11 U.S. Presidents Who Were Entrepreneurs and What We Can Learn From Them

(to Celebrate Presidents’ Day)

11 U.S. Presidents Who Were Entrepreneurs and What We Can Learn From Them

In April 1982, President Ronald Regan gave a speech before the U.S. Chamber of Congress saying: 

“Entrepreneurs are heroes of modern times. They rarely receive the credit they deserve. Treasury Secretary Don Regan recently reminded the student body of Bucknell University that it was under capitalism that mankind brought ‘light where before there was darkness, heat where once there was only cold, medicines where there was sickness and disease, food where there was scarcity, and wealth where humanity was living in squalor.’ And much of what he was talking about came into being in the lifetime of many of us here in this room. But the societies which achieve the most spectacular progress in the shortest period of time are not the most tightly controlled, the biggest in size, or the wealthiest in material resources. They are societies that reward initiative and believe in the magic of the marketplace…” (Source: Small Business Trends)

As we take this day to remember our presidents, we want to also recognize and learn from those presidents who made entrepreneurial ventures, took risks, and helped add to the prosperity of this country. Although each of them was not successful, there is something to be learned from their stories. Today we will be recognizing 11 entrepreneur U.S. Presidents along with their challenges, resilience, and successes. 

These 11 entrepreneur Presidents are from both major U.S. political parties, and I understand that some of these Presidents are controversial to some people. By including them in this article, I’m not endorsing their political views. Instead, I’m trying to learn and teach what I can from their experiences as entrepreneurs. 

1. George Washington (1789-1797): 1st President

“The harder the conflict, the greater the triumph.”- President Washington 

While most presidents were entrepreneurs before they took office, President Washington didn’t become an entrepreneur until after his final term as president. For much of his childhood, Washington lived on a farm in Mount Vernon, Virginia, which was later inherited by his half-brother, Lawrence. When Lawrence passed away, Washington leased it from Lawrence’s wife and inherited it in 1761 (Source: History.com). He later renovated the estate into a mansion, gardens, a place to lay family tombs, shops, barns, and various living quarters. Washington even turned a large portion into farms as wheat being his main harvest. He then packaged the wheat and created GW Flour, one of the very first branded food products (Source: GoodReads review of “George Washington, Entrepreneur”), which was then exported throughout the US and Europe.

President Washington’s farm manager, James Anderson, later encouraged Washington to open up a distillery on the grounds of Mount Vernon, Virginia, and “with just a boiler and five copper stills, the 2,250 square-foot distillery became profitable almost instantly.” (Source: Ondeck) By the year 1799, Washington had one of the largest distilleries in the country making 11,000 gallons per year (Source: Business News Daily).

2. Abraham Lincoln (1861-1865): 16th President

“Always bear in mind that your own resolution to succeed is more important than any other one thing.”- President Lincoln

In 1833 and at the age of 23, President Lincoln and his friend, William Berry, opened up a general store called Lincoln-Berry in New Salem, Illinois. Many sources say that they were not very successful as they purchased inventory from other stores on credit and then made a profit by reselling the items. Although the economy was doing very well at the time, the location of their store wasn’t ideal as the town stopped growing. Lincoln had to sell his share of the store as a result, and after Berry died, Lincoln received his $1,000 debt (Source: Business News Daily), which resulted in Lincoln’s bankruptcy. Over 17 years, soon to be President Lincoln was required to pay his creditors back (Source: Legal Zoom). 

“Despite it all, Lincoln was known to rise triumphantly out of failure. He went on to launch a successful law practice in 1837, and became the only president to receive a patent in 1849” (Source: OnDeck), which was for a device to lift riverboats over sandbars. 

