Top 10 Decisions That Entrepreneurs Took, Which They Regretted Later

There’s no other way to say it – Starting a company is tough, and venturing into entrepreneurship is not intended for the faint-hearted.

Entrepreneurship offers boundless potential for those who tender absolute belief in it and live by its norms. At the same time, however, it is also a way of living that can rework the entire course of your life.

An extremely fine line that separates success and failure in the field of business and Entrepreneurship offers no way around it – you either head in the right direction or not.

So what defines success if there are so many variables that can lead to failure impacting revenue, confidence, and even moral strength?

No one’s ever born an expert. Before you learn how to run, you need to learn to walk and how many times have you fallen down before you took your very first steps?

We’ve compiled a list of entrepreneurs who were initially struck down by questionable decisions. Having understood and rectified them, they are now successful entrepreneurs. Don’t you want to be one too?

There isn’t any success Manthra for an ideal entrepreneur experience. And by this article, we try to represent the strength every person needs to possess in turning defeats into victory – “The Entrepreneur Mindset”.

1.    Leo Laporte- Founder TWiT Networks

Leo Laporte had initially struggled over the course of starting the company. He developed a range of skills in multiple respects and tried to do everything on his own, which even you would be under the decision right now. This ultimately ended with him having a lot more on his plate and not finding enough time to actually run his business.

But after hiring a business partner and successful delegation of duties, he was finally able to manage the business and finally obtain a profitable turnover.

Effective leadership is when you take in your workforce into a single entity that works effectively towards a commonly manifested objective.

leo laporte- founder twit networks


“Deleted Twitter and Facebook from all my mobile devices and it feels so good!
I just dont need the drama” 


2.  Rand Fishkin – CEO of Moz, Co-Founder of

Rand was initially fond of only “big-bang” projects, ones that had a development time of more than a few years. Although a few of them clicked right away, as time went by unexpected delays caused them to shelve many of them, which took a profound toll on their revenue.

He says that “Missing something you budget and plan for by more than a year is really bad news in the startup world.”

rand fishkin ceo of moz , co-founder of

“Best way to sell something: don’t sell anything.
Earn the awareness, respect, and trust of those who might buy.”


 3.  Sandi MacPherson – Editor-in-Chief, Quibb

Sandi went almost 6 months developing a product that believe it or not, she thought she wouldn’t even use quite often. Making a product that isn’t sold brings resounding losses in money, time, and most importantly your company’s stature in the market.

Every CEO needs a distinct understanding of the market understanding the trends of sales with a fair share of experience in investing in the right opportunity.

sandi macpherson ,editor-in-chief, quibb

“The welcome email is your best opportunity to develop a relationship with
someone who’s already interested in your product..”


4.  Dharmesh Shah – Co-Founder and CTO, HubSpot

Having successfully built a software company with $10million+ revenue, Dharmesh went on ride his luck by being a parallel entrepreneur by building a different startup. That proved to be more bane than a boon for him. His initial team felt left abandoned while the new one couldn’t gather enough revenue in the market.

Startups require a lot of effort to stay successful in the market with everyone trying to better their competitors. It’s a full time- consuming job that requires your complete and vigorous passion.

dharmesh shah – co-founder and cto, hubspot

“Sleep is that time you’re working on startup problems with you eyes closed.”


5.  Hiten Shah, Co-Founder at KISSmetrics

Hiten Shah spent close to a million dollars on a web hosting company, by perfecting in all respects. However, the company failed in being a genuine crowd-puller leading to a heavy loss of revenue.

However, by focusing on the needs of the customer together with analyzing growth potential Hiten was able to co-found two highly successful analytic companies –KISSmetrics and Crazy Egg.

Starting a company with simply the initial urge will only lead you in the opposite direction. Entrepreneurship is all about choosing the smartest way to work.

hiten shah, co-founder at kissmetrics


“In my experience, human problems are the biggest threat to a company’s well-being, and it usually happens when there’s office politics, you’re too distant from your team, or you’re way too involved (two extremes).”


