Inside the Algorithm: What 5,000 Miles With Gig Workers Taught One Researcher About Power, Control, and Design
Paths of Curiosity in an AI World

What if the app that decides your Uber driver's next ride was specifically designed to make them feel free while controlling almost everything they do?

Dr. Alex Rosenblat spent seven years finding out.

In this episode, we continue our AI, Data, Behavior, and Human Systems miniseries with Dr. Alex Rosenblat, Director of Sociotechnical Research at The Markup and Cal Matters, and author of Uberland: How Algorithms Are Rewriting the Rules at Work. She rode over five thousand miles with gig workers across twenty-five cities, then did something almost no outside researcher has ever done — she went inside Uber to try to change it.

Together, we explore:

• How algorithmic management gives companies total control over workers without ever having to call them employees
• Why drivers crowdsource the rules in online forums because the platform never actually tells them what the rules are
• What dark patterns look like in the real world — from gig apps to hospital registration tablets — and how they steer choices you didn't know were being steered
• What happened when Dr. Rosenblat tried to get a copy of her own child's hospital consent forms after surgery
• Why surveillance pricing — getting charged a different amount than the person standing next to you — may be the most underreported story in tech right now
• What ethnography gives researchers that no dataset ever could

Dr. Rosenblat also reflects on what it means to study a system from the outside, work inside it, and come back out to investigate again — and why understanding how every stakeholder thinks is the skill most researchers never develop.

This conversation will change how you read every form you're handed, every app you open, and every choice a platform tells you that you're making freely.

Because in a world where design is policy, the most important question isn't what the system can do — it's what it's been built to make you do without noticing.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
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Paths of Curiosity in an AI World

For decades, banks discriminated against borrowers in person. Then algorithms inherited those same biases and made them invisible.

Aaron Klein says AI could finally fix that — or make it far worse.

In this episode, we continue our AI and Human Decision-Making: Choices, Bias, and Behavior miniseries with Aaron Klein, Miriam K. Carliner Chair and Senior Fellow in Economic Studies at the Brookings Institution, former Deputy Assistant Secretary for Economic Policy at the U.S. Treasury Department, and former Chief Economist of the Senate Banking Committee — a person who helped write the laws that govern the financial system you're already living inside.

Together, we explore:

• What actually happens in the first seconds after you apply for a credit card — and why a mysterious black box number you've never heard of may already be shaping your financial life
• How banks once decided loans in person, face to face, and why that created the discrimination that federal law was written to stop
• What your device, your email address, your shopping hours, and even your name might already be telling a lender about you — before you've said a word
• Why the same characteristic — gender — is perfectly legal in car insurance but completely illegal in credit cards, and what that contradiction reveals about how financial rules actually get made
• How AI could finally extend credit to people the current system has locked out for generations — and what's standing in the way
• Why the entire financial system is tuned to an out-of-tune oboe, and how hard it is to get everyone to retune at once

Klein also shares his own path from organizing his rundown high school in Silver Spring, Maryland to the Senate Banking Committee to the Treasury Department during the 2008 financial crisis — and why the only two professions people describe as a calling are the priesthood and public service.

This conversation will change how you think about every financial decision you make — and every decision already being made about you.

Because in a world where an algorithm decides whether you get a loan before a human ever looks at your name, the question isn't just whether the system is fair. It's whether anyone with the power to change it actually will.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
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Paths of Curiosity in an AI World

Every cafeteria, every app, and every website you use today was designed to push you towards a decision before you even knew you were making one.

And the people who built it? They're not thinking about you.

In this episode, we kick off our AI and Human Decision-Making: Choices, Bias, and Behavior miniseries with Dr. Syon Bhanot, Associate Professor of Economics at Swarthmore College and Senior Researcher at MIT's Applied Cooperation Team, whose field experiments with governments, cities, and international organizations — including the World Bank and the U.S. Federal Government — have changed how millions of people save, conserve, and make decisions about their own lives. He is the recipient of the 2024 Exeter Prize for his research on attention and decision-making.

