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Here in the United States, bail can be an enormous deciding factor on who goes to prison and who doesn’t. And for how long they go or don’t go...regardless of guilt or not. 

But do you know how the bail system really works? Who profits from it? Who is put at a detriment because of it? Likely not. So we’re dissecting the bail system—and getting real about its inherent, systemic issues. 

Today on Business Casual, I’m interviewing Adam Foss, a widely respected criminal justice reform advocate and an advisor to the Bail Project. He’ll explain precisely how the bail system fits into the broader private prison ecosystem in the United States. A small taste?

Did you know the concept of bail dates back to feudal England? And really hasn’t been meaningfully rethought since serfs were a thing?

Or that some bail funds pick and choose which incarcerated people to help, while others take an “anything goes” approach, regardless of alleged offense?

There’s so much more to learn.

And after a summer of reading the words “donate to bail funds” over and over again, it’s high time you get an idea of what bail funds actually do...and why they want to be put out of business. 

Listen now.

Is your favorite business employing what could easily be described as contemporary slavery to cut costs and push product? Would you even know if the answer were yes?

The truth is, you probably wouldn’t. That’s because the prison-industrial complex in the United States is deeply entrenched in just about every sector of the economy, from military manufacturing to apple picking. And more often than not, that prison-industrial complex is rigged against low-income Americans and people of color. 

So what do we do about it? That’s what we’re covering today on Business Casual with Ashish Prashar, a widely respected justice reform advocate and former young offender. 

Ashish explains the importance of prison labor for both corporations and state economies, the necessity of prison-industrial reform, and the hard truth of America’s incarceration problem. 

But first, he masterfully provides the historical context for prison labor as it exists today—a system which relies on a Reconstruction era loophole essentially allowing for modern day slavery. 

This is a tough conversation to have...when was the last time you were forced to reconcile your modern beliefs with a Constitutional amendment ratified in 1865? But it’s way past time to have the conversation. Ashish offers a remarkable starting point for anyone who wants to learn more about the prison-industrial complex—I hope you’ll listen now.

+ While we’re here: I drew on my conversation with Ashish to write about the prison-industrial complex in my new Business Casual column. Read that piece here and subscribe to the weekly newsletter here.

If it’s true that what matters not is the grades you make but the hands you shake...the business world could have a major reckoning headed our way.

Networking, fostering, and building relationships is key to success in corporate America and beyond...so how does doing all that change when we’re working from home, often with no office return date in sight ’til 2021?

Today on Business Casual, we’re figuring it out with Dr. Laura Morgan Roberts, Professor of Practice at the University of Virginia’s Darden School of Business and an expert in the art and science of maximizing potential for people in organizations and companies.

As Laura explains in the episode, building relationships, boosting morale, and creating culture are paramount to succeeding in business and attracting top talent. Just about none of those things happen easily in a remote work environment. There’s also the individual toll of remote work—we get lonelier more quickly than in an office, and creativity can lag. 

So what are we to do to ensure business as usual stays as usual in this very unusual time? Laura has some tips, tricks, and ideas. Listen now to level up.

The work from home revolution has arrived...but is that a good or bad thing for the business world? Let’s walk through the pros and cons.

Pros: The ability to work from wherever means more opportunity in previously underserved and non-coastal cities. Less commuting means less pollution. Three words—work from bed.

Cons: A fully distributed workforce can be tough to scale. It’s harder to build both company culture and innovation remotely. No office snacks.

Today on Business Casual, we’re putting all of that in context with Matt Mullenweg. Matt is the founder and CEO of Automattic, which is the parent company of WordPress.com. He built Automattic to have a completely distributed workforce—1,200+ employees working from 77 countries and no HQ.

As Matt sees it, “the sun never sets on Automattic.” He’s adamant that the environment, the economy, and distribution of opportunity could all meaningfully change for the better in a widespread remote workforce world.

So it works for Matt and his team, but can it work for everyone? We’re about to find out. Matt thinks the companies like Google and Facebook that have announced WFH through the rest of the year will find it hard to go back to in-office work. 

So is this the new normal? And can it change corporate America for the better? Listen to find out.

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I’m not entirely ruling IPOs out quite yet, but the case for their competitor in public market access—direct listings—is growing by the second. Here’s why.

When we consider what makes systems of capitalism work, it’s hard not to think about access for both individual investors seeking to purchase stakes and individual corporations seeking their money. Often, the equilibrium between the two is decided by a very small group of very wealthy investors participating in an initial public offering. 

A direct listing, on the other hand, removes the underwriters from the equation. Shares are listed outright on exchanges with no real price guarantee. 

Which do you think serves as a better example of granting access to participants in a capitalist society? I know my answer.

And so does today’s Business Casual guest, Barry McCarthy. He’s the architect of the modern direct listing, and he was also the CFO of Netflix from 1999 to 2010 and CFO of Spotify from 2015 to 2020—a tenure during which the music streamer went public via a direct listing.

Barry sees the process of tapping into public markets like this: The so-called “modern” IPO hasn’t changed much at all since 1971, aside from the fact the interns on the roadshow are fetching iced oat milk cappuccinos instead of black coffees. It’s a supremely outdated process. So what can be done instead?

Direct listings...maybe. Barry will be the first to point out that they’re not for everyone. Listen to the episode now to hear why.

The fate of the U.S. economy comes down to one thing: access.

If every individual who wants it and every company that needs it can’t access capital markets, both wealth and job creation skid to a stop—and with them, so too does the power behind the U.S. economy.

