Tollsmart was founded by two people who couldn’t understand why it was so difficult to obtain toll cost information for upcoming road trips. Leonid (Leo) Iogansen, who developed the original Tolls Calculator USA & Canada iPhone app in 2014, came up with the idea after running out of cash on a toll-laden trip from Baltimore to New Jersey and ended up getting a ticket. It left him thinking there must be a better way to prepare travelers for tolls in advance of a trip. He wished there to be a product which would not only display routes on a map, but would also calculate tolls expenses for these routes.

Jim Kovarik, an entrepreneur and former AOL executive, had already developed an industry-leading fuel cost calculator application (the Galculator) for Cost2Drive, and had been looking for a toll calculator to complement it given that 50,000 people were visiting the site each month in search of toll cost information, a number that was doubling every year. Jim and Leo decided to combine efforts and in April 2015 cofounded Tollsmart, a Virginia-based LLC with a mission to provide full transparency around tolls so people can make smarter, more economically-sound driving decisions.

As we were developing the API for our toll calculator application we were thinking about the many potential use cases and noticed that there were many people posting questions on Twitter regarding whether or not toll costs are included in the price estimates provided by Uber. In most instances the answer was 'no' and so we felt we could provide a valuable add-on service to Uber by providing price estimates that are inclusive of tolls.

As we further developed our Tollsmart iPhone application to where it now provides toll costs for alternative routes, it presented another opportunity for Uber customers to see which route would be the most cost-effective factoring in both toll and Uber costs. We felt this was an innovative service to enable Uber customers to make more informed suggestions to Uber drivers regarding routing.

Additionally we felt we could bring a whole new audience to Uber, those who were using the Tollsmart app in advance of driving someplace who would then see that the Uber service was available for their itinerary, and at reasonable prices thereby creating more awareness for Uber and delivering more customers.

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