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Gabe Klein

Venture Partner

In addition to his work with Fontinalis, Gabe is Co-Founder and Partner in Cityfi, an Advisory Services Firm that specializes in facilitating complex change in cities with public and private sector clients, often in the technology and mobility sectors and with triple-bottom-line outcomes. Gabe has advised governments and companies worldwide on innovation in cities including Singapore where Gabe has been a visiting fellow for the Centre For Livable Cities, working on creating a “car-lite” city-state.


Gabe is also the former Commissioner of the Chicago and Washington DC Departments of Transportation. In both cities, he revamped technology platforms and government processes while focusing on putting people first on city streets. This included launching two of the first and largest bikeshare systems in the U.S. and building protected bike lanes and better pedestrian infrastructure for vulnerable citizens citywide, as well as facilitating private services like carshare and rideshare that could help each city’s mobility goals. As DOT Chief, he worked to bring a new Riverwalk to Chicago as well as the breathtaking Bloomingdale Trail, 100’s of miles of bike lanes, new policies combined with technology solutions to revamp parking, permitting, and many other arcane government processes. Gabe honed his creativity and leadership skills working in business, including Zipcar, where he served as Vice President, Bikes USA as national Director of Stores and his own electric powered, organic food truck chain, On The Fly.


In 2015, Gabe also published Start-Up City with David Vega-Barachowitz on Island Press, a manifesto on revamping how (and how fast) we innovate in cities and rethinking public-private partnerships with a triple-bottom-line approach as technology shapes a dramatically different future. Gabe sits on the boards of Transit Screen, Carma and Streetsblog, and advises companies including Spin, Numina, Miles and Cabana.

Roles at Fontinalis Partners

  • Venture Partner

    Current role


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