Darrell Silver

THE FREEDOM TO TAKE ON RISK. When Darrell Silver left the finance world in 2008, right before the financial crisis, he wanted to do something entrepreneurial and tech-related. The day-to-day risks of entrepreneurship called to him as he craved something challenging that would demand more of him. “I like getting thrown into the deep end,” Darrell says. He was 25 years old and had a huge appetite for risk. But he acknowledges his advantage: he had been working since high school and had skills to leverage if he ran into financial trouble. “Most people don’t have that door open to them,” Darrell admits.

Darrell founded Perpetually, a web archiving company, which was eventually acquired by Smarsh, another web archiving company, which was in turn acquired by Dell. It wasn’t enough for Darrell to just work on web archiving for Smarsh, so he left to start Thinkful, an online adult education school.

“Starting companies was a way for me to build products that millions can benefit from,” Darrell says. It is hard to see the impact of simply making money in finance or making money for others, he says. “I know the world is not equitable and there is a lot we have to do to fix it, so what better thing to work on?”

Darrell saw that higher education was broken. “Education is one of the most expensive things to purchase, yet its consumers are the least qualified to make that purchase,” he says. Students have no way to evaluate whether their education will actually better their life and job prospects. The focus of Thinkful would be to provide students that return on their investment. “The goal of the curriculum is that at a minimum, you’ll get a better job,” he says.

That gambit worked. Thinkful started with just six students and was sold to education technology company Chegg in 2019 for $100m. They shared the same belief that higher education and skills-based education prices are too high, and sought to find ways to lower prices to make education accessible.“My risk appetite would have been a lot lower had I graduated with student debt. That’s fixable,” Darrell says.

WHEN IN DOUBT, SEEK OUT NETWORKS. Participating in networks is in part what drove Darrell into starting a business in the first place. “I had run into people who were new to New York who were freelancers or starting their own initiatives,” he recalls.

The gay tech community in particular has proved a strong connection. “There’s value in being out, and the community is thriving,” Darrell says. “I think we’re really building something that’s not just for ourselves, but will inspire future generations.” With fewer people needing to hide their sexuality, living one’s identity can forge a path to success, he says.

But while those networks and paths exist, an entrepreneur still has to make the effort to connect with them. “Entrepreneurship is about going through painful experiences over and over again,” he says. It’s about learning how to find people exploring new solutions when you’re stumped, and to empathize with them when they come to you, he notes. “When you open yourself up to a shared identity, your journey is not just a single process along a line; it’s a whole network moving together.”