6. David Lucatch, founder and CEO of Yappn Corp.

The initial years of Yappn Corp. were filled with the struggle for David Lucatch. However, nothing was proving to be heading in the right direction.  Failure tends to leave a mark on oneself that can only be confounded by success.

David Lucatch continued persevering and after a few months, Yappn started gaining remarkable market share.

david lucatch, founder and ceo of yappn corp.


“During these trying times, I poured all my energy and focus into doing whatever it took to succeed and leading my team by example.”


7.  Derek Sivers – Founder of CD Baby

Derek Sivers had a rather confronting experience in the past with his employees who staged a mutiny to get rid of him. They were focused primarily on benefits rather than cliental.

However, only in the future did he realize he could easily have prevented an occurrence that impacted the culture of the organization.

His words – “Fire the rotten apple in your bunch immediately”.

derek sivers – founder of cd baby


“Don’t be on your deathbed someday, having squandered your one chance at life, full of regret because you pursued little distractions instead of big dreams.”


8.  Fred Smith – CEO, FedEx Express

FedEx was able to build its business model revolutionized the shipping industry but before its success, Fred Smith’s college professor disagreed to it and he even received a poor grade on an assignment where he pitched the idea for the company. No one remembers the professor, but now everyone remembers Fred.

fred smith ,ceo, fedex express

“Leaders get out in front and stay there by raising the standards by which they judge themselves—and by which they are willing to be judged.”


9.  Leo Babauta – Best-selling author

Leo toiled at a dead-end job he hated for a long period of time and attributes it to “the fear of failure and lack of belief”.

Finally, his venture into blog writing has now made him a bestselling author and now he says, “Knowing what I know now, I’d have started a decade earlier.”

Starting late indeed is the worst-case scenario. Attributing fear to fuel your desire can certainly drive you to maintain your goal of being a successful entrepreneur.

leo babauta – best-selling author


 “Doing a huge number of things doesn’t mean you’re getting anything meaningful done.”


10. Jeff Bezos- CEO, Amazon

Before Amazon became a household name, Jeff had several failed ideas- one of which was an auction website, zShops that failed miserably. However, he repurposed the idea into what would eventually become the Amazon Marketplace.

jeff bezos- ceo, amazon

Blood, Sweat, and Tears; paired with countless sacrifices, pains and losses is what a startup is made of. Market Validation is vital because you won’t get investors if you don’t know your numbers. Your idea is your brainchild, so stick to it even when all the odds are against you.

Each and every one of these entrepreneurs you saw above is human. They take failure as stepping stones to success without losing an ounce of self-belief. Their positive reaction to defeats is what allows us to label the term “successful” before their designation as Entrepreneurs.

“We see our customers as invited guests to a party, and we are the hosts. It’s our job every day to make every important aspect of the customer experience a little bit better.”

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5 Entrepreneurs Who Rose From The Ashes To Become Success

As they say, success is not easy. While some are comparatively lucky and take on businesses that were already successful, maintaining standards may be more difficult (look at Tim Cook) as expectations are involved. For others, and they are the majority in a world where everyone is hungry for everything, it is a matter of stretching the human limits to the extremes, though they go on to show what amazing creatures humans are. Here we look at five people who started with next to nothing in the most difficult circumstances and went on to build brands that still continue to inspire us with the effort that went into their making and the heights they are continuing to achieve.

Oprah Winfrey


The 62-year-old Oprah Gail Winfrey may today be the most powerful woman in the United Sates, but that has not always been the case for her. Born in Kosciusko in Mississippi to a housemaid and a coal miner, Miss Winfrey had to endure such extreme poverty for the first 6 years of her life while living with her grandparents that she had to wear potato sacks and eat leftovers.

When she went back to live with her mother, she was violently assaulted, something she revealed to her viewers on her show much later, in 1986. At 14 years of age, she became pregnant with her first child, which ended in a premature delivery, much to her distress.

