9 min 56 sec

TV Writer Casts Himself in Lead Hustle Role

A Los Angeles based TV and magazine writer writes himself into a role of memorable audio interviews.
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What It's About

A writer who spins the stories of others using a new medium.

Business Model
Skills Required
Storytelling & Communication
Profit Potential

Words of Wisdom

A suggestion: don’t try to accommodate every request. Decide how your service works and offer it that way! Especially when it’s a different kind of thing, the burden is on you to explain why it’s important to do it your way. This creates more confidence and trust for buyers.

Fun Fact

When Dennis went to build the website for the game, he discovered that YouDontKnowMyLife.com was owned by someone else and they were asking $795 for it. That seemed too steep so he secured YouDontKnowMyLifeGame.com. A few weeks before the games were going to arrive from the manufacturer, he saw that the original website was going to be auctioned off. Dennis took a chance and bid $10. He ended up being the only bidder and the website is now his for $785 less than what was originally asked.

Notes from Chris

Episode 832
Los Angeles writer Dennis Hensley has spent his life asking unique, probing questions. A master interviewer, he began his writing career in the magazine world crafting celebrity profiles, and later transitioned to writing for television.

All was well until the labor strike in 2013.

His opportunities began to dry up and he soon found himself without steady gigs. The crisis had a negative effect on his financial, mental, and physical health. And it continued like this for several years.

In 2017, he began attending programs at the Actors Fund, a national human services organization that meets the needs of the entertainment community through emergency financial assistance, affordable housing, health care and more. He enrolled in a life-changing course called Managing Cash Flow for Artists. In this course, the instructor recommended that students listen to the Side Hustle School podcast.

Dennis was clear that he needed a side hustle, and could see how it could make a difference when crises occur (like the labor strike). He began to explore what he likes to do and what he’s good at and landed on interviewing. He had been interviewing his whole life and was really great with crafting questions. And most of his past subjects found his style to be fun and meaningful. He already had a podcast and wanted to think of a unique way to expand.

That’s when the idea for Lifecast was born. Lifecast is a digital audio interview that focuses on memorable stories. Dennis spends up to three hours conducting in-person interviews to gather details about the subject’s life.

He utilizes questions from his Observation Deck, a deck of cards featuring questions created specifically for interviews: “What makes you blush?” and “What was your worst job?” for example. He then compiles the interview into an edited audio collage with music for family and loved ones to cherish.

Startup costs came in around $2,000 to cover the cost of equipment, rights for music, and a Squarespace website. He was able to recoup his investment after a couple months of interviews. Packages range from $700 to $1,000 depending on the scale of the interview. He currently conducts an average of two interviews per month.

Dennis has recently cast himself as the lead in another side hustle. After launching Lifecast, he was inspired to have his Observation Deck printed professionally so that he could gift the deck to interviewees and sell to interested parties. He reached out to a graphic designer friend and asked for advice on where to print his cards. His friend sent him a link to MakePlayingCards.com and challenged him to “Think big and create a board game out of the questions as well!”

Dennis encourages everyone out there to look within their own skills and interests, and get creative. Think of what excites you and see what you can build from that. After creating one side hustle, it was easier to create another. These side hustles have given Dennis something that is his to own that the entertainment industry can’t take away from him.


  • Get a Life Cast: Learn more about this unique side hustle over on Dennis' website, and while you're at it, check out his card game, You Don't Know My Life! as well!
  • Actors Fund: A charitable organization that supports performers and behind-the-scenes workers in performing arts and entertainment
  • Make Playing Cards: The manufacturer that Dennis used to create You Don't Know My Life!
  • Squarespace: The website building platform that Dennis used to create his website


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Find support around you when brainstorming ideas for a side hustle or starting one. Whether that be joining a community of entrepreneurs, a society like the Side Hustle Society, or forming your own, find support to keep you motivated and in action."
—Dennis Hensley #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau