its now iconic shoebox-cum-mailer packages.
The founders, veterans of big advertising, launched the agency in 2007, excited by the idea of working with startups in utero–almost as members of their clients’ founding teams. That approach has helped reorder entrepreneurs’ priorities. First identify your brand. Then embody it.
It feels overly reductive, but Ulukaya is the face of a statistic: 51 percent of U.S. startups with revenues above $1 billion were founded by immigrants. Chobani, the Greek yogurt company Ulukaya launched in 2005, is no longer a startup. But its founder, who emigrated from Turkey in 1994, still feels like a startup guy with one of the all-time great origin and growth stories. Since 2014 he has also been spearheading an effort to hire and help refugees, and to convince other companies to do so. (Thirty percent of Chobani’s workforce are immigrants or refugees.)
So in a decade ending with a dangerous backlash against immigrants, it seems fit to spotlight this embodiment and champion of a demographic at once beleaguered and bursting with potential. (Yes, Musk is from South Africa. But immigration is not a soapbox issue for him.) Ulukaya represents other recent trends as well: the growing demand for healthy foods, the imperative to rebuild America’s manufacturing base, and the hankering for ethical leadership. His “anti-CEO playbook,” introduced this year in a TED Talk, calls for, among other things, gratitude toward employees and accountability to customers. Ulukaya preaches those things. Chobani practices them.
Jennifer Hyman and Jennifer Fleiss
For more than 20 years, the internet has changed how we buy. For the past decade, Hyman and Fleiss have influenced whether we buy at all. With fashion both fickle and expensive, Rent the Runway, now valued at $1 billion, lets its nine million subscribers rent not just big-night-out duds–its original model–but also normal, albeit super-nice, stuff you might wear to work. The business has motivated large retailers like Bloomingdale’s, Macy’s, Urban Outfitters, and Banana Republic to follow suit, and inspired other rental startups like Feather and Fernish (furniture) and Joymode (games, camping gear–anything that contributes to a fun experience).
Aspiring entrepreneurs should be encouraged that Hyman and Fleiss, who met at Harvard Business School, started the fashion technology company with no experience in either fashion or technology and managed to convince dubious designers and investors to take a flier on them. (Fleiss left the business in 2017 to work on Walmart’s digital concierge service.) Not surprisingly, the partners were inspired by last decade’s rental pioneer: Reed Hastings of Netflix, who more recently has spent his time reinventing how and what we watch on TV and in theaters.
We mean, of course, Barbara Corcoran, Mark Cuban, Lori Greiner, Robert Herjavec, Daymond John, and Kevin O’Leary. Shark Tank, which celebrated its 10th anniversary this year, transformed entrepreneurship into a spectator sport and educated millions of average viewers about concepts like liquidity, margins, and valuations. More usefully, the Sharks gave new and aspiring entrepreneurs actionable advice about pitching (know your numbers, tell a story, keep it short) and evaluating business models (think profitable, practical, proprietary). They also introduced America to compelling and ultimately fast-growth startups, including Bombas, Scrub Daddy, and Squatty Potty.
With personalities that range from sweet (Greiner) to sour (O’Leary), the individual Sharks put to rest stereotypes of entrepreneurs modeled on anomalies like Steve Jobs and Richard Branson. And because all are successful founders in their own right, they came to embody two things. First, the dream of entrepreneurship fulfilled. Second, the responsibility that comes with the achievement of that dream: to help aspiring founders coming up behind them.
Not many entrepreneurs come back from a quit-doing-that order by the federal government. But Wojcicki, the founder and CEO of 23andMe, knew that “that”–offering personal genetic testing–could arm consumers with information essential to protecting their health. So in 2013, when the FDA nixed her company’s health-risk reports, Wojcicki, a former health care investment analyst, didn’t just fall back on 23andMe’s less-contentious application of helping people understand their origins. Instead, she led her team through two years of exhaustive work, in consultation with regulators, and emerged with the first FDA-approved genetic-testing service for individuals in the U.S.
To date, the company is approved to report only on certain conditions, such as type 2 diabetes and celiac disease, but the number is growing. And 23andMe’s vast trove of genetic data–captured through spit samples sent in by more than 10 million customers–is being leveraged for drug discovery for diseases like Parkinson’s. In a controversial move, Wojcicki is partnering in that effort with GlaxoSmithKline, which last year invested $300 million in 23andMe. That relationship, and potentially others like it down the road, suggest 23andMe’s significance beyond the value it delivers consumers: as a case study of the tradeoffs among privacy, profits, and the public good.
Kevin Systrom and Mike Krieger
Aesthetic appeal. Positivity. Storytelling. Engagement. Fun. The creators of Instagram arguably were more in tune with the better angels of social media than predecessors like Facebook and Twitter, while resisting some of the industry’s demons. (Yes, Instagram can lower self-esteem and facilitates stalking and bullying. We’re talking relative harm here.)
Perhaps that’s why, emerging from a decade that began with a social media boom and is ending in a backlash, Instagram retains much of its popularity–including with the teens and young adults who are cooling on other platforms. A billion people use it every month; businesses are crazy for it; and armies of influencers owe Systrom and Krieger for their very-21st-century version of fame. (Kim Kardashian didn’t make our top 10 list. But this seems like the place for an honorable mention.)