“The best way to predict your future is to create it.”- President Lincoln

3. Andrew Johnson (1865-1869): 17th President

“I realized, there are people out there who can beat me, want to beat me. And unless I continue to innovate and evolve, I am going to learn a painful lesson from someone who has.”- President Johnson

Before becoming President of the United States and running political campaigns, President Johnson was a very successful tailor and real estate owner. His mother was also a very talented seamstress who helped Andrew find an apprenticeship in Greeneville, Tennessee when he was only 18-years-old (Source: OnDeck). His talents with tailoring flourished, he opened up a shop in 1826, which became very successful, and he started investing in real estate from there. A fun fact about President Johnson is that while working at his tailor shop, “it eventually became a gathering place for political debate, and Johnson held his first meetings as an alderman (an elected member of a municipal council) in 1829.” (Source: OnDeck)

4. Warren Harding (1921-1923): 29th President

“America’s present need is not heroics but healing; not nostrums but normalcy; not revolution but restoration.”- President Harding

President Harding was raised in a family that found interest in the newspaper. He eventually attended school at Ohio Central College, and there, according to an article by Business News Daily, “he studied the newspaper trade in college after dabbling in teaching, insurance, and law,” and graduated at the age of seventeen. Two years later, he and several partners purchased the Ohio newspaper, The Marion Star, for $300 (Source: OnDeck) while it was near bankruptcy. Their biggest challenge was owning a Republican newspaper in a Democratic area (Source: OnDeck), but Harding completely turned things around with his wife’s help in managing the newspaper. The Marion Star eventually became “the city’s official daily newspaper.” (Source: CheatSheet) 

After receiving full ownership of the paper at the age of 21, Harding became worn down and had to spend time at a local sanitarium (Source: Business News Daily). He eventually recovered, found favor in his writing from local politicians, and earned revenue to run his political campaigns (Source: FreedomVoice Blog). He was a very successful businessman and after being in the newspaper business for 39 years (Source: TIME), he was able to sell the newspaper before dying in 1923 for $550,000, which is equivalent to $7 Million today (Source: Business News Daily). “Today, the business (from the newspaper in Ohio called the Marion Star) is still alive and owned by the Gannett Company, a publicly-traded media holding company.” (Source: NextShark)

5. Herbert Hoover (1929-1933): 31st President

“Competition is not only the basis of protection to the customer, but is the incentive to progress.” – President Hoover

At the age of 40, Herbert Hoover became a millionaire (Source: FreedomVoice Blog), but he found success from his labors by being diligent and resilient. When Herbert was 9-years-old, he became an orphan along with his two siblings. His uncle eventually took them in, but according to an article by Miller Center, “the young Hoover was shy, sensitive, introverted, and somewhat suspicious, characteristics that developed, at least in part, in reaction to the loss of his parents at such a young age.” Although he had average to failing grades except for math (Source: Miller Center), Hoover was determined and attended Stanford University. According to the same source, he worked in the clerk’s registration office to pay for tuition and began using his entrepreneurial skills by creating a student laundry service. 

After graduating college with a geology degree, he got a job with Bewick, Moreing & Co working 70 hours/week in a gold mine pushing carts. Hoover then left to start his own mining consulting business called Burmese silver mines, which focused on reorganizing failing companies and finding investors to pay for developing new mines. His company quickly employed 175,000 employees (Source: Entrepreneur), and the success that he built with his company earned him the title of “Doctor of sick mines.” (Source: OnDeck) By the time that he was forty, his wealth had grown not only from his company but from publishing a leading textbook on mining engineering. Other entrepreneurial successes he had included inventing a new process to extract zinc that had been lost and starting up in the Zinc Corporation, which later became part of a larger corporation (Source: Business News Daily).

6. Franklin Roosevelt (1933-1945): 32nd President

“The country needs and, unless I mistake its temper, the country demands bold, persistent experimentation. It is common sense to take a method and try it: If it fails, admit it frankly and try another. But above all, try something.”- President Roosevelt

At the age of 39, Franklin Roosevelt became ill with many symptoms, including paralysis of his legs. Although he was first diagnosed with paralytic poliomyelitis, his symptoms were shown to be more consistent with Guillain-Barre syndrome (Source: Pubmed). Despite his physical circumstances, he refused to accept that he would be permanently paralyzed. He became president in 1933, but before his political endeavors, he founded a hydrotherapy center in 1926 for the treatment of his disease, according to the FreedomVoice Blog. It became known as the Roosevelt Warm Springs Institute for Rehabilitation and still operates, serving about 4,000 people each year with all types of disabilities (Source: Entrepreneur).

