Thesis Driven Leader Series Brad Hargreaves, Editor at Thesis Driven

While Charles Marohn began his career as an engineer, he soon realized that the problems plaguing American urban design - particularly in the suburbs - ran deep. So he quit his engineering job and began writing about how to redesign cities for livability and people rather than cars. His work - including books Strong Towns and Confessions of a Recovering Engineer - became very influential in the New Urbanist movement and the past decade of innovation in urban design and real estate development.
In this episode, Marohn joins Brad on the final episode of Season One of the Thesis Driven Leader Series to discuss the future of cities. We'll touch on the design and policy interventions that would save lives and improve our cities' finances as well as how real estate developers should approach designing better places. We'll also discuss the role that technology can - and cannot - play in making cities better.
Marohn brings a perspective and insights that will be relevant for anyone looking to innovate in the built world.

Real estate is nothing without people. Even the most beautiful, historic spaces occasionally need a boost, and Stephanie Blake is the magician making that happen. As CEO of Skylight, she’s responsible for activating spaces ranging from New York’s Moynihan Station and St. John’s Terminal to San Francisco’s Ferry Building and Detroit’s Michigan Central Station.
Blake has built a reputation working with governments, brands, and real estate developers to build a sense of place and activity in incredible and often unconventional spaces. This week, she speaks with Brad about how she uses placemaking activations to bring vibrancy, purpose, and community to real estate of all types.
Placemaking strategies have gained popularity for a variety of reasons; they help developers drive interim revenue, market a space that might be challenging for the public to understand and encourage businesses to come to an area that might otherwise be lacking. Skylight’s brand of activation is a powerful toolkit for developers and governments alike, particularly as cities reconsider the role of offices, gathering places and central business districts in a post-pandemic world.
Through her work, Blake puts her background in history to work. Each Skylight project begins with studying the context of space including both the history and the neighborhood. And it culminates working with brands to create extraordinary experiences in those spaces like NY Fashion Week, food festivals and concerts - to name just a few.
This interview is full of rich insights about how developers can position their spaces to be welcoming places from day one, including the power of a blank canvas and lessons for operators repurposing challenging spaces.

Spencer Rascoff has had an extraordinary career as a leading real estate tech founder and investor. As the founder of Zillow, he revolutionized how homebuyers, sellers, and agents market and discover listings. More recently, he launched Pacaso, a fractional ownership platform for second homes which now serves the owners of more than 1,400 homes.
Since leaving Zillow, Spencer has been a prolific figure in the real estate tech world - he’s been an active founder or executive in dozens of startups and an investor in hundreds through his VC fund 75 & Sunny and others.
We’re delighted to share Spencer’s unique perspective and predictions about the future of real estate and technology in this episode of the Thesis Driven Leader Series. In this conversation, Spencer and Brad discuss a number of topics including:
The big opportunities in real estate right now, the problems that need solvingWhat Spencer belives the most important proptech problem will be in the 2030sWhere AI can be helpful in proptech (and where it probably won’t be)His take on the DOJ’s commissions lawsuit on the brokerage industry and real estate more broadlySpencer’s experience investing and his advice about the role investors should play in portfolio companies.Enjoy! And if you’re enjoying our podcast, please visit www.thesisdriven.com for a deep dive into emerging real estate themes and the innovators capitalizing on them.

Steve Case has spent the past 40 years at the intersection of technology, cities, and innovation. He was one of the leaders of the internet revolution as the founder and chairman of AOL. Since then, he’s dedicated himself to investment in entrepreneurs and innovation as the founder of the venture firm Revolution.
Along the way, Case developed a thesis for investment and economic growth that’s a little different than that of most venture investors: a belief in the emergence of places beyond traditional tech hubs–cities that haven’t traditionally been the focus on venture investment but have tremendous potential.
Through Revolutions’ seed and growth funds, Case and his team have made “The Rise of the Rest” their guiding philosophy. They look for companies where place matters, and they like to invest in “Rise of the Rest” cities that are likely to benefit from increasing innovation and investment int he coming years. He writes all about this in “The Rise of the Rest, a book he published in 2022.
This is a fast-moving conversation that covers a number of topics. Brad and Steve discuss the characteristics of rising cities and which ones get them particularly excited. They talk about innovation districts and their particular importance as talent disperses beyond traditional tech hubs. They discuss why the next wave of startups will all have a policy aspect whether they’re healthtech, fintech, proptech or any other major tech sector. They also go into more detail about what the Revolution team looks for in startups and how they run their investments … and how their unique venture thesis has given rise to a fund dedicated to investing in real estate in rising cities.
With a worldview anchored in place and innovation, Case’s insights and predictions are invaluable to anyone with a stake in venture, real estate, innovation, the future of urban spaces and policy.
To read our weekly newsletter, please visit us at www.thesisdriven.com. Enjoy!

In 2011, without any real estate experience, Caren Maio co-founded Funnel and scaled it to become one of the leading multifamily marketing platforms in the real estate ecosystem today. Since then, she’s been an entrepreneur-in-residence at Camber Creek and President at Moved. She’s dedicated herself throughout her career to mentoring other proptech startups and is now a highly sought-after advisor in the space.
Caren brings a unique perspective to the Thesis Driven Leader Series. She has been in proptech for about as long as there’s been a thing called proptech. But much has changed since she got her start over a decade ago; for example, many of the most sophisticated real estate owners have teams dedicated to sourcing and identifying great tech. But that makes it more important than ever that founders differentiate their startups from other offerings in the problem they’re solving, their product execution, marketing / sales and customer experience.
Caren also discusses the biggest mistakes she sees real estate tech companies make, including advice for proptech entrepreneurs just getting started. We talk about the fundraising environment as well as the pitfalls of starting a company in New York City.
Caren is clearly a product person at heart and, along with real estate operators and entrepreneurs, product leaders at any tech start will find her insights practical, valuable and probably inspiring, too.
Enjoy! To subscribe to Thesis Driven's weekly newsletters, visit us at https://www.thesisdriven.com/.

For three decades, Dan Doctoroff’s vision for cities–and how technology can make them better–has shaped how we think about urban centers in the US. Perhaps more than anyone, he brought forward the initiatives that made NYC what it is today: the Highline, Barclays Center, Long Island City Waterfront, Hudson Yards and Citi Bike, among many. Doctoroff’s dreams, sweat, and speed are behind all of them.
In this conversation, hosted by Thesis Driven editor Brad Hargreaves, Doctoroff walks us through 30 years beginning with NYC’s ambitious bid to host the Olympics. While the bid failed, it became a blueprint of values and plans that would drive his priorities as NYC’s Deputy Mayor for Economic Development, the leader of the PlaNYC initiative, and the founder of Sidewalk Labs, a company dedicated to improving cities through technology.
Doctoroff draws upon his experience with large projects to discuss how he tackles complex initiatives with multiple stakeholders, including his success and failures along the way. Through it, he has advice for entrepreneurs and innovators with big aspirations, from building new cities to getting companies off the ground. He also discusses the importance of storytelling and narrative when doing anything meaningful at scale.
The conversation wraps with Doctoroff discussing the path he has taken since leaving Sidewalk Labs. Four years ago, he was diagnosed with ALS and has since dedicated himself to researching, changing and funding how science and industry approach finding a cure.
Lessons abound in this conversation for developers, legislators, entrepreneurs, investors and frankly anyone who cares about cities. Listeners will likely be inspired by Doctoroff’s optimism, tenacity, and passion.
Enjoy!