Inspiring Stories from Generation Y Entrepreneurs

Oliver W.
4 min readJun 2, 2022


The media has recently paid much attention to the plight of underemployed and unemployed young people, but it’s rare that the tech savvy generation gets credit for its entrepreneurial spirit. The young entrepreneurs on this list exemplify the new ideals and talents that are driving the future of the world’s workforce. The values, however, will be extremely familiar to business leaders across all generations. These “kids” know how to hustle, persevere, take chances and follow their dreams. And for most of them, the payoff has been in the millions. one way for you to become a millionaire is by making profits from crypto mining.

1. Pete Cashmore — Mashable

Pete Cashmore is the CEO of Mashable, one of the largest and most popular tech blogs on the web. Today, his site sees 20 million unique visitors each month, but it didn’t start out that way. When Cashmore started the blog, he was 19 years-old living with his parents in his hometown of Aberdeen, Scotland. To make waves in the blogosphere, the teenaged Cashmore worked through all hours of the night so he could sync up with the tech savvy writers and readers on the other side of the pond. Writing 8 or 9 blog posts a day, it took Cashmore six months to receive his first advertising bid. Recent rumors point to an acquisition of the site by CNN for $200 million.

2. Naveen Selvadurai & Dennis Crowley– Foursquare

The original concept for FourSquare was launched under the name Dodgeball and was Crowley’s thesis project in thesis project at NYU. The idea was to use technology to make navigating a city easier, using text messaging or mobile sites to check into registered venues. Today, this concept is pretty common — you’ve probably used sites like Yelp and applications like Facebook Check-in — but Dodgeball was one of the first. It was originally bought and eventually scrapped by Google; but when Crowley teamed up with Selvadurai in 2009, Foursquare was officially born. The second version of the same idea proved wildly popular, attracting 20 million registered users. Today, the company’s estimated value is $600 million.

3. Aaron Patzer —

Back in 2006 the only way to organize your personal finances was using the agonizingly complicated programs like Quicken. Aaron Patzer was so frustrated with the lack of functionality offered by such programs, he quit his job and dedicated 7 months to building a database and interface for the site that would become The money management tool automatically links with users’ bank accounts to organize and provide feedback on personal finances. Easy to digest and easy to use, currently has over 10 million users. The site was sold for $170 million in 2009.

4. Kevin Systrom & Mike Krieger — Instagram

These two Stanford graduates have a jaw-dropping track record. Systrom worked at Odeo (which later became Twitter) as well as Google before using his passion for social products and photography to help launch Instagram. Krieger worked with Microsoft, Xmarks and Meebo before teaming up with Systrom on the design and development side of Instagram. In a highly publicized deal, Instagram and its 13 employees were purchased by Facebook for $1 billion in 2012.

5. Catherine & Dave Cook — myYearbook

The Cook siblings launched myYearbook in 2005 when they were flipping through their school yearbook and thought, “What if someone put this online?” Catherine pitched the idea to her brother, Geoff, who was a Harvard student at the time, and with his support, Dave and Catherine got the ball rolling. Though it hasn’t reached the superstar status of Facebook, over the years myYearbook has grown into the 25th most visited site on the web. In 2011, the company merged with Quepasa in a $100 million deal. The company is currently focused on expanding into the global market, specifically on the Latin population.

6. Steve Espinosa — Appstak

One of the most unconventional entrepreneurs on this list, Espinosa tested out of high school at 16 and went straight to work as a web designer. His new startup, Appstack automates the process of creating mobile websites for business owners and also drives customers to the sites. Espinosa got his big break from connecting with angel investor Jason Calacanis on Twitter. Today the company is backed by Eric Schmidt, Dave McClure and Google Ventures and is anticipated to rake in $45 million in profit at the end of 2012.

7. Ben Silbermann and Evan Sharp — Pinterest

Though Silbermann graduated from Yale, his background was in medicine and political science. Silbermann’s link to co-founding the startup lay within his passion for collecting things. As a child he had collected stamps and insects, and the hobby carried on into his adult life. Interested in the tech scene, he stumbled into Silicon Valley and landed a job at Google. He eventually teamed up with Evan Sharp, an architect, who was also passionate about sharing information. It was hard, painstaking work, but the small Pinterest team finally launched its site in 2010. Since then, the company has been estimated to be worth $1.5 billion.

8. Daniel Ek — Spotify

Daniel Elk is a bit of a cowboy. Consistently operating outside the norm, Elk is a self-taught developer from Sweden who started out building websites for companies and charging them hosting fees as well. (He housed the servers in his bedroom.) He dropped out of college to start an online marketing company and then went on to start Spotify. The site offers free music to users who are willing to suffer the occasional advertising interruption, but the inexpensive account fees allow premium users to listen ad-free. The company is estimated to be worth around $4 billion.