3 Questions in Toronto

season 2
Written By Chip Chip

Dispatches From The International Downtown Association Conference and Marketplace

Recorded at the International Downtown Association Annual Conference in Toronto, this bonus episode brings together voices from downtowns across North America. Chip asks a group of downtown leaders what’s exciting them about the field of Urban Place Management, what’s happening in their own communities—and one question chosen at random. A quick, lively snapshot of the people working every day to make cities stronger, more welcoming, and more resilient.

https://downtown.org/event/2026-annual-conference/

Featured in this Episode

Field Guide
Tim Tompkins
Tim Tompkins

Tim Tompkins is a longtime leader in urban place management and the founder of SharedCity, a consultancy focused on helping cities and downtown organizations create more vibrant, inclusive, and resilient places. Previously President of the Times Square Alliance, his work spans public space, economic development, arts and culture, placemaking, and the evolving role of downtowns in civic life.

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Chelsea Gondeck
Chelsea Gondeck

Chelsea Gondeck is CEO of the Downtown Partnership of Colorado Springs, where she works to strengthen Downtown as the economic, civic, and cultural heart of the region. Her work spans placemaking, economic development, mobility, public space, and partnerships, including leading the award-winning transformation of AdAmAn Alley.

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Lukas Umana
Lukas Umana

Lukas Umana is Senior Director of Public Space Operations and Activations at the DowntownDC BID, where he leads work to create clean, safe, vibrant, and memorable public spaces. His work brings together placemaking, public art, events, hospitality, and creative partnerships to strengthen Downtown DC and demonstrate the economic and community value of great public-space experiences

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Kimberly Bares
Kimberly Bares

Kimberly Bares is President and CEO of The Magnificent Mile Association, representing businesses, property owners, institutions, and attractions along Chicago’s iconic North Michigan Avenue. Her work focuses on economic vitality, placemaking, advocacy, public realm improvements, and strengthening the Magnificent Mile as a vibrant destination for Chicagoans and visitors alike.

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Caroline Keesler
Caroline Keesler

Caroline Keesler is part of the team at the Tampa Downtown Partnership, working to support a vibrant, connected, and welcoming Downtown Tampa. Her work includes placemaking, public-space activation, events, and programs that bring people together and strengthen the downtown experience.

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Ivy Lupco
Ivy Lupco

Ivy Lupco is the founder and principal consultant of Third Place Makers, a Tampa-based placemaking practice focused on creating places where people feel connected and belong. Her work spans public-space activation, community engagement, public art, events, and inclusive urban experiences. She also hosts Third Place Makers Talk a podcast exploring the people, projects, and ideas shaping places and communities across the country.

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Kristi Clark
Kristi Clark

Kristi Clark is City Place Manager with Canberra’s City Renewal Authority, where she works to make the city centre more active, welcoming, and connected. Drawing on a background in events, performance, and community engagement, her work includes placemaking, programming, public-space activation, and supporting the businesses and communities that bring central Canberra to life

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Sheffia Randall-Nickerson
Sheffia Randall-Nickerson

Sheffia Randall-Nickerson, MBA is currently the Chief Engagement and Collaboration Officer at University Circle Inc., the community service corporation responsible for developing, serving and advocating for University Circle as a vibrant and complete neighborhood. Sheffia also held the positions as President and CEO of the Center for Arts-Inspired Learning, a non-profit arts education organization and Assistant Director of Community Engagement and Education at Playhouse Square in the center of the Cleveland Theatre District.

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Kate Borders
Kate Borders

Kate Borders is President of University Circle Inc., the community development organization serving Cleveland’s University Circle district. Her work focuses on strengthening one of the country’s most significant concentrations of cultural, educational, and healthcare institutions through placemaking, economic development, transportation, public space, and community partnerships.

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Kyle Carter
Kyle Carter

Kyle Carter is Vice President of Place at the Quad Cities Chamber of Commerce, where he leads work focused on creating vibrant, welcoming places across the bi-state region of Iowa and Illinois. His work connects downtown development, placemaking, public spaces, arts and culture, and economic vitality to strengthen communities throughout the Quad Cities.

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Betsy Brennan
Betsy Brennan

Betsy Brennan is President & CEO of the Downtown San Diego Partnership, where she leads efforts to strengthen Downtown San Diego as a vibrant, welcoming, and economically resilient urban center. Her work brings together business, civic, and community partners around everything from economic development and public space to clean-and-safe programs, mobility, and the downtown experience.

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Bloor West Village BIA
Bloor West Village BIA

Established in 1970, Bloor West Village became the world’s first Business Improvement Area, pioneering a model for collective investment in commercial districts that has since spread around the world. Today, the BIA continues to support its Toronto neighborhood through beautification, events, marketing, advocacy, and initiatives that strengthen the local business community.

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Chip Chip
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Small Block - Shifting the Ground