Meet The Yale Graduate Shaking Up Entrepreneurship With A Brand New Mobile App

Gary Stewart is a savvy innovator who has always been ahead of the curve.

His latest venture is an educational playground for ambitious entrepreneurs called The Nest. The mobile app, which is still in private beta provides snackable modules of entrepreneurial education, for founders, by founders that look like all of us.

Launched in December last year, The Nest has already raised more than $1 million in outside funding. Slated to officially go live in September, Stewart calls his startup a “Masterclass for founders” where users can learn the written and unwritten rules of entrepreneurship and actionable tips to replicate success.

“It’s not clear to me why accelerators and incubators use an offline model that’s not scalable and that’s exclusive when the whole point is to support technology,” says Stewart, CEO and co-founder of The Nest and former MD of Wayra UK, a tech accelerator. “By using technology we can say, anyone, anywhere with a phone should be able to access mentorship, capital, and the education and information they need. We can use technology to democratize access to capital and networks.”

Stewart’s road to success is not the most conventional, but neither is he. He was born in Jamaica, raised in the Bronx, and then spent 14 years in Spain before relocating to the UK. His cosmopolitan background taught him to aptly navigate social situations and land on his feet from a young age.

Graduating magnum cum laude from Yale University, he then went on to win a coveted spot at Yale Law School. After clerking for a few years in Washington DC, a desire to be one of those “people on the other side of the table who were having all the fun” pushed him to head over to Europe in search of something more fulfilling. In a self-proclaimed “quarter-life crisis” Stewart wanted to escape this homogenous, middle-class American lifestyle for something that would truly push him, tired of chasing a track that people told him was the correct one. These formative experiences have led Stewart to be “comfortable taking risks” necessary to pursue what “scares you but interests you.”

The Nest

The leap from New York to Barcelona and from corporate law to founder of online property directory Nuroa.com has imbued Stewart with a depth of insight into a broad cross-section of cultures and business environments. He thanks his ability to “start over and navigate a path” as well as the freedom it gave him to reinvent himself.

Being gay and black and an immigrant in America, Stewart “was always in the position to be defined, never to define [him]self.” Living in Spain, in particular, was a chance to reinvent, and gave Stewart a “different perspective, along with the ability to think more creatively and freely” as well as to see past the “taxonomies” that separate different business sectors. These skills have become vital in Stewart’s toolbox, teaching him “the rules of the game and how to leverage them to your benefit.” Any advice he’d pass on from these experiences? Stewart says: “figure out how the game is played, adapt to the game, make sure no one hates you too much and then try to win the game.”

“By using technology we can say, anyone, anywhere with a phone should be able to access mentorship, capital, and the education and information they need. We can use technology to democratize access to capital and networks.”

But not only has Stewart set out to win the game, but he’s also set out to change the game too. This energy has been fundamental throughout his career, a contagious, reassuringly confident, go-get-em’ energy that makes Stewart a change-maker. Talking about the process of disrupting the closed network that privileges white men in business, Stewart cites how crucial the digital world is in allowing us to democratize access to content. Disruption is the strategy du-jour as he rewrites the rules – “if you want to open up this system it needs to be done very differently”. To expand the Silicon Valley ecosystem of pattern recognition to include people that don’t look like your Mark Zuckerberg’s or your Jeff Bezos’ then it is “no longer about asking for permission.” “Technology gives us a way to disrupt this industry” and demand that all investors are governed by the same rules that apply to the start-ups they fund.

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Talking about how this process began for him, Stewart cites the Wayra study he conducted in 2014 (published by Forbes). By asking the questions that no one was asking about the London business ecosystem and discussing the diversity issue in UK businesses, Stewart was at the forefront of disrupting the homogeneity of this community. He describes how out of a moment of “personal curiosity” a growing network of in-bound attention from the likes of Jim McMahon, a London MP, and others who felt excluded in the UK drew traction to this movement. Stewart’s advice to directors is simple: “put your money where your mouth is”. He practices what he preaches, naturally, this ethos has carried over to The Nest and infused into “the DNA of the company.”

Indeed, Stewart’s impactful work is getting recognition. Last year he made it onto the Powerlist of the 100 most influential blacks in the UK alongside rapper Stormzy and Meghan Markle, among others.

“Over 15 years in entrepreneurship, I realized that there weren’t many people that looked like me being funded — or even considered — by VCs, angels, and accelerators. And the problem extends beyond race and sexual orientation to gender, socio-economic background, and geography.”

When we move to talk about The Nest, Stewart is all energy and drive. Perhaps unsurprisingly, the vision for The Nest is nothing short of “taking over the world!.” “If you want to be an entrepreneur, go big or go home.” According to Stewart, it all comes back to understanding the rules of the game to play successfully. Breaking down the specifics for me, Stewart explained that The Nest is going after the higher education market. With a net worth of $6.9 trillion, a minuscule 3.8% of which is online, the goal is to “rewrite the rules of education”. Starting in the UK and US simultaneously, you can expect to see The Nest in “Africa, the Middle East and parts of Asia within five years.” Stewart is creating a world in which “people don’t need accelerators or business-school when you can get a world-class education from the Nest,” and pay less for it.

“Over 15 years in entrepreneurship, I realized that there weren’t many people that looked like me being funded — or even considered — by VCs, angels, and accelerators,” said Stewart. “And the problem extends beyond race and sexual orientation to gender, socio-economic background, and geography. I realized that if you aren’t part of the solution, then you’re part of the problem. So when my co-founder, Rasha Khawaja said what problem should we be spending the next 5-10 years trying to fix together, the answer was obvious, and The Nest was born.”

Diverse founders and pioneers have already participated in educational videos on The Nest. That’s everyone from former gubernatorial candidate Stacey Abrams; Steve Blank, the “godfather of Silicon Valley;” Sander Daniel, co-founder of Thumbtack, which has raised $430 million with Sequoia as their lead investor; Hussein Kanji, co-founder of Hoxton Ventures, a venture capital fund that has 3 unicorns; and Natalie Campbell, CEO of Belu.

With an approach that combines inspiration from Masterclass, Howard Business School, and Spotify, The Nest is aiming “to be the world’s definitive library of entrepreneurial education”. Stewart tells us the app has set out to respond to the question of “How do we get people to learn and bring subjects together in a way that makes sense to learners?.” Following an entrepreneurial “life-cycle” of A-Z from creating an alpha to finding funding, through legal entity all the way to achieving product-market fit and acquiring institutional investment it’s an expansive how-to, mapped out into a curriculum that’s engaging, entertaining and academic whilst being “relevant to what normal people want.”

Coupled with his boldness and confidence are Stewart’s pragmatism and warmth. His own failures and setbacks (he wrote an article on this for Forbes entitled “How Europe Destroys Entrepreneurship”) have instilled him with simple but steadfast rules that he lives by, including retaining perspective and living life without bad karma. “As long as you’re not a dick to people when you have a low point, you will find people who will help you out.” Stewart is invested in the idea of “paying people forward:” helping others out of good-will in order to create a safety net of people mutually invested in each other’s success. He reassures us that “with age and time comes perspective.” Mantras that we can all live by.