By and large, we’re pretty okay and handing access to those looking for it—any old fool could download an app and begin trading stocks. 

But like a first attempt at homemade croissants, things could always be better. We’re facing a gaping wealth disparity problem and a pressing inequality of basic education. The first step in increasing access to public capital markets is solving for those...not an easy feat.

Adena Friedman—president and CEO of Nasdaq, the first woman to lead a global stock exchange, and today’s Business Casual guest—hasn’t let it deter her.

Adena’s been helming Nasdaq since January 2017, and during her tenure, she’s focused intently on issues of access—access for companies, access for investors, and access in general to capital markets.

In this episode, Adena will explain how we increase access in the right and healthiest ways. To her, allowing more companies and people to tap into public capital markets will necessarily level the playing field for individual and institutional investors.

But whose responsibility is it to ensure that increase in access happens? Listen to find out.

By now, you know the higher education system in the United States is broken. You didn’t need COVID-19 to prove it.

Because even before the postsecondary education industry was forced to pivot to remote learning en masse, a caste system was rapidly bubbling up within its ranks: 

The best of the best go to Harvard and become the ruling class…

While everyone else perishes in a middle-ground limboland that’s left entire swaths of the population—often low income and often minorities—robbed of the opportunity for upward mobility.

It sucks that students can’t go back to campus to do things like learn and network and party in person. But that’s not the real tragedy. This caste system is, according to today’s guest and NYU Stern professor Scott Galloway. 

As Scott sees it, the system has enabled us to completely lose sight of the importance of unremarkable students—those who might not be MIT material, but deserve a shot at college (aka the ticket to improving your socioeconomic standing).

In this episode, Scott tears apart that system (and almost every other system, for that matter) in a wide-ranging conversation about the future of higher education. Some buzzy sneak peeks:

Scott: “Harvard is a streaming video platform that costs $58,000 a year.”

He also says we’re headed toward a hybrid model of online and offline education that’ll bring with it a culling of the middle class of higher ed.

Is there a chance big tech saves higher ed...?

You don’t want to miss this episode. Listen now.

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Most years, this time in August is a boom for Target’s dorm décor section and purveyors of shower caddies and anyone selling that John Belushi Animal House poster. But 2020 isn’t like most years.

This year, higher education across the country will take place online, as COVID-19 has laughed in the face of the traditional residential college model. For anyone hoping to win back the beer pong championship belt, that’s devastating. For everyone else...it isn’t.

Moving to online, tech-forward education for the masses could be a net good for students—it makes degrees more flexible, more specialized, and more accessible, according to today’s guest: Dan Rosensweig, the president and CEO of Chegg.

But Dan thinks making higher education truly work for all means doing more than just sticking with online learning post-coronavirus. College degrees remain a fast-track ticket to upward mobility—in order to meet the needs of all who want them, we need a total reset of the industry. 

But how do you reset an industry worth $700 billion a year in the U.S. alone? It won’t be easy. And not all institutions will survive. 

Listen now to hear how we move forward.

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Olympic athletes are people, too. So how come the current business model of the Olympic Games, a commercial feat that would be entirely impossible without said athletes, fails to take them into account?

In this episode of Business Casual, we’re talking about the intersection of finance and elite athletics with Lauryn Williams, a four-time Olympian, three-time Olympic medalist, and the first American woman to earn a medal in both the Winter and Summer Olympics. Oh, and also she’s a certified financial planner.

As Lauryn told me, “The business model has needed overhaul for quite some time. I think that it's one of those things that it just started and began to snowball and nobody really knows how to undo something and start from the ground up.”

That might be where COVID can play superhero. Given an extra year between now and the postponed Tokyo Summer Games, the International Olympic Committee has the chance to rethink the support it offers athletes—many of whom are now forced to put off lucrative brand deals and pay for an extra year’s worth of intense training.

And even in normal, non-coronavirus circumstances, the cards can be stacked against them. There are countless variables that go into the viability of professional sports as a career—where you’re from, what your event is, and whose attention you get can be financial make it or break it moments.

If you make it, you’re Michael Phelps. 

If you break it, you’re stuck crowdfunding your way to competitions, working multiple jobs on top of training to be the best in the world in your sport, and even going into serious debt.

Lauryn explains it all in this episode. Don’t miss it.

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The Olympics as we know them have been around for 124 years. A lot has evolved since 1896, but it seems the business model of the Games is one thing not even time can’t change. 

With the Tokyo 2020 Olympics being postponed to next year (for now), it’s time to take the interim 12 months to reevaluate the economics of the Games. Because they don’t always make complete sense…

Hosting the Olympics is more often than not a money-losing endeavor. Did you know that it took Montreal until 2006 to pay off the last of its debt from the 1976 Games?

Tourism for host cities actually takes a hit when they welcome the Games. 

I learned that (and a whole lot more) from Andrew Zimbalist, today’s guest on Business Casual. Andrew is the best of the best in the field attempting to understand the economics of sport. He’s taught econ at Smith College for decades, specializing in the Olympics and the impacts the Games have on host cities and their economies.

In this episode, Andrew helps me tear apart the Olympics business model, taking into account the perspectives of host cities, athletes, the International Olympic Committee, and more. In addition to understanding what’s broken, we’ll talk about how we fix it. (Hint: Anyone at the IOC listening? We’ve got some thoughts.)

And most importantly: We’ll also parse out the causes, effects, and impacts of postponing Tokyo 2020 due to the coronavirus.

You don’t want to miss this one. Listen now.