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Thesis Driven Leader Series

Author: Brad Hargreaves, Editor at Thesis Driven

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At Thesis Driven, we research and write about trends in the built world. Join Thesis Driven founder Brad Hargreaves as he interviews the leading voices at the intersection of real estate, cities, innovation and technology. Guests include innovators like Zillow founder Spencer Rascoff, the renowned East Coast developer MaryAnne Gilmartin, AOL founder and real estate visionary Steve Case and many more top change makers in real estate. Check out our newsletter at

“Thesis Driven is the best source for substantive insight into innovative GP strategies, data-driven real estate investing, and the lesser-known stuff that makes real estate go. ” -Moses Sternstein, Random Walk

“If you like it here in the Asphalt Jungle, you'll like what Brad Hargreaves is doing over at Thesis Driven.” -Eric Weatherholtz, Asphalt Jungle

“Emerging real estate development trends” -Fed Novikov, Really Good Buildings

11 Episodes
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 Co-founder and 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 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 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
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!
.Welcome to the Thesis Driven Leader Series! Thesis Driven editor Brad Hargreaves speaks with Dave Eisenberg, Founding Partner at Zigg Capital. It’s a great conversation about the convergence of venture and real estate investing. And it’s a unique opportunity for investors and entrepreneurs to glean thoughtful - and actionable - insights about innovation, economics and growth in the proptech startup world.Dave and Brad start by digging into a major topic in real estate tech:  decoupling investment in the operating company (“opco”) from investment in the real estate or assets (“propco”). Blending the investment structures has historically been disastrous for startups whose real estate holdings are a powerful and differentiating asset but simply can’t generate venture returns at venture speed. Through his VC fund Zigg and their partner real estate fund Watchung Capital, Dave and his colleagues are optimizing for serving a wide variety of proptech startups, including those that need both venture and real estate capital.Listeners will also learn about how venture investors like Dave source deals and what they are looking for in future portfolio companies. Dave details how he and his colleagues evaluate deals and the founders behind them and why he values humility over bravado. He also provides some helpful hints to founders about what they should be looking for and expect in future investors.Brad and Dave also discuss gaps in the real estate tech markets and areas that are ripe for innovation. Investors like Dave believe in proptech and its value to the economy and the future of how we live. So if you have an idea, it’s time to go for it.To get our weekly newsletter with research and insights about the built world, head over to Enjoy!
A pioneer in the world of real estate crowdfunding, Jilliene Helman joins Brad on the Thesis Driven Leader Series this week. She’s the founder of RealtyMogul, an online investment platform that gives members access to real estate deals traditionally reserved for larger investors. Late last year, RealityMogul announced that more than $1 billion has been invested on their platform. Through her platform, Jillian has made real estate investing more accessible to individuals who want to diversify their portfolios.This episode explores Jilliene’s experience innovating in the real estate investing world and the key lessons she’s learned as a successful proptech entrepreneur. The conversation kicks off with her insights from the 10 years of work behind the first $1 billion, including how her team won over raving fans, designed product and UX for retail investors, and found investors who were a great fit. Jilliene and Brad go on to discuss how Jilliene plans to achieve the next $1 billion and why educating new customers about the space and building trustworthiness are essential parts of those operations.  They also talk extensively about the unique landscape of real estate investing, the rise and fall of their competitors and why RealtyMogul’s focus on individual investors has been critical to their success.This is a great conversation for anyone working at the intersection of real estate, investment and innovation. But it’s a must-listen for proptech entrepreneurs. Jilliene shares invaluable insights that will help them immensely on their journey. Enjoy!
It’s hard to find a more ambitious, thorny, crazy, fascinating, optimistic example of innovation in real estate than what Jan Sramek is doing in California. He’s the founder and CEO of California Forever, the company building the increasingly famous - and at times infamous - new city northeast of San Francisco in Solano County.In this episode, Jan shares why he decided to start a new city  and how he has shepherded it through raising $900 million from some of the biggest names in Silicon Valley, purchasing 62,000 acres in Solano County, and planning a thriving, walkable urban center. And we discuss some of the challenges on the horizon, including garnering community buy-in, overcoming regulatory hurdles, and facing a November ballot referendum which will decide the ultimate fate of his city. This is an exciting listen from start to finish. Here are some additional topics Brad and Jan cover:Why building a new city can be a practical solution to the housing challenges facing California.California Forever’s approach to transportation within as well as to and from the city.How Jan pitched and won over the who’s who of Silicon Valley on a project that doesn’t walk or talk like any other VC-backed company.Plans for building after the ballot initiative and how the team is solving the nuts-and-bolts of the an extraordinarily ambitious real estate project.How Jan and his investors are viewing the project from a real estate finance and returns standpoint.Design strategies for encouraging unique, organic architecture while discouraging cookie cutter neighborhoods and sprawl.The reasons Jan and his team are proactively pursuing environmental reviews even where they’re not necessarily required.How California Forever has managed relationships with the local community - including the largest west coast Air Force base - and factored in their interests to design the new city. Enjoy the talk! To view plans for California Forever, including the ballot initiative, visit and, to subscribe to the Thesis Driven weekly newsletter, check us out at
