John Berkowitz, co-founder of Yodle and OJO Labs.

In 2005, John Berkowitz was getting ready to graduate from George Washington Unviersity and was exploring what to do with his life.

His childhood friends, Ben Rubenstein and Nathaniel Stevens, convinced him to join them in building Yodle, a provider of online advertising and marketing services to small businesses.

Eventually, they grew Yodle into a company with more than 1,500 employees and $200 million in revenue and in 2016, bought Yodle for $342 million.

At Yodle, Berkowitz served many roles including launching and managing its $50 million enterprise division and most recently managing all strategic relationships for Yodle as vice president of business development.

Today, Berkowitz is CEO and Co-Founder of OJO Labs, based at WeWork on Congress.

Berkowitz recently discussed his entrepreneurial endeavors on the Ideas to Invoices podcast.

In 2005, moving small businesses from print media to the online world was fairly novel, he said. With Yodle, they were in the right place, at the right time with the right idea and they had the background to understand the problem they were trying to solve.

Berkowitz is the son of a CEO and founder of a small construction company in New Haven, Connecticut. Rubenstein is the son of a lawyer and Stevens is the son of a car dealer.

“So we deeply understood the pains of small business owners,” Berkowitz said. “The idea resonated. We did some research and found there was a large market of these small businesses that had huge needs. Jumped off the cliff and started building the company.”

They walked right in through the front doors of small businesses to pitch their idea.

“People were spending so much money in a place that people were going to less and less,” Berkowitz said. “The idea of I’m going to move you from the print Yellow Pages to Google was novel enough that we got their attention.”

They faced a lot of challenges in the early days. In 2005, there was a lot less documentation and best practices for starting companies like how to incorporate, Berkowitz said.

“Frankly I think It was as hard then as it is now to figure out the right business model, get the right people and get the resources,” Berkowitz said.

They tried different go to market strategies like knocking on doors, dialing for dollars and going to trade shows.

It was pretty early on when they realized that they had an immediate product and market fit.

“We knew we had a problem that needed to be solved and that customers readily identified with that problem,” Berkowitz said.

Next, they had to figure out how to effectively scale the business before other competitors. Some huge Yellow Pages companies and large publicly traded companies were entering the market.

“It was very much a David vs. Goliath kind of market grab scenario that we had to adjust to,” Berkowitz said.

They raised a $3.5 million Series A round of venture capital after a year in business from Bessemer Ventures to scale Yodle.

The company faced a lot of rejection from venture capitalists, customers, and others in building the business. Berkowitz still doesn’t like rejection but he learned to accept it and draw strength from it.

In 2011, New York-based Yodle entered the Austin market with its acquisition of Profit Fuel, a company that specialized in search engine optimization for small businesses founded by David Rubin, who is Berkowitz’s co-founder at OJO Labs today.

“They fit perfectly with Yodle’s culture,” Berkowitz said.

Austin became Yodle’s biggest office, growing from 200 employees in 2011 to more than 900 employees.

Berkowitz came to Austin in 2011 for six months but he fell in love with a woman, who became his wife. And he fell in love with Austin. He decided to launch his next venture here because Austin is a great place to launch a startup with lots of talented and experienced executives.

OJO Labs builds an AI technology that automates conversations and creates data driven personalized experiences to help consumers make better decisions and can be used by companies to create deeper engagement with consumers and provide more value to them. It is focused on the real estate market right now. Its personal assistant is based on true artificial intelligence.

Real estate agents and consumers are using its product in a limited way today. They plan to scale nationwide in the fall.

OJO Labs raised a $5.8 million Series A round led by two Austin venture capital funds: LiveOak Venture Partners and Silverton Partners. The company also made the Austin Chamber of Commerce’s A-List of the Hottest Startups in 2016.

Berkowitz said OJO is the biggest opportunity he has seen in his career.

“The incredible team working on OJO has built a truly revolutionary product,” he said.

For more on Berkowitz’s interview, listen to the full Ideas to Invoices Podcast.

Editor’s note: Ideas to Invoices would like to thank WeWork on Congress for hosting us this week.