Josh Shipp Used to Get Kicked out of Class for Talking: Now he Gets Paid to Talk

by / ⠀Entrepreneur Interviews Startup Advice / May 5, 2022
josh shipp

U30: You’ve appeared on TRL, FoxNews, Comedy Central and Cosmo Girl.  How’d you score the press?

I started all this as a professional speaker- going around to high schools and colleges and speaking to large audiences. But that doesn’t translate to media. A speech is one person to five hundred.  Media is one person to one person times give hundred.
Once I understood this, I knew I needed to pitch myself to the media a teen communication expert or teen advice guy.  Not a “motivational speaker” shoot me.  That, and you need to be unique.  Not in content or message, but in delivery.  It’s not what you say- it’s how you say it.

U30: What is some advice for young entrepreneurs who want to start diving into online video themselves?

Just do it.  Seriously. Stop thinking. And strategizing. And formulating your dream board and just turn on a camera and go.  My first videos were awful. I mean horrible. But my fifth one was a bit better, and video #50 was pretty solid. Practice makes improvement.

U30: How did you book your first paid speaking engagement? How do you make the leap from non-paid speaking to paid speaking?

How did I make the leap from non-paid to paid? Watch: I asked to be paid. At first $500. Then $1,000. Then $2,500. Now $5,000.
If you’re good at what you do, you’ll find the more you charge the more demand you’re in and the better clients you’ll get.  You get what you charge for.

U30: How well does social media work to engage with teens? They are on it to talk to their friends, but they don’t seem to be into Twitter or blogging.  How do you reach your demographic online?

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I’m anywhere they might be. Myspace, Facebook, Twitter, Youtube, etc.
Most of my audience is on Facebook.  But some are still holding onto myspace and some are early adapters to Twitter.  Why this works for me: Number one, I authentically like Facebook. I know how to use it. I like it. It’s me. So I don’t appear to be some suit on there trying to sell crap.  Number two, It’s where my audience is at.
Don’t always ask your audience to go to YOUR blog or YOUR website or YOUR site.  Go to theirs.

U30: You are insanely passionate about what you do.  What advice do you have for young people trying to find their passion?

You know what it is.  If you say you don’t – I don’t believe you. You just don’t have the guts to pursue it. Neither do I. Neither did anybody.  Take a deep breath and jump.  You’ll be scared out of your mind but the confidence will build once you pursue your passion- instead of sit around and dream about it.

U30: Who are your mentors and how can young entrepreneurs go about finding their own?

Many.  The best way to learn is from someone who’s been there.  My virtual mentors include Jamie Oliver, Kevin Carroll, Mark Sanborn, Frank Kern, and Tony Hawk.  I also have mentors you’ve never heard of, but that are incredibly successful and teach me something.
The best way to approach a mentor is: try to find an introduction point from someone you know, don’t waste their time, prepare questions in advance, and actually be pursuing and making progress in your field.

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U30: You just scored your own TV show called Jumpp Ship.  What did you do to land a deal?

It takes ten years to become an overnight success.  Lot of hard work, airline miles, and networking to become the go to guy for advice for young adults.  It’s all about have a unique delivery in a niche.  That’s attractive, especially for non-fiction reality TV.
If you wanna have a TV show, think about what you can do today that will help you get that show in 5 years.  I wanted a show five years ago, but honestly wasn’t ready.  Are you good on camera? Do you have a unique way of delivering your message? Have you written a book? Been quoted in articles?  Get on it.

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, 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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