Facebook owes it, too. The Social Network’s $1 billion acquisition of the then-13-employee social network induced vertigo among industry observers in 2012. But Systrom and Krieger–who came together while working on Instagram’s predecessor, a more feature-dense app called Burbn–generated buckets of money for Facebook while significantly boosting its mobile, visual, and narrative abilities. Last year Systrom and Krieger, frustrated by life under Zuck, sought the door. Their empire of self-expression remains.
No one this decade has influenced the blocking and tackling of startups as much as Ries, a serial entrepreneur and one-time venture adviser at Kleiner Perkins. His 2011 book, The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, laid out a customer-centric, experiment-heavy, waste-light approach to building businesses that provided a welcome alternative to the capital-guzzling practices of some venture-funded firms. Today, coffee shops and co-working spaces around the country thrum with a new vocabulary: “minimum viable product,” “A/B testing,” “product/market fit,” and–most powerful of all–“pivot.” (The lean startup builds on Steve Blank’s formula for customer development and Alexander Osterwalder’s popular business model canvas, which clarifies a startup’s elements and activities to improve decision-making. Hat tips to both.)
Now Ries is making his mark on exits as well as starts. The Long Term Stock Exchange–his attempt to reduce the kinds of quarterly number-driven behaviors that hurt many public companies–was approved by regulators in May. If the new exchange succeeds, it could be a boon for innovation, social responsibility, and founders who fear selling their souls.
Born in the years of recession, companies like Airbnb, Uber, and Thumbtack generated new income streams for the freshly un- or underemployed. The gig economy expanded along with the larger economy and is now, by some estimates, 60 million strong in the U.S. Some call it the future of work. While Brian Chesky of Airbnb and Travis Kalanick of Uber attract the lion’s share of credit/condemnation for this phenomenon, Busque was there first, if only by a matter of months. Her company, TaskRabbit, is an online marketplace for services like moving furniture, walking dogs, raking leaves, and picking up groceries–things, in Busque’s formulation, that neighbors do for neighbors.
Formerly a software engineer at IBM, Busque conceived of TaskRabbit before the crash and assumed the business (originally called RunMyErrand) would chiefly attract college students. Today, more than 140,000 people ranging from skilled labor to PhDs earn, on average, $35 an hour offering services on the site. (Ikea acquired the company in 2017, and Busque joined early-stage fund Fuel Capital.) And TaskRabbit’s human legacy may be more enduring than its larger peers. Landlords may subvert the intent of Airbnb and self-driving cars may someday make Uber and Lyft drivers obsolete. But it takes a human being to fix your toilet.
Blake Mycoskie, Scott Harrison, and Ben Rattray
If you want people to do the right thing, appeal to their ideals and their consciences, sure. But then you have to make it easy. That insight is inspiring entrepreneurs to devise frictionless approaches to philanthropy and activism: either incorporating them into the buying experience or just making participation so painless there’s no good reason not to. Mycoskie has given away close to 100 million pairs of shoes since founding Toms in 2006. His buy-one-donate-one model was adopted by companies like Warby Parker, and spawned dozens of socially conscious imitators, including Love Your Melon (beanies) and Figs (medical scrubs). Many of those have since adopted more sophisticated formulas for giving, but they are still simple and purchase-based.
Harrison, the founder of Charity: Water, popularized the neat idea of having people invite friends and family to make donations to the cause–providing potable water in developing nations–in honor of their birthdays. Facebook is one of several organizations now allowing users to create birthday pledges. Rattray’s Change.org, meanwhile, has become a more orderly megaphone than Twitter for amplifying both outrage and good intentions. Its online petitions have enabled more than 265 million people globally to make their voices heard on human rights, economic justice, and the environment. No screaming. Just signing.
Most entrepreneurs don’t become famous. They toil away in obscurity doing the important work of creating jobs and serving customers. Some also leverage creativity and scant resources to help their communities or industries in ways that rarely make headlines outside hometown papers. They, too, are among the decade’s most significant faces of entrepreneurship.
Here are just a few: Grace and Kevin Reynolds, founders of Handmaid Cleaning, in Walla Walla, Washington, preside over a Facebook community of more than 19,000 housecleaners–many of them financially struggling and disrespected–who support one another with advice and encouragement.
Frank Diaz, founder of Tin Hut BBQ, in Honolulu, hires (and sometimes houses) veterans with PTSD for his food-truck business and is developing a center to provide vocational training and other services to that troubled population.
Mark Tilsen and Karlene Hunter launched Native American Natural Foods to create jobs on the Pine Ridge Reservation in South Dakota and–with their Tanka Bars–a new market for embattled buffalo farmers.
Tony Vu is using his Asian-fusion restaurant MaMang as a springboard to mentor aspiring chefs in Flint, Michigan, and help them get started in pop-ups or food trucks.
And Eric Williams is the founder of the Silver Room, a jewelry, apparel, and home goods store in Chicago. Williams attracts tens of thousands of people and generates north of $1 million each year for local vendors with the block party he created to–among other things–spotlight more artists of color in community events. Hat tips to all.