Things got better only when she went to live with her father, a man who was very strict and who was unwilling to settle for anything that he thought was not good for his daughter, in spite of the poverty. She won a full scholarship to the Tennessee State University.

The start to what was later to become one of the most successful careers in history was the job of a news anchor she got at the age of 19 at a local radio station for the black community in 1983.

Since then, there was no looking back for this woman, who found fame as the host of the most popular TV show of the time ‘AM Chicago, which is now known as The Oprah Winfrey Show, and is the most successful chat show in American television.

She changed the course of television chat shows, through what is now known as the ‘Oprah Effect’, by shifting the focus to a confessional mode, often making it a cathartic experience for the participants. The ‘Oprah Effect’ was felt the most in the 2008 presidential elections, where her support drew in 42000- 1600000 votes for Obama in the Democratic primary alone.

Some of the most memorable moments of her show are the coming out of Ellen DeGeneres, another hugely successful chat show host, as lesbian, and the public confession of Lance Armstrong.

By 1988, in spite of the enormous success she had attained, she felt tired of working for others, not being in control of something which meant so much for her. So she founded her own production company Harpo Studios, which today has more than 250 employees, and for which she was named the most powerful woman in entertainment in 2008 by The Hollywood Reporter.

She is also an enthusiastic supporter of philanthropy, having created Oprah’s Angel Network in 1988, and the Oprah Winfrey Leadership Academy for Girls in Johannesburg, a school spread over 22 acres where she still teaches via satellite.

Steve Jobs; Apple


Born to a Syrian immigrant father and a Catholic mother and given up for adoption to parents who were too scared to love him for the first few years as they thought he would be taken away due to legal complications, Jobs’s success story is truly phenomenal.

And that Steven could be adopted by the Jobs couple only after they promised that they would provide him with a college education, became ironical when they could no longer afford college for the already disinterested Steve.

Jobs’ first job was to be a video game designer with Atari, which he left within a few months to run away to India to seek spiritual enlightenment. A thing called Apple Computer was started by the 21-year-old Jobs and his friend Steve Wozniak in 1976 in the garage at Jobs’ place, and it was funded by the selling of Jobs’ Volkswagen bus and Wozniak’s scientific calculator.

Debuting with Apple I at $774,000, the company went on to have a 700% growth with $139 million in Apple II. In 1980, the company was valued at $1.2 billion on the first day of trading as a publicly traded company.

This unbelievable rise was not to last long, however. The next few products failed to cut through the public, and IBM took a sudden leap, something which even the Macintosh of 1984 could not salvage in a world where it was now required to have an IBM support system. This, in spite of being superior in quality and performance when compared to the IBM PCs.

This gradually culminated in the expulsion by the executives, headed by the CEO John  Sculley, of the man who had co-founded the company where he had no official position, in the year 1985. Again ironically, Sculley, previously the marketing expert of Pepsi-Cola, had been appointed by Jobs.

Not a man to take defeat lying down, what Jobs did next is a matter of fairytales. He began a new hardware and software venture called NeXT, Inc. In 1986, Jobs purchased an animation from George Lucas which went on to become Pixar Animation Studios, where he invested $50 million out of his own pocket.

Pixar proved to be hugely successful, with the first animation movie Toy Story, and has grossed $4 billion with movies like Finding Nemo and The Incredibles. In 2006, it was to merge with Disney, making Jobs the largest shareholder of the latter. But this was after the fizzing out of NeXT, Inc, which failed in marketing its specialized operating system.

NeXT, Inc. was bought by Apple for $429 million in 1996, and Jobs returned in 1997 as Apple’s CEO at a time when the company was still struggling to gain back its former glory. Armed with a new management squad, changed stock options, and an annual salary of $1, Apple was brought back on track with products like the iMac, good and efficient designs, and effective marketing.

