Part of a seven-part series exploring what 100+ independently written letters from America’s business community reveal about the country and its people at 250. Read more in the series.
America was founded in part over a fight about commerce and the right to trade and sell without the Crown taking its cut. Free enterprise has been bound up with the American idea from the start.
Two and a half centuries later, that idea has held up better than almost anything else the founders argued about. A 2026 Gallup survey found small business is the most popular economic concept in America, viewed positively by 95% and unchanged since 2010. Free enterprise ranks second at 77%.
But free enterprise has slipped nine points since 2010. The business leaders who wrote Birthday Letters to America take that seriously. Taken together, they make a distinctly American case for enterprise. It rewards initiative, but it also depends on conditions no single entrepreneur controls: fair competition, public trust, and the rule of law.
The promise at the center of it was never success. It was the chance to try.
What America promised
Dan Withrow, CEO of CSS Distribution Group in Kentucky, started working at 11, delivering newspapers. His parents both became successful business owners, and so did his older brother.
“I have not simply heard about the American Dream. I have lived it. ... America never promised me success. What it promised was opportunity—the freedom to dream, to work, to fail, to learn, and ultimately to succeed.”
His own path zigzagged until he found a passion for sales and helping manufacturers solve packaging challenges. After 25 years of building relationships and earning trust, one customer gave him the opportunity to start his own business. Twenty years later, that customer is still a customer.
“Entrepreneurship was not something we simply admired—it was something we lived. Watching my parents build their own businesses taught me that success is rarely handed to anyone. It is earned through hard work, perseverance, integrity, and a willingness to take risks.”
Withrow doesn’t treat the payoff as the finish line. He credits the employees, customers, vendors, mentors, and family who believed in him before he had much to show for it — and writes that passing along what he’s learned may be one of the greatest responsibilities he has.
The people in between
Eric Hoplin, president and CEO of the National Association of Wholesaler-Distributors, travels the country every week meeting distribution leaders. It’s the business that sits between the people who make things and the people who need them, and almost nobody notices it. He calls them “America’s unsung heroes.”
“Distributors operate behind the scenes, serving as the backbone of our supply chain and the connective tissue of our economy. They keep hospitals, schools, manufacturers, retailers, restaurants, and every other industry sector stocked with the critical supplies needed to serve our communities.”
What strikes him isn’t what distributors carry. It’s who they are. Across every line of trade, he finds the same character.
“They are entrepreneurs, they work hard, they are patriotic, they have grit and determination, they are innovative, they care deeply about their customers and employees and they take great pride in the important role they play in helping millions of people live their American dream.”
Enterprise isn’t only the companies people can name. Every one of those distributors was once a bet somebody made, and most of us will never know their names.
The most audacious startup ever launched
Jill Johnson is a fourth-generation entrepreneur. Her great-grandfather, grandfather, and father each bet on an unproven idea, and when she started her own management consulting business, she was making the same bet. So it’s no surprise she sees the Founders as entrepreneurs.
“Your founding 250 years ago did not promise success or wealth to your people. But you did promise that we all had the chance to try. Now two and a half centuries in, you are still the most audacious and impactful startup ever launched.”
Entrepreneurs don’t wait for permission, she writes, and neither did the Founders. In her consulting work, what moves people past being stuck is the moment they give themselves permission to think differently.
“That fearless willingness to try is among the most patriotic acts any of us in business will ever take. Our Founders understood this. They were consultants too. They were just focused on nation-building.”
If the founders were entrepreneurs, the country was always a venture: unproven, uncertain, and built to survive its own failures.
Liberty to innovate, opportunity to compete
Trey Richardson is managing partner at Sagac Public Affairs, an Oklahoma firm that helps employers and trade associations make their case on federal policy — work he describes as protecting the competitive marketplace.
“Our American experiment began with a profound and audacious premise: that free individuals, granted the liberty to innovate and the opportunity to compete, could build the most extraordinary nation on earth. ... The true strength of this country has never resided in its federal institutions or the halls of government. It lives among entrepreneurs willing to take calculated risks, employers creating jobs, the workforce driving our economy forward, and the communities solving problems through local action.”
In his view, a free economy isn’t self-running. Prosperity depends on people willing to take part in the decisions that shape it.
“As we celebrate America, we reflect with deep gratitude on the foundational freedoms that make our work possible: the freedom to build, to compete, to advocate, and to meaningfully contribute to the governance of our republic.”
For Richardson, enterprise isn’t practiced apart from the country’s rules — it’s practiced inside them, and keeping the field open takes people who show up to help shape it.
Trust is the price
Erik Wohlgemuth, CEO of Future 500, studied American history and westward expansion, and came away believing the national story has always been one of imperfection and continual striving to close the gap. He admires what business has built. He’s also clear that the system depends on conditions it can’t guarantee for itself.
“Capitalism is not self-executing. Markets flourish only when they are grounded in trust, fair competition, and the rule of law. Left unchecked, economic success can become economic privilege. Wealth can concentrate into power. Competition can give way to cronyism.”
He doesn’t treat those as failures of free enterprise, but as warnings about what happens when the values sustaining it get neglected — and he puts the responsibility squarely on business leaders.
“As America enters its 2nd quarter century, the measure of business leadership will not simply be the wealth it creates, but the trust it earns. The founders gave us a framework for liberty and free enterprise. It falls to our generation to renew it—to ensure that capitalism does not devolve to cronyism but remains open, competitive, innovative, and worthy of public confidence. This is not a partisan calling. It is an American one.”
The test of free enterprise isn’t only how much it produces. It’s whether people still believe it’s open to them.
A chance, and a responsibility
Five writers, working independently. A paper route in Kentucky that turned into a distribution company. An industry nobody notices that keeps the shelves stocked. A fourth-generation entrepreneur who looks at 1776 and sees a startup. A lobbyist who thinks the freedom to compete and the freedom to vote are the same inheritance. A CEO warning that none of it runs on its own.
All five landed in the same place: the promise was never success. It was the chance to try. Two hundred and fifty years in, that chance is still the thing worth protecting.
