Building a Playbook

On How to Win in the Midwest

I am a business media sicko. That is probably implied because you are reading my business/technology/deals blog. I like reading about how the world of business operates because it helps me view the work that I do on a day-to-day basis in a clearer light. And over the years I have consumed a lot of content that has changed the way I think about the world. Be it the acquired podcast, eboys, The Power Law, The Cold Start Problem, Play Bigger, The Mom Test, The Founders Podcast, The All-In Podcast, The Fish that Ate the Whale, Americana: A 400-Year History of American Capitalism, Bad Blood, Hamilton Helmer’s 7 Powers, Creativity, Inc., The Innovator’s Dilemma, Zero to One, the TBPN Podcast, and many more - I would say that my “content diet” leans heavily into understanding how business works. Even when I watch television or movies for leisure, I find myself attracted to the stories that talk about entrepreneurship and building something (s/o season 3 of Mad Men, maybe the GOAT). I just like learning about business.

But there is a problem: with the exception of Sam Walton’s Made in America (which I HIGHLY recommend), basically none of these have anything to do with the Midwest. I can’t even find a reliable history of Kroger or P&G, companies that have been around forever and have pretty interesting founding stories. Instead, most of my consumption has to do with tech (makes sense considering my career), or some stupid company on the coasts. And look, I have nothing against either coasts, but I am not sure I really care what happens on the coasts in relation to my own career or the companies I invest in. Sure, if you can make it in New York, you can make it anywhere, but I have also seen plenty of great Midwestern companies bought by New York PE firms sputter along and not really define success.

When I look around at successful companies in my backyard, they look pretty different than the successful companies we read about on the front page of the Wall Street Journal, or get air time in your favorite business Newsletter, or get featured on your favorite business YouTube channel. Sure, they have some overlapping characteristics, like an interest in cash flow and profit (although, that’s not always true / similar). But how they have been built always seems slightly different.

Unfortunately, I haven’t been able to find anybody who tracks or explains these differences effectively. There is no universal, overarching theory about what makes a Midwestern company successful. Of course, there are theories about the decline of the Midwest (read: the Rust Belt), but most of those are high-class BS, speaking from first hand experience.

But, sure, I live here but nobody else does, so does that even matter?

WRONG.

I have already written about the Economic Viability of the Midwest. The punchline for those who don’t want to double dip on my brain today is that the Midwest is very economically viable, it’s a huge economy, it has a ton of economic diversity, and there are some interesting trendlines that should get locals excited.

The Midwest contains ~70 million people, or more than 20% of the U.S. total population. And if you turn back the clock, from 1880 to 1970, the Midwest was the center of America, literally and metaphorically. The industrial base in our country was BOOMING, population was booming, and this was where the opportunity in our country existed. Detroit was the richest city in the country and Chicago actually was our SECOND city.

But then globalization happened, and our nation’s economy shifted away from blue collar, industrialized epicenters, to more white collar, services based industries. People moved South and into suburbs (I think the entire state of Florida is America’s Suburb, but that’s a different article, a different blog). In 1969, the Industrial Midwest had 33% of all US Manufacturing jobs, despite having less than 25% of the population. In 1900, the Midwest had 36% of the US population, but by 1980, that number had shrunk to 26%. US Manufacturing in general shrunk over that period, from 19.6 million jobs in 1979 working in manufacturing in the total country (a peak), down to 12.8 million in 2019. Most of that decline was absorbed by the Midwest. Illinois machinery employment dropped by 46% from 1990 - 2019. Ohio machinery employment dropped 32% and Michigan dropped 23% during that same period.

Even the largest companies in the world were largely based in the US. In 1970, 40% of the Fortune 50 were based in the Midwest. Today, that number is 16-20%. In 1970, we had Detroit auto OEMs, Chicago large industrial and retail, Ohio had consumer and industrial companies.

The summary narrative is that the Midwest has one foot on the banana peel and another in the grave, as my Uncle Nate likes to say. The trendline has been pointing downward for 50+ years.

But, critically, the region hasn’t gone to Zero - far from it. While the trendline fell off a cliff in the late twentieth century, it has mostly leveled off. The Midwest is still the leader in US manufacturing and dominates the freight and logistics industries and anchors food production. It is the logistical switchboard of our entire country. And the things that made it great once, largely still exist: dense infrastructure, navigable waterways, rail network, interstate connectivity, great engineering talent, and general purpose industrial know-how.

Not only that, but it’s just better to live here. Sure, it’s less expensive, but that’s not the only thing. Schools are good, lifestyle is actually enjoyable, climate is moderate, values are strong, and the list goes on.

And in 2024-2025, the Midwest was the ONLY census region where every state gained population. People want to be here. You can tell because people are increasingly here, especially as of late. And it’s not just one city booming and driving it forward for everyone else, like parts of the Sunbelt or the West.

And not to mention, the total economy in our country has BOOMED, unequivocally. So sure, on a relative basis the Midwest economy it has declined, but on a nominal basis, the Midwest GDP has grown by 2.5x since 2000, from $2.7 trillion to $6.5 trillion in 2025, approximately. Roughly comparable to Japan, Germany, or India. The story has less to do with Midwest decline and really the Sunbelt & West’s rapid rise.

So the question is not whether or not the Midwest is relevant. The answer is fairly obvious - of course it is. It’s one of the central nodes of the largest economy in the world, one of the greatest bastion’s of economic activity the world has ever seen.

The questions are: why isn’t anybody studying it? What makes this region different from everywhere else?

And maybe more importantly, what does it take to win here?

Again, I don’t think the same playbook that is applied to Northeast conglomerates or west coast media and tech companies applies to Midwestern success stories. I just see too many differences when comparing comapnies across the region. But I can never find data on how they are different and what different strategies need to be applied here versus elsewhere. Hiring is different, pay is different, account management is different, and so much more.

So again, what’s the playbook for winning in the Midwest?

That’s an endeavor I am deeply motivated to try and tackle. My pal, Sean Cox, and I are doing our best to try and answer that riddle. We have recently launched our podcast, How to Win In the Midwest, with the express intent of discovering what makes a great midwestern company so great, and, maybe more importantly, what lessons can the next generation of businesses and business leaders apply to themselves to achieve greatness.

We are not going to publish weekly - at most we will be doing this monthly. This is largely because we want to go deep on the topics we are covering. I highly doubt we will have any guests on, but you never know. I don’t plan on running any specific podcast best practices to grow the audience. I just want to figure out what makes a great midwestern company great. That’s it. This is a research project. I am guessing I will be publishing a lot of my findings in this blog along the way, but no promises.

If you are also interested in figuring out this playbook, I hope you will join along.

Find it here: