Online-content startup makes CEO switch

Veteran Chicago ad-buying executive Lisa Weinstein is stepping in as CEO of a digital-media startup.

Weinstein took over, a Chicago-based spinout from the Discovery Channel. The site focuses on stories that educate readers about a particular topic or person. Current selections include: “To maximize your focus and achieve your goals, try Warren Buffett’s 2-list strategy,” and “How do noise-canceling headphones actually work?”

The startup is backed by several Chicago venture capital firms, including Pritzker Group Venture Capital, Origin, Corazon Capital, Chicago Ventures and Hyde Park Angels. Founder Gabe Vehovsky, who recruited Weinstein as an adviser a couple of months ago, becomes an adviser to the company.

“Gabe did an amazing job building the team and the platform and audience,” says Sonia Nagar, a vice president at Pritzker Group. “Now it’s time to turn on the monetization.”

Since raising $6 million three years ago, Curiosity has evolved from a site that mostly aggregated content to also producing original content for advertisers, such as Skillshare,an online-learning company. It also sells advertising on the site. Customers include Motorola, Coursera and Masterclass.

The company also raised another $1 million from Pritzker Group, Origin, Chicago Ventures and Hyde Park Angels.

“Gabe and the board recognized, as we were looking to pivot and ramp up revenue growth, that perhaps someone with my background in media would be an asset,” said Weinstein, 43.

She recently built Engine Media, a media-services company, through acquisition for Chicago investment fund Lake Capital. Weinstein previously was president of digital, data and analytics for ad-buying and planning firm Starcom Mediavest. She was CEO of the Chicago office of media buyer Mindshare, working with clients such as Motorola, Discover, Abbott and American Family Insurance.

“She knows how to talk to advertisers,” Nagar said. “She can bring a lot to the table.”

Making a living from online advertising, which has been commoditized in a world where available space exceeds demand, isn’t easy. “Ad-supported models are challenging,” Weinstein acknowledged. She’s banking on’s audience to give her an advantage. “We have a really engaged audience that spends a lot of time with our content,” she said, adding that the average engagement time is nearly 3.5 minutes and users are opening its app six to seven times per month.

“If you know what you’re looking for and go there, there’s content,” says Rolin Moe, director of the Institute for Academic Innovation at Seattle Pacific University, who researches open education resources, such as TED and “It’s aesthetically well produced. What is the endgame to capitalize on that? It’s not clear. It’s more content in a sea of readily available content. Companies that are providing content to users for free are seeing the most success in building audiences. But they have to find alternative sources of revenue. I don’t see how the advertising is going to allow them to recoup their costs.”

Most of Curiosity’s content is text, but it’s quickly moving more into video, where ad​ rates are higher.

“As the definition of TV changes and video content is consumed in new ways and via new distribution points, there are openings for new content creators/aggregators,” said Matt Spiegel, a Chicago-based digital-advertising veteran who is managing director of consulting firm Media Link. “The keys to success are aggregating a recurring large audience and having content that consumers want to return to regularly. Neither are easy, but it is doable.”

Originally featured in Crain’s.