Four CEOs that Overcame Incredible Adversity

In the world of entrepreneurship, the leadership behind a corporation is extremely important. The CEO of a company can either lead it to crash and burn or to unfathomable heights. One thing is for certain — all successful CEOs do not give up easily in the face of adversity. This article will rank the top 4 CEOs of this decade that had the grit necessary to be successful in his or her career.

4) Sallie Krawcheck

Sallie Krawcheck didn’t start off her career as an entrepreneur. She began her career as an equity analyst for Sanford Bernstein. Within six years, she became the chairwoman and CEO of the company. She was dubbed by Fortune as “the Last Honest Analyst” because of her impartial advice. Krawcheck was later named CEO of Citigroup’s Smith Barney unit, and was at that time one of the most influential people in the world. A few years later, she became the CEO of Citi’s wealth management business.

However, her meteoric rise to the top was certainly no coincidence. In an industry dominated by men solely driven by money, she stood out. She carried integrity and creativity. She brought a perspective that was unique on Wall Street, and most importantly, she was driven by meaning and purpose. There was certainly no doubt about her abilities. When the financial crisis hit in 2007, Krawcheck’s unit contributed $12.9 billion of the bank’s $81.7 billion revenue. Her unit became one of the brightest spots in Citi’s gloomy days.

However, in February 2008, two Citigroup-sponsored hedge funds, Falcon and Asta/Mat both lost most of its value. Falcon lost 80%, and Asta/Mat lost almost everything. Krawcheck insisted that investors should be compensated for their losses because those were extraordinary declines and the risks of the funds were misrepresented to investors. Showcasing her vision and her sense of purpose, she believed that a lack of compensation would result in lawsuits and angry clients who would threaten to leave the bank. Even though Citigroup eventually compensated their clients, they did so reluctantly, and this led to Krawcheck’s first strike with CEO Vikram Pandit. Over the next few months, Citigroup had a tumultuous time, and every time a tough decision had to be made, Krawcheck had clients in mind, and Pandit had money in mind. In the testosterone-filled world of finance, Citigroup turned a blind eye to Krawcheck’s insights and eventually got rid of her.

Soon after, she got hired by Bank of America to head Merrill Lynch in 2009. Despite having an incredibly successful two years as president of Merrill Lynch’s wealth management unit, she was once again driven out due to “restructuring”.

Through her own experience of discrimination in the apex of the financial world, she has since founded Ellevest. Ellevest is a digital investment platform for women that helps to close the gender gap in investing in the U.S. She features on our list because she is never gave up on her focus on clients despite it costing her job, and when none worked out, she created something to fix the problem not just for herself, but for women all around the world.

3) Charlie Kim

Number 3 on our list is Charlie Kim, the CEO of Next Jump. Charlie started the company from his dorm in Tufts University in 1994. As he was in long-distance relationship, his phone bill began getting expensive, which prompted him to go into business to curb the costs. He started convincing merchants and companies to buy advertising in directories that he would then distribute around school.

Starting from paper directories, he eventually went online during the dot-com era. He managed to raise about $15 million from angel investors for Next Jump, and hired around 150 employees. His business began booming. He had offices all around the states in Boston, D.C., Chicago, San Francisco, and New York.

However, the dot-com bubble burst not long after. He could no longer afford to pay any of his employees. Eventually, he was nine months behind on rent, and his mailbox was stuffed with eviction notices. Debtors began suing him directly because his company was broke. He recounts that he woke up for sixty days in a row with a nosebleed. Using his charisma and creativity, he managed to convince his landlord to let him use an empty space in the building.

It was at this time that he gathered a small team, and he set out to rebuild his company from scratch. By being opportunistic, he was able to acquire the customer list of a top competitor, which helped his company grow at an incredible rate. He remained optimistic that he would succeed, and he was not wrong. He has already rejected offers in the billions, so that he can continue working at the company he worked so hard to build.

2) Dawn Halfaker

Dawn Halfaker is the founder and CEO of Halfaker and Associates. Her company provides professional services and technology solutions to the federal government. Dawn is more than just your average CEO. She was a military police captain that served in Iraq, leading troops into combat. However, she no longer serves in the military due to an ambush in Iraq, in which she lost an arm.

According to an interview with Huffington post, “It was a routine, 3-hour patrol mission looking for enemy activity on a relatively quiet night until, after about two and a half hours, we drove right into an ambush. I was in the first vehicle of the convoy, and one of the rocket-propelled grenades hit me and one of my squad leaders, severely injuring both of us. I was deafened from the sound, blinded by the flash, and incapacitated by the pain. I looked around, trying to assess the damage, but didn’t really look at myself. I remember getting back to the police station, being pulled out of the vehicle, lying on the ground and eventually getting loaded into a medevac helicopter. That was the last thing I remembered of my tour in Iraq.”

When she woke up from her coma, she had been transported back to the United States and her parents were by her side. It was only then did she learn that she had lost her arm. At that time, she felt like her life was over. She was struggling to come to terms with the fact that not only did she lose her arm, she also lost her career.

Knowing that she wanted absolutely no contact with politics having interned at Capitol Hill in the past, she applied to a job at the Defense Advanced Research Projects Agency. It is a research agency that seeks to bring cutting-edge technology to the U.S. military. Her focus was on medical technology, and that was how she came up with the idea for her startup.

Currently, half of her employees are veterans and 10% of them are wounded warriors. She does this because she understands the difficulties that veterans face after returning from a warzone. She says, “In the military, we’re not focused on climbing the corporate ladder or finding jobs, so it’s often difficult for veterans to figure out how to transfer our skills.”

1) Oprah Winfrey

Oprah is number 1 on our list because the amount of hardships she had overcome as a child is quite mind-boggling. For her to be the billionaire she is today, it took a dash of luck, as well as incredible discipline, brilliance, and ability to overcome.

Oprah was born to an unwed teenage mother, which resulted in her spending her first years on her grandmother’s farm in Mississippi while her mother looked for work in the North. On the farm, her grandmother taught her how to read at an early age. She was an incredibly gifted child. By the time she was three, Oprah could recite poems and Bible verses in local churches.

However, her world took a turn for the worst when she turned 6. She began living with her mother in Milwaukee in an inner city apartment. During the days when her mother was working long hours, she was repeatedly molested by male relatives as well as another visitor. The sexual abuse she took lasted from when she was 9 to 13. Due to the emotional devastation she suffered, she tried to run away from home to live in a juvenile detention home, but was rejected as all the beds were filled. At 14, she left home and was completely on her own. Not long after that, she gave birth to a baby who died in infancy. After that trauma, she went to Nashville, Tennessee to live with her father.

Vernon Winfrey was a disciplinarian. He was strict, but he was able to provide the secure life that Oprah so badly needed. He also developed her genius by requiring her to read a book a week and write a book report on it. Under this structured environment, she flourished by becoming an honor student, and an award-winning orator.

After Oprah turned 17, she won the Miss Black Tennessee beauty pageant, and was offered her first on-air job at a local radio station, WVOL. She got a full-ride scholarship to Tennessee State University, and after she graduated, she went back to work at WVOL, and her broadcasting career took off. Since we all know how successful Oprah turned out, I will not delve into her countless achievements. Just bear in mind that not only did she overcome her childhood atrocities, she also defied all odds by being a successful black woman in the entertainment industry, an industry generally dominated by white folks. Since this is an article about CEOs, Oprah is the founder and CEO of Harpo Productions, which produced “The Oprah Winfrey Show”, “Dr Phil”, and many other world-renowned shows. She is also currently on the board of directors at Weight Watchers.

Originally published at on July 6, 2016.

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