10 Gutsiest Moves in Entrepreneur History

by / ⠀Entrepreneurship / January 14, 2014

The common thread that binds all wannabe’s, first timers and serial entrepreneurs, is belief in an audacious notion or idea, and the courage to make that idea a reality. The 10 decisions made below were extremely tough decisions, which could have ended terribly, but later resulted in some of the biggest payoffs in tech history.

1. Elon Musk bets on Tesla Motors

elon-musk-tesla

When Tesla ran out of money in 2008, Elon Musk put the money he made from the sale of PayPal into Tesla. If it had failed, he wouldn’t have had a cent left to his name. Good thing it didn’t.

2. $1.65 billion for YouTube

youtube

YouTube had been struggling with legal issues and had no revenue. Google’s offer couldn’t have come at a better time. On the other hand, Google (who already had a video sharing site) looked to be taking a pretty risky investment. Today, Google generates a reported $3 billion yearly from the premier video site on the web.

3. Facebook turns down a combined $16 billion

facebook

While only two years old and still in its initial stages, Mark Zuckerberg was $1 billion for Facebook by Yahoo!, an offer he turned down. A year later, Microsoft offered him $15 billion, but still he said no. According to Zuckerberg, he still had “some work to do on the site”. It was a risk worth taking as his personal net worth is now higher than those original offers, and the company he built is valued at around $100 billion.

4. When Twitter rejected Facebook

T-vs-F

Just as Zuckerberg rejected Microsoft and Yahoo!, Twitter also refused to sell out to Facebook, not once, but twice, and for the exact same reason. Twitter is currently valued at over $8 billion.

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5. Putting all your eggs in one basket

installshield-professional-3

InstallShield was just a small tech company, working out of a 10′ x 10′ office when CEO Viresh Bhatia decided to sink every dime the company had into one full-page color ad in PC Magazine. Their competitors were strong and well established, but he seemed spurred on by that fact and insisted the ad was located directly opposite Microsoft’s. Being placed next to the big boys showed customers they were at a similar level to them in the market place, and Bhatia later sold the company for $78 million.

6. Intel abandons memory chips

 Intel

Until 1981, Intel built memory chips. However, due to competition from the Japanese market, they saw their profits fall from $198 million to just $2 million, making the memory chip business near impossible to conquer. They decided to completely change direction and move from memory chips to microprocessors, a move that paid off and has made them world-renowned industry leaders.

7. Launching the first iPhone

iphone 3

Not only did Apple have to build a phone from scratch with no previous phone experience, they also had to convince consumers that it was worth the buy. Having spent billions to get to the launch of the first ever iPhone, one insider said “The entire company was riding on the release being a success.” Fair to say, it was quite a success.

8. Microsoft makes games

original-microsoft-xbox

While Microsoft knows a thing or two about software development, hardware was not its strongest suit. This was proven by the $4 billion loss they endured when they launched their first console. They got better and today, the Xbox 360 generates several billion dollars each year.

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9. Investing in Photobucket

Photobucket_splash

Chris Sacca earns a spot on the Midas list for his investment in Photobucket. At the time of investment though, he didn’t have any money. So, he took the speculative move of using his student loans and credit card to get the cash. Thankfully for him, the photo sharing site has grown in leaps and bounds and was acquired by MySpace for $250 million.

10.  $1.6 million mortgage to buy a super bowl ad

hotjobs Richard Johnson, the CEO of Hotjobs decided to take out a mortgage on his house to buy one single ad during the Superbowl. The response was immediate and HotJobs moved from being a struggling fledgling company in 1999, to being acquired by Yahoo 2 years later for half a billion dollars.

Image Credits: www.businessinsider.com, installshield-professional.en.softonic.com, logos.wikia.com, h30495.www3.hp.com, mediabuzz.monster.com 

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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