ECONOMY & WORK
MONEY 101
NEWS
PERSONAL FINANCE
NET WORTH
About Us Contact Us Privacy Policy Terms of Use DMCA Opt-out of personalized ads
© Copyright 2023 Market Realist. Market Realist is a registered trademark. All Rights Reserved. People may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.
MARKETREALIST.COM / NEWS

Founder of SparkNotes and OkCupid Shares Key Lessons From His Entrepreneurial Journey

After 25 years, Yagan, who is now a prosperous investor and entrepreneur, claims that his worst professional error was not buying SparkNotes back.
PUBLISHED MAR 7, 2024
Image Source: Sam Yagan (left) attends the 2013 Ninth Annual Time 100 Gala| Photo by Lars Niki/Corbis | Getty Images
Image Source: Sam Yagan (left) attends the 2013 Ninth Annual Time 100 Gala| Photo by Lars Niki/Corbis | Getty Images

Back in the 1990s, when the internet was just starting to become a big deal, a young entrepreneur named Sam Yagan and his buddies, Max Krohn, Chris Coyne, and Eli Bolotin, got together in their college dorm room to start their first company. As they studied arithmetic together, they questioned why there weren't any online study aids similar to Cliff Notes. Thus, they developed SparkNotes.

Image Source: Photo by Lars Niki/Corbis | Getty Images
Image Source: Photo by Lars Niki/Corbis | Getty Images

Remarkably, after just seven months, their small product began drawing interest from large corporations interested in purchasing it. Yagan saw an abrupt change of fortune when he sold his startup during the dot-com boom. Before that, he was a penniless college student earning $4,000 each semester. But after that, things quickly became worse.

After SparkNotes' purchase, the company's stock price dropped and SparkNotes was relisted for sale. It would have been easy for Yagan and his buddies to buy it back, but they chose not to. After 25 years, Yagan, who is now a prosperous investor and entrepreneur, claims that his worst professional error was not purchasing SparkNotes back. He now uses that experience as a teaching tool for the business owners he assists.

Yagan and his partners founded the business in March 1999 and sold it for $30 million, with half of the money paid upfront and the remaining amount paid over time, to iTurf, another online startup. Regretfully, this happened right before the February 2000 dot-com bubble burst. About a year later, iTurf was still in debt to Yagan and his team, having had financial difficulties. They consequently decided to sell SparkNotes to pay off their debts. Barnes & Noble had the chance to pay iTurf $1.75 million to recover full control when they made an offer of $3.5 million—a meager 5% of the true value. 

Hands holding US Dollar bills | Pexels | Photo by Karolina Grabowska
Hands holding US Dollar bills | Pexels | Photo by Karolina Grabowska

Sam Yagan, born in 1977 in Chicago, Illinois, is an American entrepreneur famous for co-founding tech start-ups, including OkCupid in 2003. Raised by Syrian immigrants in Chicago, Yagan graduated from the Illinois Mathematics and Science Academy before attending Harvard University, where he earned a B.A. in applied mathematics and economics in 1999. During his time at Harvard, he co-founded SparkNotes, later selling it to iTurf for $30 million in 2000.

After leaving Barnes & Noble in 2002, Yagan led the development of eDonkey, a peer-to-peer file-sharing network until legal issues arose in 2005. He then reunited with his SparkNotes partners to launch OkCupid, known for its innovative matchmaking approach. In 2011, OkCupid was sold to IAC/InterActiveCorp for an estimated $90 million. Yagan held various leadership positions within IAC, including CEO of Match, Inc., and later CEO of the Match Group, overseeing its successful IPO in 2015.

In 2014, Yagan co-founded Corazon Capital LLC, a venture capital firm focused on supporting local tech start-ups. One of its investments, Rocketmiles, was acquired by the Priceline Group for around $20 million in 2015.

Looking back, when Yagan reflects on that time, he realizes that he was so overwhelmed by the stock market crash that he couldn't fully grasp the internet's long-term importance. Despite the tough decisions they would have had to make, like letting people go, they could have persevered. Keeping hold of SparkNotes would have allowed them to introduce OkCupid to a wide audience. Just picture being able to announce the launch of a new dating service like OkCupid directly to SparkNotes users. They would have named it SparkMatch.

MORE ON MARKET REALIST
Once again, Ken Jennings proved that players can have a lot of fun on the serious game show.
19 hours ago
While Harvey was expecting to hear some funny responses, the ladies blew his mind with their powerful answers.
23 hours ago
The player, Clint Ingalls' disastrous choice of letters gave him no chance in the end.
1 day ago
The show's expert, Alan Fausel, was astonished by the fabulous Richard Cosway drawing.
1 day ago
The high school teacher could barely contain her excitement after cracking the Bonus Round puzzle.
1 day ago
The founders of Vade Nutrition couldn't the refuse the offer from Mark Cuban and Alex Rodriguez.
2 days ago
The creator claimed that the Costco avocado didn't feel or taste real, especially when compared to a ripe, organic one.
2 days ago
The player, Kenneth Blount-Hames, was stumped by a simple, everyday phrase in the final round.
2 days ago
The painting had been with the guest for 30 years, and she was curious about it.
3 days ago
It was hard for Harvey to digest what he was hearing from the senior players.
3 days ago
The best friends, Hanna Chung and Laura Tarpley, got tricked by just one word in the end.
4 days ago
The player, Shannon Hunt got the host excited before missing the puzzle by a few letters.
4 days ago
The founder of Hairfin managed to make it through the heckling to get a deal.
4 days ago
The player, Jeff Richardson put up a stunning performance to drive home a new car.
5 days ago
Since Kevin O'Leary made the offer just to mess with Corcoran, the deal hit the Shark where it hurts.
5 days ago
Harrison chose to pass on the most important item of the collection for a strange reason.
5 days ago
The contestant, Alexa Kalanz was doing well throughout the game despite a rough start.
5 days ago
Despite having just 25% ownership of her company, Meagan Bowman managed to bag a $400,000 deal.
6 days ago
In the end, Harrison felt like he hit the jackpot as he knew every collector would be after the item.
6 days ago
Former players and audience members shared how the show deals with controversial statements.
7 days ago