Welcome back to the Thesis Driven Leader Series! In this episode, Thesis Driven editor and host Brad Hargreaves is speaking with one of the preeminent developers of our generation, MaryAnne Gilmartin. She’s known for building Brooklyn’s Barclays Center, Atlantic Yards, and the New York Times building, to name a few. And she’s now expanding beyond New York City to develop the Baltimore Peninsula - a 177 acre project which includes 14 million square feet of new development and 40 acres of publicly accessible open space.In this interview, you’ll hear about the exciting details of her emerging new development on the Baltimore Peninsula as well as why this project is an excellent model for urban spaces - from the details of the master plan to the urban geography to the role of placemaking to the motivations of each stakeholder. MaryAnne and Brad also discuss the current development environment in New York City. MaryAnne shares her thoughts about the policies and politics that have added headwinds to new housing construction and what the city and state need to do to dig out of the housing crisis. She also shares why she’s optimistic about the city and many New York politicians and why, ultimately, she’d still bet on NYC over any other city in the world.This interview will be inspiring to any lovers of great real estate projects and development. MaryAnne has a wealth of insights on what it takes to thrive (and survive) as a developer and what key elements make a project valuable and promising. She has a palpable passion for cities and creativity and vision for the future of the built world.Excited to see you on the next episode of the Thesis Driven Leader Series - till then, check out the Thesis Driven weekly newsletter at
In this week’s episode, Thesis Driven Editor Brad Hargreaves speaks with one of the most respected thinkers on the future of work and real estate, Dror Poleg. Dror is the author of the acclaimed books After Office (2023) and Rethinking Real Estate (2019). Through their conversation, Brad and Dror dive into how macroeconomic factors and advances in technology influence how businesses source, value and manage talent which in turn drives how we work, where we work and where we want to live. More from the episode …  Why “WFH” isn’t just a pandemic trend but the most recent chapter in two decades of shifting how we distribute workforcesHow technology has fundamentally upended the linear, predictable nature with which we once approached investment expectations, upside / downside risk, talent priorities, management … and yes, office space.How this will impact the ecosystem of office real estate from how developers and owners evaluate deals to how banks underwrite risk.Why the future of office winners will not be who calculates the optimal ratio of in-office vs. WFH time but those who strategically use office space to solve (dynamically) for the specific needs of specific teams and specific times.Why the office market will start to look more like the hotel market.The critical importance of central business districts and who is getting it right.Why the better conversation is less about the future of the office but more about the extraordinary opportunities that spaces of the future will present as our work patterns and lifestyles change - and why value will accrue to the real estate leaders who move beyond increasingly outdated worldviews about urban and office spaces.Why the future of cities is still bright.Headlines and popular opinion lean “doom and gloom” on the topic but Poleg’s takes in this podcast - as in his books - will likely leave you feeling more inspired and creative about how you’re thinking about the future of work. Keep up with Dror on X or sign up for his newsletter on his website: to see you on the next episode of the Thesis Driven Leader Series - till then, check out the Thesis Driven weekly newsletter at
Rhett Bennett and Moses Kagan are co-founders at ReSeed Partners, a new firm at the frontier of real estate development and investment. They're taking a novel approach that echoes venture accelerators like Y Combinator. They're joining Brad for our first episode of the Thesis Driven Leader Series to share insights why they launched ReSeed, how they went about assembling their first cohort, what they learned, and what's on the horizon.To learn more about ReSeed Partners, visit to get newsletters from Thesis Driven? Go to
Welcome to the Thesis Driven Leader Series hosted by Brad Hargreaves. The Leader Series Podcast is an accompaniment to our weekly Thesis Driven newsletter, one of Substack's top 15 business newsletters. podcast will feature conversations with the leading voices at the intersection of real estate, cities, innovation and the built world. We'll talk about how technology is going to shape real estate investing over the coming years, what new sectors and consumer preferences changes mean for real estate development and how entrepreneurs might be able to play to these trends.Here are some of the outstanding real estate leaders we'll speak with over the next three months:Spencer Rascoff, the Founder of Zillow, Pacaso and heyLibby. Spencer is one of the most successful tech entrepreneurs in real estate and has a wealth of insights for real estate investors and innovators alike.MaryAnne Gilmartin, the Founder and CEO of MAG. MaryAnne is one of the top real estate developers in New York City and now she's taking her show on the road and redeveloping a substantial part of downtown Baltimore.Dan Doctoroff, the founder of Sidewalk Labs and the former NYC Deputy Mayor for Economic Development and Rebuilding. Dan is the foremost expert on improving life in cities for everyone through the application of technology to solve urban problems.Please join us for 12 weekly episodes this season!
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