Student Loan Hero founder abandoned first startup idea, sold second

Student Loan Hero CEO Andy
Josuweit.
Courtesy of Andrew
Josuweit

• Student Loan Hero, a personal finance site, was
  acquired for $60 million this week.
• That milestone never would have happened if CEO Andy
  Josuweit stuck with his original idea for a company.
• Josuweit says learning from failure is key to finding
  success as an entrepreneur.

Part of being a successful entrepreneur is knowing when to give
up on a bad idea.

Andy Josuweit learned that on the fly when he founded Student Loan Hero, a personal
finance site dedicated to helping people manage their student
loan debt.

This week, Student Loan Hero was
acquired by LendingTree for $60 million. But that milestone
never would have taken place if Josuweit stuck to his original
idea for the company.

In 2012, Josuweit and his business partners won a $40,000 grant
from the incubator Startup Chile for their idea for a service
called Toolbox. As Josuweit told Business Insider, Toolbox was to
be an online space where professionals could build profiles
around the products and equipment they use for their jobs. Users
would be able to compare the products recommended by people they
follow, and they would earn commission from purchases made
through their profiles.

But Toolbox never came to fruition. A few weeks into the
incubator program, Josuweit realized he had an even better idea,
one that addressed an issue that hit close to home. 

“We were playing with that idea and we saw some fundamental
issues with it. We wrote down all our problems on a piece of
paper in a spreadsheet and talked to advisers,” Josuweit told
Business Insider.

“At that point, my student loans were growing from $74,000 to a
little over $100,000,” he said. “I thought, ‘Hey, this is my
cancer, I’m bleeding right now. I need to solve this problem. And
there are a lot of people like me out there.'”

Josuweit and his partners put Toolbox on hold and came up with an
idea that eventually would become Student Loan Hero. The service
provides financial comparison tools for student-loan holders and
gives users personalized advice on paying off their debt. 

Launching Student Loan Hero wasn’t quite so simple — it took a
week for Josuweit and his partners to convince their Startup
Chile advisers to allow him to go forward with the new idea, he
said.

But once it was approved, the new project quickly became personal
for Josuweit. He said that as his student loans mounted, he began
to feel pressure from his family to succeed. His parents had
cosigned on some of his loans, and his failure to pay off the
loans was starting to affect their credit.

“It created a lot of stress and pressure in my family,” he
told Business Insider. “There was almost a year where I didn’t
talk to my dad, and it was pretty traumatic.”

He continued: “That’s what created pressure, like, ‘Hey, we
have to make this work. We don’t have a choice.’ When you have a
gun to your head, your have to push and you have to
fight.”

LendingTree’s acquisition of Student Loan Hero not only validates
the early financial struggles for Josuweit, it reaffirms his
decision in 2012 to completely change courses after finding a new
idea.

“You’re going to fall on your face a few times, you’re
going to screw up and fail. You’re going to learn from the
failures. It takes time,” he said. “But if you are willing, have
the determination, have the grit, ultimately it’s inevitable you
will succeed.”