BOSS TALKS: Jen DeLeon Talks Overcoming Self-Doubt, Authentic Instagramming, and Being About Her Business

Jen talking with Jeezy.

Jen talking with Jeezy.

Jen with Wiz Khalifa.

Jen with Wiz Khalifa.

Jen DeLeon is a true Renaissance-woman. She serves as Dash Radio’s Chief of Staff, runs her own consulting business DeLeon Direction, is a booking agent, vlogs, and writes Church Notes that she sends out regularly. But despite her heavy workload, Jen stays about her business. She even showed me her meticulous planner (believe me, she’s not missing a date) that she created, color coded and all. And yet, she still found time to share some of her notorious inspiration with me.

“Whatever people are posting [on Instagram] for likes, that’s fantasy”.

From first glance at her Instagram, you can tell that Jen is intentional. She believes strongly in authentic instagramming, and broadcasts her doubts just as much as her successes.

“I am aware that I write lengthy-ass captions. It’s the only way for people to really understand the story behind each post.” She talks about overcoming her self-doubt when she was beginning her career as a booking agent, starting big with Lil Wayne.

“I realized these opportunities kept coming to me. And it was easy, because I’m very protective of all my relationships, so I knew it was going to be an easy thing. I just wasn’t sure if it was for me or not. So I got over that doubt once the Wayne thing, there was contracts signed. I must’ve been doing this for 3, 4 months, but I never said anything to anyone” we signed [the contract] in December, and I didn’t say anything until the show was over, end of July. I overcame that doubt when [bookings were] consistently happening. I overcame all the craziness from the Wayne booking, so I am very confident when it comes to booking. I’m working on a lot of booking for next year, and I’m really excited about that.”

“I had the worst anxiety up until that second. I was so worried that everything was going to go wrong that I didn’t even Vlog the experience. All I have from that day is that picture. It’s not easy, and I really hate when I see people on social media acting like everything is perfect and everything was handed to you. No, it wasn’t, so that’s why I chose to be very transparent. Probably a little too transparent”, she laughs.

“I’ve been on unemployment, I’ve been through heartbreak, I’ve made dumb-ass decisions”.

Deleon makes it known that her come-up wasn’t linear. She moved to LA from a remote suburb of Chicago, with no plan but her passion. Now, as a prominent figure in the music industry, Jen Deleon gives props to all of the things that lead to her success.

“Im very open about it because that’s the only way people are going to relate to you” how is someone going to be able to relate to me if I show Lil Wayne in a picture and say, ‘Just randomly booked this man for a festival, woo, fire emoji’.”

“I was having major anxiety...I have to send my Church Notes today.”

“I never take credit for anything that I’ve done.” Deleon attributes her success to God and to the team of people who have helped get her where she is today. “I don’t make money off of it, but I wouldn’t be where I am today if it wasn’t for God. So I never take credit for myself and I really hate when I hear people say ‘Oh I did it by myself’ cause no you didn’t. God gave you that blessing, and there are people who are part of that process who also helped you get that blessing, so I never take credit for anything that I’ve done, anything I accomplished was from God and the people that help me get into these blessing and opportunities.”

“The industry is like high school”

Deleon says she has had to turn down the advances of men that hit on her in the industry. “If you set that boundary, people know what you’re about. If you get that respect, you get that respect forever”.  So she set that boundary. “The industry is like high school” Deleon says, “Whatever your reputation is, if you screw someone over, trust me, the whole industry knows…you’ve got to be very careful about who you let in your circle and who you affiliate yourself with”.

So, women in the music industry, if Jen leaves you with anything, she wants you to know: be about your business. If you’re about your business, everyone around you will know it.

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