7. Harry Truman (1945-1953): 33rd President

“I studied the lives of great men and famous women, and I found that the men and women who got to the top were those who did the jobs they had in hand, with everything they had of energy and enthusiasm and hard work.”- President Truman

Due to medical issues, President Truman is the only president elected after 1897 who did not earn a college degree (Source: Business News Daily). He then served in France during WWI and upon returning home, Truman and his wartime friend, Eddie Jacobson, opened up a men’s clothing store in Kansas City, Missouri, which was successful for three years before failing, due to the postwar recession. “After his shop went bankrupt, it took him 15 years to pay off his share of the firm’s debts. Nevertheless, the store established Truman’s reputation as a respected businessman, which in turn set him on the path to civic engagement.” (Source: OnDeck) This new path paved the way for greater success in other offices. According to the same article by OnDeck, he even joined the Triangle Club, which is an association of businessmen committed to improving the city, and became involved in activities with the American Legion. 

8. Jimmy Carter (1977-1981): 39th President

“It’s not necessary to fear the prospect of failure but to be determined not to fail.”- President Carter

When President Carter was 10-years-old, he stocked his family’s peanut farm with produce and took it to town to be sold. He continued to save the money he made, and by the age of 13, “he bought five houses around the plains which the Great Depression put on the market at rock-bottom prices. He then rented the homes to families in the area.” (Source: Abby Connect) 

The risk of losing the 2,500-acre peanut farm became very high when his father died of cancer in 1953. According to an article by Entrepreneur, Carter then returned home from the Navy to manage the struggling peanut farm. “Carter reportedly threw himself into farming the way he had with his naval duties, and hard work and effective management made the Carter farm prosperous by 1959.” (Source: Entrepreneur) 

In 1971, a sudden drought hit, bringing another risk to the farm, so Carter bought local farmers’ peanuts and sold them in bulk to big processors. “This led Carter Warehouse to gross $800,000 annually by 1971, up from a mere $184 when Carter started.” (Source: TIME)

9. George H.W. Bush (1989-1993): 41st President

“No problem of human making is too great to be overcome by human ingenuity, human energy, and the untiring hope of the human spirit.”- President George H.W. Bush

President George H.W. Bush found much entrepreneurial success from the oil industry, after graduating from Yale with an economics degree. He first started in oil as a salesperson for Dresser (Source: Time), then later formed a partnership with his neighbor, John Overby, and created the Bush-Overby Oil Development Co. in 1951. Due to family connections, the company was financed with nearly half a million dollars from Bush’s uncle (Source: Entrepreneur). 

The success of the company grew, and in 1954, Bush-Overby Oil controlled 71 wells, which produced 1,250 barrels of oil per day (Source: LegalZoom). By 1953, their company then merged with another independent oil company to create Zapata Petroleum, of which Bush became president (Source: Entrepreneur). After years of growth and in 1966, Bush was able to sell his holding and made about $1 Million doing so (Source: TIME).

