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Karis: A hole-in-one is a once in a lifetime experience for a golfer–if you’re lucky. Now, one startup wants to turn that luck into cold hard cash by letting golf courses offer payments as high as $25K for a hole-in-one.

Jim: Digital Golf Technologies helps golf courses offer fully automated hole-in-one contest as a way to generate additional revenue and give golfers some added excitement on the course.

DGT, which launched in 2015 and is founded by Redbox founder and former CEO Gregg Kaplan, currently works with around 150 golf courses across the US that install the startup’s HD cameras and ball tracking technology at one of their par 3 holes. Players pay an additional $5 for a chance at $10K, or $10 for a $20K payout. There’s flexibility in the pricing model, CEO Mike Jakob said, and some courses build the fee into the cost of the round so all players are eligible.

Karis: Despite its popularity among its most avid fans, the golf industry in general has been flat over the last few years. The number of US golfers playing traditional courses has been stagnant–about 25 million people a year–over the last five years, and the US golf equipment totaled $2.55 billion in 2015, down 3% from the year before.

DGT sees its technology as a way for courses to generate new revenue, recapture some of the casual fans, and capitalize on some of the wagering that’s happening between golfers on the fairway already.

To grow its team and get its tech in more courses, DGT just raised $4M from VC firms including Modjule, MATH Venture Partners, Hyde Park Venture Partners and other investors. DGT plans to add more features to its gameplay, allowing for closest-to-the-pin, longest drive, and other contests courses can offer at their holes. [More here]

Karis: Canadian healthtech startup League just chose Chicago as its US headquarters. The Toronto-based startup, which provides customizable health benefits plans, will move into an office in River North and has hired Brian Ancell as US President. The move comes as League is looking to expand across the US: The platform is now live in Illinois and Washington.

Jim: Chance the Rapper is the star of a new ad for Twitter. In the 1 minute spot, the Chicago-based rapper tweets that he’s looking for requests for the night’s concert. The commercial follows the reactions of fans and musicians arguing over favorite songs and posting opinions about the state of the music industry. The idea is to show that Twitter is an open forum for all perspectives (though I’m guessing there won’t be a spot featuring egg avatars any time soon).

Karis: The Pokemon Go phenomenon is far from over, if a Chicago fest is any indication. According to the Tribune, the Official Pokemon Go Fest celebrating the AR game’s one year anniversary, set to be held July 22 in Grant Park, sold out in a matter of minutes with resale tickets going for as high as $400.

Queer Tech Club is hosting a special Pride Month Meetup/Happy Hour at Networked Insights, a local big data startup transforming the way companies connect with their customers. Get the info on this event and more in our June edition of Chicago Inno Approved.

Uptake founder Brad Keywell on the fourth industrial revolution:

“As difficult as it may be, the future of work looks very different from the past. I believe people with grit, creativity and entrepreneurial spirit will embrace this future, rather than cling to the status quo. People can be better at their jobs with the technology of today—and the technology that is yet to come—rather than fearing that their human skills will be devalued.”

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Karis: NowSecure, a Chicago-based mobile app security software company, announced it has hired Alan Snyder as the company’s next CEO. Snyder was previously CEO of BoxTone, a mobility management platform that was acquired by Good Technology. NowSecure’s founder Andrew Hoog will continue with the company and “focus his energy on product innovation, sales enablement and business strategy,” according to a news release. NowSecure has raised $12.5M since it was founded in 2009.

Karis: As part of its “180 days of change” Uber is introducing tipping…in three cities (full rollout by the end of July, the company says).

Sigh. For all the chest beating about Uber’s ability to grow quickly, I find it a little odd that they can’t yet manage to offer a widespread roll out of a feature that their users and drivers have demanded and their competitor has had for years. It’s about time to fast-track the good stuff, Uber.

Jim: It’s embarrassing that it took so long for Uber to roll this out. Lyft drivers, meanwhile, have earned more than $250M in tips.

Karis: I was blown away by the Takashi Murakami exhibit at the Museum of Contemporary Art this weekend, and came thiiiiisss close to dropping $40 on a commemorative t-shirt. For now, I guess I’ll have to be content to adorn my selfies with Murakami-inspired photo effects and frames.

Jim: It’s cool to see Takashi Murakami embrace his work being used on Facebook. He probably didn’t expect selfie frames to be a place for his art.

From Karis’ story on the new Facebook Messenger frames based on the MCA’s Takashi Murakami retrospective:

“It’s natural for the MCA and Facebook to work together because we share a commitment to providing today’s audiences with experiences that are cutting edge, enticing, and participatory.”

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