Episode Summary
Executive Summary: Redfin CEO Glenn Kelman and Jason Calacanis discuss how remote work and migration are reshaping housing, worsening affordability in destination cities while weakening demand for downtown offices. Kelman argues that restrictive zoning and NIMBY opposition deepen the crisis, while housing and proptech innovation—from integrated services to instant cash offers—could make moving easier. They also debate workplace culture, equity, real-estate commissions, listing transparency, and whether founders should engage with critical media.
Main Topics: Remote work, migration, and housing affordability: Kelman says remote work has enabled workers with high-cost-city salaries to move to cheaper regions, rapidly raising prices and displacing local buyers. The migration broadens opportunity but disrupts communities and shifts economic and political influence. Housing supply, zoning, and NIMBYism: Both speakers argue that insufficient construction contributes to rising prices. Kelman criticizes neighborhood opposition to density, contending that building more homes—including market-rate units—can improve affordability and diversity. He points to Nashville and Vancouver as development examples. Remote work and the future of offices: Kelman expects lasting weakness in downtown commercial property as companies reconsider leases and employees value flexibility. He sees remote work as beneficial overall, while acknowledging losses in mentorship, social connection, and shared purpose, especially for new hires. Proptech, iBuyers, and a more integrated moving process: Kelman describes the industry’s evolution from online listings to brokerages, lending, title services, and iBuying. Companies use data to make rapid cash offers, trading some sale price for convenience; integration and corporate access to capital may make transactions faster and provide bridge financing. MLS access, pocket listings, and commissions: Kelman defends MLS systems as a way to share listings, but condemns agents who withhold homes from the open market. He supports greater transparency about buyer-agent compensation and discusses a DOJ challenge to the customary system in which sellers pay both agents. Work, startup equity, and accountability: The speakers consider changing employee expectations, the value of purpose-driven work, and cynicism caused by debt and unequal startup equity. They also disagree about whether founders should speak with major news outlets: Kelman emphasizes accountability and visibility, while Calacanis warns of unfair framing.
Key Arguments: Remote work has accelerated migration from expensive coastal cities to lower-cost markets; incoming buyers can afford prices that exclude longtime local residents. Restricting housing supply raises prices. Kelman argues that additional homes at different price points contribute to affordability, while exclusionary neighborhood opposition can protect existing owners at broader social cost. Remote work is likely to reduce demand for downtown office space, and converting offices to housing may not restore their former value because the location advantage of being near employers has diminished. Proptech companies can use integrated services and access to capital to reduce the friction of moving, including buying a seller’s home or offering bridge financing when consumers struggle to carry two mortgages. Pocket listings reduce competition and transparency; Kelman argues sellers benefit from broader exposure and that open access to listings supports fair housing. Making buyers directly responsible for their agent’s fee could make them more price-conscious and put downward pressure on commissions, while still allowing agents to be paid for valuable service. Kelman argues that meaningful work and collective purpose motivate some employees, but recognizes remote work can weaken connection and that workers may reasonably prioritize flexibility and family life.
Data Points: In-migration compared with out-migration: Florida: 7 to 1; Texas: 5 to 1; lower-cost states generally: 4 to 1 - Kelman’s estimates of the ratio of people moving in for each person leaving. Home-price comparison in Austin: $1 million versus about $600,000 two years earlier - Illustration of how a remote worker may see an Austin home as affordable while local buyers view the price increase as steep. U.S. adults qualifying for a loan: Kelman says about half of America cannot qualify - His explanation for why consumers may struggle to finance two homes while property-technology firms can access substantial capital. Redfin commission refunds: $1 billion - Kelman cites commissions Redfin has refunded as evidence of its effort to challenge traditional costs. Redfin high-end listings: Tripled year over year - Kelman says Redfin increased its share of high-end listings by improving agent compensation and incentives. Traditional buyer-agent commission: Often 2.5%–3%; Kelman says business sellers may pay roughly 1%–1.5% - The discussion contrasts customary residential commissions with lower rates paid by institutional sellers. Real-estate transaction scale: Six months to move versus a goal of completing transactions in weeks - Kelman argues that integrated services and bridge financing could shorten the moving process.
Pivotal Quotes: "We just need to build more housing." — Glenn Kelman: His central prescription for addressing housing affordability and the effects of restrictive development. "Running the housing market is a public trust." — Glenn Kelman: His argument against pocket listings and for broad, fair access to homes for sale. "I think it hurts new hires who are just trying to learn the lay of the land." — Glenn Kelman: His qualification that remote work benefits many employees but can hinder onboarding, mentorship, and connection.
Implications: Housing affordability will depend not only on migration but also on whether cities allow more construction. Remote work may permanently redistribute both residents and office demand. Proptech could simplify transactions, while listing transparency and buyer-paid agent fees may reshape brokerage economics.
About This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.