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During times of economic crisis, a system that squeezes out free airline flights from unmanaged frequent flier miles may be worth a few bucks. In this segment, we look at such a new service. We also dive into the self-study market by looking at a startup that’s creating a self-study language app for mobile phones. Guy Kawasaki, author of newly-published Reality Check, venture capitalist and founder of AllTop, was our guest host again, to help us evaluate Travelfli and UrbanPlanetMobile.

We started with Travelfli, a Boulder, Co.-based startup backed by David Cohen‘s TechStars. Travelfli is addressing the 17 million elite frequent flier travelers who may need assistance managing their frequent flier miles. Apparently, there are 10 million unused miles each year. Both Guy and Ezra Roizen, digital media investment banker and Vator Box regular, weren’t convinced that there was a real pain point when it came to managing miles, partly because elite travelers likely used the same airline, or would care about saving $500 for a free ticket.

In our exit and liquidity scenario portion of the show, Liquid Scenarios looked at Mint, Sidestep and Kayak for its analysis of options and possible outcomes for Travelfli.

We then focused on UrbanPlanetMobile. This startup received rave reviews from Ezra, mostly because of the opportunity and the platform. 

In our exit and liquidity scenario portion of the show, Liquid Scenarios pointed out that the language instructional market is $83 billion, and that 40% went to self-study programs. We also point out that comparable companies include italki, Proxis and SharedTalk.

It’s very costly to serve this self-study market. To this end, UrbanPlanetMobile may be well positioned — to the extent that it provides cost efficiencies – to be a potential partner or acquisition target for Rosetta Stone.

(Our next guest host will be Brian Ascher from Venrock, followed by Google’s Marissa Mayer and then Zynga’s Mark Pincus.)

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