When Steve Jobs died in 2011, he had seen Apple rise to have a record-breaking stock value, and being ranked No. 1 on lists compiled by Fortune magazine. In November 2014, the company became the largest publicly traded corporation in the world by market capitalization, in addition to becoming the first American company to be valued over $700 billion.

And though it lost the man who made it, the company is worth $586 billion as of May 2016 under CEO Timothy Cook, who took over from Jobs. In May 2015, activist investor Carl Icahn had alleged that the company has assets worth $1.4 trillion, and thus should boost its share buyback program.

Richard Branson; Virgin


Richard Branson, knighted in 2000, and today the 4th wealthiest man in the UK, started with £300, and now is worth $5.2 billion, with $12 billion in sales.

Branson, with his love for adventure and perseverance, serves as an inspiration to many people worldwide, especially young children, for his fight with dyslexia, which he conquered at a time when people did not even know what dyslexia was.

His first venture was a magazine called Student, which he started as a sixteen-year-old college dropout. The Student was successful, making him earn good revenue, but it was not without its share of trouble. He was arrested for publishing information for treating venereal diseases, which was legally prohibited.

Virgin was started in 1970 as a mail order record retailer from the crypt of a church, with the name being chosen to signify Branson’s being new in business.  His first brick and mortar outlet was opened at Oxford Street, and the success he achieved made him sign Mike Oldfield as the first ‘Virgin’ musician. In 1977, Virgin Records added the Sex Pistols to its folds.

Its success notwithstanding, Virgin Records was beset with cash-flow problems, and Branson had to pretend that he was buying records for export in order to get over the excise tax on sales. In 1992, Virgin Music had to be sold to EMI for $500 million in order to keep the airline company functioning in the face of rising fuel costs and recession. Later, he said that after the completion of the deal, he wept at having lost the very first venture of his empire.

V2 Records was created in 1996 by Branson as an effort to re-enter the music business, and he owned 5% of the shares. It was sold to Universal Music Group in August 2007 for $7 million.

The airlines business was started in 1984 with Virgin Atlantic. And it was riddled with misfortunes from the beginning, when birds flew into an uninsured engine during the Government certification flight, causing an explosion. This forced Branson to gather cash from his overseas investments in order to rebuild the company.

This was soon followed by a legal dispute with British Airways, whom Branson claimed was trying underhand methods to steal passengers.

Today, all this is hopefully history, with Branson having ventured into space tourism following telecommunications. Having dabbled in over 200 companies, Branson today is in a position to join Giving Pledge, the $500 billion philanthropy club co-founded by Bill Gates.

The members of this club, which includes the likes of Gates, Warren Buffett, Azim Premji and Patrice Motsepe among others, pledge to give more than half of their wealth to philanthropic causes.

Walt Disney; Disney

os-walt-disney-birthday-2014 (1)

Once told to be a man lacking imagination and good ideas by a reporter, it was not easy to gain acceptance for this man who had wanted to be a newspaper cartoonist from a very young age, when he used to draw paid pictures for his neighbors and cartoons for his school newspaper.

Frustrated, Disney decided to tackle things head-on by founding his first cartoon studio as a 22-year-old. It was such a big failure that he was pushed towards bankruptcy.

Having suffered failure, Disney flew off to Los Angeles to be an actor, only to be disappointed yet again. But here, the Disney studios which he founded with his brother Roy soon became a success, starting with advertisements before graduating to animating Walt’s own cartoons.

It was not a smooth transition. Soon after, Disney discovered that Margaret Winkler, the New York distributor who distributed the Disneys’ Alice cartoons and looked into the invention of Oswald the Lucky Rabbit, had stolen the rights to the latter along with her husband. She had also been able to take in all of Disney’s animators.

This made the Disney family immediately get into work with Mickey Mouse, whose first animated short films Plane Crazy and The Gallopin’ Gaucho, failed to find any takers as they were silent films at a time when the genre was fast fading.

Soon, Disney created Steamboat Willie, the third film of the franchise with sound and music and having Walt as the voice of Mickey. The cartoon became an instant hit with the audience, and that was the beginning of what was to be the most phenomenal cartoon show of all times.

