The Next Generation of Business Leaders on the Secrets Behind their Startup Success

As the digital economy has expanded, so too have opportunities for forward-thinking entrepreneurs to start and scale companies in record time. Technology has reduced the need for significant early-stage capital, and with it, the rigid human resource hierarchies and risk-averse strategies that were once the hallmarks of a successful business model. Now, a new generation of founders and CEOs are finding success by keeping their digitally-advanced startup companies adaptable, flexible, and inventive—and by encouraging their team members to work that way, too.

Here are four stories of business leaders who helm companies that are not only disrupting their industries, but also setting new standards for productive work cultures, engaged employees, and meaningful impact. We explore their journeys and relay the personal insights they’ve shared on what makes a good leader, great company, and cutting-edge success in the 21st century.

Adam Neumann, CEO and Co-founder, WeWork

Founded in 2010, WeWork is a global network of dynamically programmed, well-designed environments that give companies both large and small the opportunity have space, share services, collaborate with one another, and create communities. With an estimated worth of around $20 billion, it is considered among the most valuable startups in America. WeWork’s website states that they are “a movement toward humanizing work,” that reimagines the day-to-day employee experience as a more supportive and meaningful one by offering well-lit, beautifully curated spaces with benefits like yoga programs, art installations and on-hand refreshments for their 210,000 members and their own employee teams, too. They also build the digital underpinnings of their office environments, from the software that powers their keycards to guest registration technologies, to keep employee experiences streamlined and smooth.

CEO Adam Neumann is a 39-year-old serial entrepreneur who began a children’s clothing line and co-founded New York coworking space Green Desk with Miguel McKelvey before they worked together to launch WeWork. He attributes his company’s success to being mission-driven, globally-minded, and deeply committed to recruiting the right employees. In a 2015 interview with Inc.com, Neumann explained how he built his billion-dollar company, touching on his five previous startups, and relaying his belief that if professionals want to find success, they need to “be able to fail, learn why you failed, be better for it, and start again.”

His advice for would-be leaders? “Build something you love, build something with intention,” he says, “and the money will follow.”

Ben McKean, Founder and CEO, Hungryroot

Hungryroot is a subscription service that delivers vegan, gluten-free food directly to consumers’ doorsteps. Driven by a mission to “create healthy foods that people crave,” they provide customers with a customizable and highly convenient experience, allowing them to order dozens of offerings including “almond chickpea cookie dough” and “sweet potato mac’n cheese,” on an easy-to-navigate website. To date, Hungryroot has raised more than $35 million from investors, including $22 million from a Series B funding round that closed earlier this year.

But the road to success hasn’t been smooth for Hungryroot or its CEO. In a piece on Medium published in March 2018, McKean discusses celebrating early achievements, but quickly realizing that as the company began to scale, it would be severely limited by the operational complexity of producing and delivering a wide-range of high-quality food on massive scale. “By early 2017” he writes, “we had grown to a position where we could no longer take on new orders,” and McKean made the drastic decision to cease deliveries for six months in order to find a more sustainable solution. Pivoting was tough, he writes, but critical to the health of the company. “We came together as a team and embodied our company values of being positive, proactive and transparent,” ultimately finding supply chain and manufacturing solutions to rely on over the long-term. Hungryroot is now profitable - an important benchmark, he reports, and has grown 300% beyond the scope of its initial success.

His thoughts on making tough decisions?

Neil Blumenthal and David Gilboa, Co-Founders, Warby Parker

Neil Blumenthal and David Gilboa, along with co-founders Andrew Hunt and Jeffrey Raider, have taken eyewear e-commerce company Warby Parker from a five-person operation in Blumenthal’s Philadelphia apartment to the $1.75 billion-dollar company it is today. Begun eight years ago as an online retailer offering an affordable direct-to-consumer alternative to traditionally expensive eyewear, the company (that now, in addition to its web presence, boasts more than 70 traditional retail locations across the U.S.) sold its first million pairs of eyeglasses by 2014.

Over the years as Blumenthal and Gilboa have discussed Warby Parker’s meteoric rise, they often come back to the company’s clear core values, and how important it is to treat them like “strategic imperatives” that can be applied in concrete ways to encourage employee engagement and effectiveness. “It’s so important that you stay agile when it comes to creating an environment and culture that make people excited to come to work every day” Gilboa recently said in an interview with firstround.com. Gilboa and Blumenthal swear by their commitment to diversity in hiring, maintaining open communication channels, fostering positive onboarding experiences, making employee work feel meaningful, celebrating achievements, and creating a company environment where people can Learn, Grow, Repeat. “Smart people enjoy learning. Active brains thrive on stimulation. Creativity flows when curiosity is stoked” Blumenthal wrote in 2017, and that creativity leads to good things for their bottom line.

The takeaway?

“Investing in your team and keeping your employees thrilled to come to work is the best way to make remarkable results possible” Gilboa told firstround.com. “That’s not just the right thing to do — it’s also good business.”

Steph Korey, Co-founder and CEO, Away

Away is a modern travel brand designing thoughtful objects to make traveling more seamless. Since Away launched in 2016, the company has grown from a team of four to over 150, opened several retail locations, expanded internationally, been named one of "The Worlds Most Innovative Companies" by Fast Company in 2018, and sold more than 300,000 suitcases.

Away was founded by friends and former colleagues, Steph Korey and Jen Rubio. They started the company because they saw a huge gap in the luggage market (luggage was either cheap but poorly made, or it was more expensive than the trip you were planning to take it on) and an opportunity to tell a broader story about travel—one that got people excited about where you could go with your luggage and what you could do with it. Through Away’s direct-to-consumer model, they’re able to create top quality products at a fraction of the cost.

Away’s thoughtful, innovative business model and approach to reimagining the travel industry aren’t the only reasons Steph believes the company has seen the success it has, though. It’s the team at Away and what they’ve been able to accomplish, together, that has propelled Away from a startup to a global brand in just over two years. In her new class on Skillshare, Steph discusses how being a great leader is similar to being a good coach, and the management principles she’s implemented to lead the team at Away, creating a supportive company culture that makes the business more agile, responsive, and productive.

“We’ve worked to build a team of people with diverse background and perspectives, which allows everyone in the company to catch each other’s blind spots... and offer a fresh perspective on projects and obstacles,” Steph wrote in Time earlier this year. She credits the driving forces behind Away’s achievements to a thoughtful culture and work environment that: embraces collaboration and encourages lots of questions to gain shared context; shares consistent and helpful feedback in real-time; and leans into mistakes as a business advantage and an opportunity for the team to always learn and grow.


Want to hear more of Steph Korey’s secrets to success? Check out her new class, Leadership Today: 3 Principles to Steal from Coaches, now on Skillshare!