Together, we explore:

• How a text message and a wristband made people two-thirds more likely to finish tuberculosis treatment in Kenya — and what that tells us about why we fail to do even the things that matter most
• What TikTok and Instagram actually know about your psychology — and why calling you a "user" is no accident
• Why telling people they're losing a water conservation competition caused them to use more water, not less
• The moment money ruins everything: why adding $11 to helping a friend move makes you less likely to show up
• Why the happiest people aren't optimizers — and what that means for every major decision you're about to make
• What AI nudging looks like when the system doing the nudging answers to an advertiser, not to you

Dr. Bhanot also shares his own winding path from a year at a refugee camp in Kenya to stumbling into microeconomics in grad school to running experiments that shape federal policy — and why the best metaphor for a career is surfing, not planning.

This conversation will change how you think about every choice you make — and every choice that's already being made for you.

Because in a world where algorithms, platforms, and institutions are all nudging you somewhere, the question isn't just whether you're being influenced. It's whether anyone nudging you actually has your interests in mind.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
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AI, Power, and the Laws That Haven't Caught Up Yet: A Miniseries Recap
Paths of Curiosity in an AI World

A 17-year-old boy had never been arrested. Never charged with anything. Never convicted of anything. But he was in a secret intelligence file, flagged by an algorithm as likely to become a criminal — and officers were showing up at his door before he had done a single thing wrong.

This is one story from one county. Seventeen thousand kids had their data in that system.

In this recap episode, Alora and I revisit all six conversations from our AI, Power, Law, and Civic Life miniseries — and ask what they add up to.

Together, we work through:

• Why winning a landmark Supreme Court case on digital privacy didn't actually close the door — and how law enforcement found a workaround before the ink was dry
• What algorithmic wage discrimination means for anyone who has ever picked up a gig shift, and why there is currently nothing stopping platforms from using a desperation score
• How a deepfake audio clip requiring minutes to generate and nothing to detect could already decide a custody case
• Whose values actually get encoded into the platforms billions of people use — and what happens to democracy when algorithms replace shared reality
• Why the kids being flagged by predictive policing were the same kids the system had already failed
• What it means that lawyers are only reaching ten percent of the Americans who need them — and whether AI finally changes that math

We also trace the career paths of all six guests, because none of them were straight. A field organizer who became a Supreme Court advocate. A clinical psychologist who went back to law school in her thirties. An engineer who spent six months on the Silk Road with cassette tapes and came back asking different questions entirely. The combination that feels random right now might be exactly what makes you irreplaceable later.

This conversation is for anyone who has spent this quarter wondering where they fit in a field being rewritten in real time.

Because the legal frameworks for the AI era are being written right now. The tools that courts will use are being designed right now. The policy decisions are being made right now.

By people — which means students who are curious have a place in this.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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AI, Access, and the Future of Law: Why This Might Be the Best Time Ever to Become a Lawyer
Paths of Curiosity in an AI World

What if the biggest crisis in American law is also its greatest opportunity?

Right now, less than ten percent of Americans who need a lawyer can actually get one. Jennifer Leonard thinks AI might finally change that.

In this episode, we continue our AI, Power, Law, and Civic Life miniseries with Jen Leonard, founder of Creative Lawyers and former Chief Innovation Officer at Penn Carey Law School, where she taught generative AI in law practice and design thinking to future lawyers and Wharton executives alike. She has spent her career asking one question the legal profession has been slow to answer: why does a system built to serve people reach so few of them?

Together, we explore:

• Why AI won't replace lawyers — and why the number of lawyers might actually grow
• How junior associates once spent weeks in conference rooms flipping through banker's boxes, and what AI does to that reality now
• Why solo practitioners and small firms could finally compete with the biggest names in Big Law
• What it means that law schools are still training lawyers for a world that no longer exists
• The unexpected psychological cost of learning to think like a lawyer — and how to protect yourself from it
• What job titles that don't exist yet will define the next generation of legal careers

Jen also shares her own winding path from a law firm she didn't love to building something entirely her own, and why the best career advice she never got was simply: don't be afraid to take the risk.

