This podcast serves as an internal ombudsman for progressives, working to find areas where they can do better, especially for the most vulnerable amongst us. It’s hosted by Ravi Gupta, former Obama campaign and administration staffer turned charter school principal. He and guests ask difficult questions about where progressives have been, and more importantly, where they are going. How do we serve kids better? Or lower the cost of housing? And why is it that blue cities do such a poor job of serving the homeless? The Regressives podcast tackles these questions and much more.


Ep. 13 – The End of Education Reform

Listen on

Ep. 12 – How We Solve Housing and Homelessness

America faces two inextricable problems: a growing homelessness crisis, and a dire lack of affordable housing. As the gravity of those issues grows more visible, lawmakers are under increasing pressure to solve them. We sat down with The New York Times’ Binyamin Appelbaum to talk about how the state of California — so often the poster child for how not to handle homelessness — is making gradual progress, taking a critical yet hopeful look at what the rest of the country can learn from their example. We discuss the unique position land occupies in our society, the persistent phenomenon of NIMBYism, and why the first step to fighting homelessness is both hugely complicated and squarely simple: build more housing.

Leave us a voicemail with your thoughts on the show! 321-200-0570

Ep. 11 – Empty Nests: Why Do Blue Cities Fund Stadiums?

In 2022 the NFL’s Buffalo Bills announced a deal with the state of New York to build a brand new $1.4 Billion stadium in Erie County. The passage of funding between the state, the Buffalo Bills, and the NFL requires that New York taxpayers front a whopping 60% of the project – or about $850 dollars. This reignited a debate that has been raging in the US for the past two decades: Should taxpayers front the costs of large scale stadiums for billionaire owners? The answer is not easy, as every major sports league in the country has leveraged their teams to push secure taxpayer funding and the problem only seems to be getting worse.

In this episode Ravi speaks with Victor Matheson, a sports economist and professor at the College of Holy Cross, who has studied stadium financing for over two decades. They discuss the history of sports stadiums in America, the arguments for and against public financing, and why this disturbing trend may not be going away. You won’t need to be a sports fan to enjoy this conversation.

Ep. 10 – Is The News Really “Woke?”

Long before Donald Trump, Ron DeSantis, or the birth of “fake news,” Americans had already started to lose their faith in American journalism. The feeling that something had shifted in the media’s discourse had become hard to ignore because mainstream news was no longer just liberal; it was “Woke.”
In this episode of Regressives, Ravi interviews Batya Unger-Sargon – the Deputy opinion editor at Newsweek and author of the book “Bad News: How Woke Media Is Undermining Democracy” – which examines how over the course of a century, journalists shifted their focus away from the working class and toward the concerns of their affluent, highly-educated peers. We discuss that shift, whether the media truly has a bias, and whether it can even be described as a monolith anymore.

Ep. 9 – The Problem with College Admissions

In our last Regressives episode, we went over affirmative action and why it might soon be a thing of the past. Today, we’ll go through a less-discussed practice in college admissions: legacy admissions. For a century, it’s allowed elite schools to cater to elite families, giving blatantly preferential treatment to the nation’s wealthiest sons and daughters. It’s created a hyper-exclusive pipeline, designed to keep donations flowing to universities while ensuring the most qualified students aren’t the only ones getting in. On this episode of Regressives, Ravi dives into the past, present, and future of a practice that the American aristocracy would rather leave undiscussed.

Ep. 8 – A Funeral For Affirmative Action

By all expectations, affirmative action is about to be a thing of the past. In a pair of landmark college admissions cases before the Supreme Court, a newly conservative majority is all but certain to roll back a major pillar of American life since the Civil Rights movement. Through talking to the plaintiffs in those cases, activists, legal experts, academics, and everyone in between, we revisit the history of affirmative action, how it was borne out of a desire to redress inequality, and why progressives are loath to acknowledge how it came to exacerbate the discrimination it sought to solve.

Ep. 7 – An Education Miracle Maker

John White is an educator and public official who served as the Louisiana Superintendent of Education from 2012 to 2020. John arrived in Louisiana in the aftermath of Hurricane Katrina and was tasked with reinventing an education system that was routinely ranked at very bottom of the United States. He used the crisis to push through reforms that transformed the lives of Louisiana students, putting them on a path that many thought inconceivable just a few years before.On this special episode, Ravi speaks with John White about how he was able to pull of en education miracle, and what bureaucratic and political challenges he had to overcome to help children of Louisiana.

Ep. 6 – The Progressives Pull From Public Infrastructure

A century ago, New York City was the infrastructural envy of the world, boasting a newly built subway system and an expansive network of bridges and tunnels. Today, the city’s vital arteries lag behind modern standards as prohibitive costs and red tape hold back innovation and progress. The New York Times’ Brian Rosenthal, winner of the 2020 Pulitzer Prize for investigative reporting, joins Ravi to diagnose the sticker shock and regulatory hurdles standing in the way of infrastructure progress in New York and the U.S. as a whole.

Ep. 5 – Progressive Hypocrisy on School Choice

“School choice” is among the most politicized phrases in America, mainly because it means different things to different people. Charter schools are at the heart of that divisive debate, pitting progressives and conservatives against one another in a shouting match over what “choice” truly means and who deserves to have it. Ravi sits down with Shavar Jeffries, the president of Democrats for Education Reform, to talk about fighting for charter schools, the many progressives who resist school choice, the sweeping influence of teachers unions, and the most important factor in this and all discussions of education: what’s best for students.

Ep. 4 – The Nonprofit Industrial Complex

In America, it’s all too common that we measure success by whether you leave the town you grew up in. The best and brightest, it’s assumed, are those that get out. Why do we accept that as a country? Urban revitalization strategist Majora Carter says we shouldn’t, and we won’t see real improvement in our low-income neighborhoods until we approach them differently. Ravi and Majora get into a wide-ranging discussion about flawed community outreach, the “non-profit industrial complex,” gentrification, affordable housing and urban renewal.

Ep. 3 – The Most Important Education Story You’ve Never Heard

Camden, NJ was once among the lowest performing school districts in the country. A system that had thirteen superintendents in twenty years and that routinely ranked in the bottom of New Jersey school districts. That changed in 2013, when an unlikely coalition united behind a different kind of education leader and playbook. We look back to one of the most overlooked and important education stories of the past few decades. 

Ep. 2 – Blue State Hypocrisy on Housing

America has a housing crisis, and it cuts both red and blue. But blue strongholds like Illinois, New York, and California struggle even more than their red counterparts to live up to a progressive policy ideal: affordable, equitable housing. Ravi interviews the New York Times’ Conor Dougherty, whose new book, “Golden Gates: The Housing Crisis and a Reckoning for the American Dream” takes a critical lens to San Francisco’s housing crisis and the liberal hypocrisy that perpetuates it. They discuss the unique position land occupies in our society, what really defines a ‘progressive city,’ and the stubborn nature of Nimbyism.

Ep. 1 – The Worst School Board in America?

San Francisco’s school board is facing a recall as parent anger boils over about school closures and efforts to promote ‘equity.’ What does this fight tell us about our national debates about covid restrictions, critical race theory, and teacher’s unions? Ravi interviews parents and experts — and even sits down with the school board’s chair (a target of the recall) to discuss what’s driving frustration and why it’s a cautionary tale for progressives.


Sign up for our newsletter

© 2022 Lost Debate Media. All rights reserved. EIN: 86-2659851