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SEO.com was recently invited to take part in a unique event featuring Daymond John from the popular show ‘Shark Tank’ and hundreds of high school students from around the country. Mr. McCauley, an amazing business teacher from Davis High School in Kaysville, Utah, started tweeting Daymond over a year ago to ask the business celebrity to make a guest appearance via Skype for his Entrepreneurship students.

As busy schedules go, nearly a year later, McCauley and Daymond arranged a hangout on Google+ but took it a step further by inviting hundreds of high school business classes to participate. The team at Google+ graciously came through at the last minute to extend the normal 10 person hangout limit so students around the country could participate.

The 45 minute Q&A session between the successful entrepreneur and aspiring high school students left us with several valuable lessons:

1. Fail, Fail and Fail Again

Unknown to many, Daymond John closed down his clothing brand, FUBU, three times in the early days in the early 1990’s. FUBU later went on to become a major pop culture brand and do millions in sales each year. This story is not uncommon to some of the most famous successful brands and entrepreneurs.

From a recent article on FastMoney.com:

Pinterest is one of the fastest-growing websites in history, but struggled for a long time. Pinterest’s CEO recently said that it had “catastrophically small numbers” in its first year after launch and that if he had listened to popular startup advice he probably would have quit.

James Dyson failed in 5,126 prototypes before perfecting his revolutionary vacuum cleaner. Groupon was put on life support and nearly shut down at one point in its meteoric rise.

The ubiquitous WD-40 lubricant got its name because the first 39 experiments failed. WD-40 literally stands for “Water Displacement–40th Attempt.” If they gave up early on like most of us do, we’d sure have a lot more squeaky hinges in the world.

The key to Daymond succeeding after closing his business multiple times was that he kept hustling and kept selling. Daymond recounted the story about him approaching rappers to wear his shirts in their videos and then he’d take the shirt back and go to the next video set. He did this over and over until 3 years later his brand was major success but very few people knew that for many years, he only had 10 shirts.

2. Know Your Numbers, Know Your Business

To an investor like Daymond, nothing is a quicker turn off than being pitched by an entrepreneur who doesn’t know his numbers. If you’ve ever watched Shark Tank, you’ve likely seen the Sharks tear apart entrepreneurs who come unprepared or dodge the important questions.

Knowing your numbers applies at many levels. As an entrepreneur seeking investment, you should obviously be prepared with numbers regarding sales, pending orders, profit, expenses and market opportunity. The same principle applies as an employee of a company or as an agency offering consulting. Knowing your key numbers and key performance indicators is a valuable trait whether you work at one of the greatest SEO companies in the world or are in the early stages of launching one of the next greatest brands.

3. Analysis Paralysis & Common Sense

One thing that really struck me while listening to Daymond was how much gut feel and common sense play into his businesses and investments versus raw analysis of data and numbers. As mentioned earlier, you need to know your numbers but Daymond recommends avoiding analysis paralysis or over analyzing a situation. Sometimes you just need to dig in and get your hands dirty to learn or determine if an opportunity is good.

Daymond also discussed how the Sharks heavily consider the person when they invest, not just the business opportunity. They know that a given business may not work out but putting your money behind a hard working, smart entrepreneur is the safest bet they can make. Daymond, in particular, looks for a “hungry person with a great idea and a lot of desire”.

4. Born to be an Entrepreneur

Entrepreneurship and innovation is something that’s been on many people’s mind since the passing of Steve Jobs. As one of the world’s most innovative thinkers, Steve Jobs lived Apple’s slogan of “Think Different”.

The following quote from an inspiring video of Steve Jobs gives a very revealing look into his mind and how he sees the world of business and innovation.

When you grow up you tend to get told that the world is the way it is and your life is to just live your life inside the world, try not to bash into the walls to much, try to have a nice family life, have fun, save a little money but that’s a very limited life.

Life can be much broader once you discover one simple fact, and that is, everything around you that you call life was made up by people that were no smarter than you … the minute that you understand that you can poke life … that you can change it, you can mold it … that’s maybe the most important thing. Once you learn that, you’ll never be the same again.

Daymond John echoed these feelings by Steve Jobs during his Google hangout when answering a student’s question about when he knew he was going to be an entrepreneur. Daymond stated that he believes were were all born thinking like entrepreneurs but society teaches us not to be entrepreneurs by correcting us at an early age and telling us how things are supposed to be or how we’ll embarrass ourselves by failing.

5. The Future of Education is Bright

Mr. McCauley of Davis High School is leading the way by utilizing technology and social media to go beyond the text book and provide his students with a cutting edge education. Social media platforms have allowed him and others to reach out and get in front of celebrities and industry experts like Daymond John. With simple and innovative technology like Google+ hangouts, these celebrities and experts can now quickly and effortlessly communicate with students, fans and anyone else interested.

I’d like to commend Mr. McCauley for going above and beyond for his students and hundreds of others that were able to tune in. I also have much respect for Daymond John who willingly took an hour out of his busy schedule to give back to students who regularly tune in to Shark Tank and look to Daymond and others for advice as they become the next wave of entrepreneurs and Sharks.

The Full Daymond John Google+ Hangout