Snow White and the Seven Dwarfs, the first full-length animated film, premiering on December 1937 in Los Angeles, managed to rake in $1.499 million though it was the Great Depression, and won eight Oscars.

Disney did not remain untouched by the war though. During the Second World War, the Disney studios were taken over by the US army and converted to a repair shop for tanks and artillery. All his animators and Disney himself were required to join the war effort. It was bleak after the war ended as well, and the company ran up a debt of more than $4 million due to slow growth in business.

A strike by the animators in 1941 added to the woes, and ended with many resigning. Disney managed the difficult post-war decade with ‘packaged features’ and overseas investments, when the company was recuperating, but by 1950, he was back to his former self with his full-length animations.

Even the opening day of the first Disneyland theme park was not without setbacks. The park which was to be the first of many of Disney’s theme park ventures (to fund which he entered television with shows like The Mickey Mouse Club), was opened by actor and future US president Ronald Reagan, and involved the distribution of thousands of counterfeit invitations.

In 1966, when a new theme park and Experimental Prototype Community of Tomorrow in Florida was under construction, Disney was diagnosed with lung cancer. When he passed away in December the same year, he had won 22 Academy Awards from the 59 nominations he had received, one Emmy Award and three Golden Globe nominations.

At present, with a price of $94 per share, the company’s market capitalization is at roughly $150 billion.

Henry ford; Ford Motor

A celebration of the 150th anniversary of the birth of company founder Henry Ford will be held throughout 2013. Go to for an interactive timeline of Ford's life, tours, a calendar of 2013 events and information about efforts to preserve Henry Ford's heritage. (12/11/2012)

Although Ford did not invent the automobile, he was the man behind the manufacture of the first affordable vehicle for the middle class American.

He came from a family of farmers who had immigrated from England and Ireland. He displayed interest in mechanics from an early age when he dismantled a timepiece given to him by his father just to see if he could put it back together. The resulting success made him confident enough to proceed with other people’s watches, and he soon took to repairing.

After his mother’s death in 1876, he refused to join the fairly successful family farm business and instead completed apprenticeships with James F. Flower & Bros., and Detroit Dry Dock Company.

Though initially he thought of partnering with Thomas Alva Edison, he chose to found his own company, Detroit Automobile Company, backed by William H. Murphy, where he could work on his own conditions. This soon proved to be a failure, with the vehicles being produced not meeting Ford’s expectations, and the company going bankrupt.

This did not dishearten him, who re-structured the remnants of this failed venture to form the new Henry Ford Company. Sadly, this too did not last owing to a dispute with Murphy when the latter brought in Henry M. Leland as a consultant. After Ford’s departure, Murphy changed the name of the company into Cadillac Automobile Company.

In 1903, the Ford Motor Company was formed, and by 1918, half of all the cars owned by Americans were the Model Ts manufactured by the company. This phenomenal success, however, prevented Ford from looking into the new features being developed by rival companies for a long time. Finally, it was the declining sales that resulted in the release of Model A, which thankfully was a success.

Though having an ill-repute for being anti-Semitic, Ford introduced many progressive measures like the five-dollar wage and the five-day workweek. When the company almost faced a government takeover in 1945, he managed a turnabout by taking some wise business decisions.

The sales for Ford Motor as of May 2016 are estimated at $149.56 billion, and the company is worth $54.2 billion. Henry Ford is placed no. 9 in the list of the top 10 richest people of all time, with a current valuation at $199 billion.

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As Steve Jobs once said, people don’t know what they want unless they have it in their hands. Yet, we cannot forget that this was coming from a man who had a range of vision to include others in this world where he believed that most could not even look at themselves. True, it may sound dangerous when considering the prospects of exploitation, but maybe men and women like Jobs and Winfrey could find a footing for themselves only by realizing the hard truths. A valuable lesson for us to learn as humans.

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