5 Epic Entrepreneurs Overcoming Obstacles & Real Rejection


If you're a bootstrapped business owner or co-founder, you are quite familiar with humble beginnings and bootstrapping your business to greatness. No matter how great your startup ideas are you'll face stormy skies, rough roads, flash floods, obstinate obstacles, and real rejection during your quest to grow your company. While the challenges are inevitable, how you react to obstacles and rejection in business is what really counts. 

We've all heard of the rags to riches stories that so many entrepreneurs have lived to tell about... if they're lucky and incredibly persistent. Some have lived in their cars and others have maxed out a dozen credit cards just to give themselves a shot at business success. Here are the stories of 3 incredible and motivating business successes that plowed through obstacles and painful rejection. 

Jeff Bezos of Amazon

One of the most impressive of these frugal beginnings has got to be Amazon's founder and CEO Jeff Bezos. The picture above shows the world's richest or second richest man (along with Bill Gates depending on the prices of Microsoft and Amazon stock on any given day) in his office in 1999. He started his business in the mid to late 90's when the internet began, was laughed at, but then picked up steam after the dotcom bubble burst. Now Amazon is one of the most valuable brands on earth with incredible innovations in ecommerce algorithms, shipping, inventory management, customer service, and subscription services. You might need to live lean and humble early on, but it can pay off like you never could imagine!

Jamie Siminoff of Ring

Just because a product or business isn't purchased on Shark Tank by one of the cut-throat investors, doesn't mean it's destined to fail. Copa Di Vino comes to mind after two "failed" pitches on Shark Tank but now enjoying $10+ million in annual sales. But nothing is quite as impressive as Jamie Siminoff's company "Ring" (originally called DoorBot). This smart doorbell with audio and video options was pitched at $700,000 for 30% of the company and it was rejected by the sharks at that valuation. But Siminoff stayed strong, didn't give up, and leveraged the exposure from Shark Tank, growing product sales to millions of dollars per year. Just this year Amazon acquired Ring for between $1.2 and $1.8 BILLION dollars! This goes to show that determination breeds success.

Brian Acton of WhatsApp

Brian Acton was a software engineer that was looking for a new opportunity but was met with the obstacle known as rejection. While he worked for over a decade at Yahoo & Apple, he got turned down by Twitter and then Facebook. These days both of those companies sincerely regret that decision. When Brian Acton couldn't find work at another big-name company, he took his chances on the start-up route instead. Teaming up with another Yahoo alum Jan Koum that helped build messaging app WhatsApp. In 2014 Facebook bought WhatsApp for a stunning $19 billion in stock and cash. What will you do next time you're rejected? Persistence and resiliency could be worth billions!

Oprah Winfrey of OWN

Oprah is such a household name and a multibillion dollar success story that many people often forget her humble beginnings. She overcame a horrendous childhood, the challenges of being a black woman in the 1970's, and being fired from her news anchor job because she was "unfit for television". But she refused to give up on her dreams and we all know how that turned out!

Steve Jobs of Apple

Steve Jobs was an incredibly successful and wealthy pioneer of the personal computer revolution when his company Apple started floundering and he was fired from his own company. Many people at that point may have been content to live off their wealth but Steve Jobs was not most people. He founded a new computer platform NeXT, and acquired the innovative company Pixar. He sold NeXT to Apple in 1997 for $400 million and worked his way back to a position as the (interim then permanent) CEO of Apple. He then took the company to unimaginable new heights with new operating systems, the iPod, and the iPhone. Jobs passed away in 2011 after forever changing the personal computer and smartphone industries and making billions in the process. 

These stories are proof that when you can overcome any obstacle or rejection to reach the promise land of startup success. Consider these business lessons and you could be rewarded with the same accolades and riches while disrupting stagnant industries.


I hope you enjoyed this article how to overcome startup obstacles and rejection to succeed in business.

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