TV Writer Casts Himself in Lead Hustle Role

This transcript was generated from the episode audio and may contain minor errors.

Everybody's got a story worth telling. Everyone has something of value in their life, some good memories, something that is interesting to delve into, perhaps reclaim or relive. That's what today's featured case study believes. And I agree. It doesn't matter if you think nothing exciting has ever happened in your life, if you spent 40 years working as a clerk in the post office or whatever your equivalent of a boring job is, a good interviewer can usually ask the right questions to discover all sorts of gems.

And to me, it's like the statement I often hear at events when we're having a group conversation about starting a side hustle or a little business, or somebody wants to be a full on entrepreneur. And they say something like, "I don't have any marketable skills," or, "I know how to do my job that I do for a company, but I don't have any marketable skills that I could use on my own." And my response is always, "I'm pretty sure that you do, actually. If we ask the right questions, we can usually figure out what they are." So it can be kind of a fun process to talk somebody through that. And almost inevitably, we end the conversation with the person realizing like, "Oh, I actually am good at more things than I thought," or, "There is something in my life that can be transferred to a different skill," or whatever it is. So getting back to that point of everyone's got a story worth telling, in this story, everyone I'm going to tell you today, a Los Angeles based TV and magazine writer writes himself into a role of memorable audio interviews.

He creates a service that I'll tell you about, currently earning a nice extra income, and then the service leads to his second hustle, which is just now getting started. One thing often leads to another. This is an illustration of that fact. So stay tuned for this story, and I might have a suggestion for him at the end as well. Los Angeles writer Dennis Hensley 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 soon he 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, healthcare, 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. "Hey, what's up? Thanks, instructor." Dennis was clear that he needed a side hustle, and he could see how it would make a difference when crises occurred, like that 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 subjects found his style to be fun and meaningful. He already had a podcast and wanted to think of a 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 own observation deck to deck of cards featuring questions created for interviews. Questions like "What makes you blush?", "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. In the fall of 2017, Dennis held a launch party to share his idea with family and friends and scored his first client. A friend hired him to interview her parents for their 50th wedding anniversary.

Prior to the LifeCast interview, Dennis had a couple of select questions from the observation deck that they thought would be fun to answer. It worked like a charm, and it brought up fun stories from the couple that otherwise might not have surfaced. After he had his first interview under his belt, Dennis was inspired to expand to include in-person events and parties, like weddings, birthday parties, and barber-bot mitzvahs. Those in-person events create a unique opportunity to interview attendees about the guest of honor and collect any funny or scandalous stories. The audio captures the feeling of the event so the guest of honor can remember that experience for a lifetime.

For the most part, LifeCast has been a smooth endeavor, albeit with just minor challenges. Dennis struggled with getting his audio right in the beginning, and has found it difficult at times to balance time spent on marketing with time spent on interviewing. Start-up 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, and he currently conducts an average of two interviews per month.

Flushed with the confidence of his first success, 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 it to interviewees and sell it to interested parties. He reached out to a graphic designer friend and asked for advice on where to print the cards. Dennis's 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 went into action and enlisted a professional game designer to help him.

They started playing around with the questions from the observation deck and thinking about ideas of how the game could be played. They also landed on the name "You Don't Know My Life." After several test plays, Dennis knew he was on to something. He launched a friends and family pre-order campaign to raise money to print it, and the game arrived to everyone who pre-ordered by Christmas. This was just in 2018. In January 2019, he began selling it on Amazon.

Dennis encourages everyone out there to look within their own skills and interests and get creative. Think about what excites you and see what you can build from that. After creating one side hustle, it was easier to start another. These projects have given Dennis something that is his to own, and no one can take it away. Awesome, I love this project.

Dennis is a one-man storycore. I do have a suggestion for him based on his website and also a fun story to share. The suggestion, which I'll tell you first and give the example, suggestion in general. If you have a service, don't try to accommodate every request. Decide how your service works and offer it that way.

This is especially important when it's a different kind of thing, something that's unusual, perhaps or unconventional. The burden is on you to explain why it's important to do it this way. I think this actually creates more confidence and trust for buyers. I just mention this because on his website, which is otherwise great, is really clear about who it's for, what it's about, etc. On the Frequently Asked Questions page, there's a couple places where he seems a little uncertain.

People are asking questions like, "Oh, can you do this by Skype?" His answer is, "Well, it's better if you do it in person in Los Angeles, but maybe with Skype or maybe I can travel, etc." Just depends on the budget. And the next question is, "Can you videotape this session?" And he said, "Well, I don't really do that, but I can go and ask a friend if they do it and get a quote from them, etc." I just think, again, don't try to accommodate every request. Decide for yourself this is how the service works and offer it that way. And if I'm looking to purchase the service for a grandparent, perhaps, which I think is a wonderful use for something like this, I just want to be told here's how it works. Just a suggestion.

Now, here's a fun story. When Dennis went to build the website for the game, the second project he's starting, he discovered that YouDon'tKnowMyLife.com was owned by someone else and they were asking $795 for it. That seemed too expensive, so he secured YouDon'tKnowMyLifeGame.com. But a few weeks before he was ready to launch, he saw that the original website was going to be auctioned. He took a chance and bid $10.

He ended up being the only bidder, so the website is now his for $785 less than what was originally asked. So a great little lesson in side hustle resourcefulness there. All right, as I said, really great project. I love what Dennis is doing, and it's always fun to see all the different creative projects that you guys come up with. Our listeners are doing some really awesome stuff out there.

Can't wait to bring you more. Inspiration is good, but inspiration with action is better. The show notes for today, including links to everything I mentioned are at sidehustleschool.com/832. That's episode 832. Thanks so much for listening.

My name is Chris Guillebeau. This is Side Hustle School. From the Onward Project.