On this week’s episode of Keep Going I talked with Theron McCullough, who calls himself a venture futurist and ecosystem engineer. That label sounds vague until you hear his path. First Techstars class in 2007. A small exit in 2010. A few years in Europe building paragliders and jumping off cliffs for a living. Then enterprise software at Pivotal, his own consultancies, a startup called Fifi that tried to become the system of record for private investors, then a tour through innovation banking at SVB, First Republic, and Citizens.

From the outside it looks scattered. To him, it is one straight line through startups, capital, and risk...

Some talks stick under your skin. This one did.

On this week’s Keep Going I sat down with Mechele Dickerson, a law professor at the University of Texas at Austin School of Law. Her new book is called “The Middle Class New Deal: Restoring Upward Mobility in the American Dream.” It comes out in January 2026.

I picked up the pitch because I have the same nagging feeling everyone else has. The middle class we grew up hearing about feels thin now. Like an old photograph in a cracked frame.

Mechele has spent more than a decade trying to write this book. That part alone makes her a good guest for a show about success and failure.

She started years ago with a book on homeownership. While she worked on that, she kept seeing a larger pattern. Families were not just locked out of houses. They were locked out of everything we used to connect with a stable life. She saw people who made a decent wage yet could not do basic “middle class” things without strain.

So she built a bigger project. She sold the first version of the book to a press. The idea was clear. It is harder than ever for lower and middle income people to become and stay middle class. It is even harder if you are not white. Then the world started shifting under her feet.

The 2016 election hit. Commentators suddenly cared about “middle class anger” and “anxiety.” She did not buy the story as it was told, but she knew she had to respond to it. So she rewrote the book to fit that moment.

Then 2020 arrived. A pandemic tore through the same families she had been studying. You cannot write about money, housing, and work in this country and ignore those years. She rewrote again. That second rewrite blew up. Reviewers tore it apart. The publisher walked away. A decade of work, gone in one email.

This is the point where many people quietly give up. Mechele did something different. She took the hit, walked away for a season, enjoyed Thanksgiving and Christmas, then came back and started from page one. A third draft. New press. New title. Same core idea.

That alone is a lesson. Sometimes the work is right and the timing is wrong. Sometimes you are right and the gatekeeper is wrong. You rest. You come back. You keep going.

The rest of the talk dug into what “middle class” even means. Mechele uses a simple income band, roughly seventy five to one hundred thirty thousand dollars a year. She picked it for a practical reason. It is the range many universities use when they hand out tuition breaks to families they see as “middle income.” It also adjusts over time, which matters.

She is quick to note that income does not land the same in each place. That money looks one way in Abilene, Texas, and another in Austin. Still, the markers are familiar. A home you can afford. A job with health care and some sort of retirement plan. The ability to send your kids to college without wrecking your own future. Maybe a bit put aside for shocks.

Her bluntest point is simple. We did not arrive here by magic. The old middle class was built by policy. The GI Bill sent people like my dad to college. New mortgage rules turned owning a house from a rich person’s trick into something workers could reach. Employers built health and pension plans when they could not raise wages during the war.

We treat those pieces as background now. They are not. They were choices. They could be made again in new forms.

Instead, college costs have climbed far faster than inflation since the eighties. Need blind admission is fading. “Merit” scholarships tilt money toward kids from richer families who look good on paper. Employers use a bachelor’s degree as a filter, so a diploma has become a ticket to even knock on the door.

On housing, the ladder keeps moving up. The average age for first time homebuyers is rising. People float the idea of fifty year mortgages, which Mechele, quite correctly, calls “rent” with different branding. If you buy at forty and pay for fifty years, do the math.

She walked through how zoning locks people out. Large minimum lot sizes. Rules that make it hard to put up multifamily units. Homeowners’ associations that wrap it all in “protecting values” while making sure cheaper units never appear. At city level, at state level, we have built a system that slowly pushes normal families away from the places where opportunity sits.

I pushed the conversation toward entrepreneurship, because the show often goes there. For a lot of kids, the fantasy now is that a startup will be their scratch off. You cannot count on a steady wage to get the markers. So you dream of building the next app, or site, or whatever, to leap straight over the grind.

She agreed with the feeling, but brought it back to ground. Starting a business takes capital. Capital comes from family wealth, or from a house you can borrow against, or from a system that lends to people with no cushion. If your parents do not have money and you do not own a home, you are playing with thinner odds. That does not mean you should never try. It does mean we should be honest about the risk.

Near the end I told a story about my own family. My grandparents in Ohio, steel town on the edge of West Virginia. They had a house. They had food on the table. My cousins had pools, big televisions, a couple of cars in the drive. All on a worker’s paycheck or a small business. Nothing lavish. Just steady.

Standing in modern Chicago or New York, you do not feel that world anymore. The core feels like a stage set for the very rich. Everyone else services it from the outside.

So I asked the question out loud. Can we go back. Or is that period gone for good.

Her answer was measured. We cannot rewind time. But we can recognize that the old middle class was a choice. It came from rules and programs that treated stability as a public goal. We can make new choices. Tighter rules around predatory loans. Better ways to fund college so a degree is not a lifetime chain. Zoning that lets builders put up real housing, not just luxury towers and big lots.

None of this is easy. None of it fits on a bumper sticker. It is easier to bark about culture than to rework tax codes or housing law. That is why very little changes. But the path is not mysterious. We have done it before.

As we wrapped, she circled back to why she kept going with the book. She is not writing for one side. She wants people in both parties to see that a strong middle class is not just a feel good phrase. It is the base of a stable country. It is who buys the toaster ovens, the cars, the fridges. It is who keeps the lights on in the real economy.

For me, this conversation lit up a vague anger I have carried since walking those polished streets in big cities. The feeling that something is off, that the store window that used to be for everyone is now for a tiny slice at the top. Mechele’s work gives that feeling names and numbers and a path forward.

Her book is “The Middle Class New Deal: Restoring Upward Mobility in the American Dream.” It lands in January 2026. When it does, I think it will give a lot of people language for what they see and cannot quite explain.

In the meantime, the lesson is simple and personal. If she can drag a book through three full rewrites, one public rejection, and a changing world, the rest of us can take one more swing at whatever hard thing is sitting on our desk.