This conversation will change how you think about law school, legal careers, and what it means to build a profession around access rather than exclusivity.

Because in a world where AI can finally put a lawyer in everyone's pocket, the real question isn't whether the legal profession will survive — it's who it will finally be built to serve.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
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Paths of Curiosity in an AI World

What if the police showed up at your door — not because of anything you did, but because an algorithm predicted you might?

That's not a dystopian novel. It already happened to 17,000 children in a Florida school district. And most of them never knew why.

In this episode, we continue our AI, Power, Law, and Civic Life miniseries with Clarence Okoh, Senior Attorney for Civil Rights and Technology at Tectonic Justice, co-founder of the NOTICE Coalition, and former civil rights litigator at the NAACP Legal Defense Fund, whose work exposing algorithmic injustice in schools, hiring, and courts has shaped policy at the state and federal level.

Together, we explore:

• The Florida school district that secretly built predictive criminal profiles on thousands of children using their grades, attendance records, and abuse histories — and used those profiles to harass families out of their communities
• Why facial recognition in schools isn't just inaccurate — it's unconstitutional, and how error rates as high as 85% mean the student flagged is almost certainly innocent
• What Ruha Benjamin's "New Jim Code" actually means: how AI encodes the same racial hierarchies as Jim Crow — but hides them behind the appearance of neutrality
• What is likely happening to your résumé right now — before a single human being ever reads it
• Why the "AI is colorblind" argument is not just wrong, but dangerous, and what proxy discrimination means for every job application you'll ever submit
• What a digital underclass looks like — and why we may already be building one

Okoh also shares his own path from a fourth-grader in Alabama who wanted to be both a Supreme Court Justice and the head of NASA, to one of the country's most urgent voices at the intersection of civil rights and emerging technology — and why the most important thing he learned was that the jobs worth doing often don't exist yet.

This conversation will change how you think about every system quietly scoring you.

Because in a world where algorithms decide who gets housing, who gets hired, and who gets policed — the question isn't just whether the system is biased. It's whether anyone is allowed to find out.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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Paths of Curiosity in an AI World

Every time you open TikTok or YouTube, a system you didn't choose has already decided what you're going to believe today.

And the people who built it? They're not thinking about you.

In this episode, we continue our AI, Power, Law, and Civic Life miniseries with Dr. Ramesh Srinivasan, Professor at UCLA and founder of the Digital Cultures Lab, whose research on algorithms, power, and democracy has taken him to nearly 80 countries and into conversations with the White House, the European Union, and governments across four continents.

Together, we explore:

• Why no algorithm is neutral — and what it actually means when a platform claims to just show you "what you like"
• How the same platform can present two students sitting next to each other with completely different versions of reality
• What people in Afghanistan, Egypt, and rural India told him they actually want from technology — and why Silicon Valley isn't listening
• The bait and switch at the heart of the data economy: why these platforms would be worth nothing without your data, and why you've never been paid a cent for it
• How algorithmic fragmentation is fueling nativism and authoritarianism across the globe
• What transparency, accountability, and democratic governance of AI would actually look like — and why social media proves what happens when we skip that step

Dr. Srinivasan also shares his own non-linear path from college radio DJ to Stanford engineer to globally recognized scholar and activist, and why the most important thing he ever learned was to stay true to who he is as a human being first.

This conversation will change how you think about every feed, every recommendation, and every platform that claims to know you.

Because in a world where algorithms decide what's real, the question isn't just what you're being shown — it's who decided you should see it, and why.

Paths of Curiosity in an AI World Exploring tomorrow's careers through the lens of AI

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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Paths of Curiosity in an AI World

What if the video used to convict someone never actually happened?

That's not science fiction. With today's deepfake technology, it could happen in any courtroom - and soon!

In this episode, we continue our AI, Power, Law, and Civic Life miniseries with Dr. Maura Grossman, Research Professor of Computer Science at the University of Waterloo and Adjunct Professor at Osgoode Hall Law School, whose work at the intersection of AI, law, and evidence has made her one of the most sought-after experts in courtrooms on both sides of the border.

