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Welcome to episode 21 of VB Engage, or, as we like to say — VB Engage 021 — because we are going to have hundreds of these things. So you’re just going to have to deal with it.

In this episode, we talk to the cofounder of Hipmunk, Adam Goldstein, just days before the company’s big acquisition announcement. And don’t forget to check out last week’s episode with Mark Organ, CEO of Influitive.


In this week’s weekly news segment, which happens every week, we discuss Snapchat for more than ten seconds.

Stewart spent part of last week at the first ever Snaphappen conference and awards ceremony (The Ghosties). There he discovered that his snaps are a bit dull, and he’s now feeling peer pressure from all the creative people out there creating epic snaps.

Announced this week at Snaphappen, a new analytics tool, called Snaplytics, has entered the fray. Did you see what they did with the name there? Clever. This tool is built to identify key metrics around snaps and Snapchat influencers. Brands will be able to pay for the analytics to see which influencers are most influential. Of course, keep in mind that just because someone is big on one platform doesn’t mean that they are influential on all platforms.

Travis may be big on Twitter and huge in China (no seriously — he is a large man) but just because he is an influencer on Twitter, doesn’t mean that anyone on YouTube cares about him. Not everyone treats every channel the same.

Snaplytics is currently limited to helping brands find the best influencers on Snapchat, and one of the best tools for finding Twitter influencers is probably Little Bird. Coincidentally, the CEO of Little Bird, Marshall Kirkpatrick, is on with us next week.

We then tease the news that Stewart is heading out to New York City for Advertising Week — or AdWeek, if you’re cool — so get ready for next week’s episode when we find out what is happening in the advertising technology world.

Finally, we talk about how smartphones are affecting retail purchases. Did you know that 70 percent of in-store purchases are driven by online research? It’s amazing how many people are making informed decisions these days.

Customers use smartphones to do the research in stores, though many times, they go back to the desktop to actually buy the product. Some people do still buy products in actual stores, but those people are dorks. Or impatient. Which reminds us, right around the corner, we’ll be seeing Black Friday advertising.

As this week’s main course, we have our interview with Adam Goldstein, the CEO and cofounder of Hipmunk, that cool airfare tool with the cute chipmunk logo.

What’s interesting about the airline travel industry is that the number of parameters involved makes creating a conversational chatbot a big challenge. Factoring in the time of day, destination, prices that change constantly, and other variables, you need a lot of machine learning power.

Hipmunk successfully launched a chatbot that, unlike some, is 100 percent A.I.-driven. The company has released this bot on a multitude of platforms, including Facebook Messenger, Slack, WhatsApp, and others.

Goldstein tells us that instead of hiring a bunch of humans to answer all of these travel questions, Hipmunk hired people to train the chatbots.

And what kind of questions does a chatbot answer? Goldstein describes one request he saw: “I want to fly from San Francisco to Taipei sometime in October. And I want to travel for five days, and I want to see the cheapest fares in coach and business class, and I want to avoid flying on a Chinese airline.”

That was when Goldstein knew his team would have to upgrade their natural language processing, machine learning, and A.I. Goldstein tells us how Hipmunk managed to crack such a thorny problem.

We also ask a few general travel questions, and Goldstein doesn’t spare anyone’s feelings when he explains exactly what type of airfare you should avoid.

Tune in next week for our interview with former tech journalist-turned-entrepreneur, Marshall Kirkpatrick of Little Bird.

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