“Be bold in your caring, be bold in your dreaming and above all else, always do your best.”- President George H.W. Bush

10. George W. Bush (2001-2009): 43rd President

“Prosperity results from entrepreneurship and ingenuity.”- President George W. Bush

George W. Bush earned his bachelor’s degree from Yale and then became the first US president to earn his MBA, which he received from Harvard. After school, he followed in his father’s footsteps in the oil industry, but took a different approach as he “searched mineral-rights titles in county courthouses around West Texas and then would see if the owners would lease those rights to oil companies.” (Source: Time) In 1977, he then founded his own company called Arbusto (Spanish for Bush), which focused on low-risk, low-return wells, and found a relatively low gas field (Source: Abby Connect). Eventually, the price of oil dropped, and their company became very high-risk. Spectrum 7 Energy Corporation jumped in and rescued their company, merging the two in 1984 with Bush as the CEO, according to an article by LegalZoom. “After losing $400,000, it was purchased by Harken Energy Corporation, and Bush served as a consultant to Harken,” (Source: LegalZoom)

After working in the oil industry for many years, Bush decided to move into sports and invested in the Texas Rangers MLB team with $600,000 (Source: Entrepreneur). According to the same article by Entrepreneur, he then sold his stakes for the team in 1998 for $15 Million, a 2,400% ROI.

11. Donald Trump (2017-2021): 45th President

“As long as you are going to be thinking anyway, think big.”- President Donald Trump

Donald Trump is a real estate guru. He studied real estate at the University of Pennsylvania Wharton School and invested in Philadelphia real estate while studying there. He took over his family’s company to develop it into an international brand and according to Abby Connect, in the 1970s he began branching into Manhattan skyscrapers and renamed the company Trump Organization. He’s built luxurious hotels such as the Grand Hyatt Hotel and Trump Plaza, Trump’s Tower on Fifth Avenue, as well as the Trump headquarters. In the 1980s, he started placing casinos in Atlantic City, adding to Trump Plaza, and Trump Castle. In 1990, he even opened up his own Trump Taj Mahal, known as his own “eighth wonder of the world.” (Source: Abby Connect) 

According to Time, Trump appears to own or control more than 500 businesses in some two-dozen countries around the world! He has been very successful, but not without several bankruptcies, according to Abby Connect. Amidst his many businesses all over the world, he has also published books, opened up golf and hotel resorts, owned beauty pageants, and created his own branded products such as Trump steaks, Trump University, Trump shuttle, and Trump Success Eau De Toilette (Source: Business News Daily). 

“Get going. Move forward. Aim High. Plan a takeoff. Don’t just sit on the runway and hope someone will come along and push the airplane. It simply won’t happen. Change your attitude and gain some altitude. Believe me, you’ll love it up here.”- President Donald Trump

Key Takeaways

Here are some of my key takeaways from this episode:

1. President  Washington the greater the conflict, the better the triumph. We savor the hard-won victories even more. 

2. President Lincoln taught us to not let failure stop us. Perseverance is a key attribute of successful entrepreneurs.

3. President Johnson taught us that unless we continue to innovate and evolve, we’re going to learn a painful lesson from someone who has. This is so true with tectonic shifts. 

4. Don’t be afraid to take risks. Be determined, don’t get caught up in the circumstances, and press forward as President Harding did. 

5. Current circumstances will not remain forever. Diligence and resilience go on a long way as President Hoover has proven. 

6. President Roosevelt encouraged us to be bold and persistently experiment. Try something. If it fails, pivot or move onto another.

7. President Truman taught that those who made it to the top were those who did the work, with enthusiasm and everything they had. Whatever we do, we should do our best and give it all we have.

8. President Carter taught us that we don’t need to be afraid of failure, we just have to be determined no to fail. 

9. President George H.W. Bush taught us to be bold in our caring and dreaming.

10. President George W. Bush taught us that prosperity comes from entrepreneurship and ingenuity. 

11. President Trump taught us to move forward, aim high, and create a plan. We shouldn’t wait around for others to do the work for us or to make things happen.

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If we desire monetization we have never before achieved, we must leverage strategies we have never before implemented. I challenge each of us to pick one thing that resonated with us from today’s episode and schedule a time this week to implement it to help achieve our monetization goals.

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    About the author

    Nathan Gwilliam

    Nathan Gwilliam

    I help organizations navigate tectonic shifts that are transforming the business landscape, so they can optimize marketing, accelerate profits, and make a greater difference for good.

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