Together, we explore:

• Why deepfakes have changed evidence manipulation from a skilled crime to something anyone can do in five minutes for free
• The nightmare scenario: what happens when fabricated audio or video shows up in family court, and no one can tell it's fake
• How Dr. Grossman is building a deepfake detection tool specifically designed for the justice system — and why explainability is non-negotiable
• Why "black box" AI has no place in a courtroom where someone's freedom is on the line
• What metadata, physics, and shadows can reveal about whether a video is real
• Whether juries will ever be able to trust video evidence again — and how soon that moment of no return might arrive

Dr. Grossman also shares her remarkable non-linear path from clinical psychologist to elite litigator to computer science professor, and why the best career advice she ever received was to stop being a generalist.

This conversation will change how you look at every video you've ever trusted.

Because in a world where anyone can fabricate a confession, a threat, or a crime — the real question isn't just whether the evidence is real. It's whether we'll ever be able to know.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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AI, Wages, and the Algorithm That Knows How Desperate You Are

Paths of Curiosity in an AI World

What if the app deciding how much to pay you already knows how little you're willing to accept?

For millions of gig workers, that's not a hypothetical. That is your typical day. 

In this episode, we continue our AI, Power, Law, and Civic Life miniseries with Dr. Veena Dubal, Professor of Law and Anthropology at UC Irvine, whose research on algorithmic labor control has been cited by the California Supreme Court and covered by the New York Times, NPR, and CNN. TechCrunch called her an unlikely star in the tech world — and once you hear what she's uncovered, you'll understand why.

Together, we explore:

• How gig companies legally stripped millions of workers of basic protections by classifying them as independent contractors
• What algorithmic wage discrimination actually means — and why two drivers doing the same ride can be paid completely different amounts
• The desperation score: what it is, why workers believe it exists, and why there's nothing stopping companies from using one
• How gamification and intentional psychological design keep workers accepting bad offers
• Why the "supply and demand" defense doesn't hold up — and what these platforms are really doing
• What it will take for algorithmic wage discrimination to finally become illegal

Dr. Dubal also shares her journey from public interest law to becoming one of the most recognized critics of Silicon Valley's labor practices, and why writing — real, effortful writing — may be the most important skill you can build in an AI-shaped world.

This conversation will change how you look at every app that pays people on the other side.

Because in a world where algorithms set your wages behind a black box, the real question isn't just whether the system is fair — it's whether anyone is allowed to ask.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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AI, Surveillance, and Your Rights: The Case That Changed Privacy Forever
Paths of Curiosity in an AI World

What if the government could track everywhere you’ve been, everyone you’ve contacted, and everything you’ve searched, without ever asking permission?

For years, that was dangerously close to reality.

In this episode, we launch our AI, Power, Law, and Civic Life miniseries with Nathan Freed Wessler, Deputy Director of the ACLU’s Speech, Privacy, and Technology Project, who took this question all the way to the Supreme Court and won.

He argued Carpenter v. United States, a landmark case that established a critical rule for the digital age: law enforcement must get a warrant before accessing your cell phone location history. But that victory is just one piece of a much larger story.

Together, we explore:

•  How AI-powered surveillance is transforming what governments can know about you 
•  Why your phone is one of the most powerful tracking devices ever created 
•  The hidden world of data brokers buying and selling your location information 
•  How facial recognition can lead to wrongful arrests, especially for people of color 
•  Why “I have nothing to hide” misses the point entirely 
•  What’s at stake for your future if privacy laws don’t keep up with technology 

Nathan also shares his journey from political organizing to arguing before the Supreme Court, and why the most important career decisions often can’t be planned.

This conversation will change how you think about your phone, your data, and your rights.

Because in a world where surveillance is becoming effortless, the real question is not just who is watching — but when they’re allowed to.

Paths of Curiosity in an AI World
Exploring tomorrow’s careers through the lens of AI
Follow us: @pathsofcuriosity

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