By Chanelle Bessette
January 15, 2014

FORTUNE — Zach James has a bachelor’s degree in business from Brigham Young University, but when it comes to entrepreneurship, he thinks business school is “almost the opposite” of what people need. His advice? “Go join a startup for two years.”

A former investment banker for Credit Suisse, James looked for Internet startups that had big business potential and sought acquisition opportunities for them. Google’s purchase of YouTube for $1.65 billion was just one of deals James was involved with. Later, he co-founded Movieclips, a Venice, Calif.-based startup that curates professional YouTube videos by others, then provides their creators with social marketing and rights management tools. Movieclips later re-branded itself as ZEFR.

James likes to encourage fun in the workplace, and has supported events like an annual company-wide trip to Comic Con, a team Halloween costume contest, and playing host to a community TEDx talk.

He spoke with Fortune.

1. What was your biggest missed opportunity?

I could have possibly joined YouTube when it had 15 employees. Early on, I always had my eye on the platform, and had the sense that they would be important. It’s been serendipitous that we are working together and our paths continue to cross.

2. What other companies do you admire? Why?

Amazon. The company is constantly leveraging its strengths and assets to find the next big thing. I’m excited to see what happens now with grocery delivery.

3. What technology sector excites you most?

Kids’ entertainment on devices. It is so fascinating to watch how early kids master devices, but they need more compelling content.

4. What is the best advice you ever received?

Work your first five years like no one else will, [then] live the rest of your life like no one else can.

5. What would you do if you weren’t working at your current job?

I would own a dude ranch in Wyoming. My alter ego is a cowboy.

6. What has been your biggest failure?

Fifty “no”s in my series A [funding round].

7. What is one goal that you would like to accomplish during your lifetime?

Baja 1000, Navy Seal training with my brothers, ride a horse from the top of South America to the bottom, cycle Europe, restore a hot rod truck, heli-skiing, and travel the world with my wife and babies.

8. Describe an ideal day.

I wake up, wrestle with my three-year-old son, give my nine-month-old daughter her bottle, go surfing or do some type of workout with friends, work hard on big ideas with really great people, put my babies to bed at 9 p.m. or so, hang out with wife, read an inspiring book or watch a favorite show…and sleep without my three-year-old peeing on me.

9.  What do you do for fun?

I like to bet people to do awesome things. The last one was to jump into the Bellagio fountain.

10. What is one unique or quirky habit that you have?

I drink Mountain Dew for breakfast.

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