Jenna Rainey


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hey friend!

I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



                                              Take the quiz to get your flow back! 
Feeling creatively stuck?  
Let's be friends!

I’m an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.

(with me)

about me



It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

Wanna Learn Watercolor?

i wrote some books

Hey I'm Jenna!

"I'm undeniable proof the 'Starving Artist' narrative is made to be broken."

How to Make a Living with Your Ideas with Jeffrey Madoff

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Have you thought about taking your hobby or side gig and making a living out of your creative creative? Do you have doubts, concerns, fears about taking the leap?

You’re not alone. I’ve been there and my guest on this episode has some insights and inspiration to share.

Jeffrey Madoff is the founder of Madoff productions in New York City. His company collaborates with ad agencies, public relations firms, and directly with clients to produce commercials. He’s worked with Victoria Secret, Ralph Lauren and more.

Jeffrey began his career as a fashion designer and was named one of the top 10 designers in the US before switching careers to film and video production.

He also teaches a popular course at the Parsons School of Design and recently published a book by the same name—Creative Careers: Making a Living with Your Ideas.

In this episode, we’re his students for a short lecture and I can’t wait for you to soak in all the wisdom.


Stellar insights

  • [03:11] Jeffrey says motivation, desire, and a compelling need to express is what led him pursue a wide variety of creative endeavors.
  • [04:36] Jeffrey’s career started with creative a clothing company at 21.
  • [07:03] Why proof of concept is important
  • [09:58] One of the largest obstacles for creatives is fear of failure
  • [10:55] The eye of an artist “can see something that other people look at all the time, but see something special in it and see another way to express it.”
  • [15:56] When pursuing a creative career, first ask yourself: Why do you want to do it?
  • [16:56] The second step is defining success for yourself.
  • [22:37] “The only stupid question is the one you didn’t ask.”
  • [23:56] Jeffrey shares some of the biggest mistakes in his career.


Rapid Fire Questions

What is your favorite resource that has helped you grow your business?

Meeting good people. Because good people know other good people and you start building a network of really good people that can be helpful, that you can learn from maybe even do business with.

What is the best piece of advice you’ve ever been given?

Be curious. Be present. And listen.

What’s the last book you read?

The Attention Merchants by Tim Wu. And it’s really interesting because the subtitle is after The Attention Merchants: The Epic Battle to Get Inside Our Heads. And it’s about social media and the most precious commodity out there is our attention. And it goes back starting with penny newspapers all the way through to social media today. And he’s a professor at Columbia university and it’s a fascinating, fascinating book. 


Subscribe & Review

If you had an ah-ha! moment or learned just ONE new valuable bit of information, I’d be so grateful if you would leave a 5-star review and tell me what you love most about this podcast. It’s a HUGE motivator for me to keep creating this for you. In addition, it helps our raking in iTunes so that more people discover this show.

And to make sure you never miss an episode (including any pop-up bonus episodes), click here to subscribe on Apple iTunes!


Links mentioned

*This is an affiliate link which means that I may receive a small commission at no extra cost to you. This helps me be able to produce free, valuable content for you. Thanks for your support!


Related Episodes

Episode 9: Tips for Overcoming Imposter Syndrome
Episode 21: The Legal Crash Course Every Business Owner Needs to Hear with Grant Atkinson
Episode 35: How to Create the Business You’ve Always Envisioned with Kelsey Murphy
Episode 37: The Importance of Curiosity and Creativity with Brit Morin
Episode 42: How to Build a Profitable Business with Tracy Matthews


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