NEW CANAAN — When he was just 25-years-old, Rich Riley, then a Wall Street investment bank analyst, sold his startup company to Jerry Yang of Yahoo for several million dollars. It was the unexpected start of a massively successful career as an internet executive for the native Texan who, for the past four years, has called New Canaan home.

“I was never super-techy. And I still am not a software developer. But I think I’ve always liked it and liked being around it,” said Riley, CEO of music identification mobile app Shazam, on Friday, Dec. 9.

His app would become the Yahoo toolbar and would lead him away from his career on Wall Street, where 70 to 80-hour work weeks were customary, and into the business side of tech, a career for which he had been preparing since his adolescence.

“Starting around 12-years-old I mowed everybody’s lawn in my whole neighborhood. I took care of over 30 yards. I had graphs of the revenue and I actually have my first financial statement from that time, with stocks I owned and how much cash I had. I was definitely sort of financially motivated and entrepreneurial as well,” Riley said of his childhood in Austin.

He went on to the Wharton School of Business at the University of Pennsylvania, where he played football and studied entrepreneurial management and finance around the time the modern internet was beginning to coalesce, before landing his job out of college on Wall Street.

“I always wanted to go to Wall Street so for me it was like mission accomplished. It was the kind of role where you worked in this amazing office on Park Avenue and got paid an amazing amount of money for your first year out of college. But if you weren’t there by 10 a.m. on a Saturday, somebody was calling you like, ‘Dude, where are you?’ It was hardcore. But I kind of like that. I worked around the clock, traveled a lot, saw a lot. I met really interesting people, met brilliant people and I met obnoxious people,” Riley said.

But it wasn’t long before he collaborated with a friend and began Log-Me-On.com, moved to San Francisco and began his career in tech.

“Yahoo was one of the first companies where the offices were open and there was crazy stuff on the walls, and people are riding scooters, and in shorts and drinking beer,” Riley remembered. “It was a lot of fun because it was the early days of the internet. This was when people were really starting to use the internet and we were just thinking, ‘What are we going to create next?’”

Over the next 13 years, Riley lived for stints in London and Switzerland before being transferred back to Manhattan and settling in New Canaan roughly four years ago, around which time he began his career at Shazam.

According to Riley, Shazam already had a good business model and a large user base. But in less than five years Riley has helped the company to move away from their former model in which selling MP3s downloads was their largest business, toward a business model that is advertisement based, and has found an increasingly larger user base.

“One of the things we’ve done pretty intelligently is we have really been the Switzerland of music. We partner with Spotify, we partner with Google, and Apple, and Napster. So however you want to consume music, we’re like, ‘great.’ We connect with all of them,” Riley said.

In addition, Riley is trying to build closer relationships with artists through the app in a way they can connect directly with fans and share songs they’ve discovered themselves.

“There are over a million apps on the App Store. Most people use less than 20 apps per month. So, it is really, really hard to break through. And even if you do, in most cases the person won’t really adopt it, they’ll delete it a few days later. So you have to really earn a spot. Fortunately for us, on hundreds of millions of phones we’ve earned that spot. But every day we have to re-earn it,” Riley said. It’s an everyday effort to make the app faster, easier to use and more essential to the user.

The job comes with no small amount of pressure, but it’s not without its rewards. According to Riley, Shazam is filled with staffers passionate about music, many of whom are handy with an instrument, though Riley admits he’s a fledgling guitarist.

“All Shazam meetings start with a musical performance. What’s lucky for me is the company is full of really talented musicians. So I can sit there doing my very basic guitar playing and they totally carry me,” Riley said.

A beginner though he is, Riley recently found a signed electric guitar and amp from country music star Keith Urban instructing him to “keep picking.”

Increasingly, Riley is rubbing shoulders with musicians, who are frequently in the office, which has helped him points with his family. On his daughter’s 13th birthday, he was able to introduce her to Taylor Swift. He’s also used his recent focus on music to start his four children - a daughter, now 14, and three sons, aged 12, 10 and 7 - playing instruments.

“I’m trying to get my kids into music so we can have a family band,” Riley joked.

Away from his world as an internet executive, Riley regularly donates to the New Canaan and Darien land trusts, the New Canaan Historical Society and the New Canaan Beautification League. His home sits on the New Canaan/Darien border, on the old Mather Farm, where he and his children bring their metal detector to search for treasures like old horse stirrups.

“If we can preserve some of our open areas and preserve some of our history, I think that’s great for the community,” Riley said.

But even on the old Mather Farm, his mind is never far from work.

“My two oldest have phones and Shazam. And I make all their friends have Shazam,” Riley said. “I do random phone checks, so you can’t come to my house unless you have Shazam. It’s kind of fun.”

justin.papp@scni.com; @justinjpapp1