How Two Hollywood Producers Left their Dream Jobs in TV to Help Students Find Their Career Path

by | Aug 21, 2017 | Uncategorized | 0 comments

Meet Lisa Hennessy and Alex Boylan, the co-founders of the opportunity platform for students called DreamJobbing.

Lisa is an Emmy nominated producer and female powerhouse. She’s one of the founding members of Mark Burnett Productions; the company that produces hit shows like Survivor & The Voice. Lisa has a credit list that could fill this entire article, but here are just a few shows she has executive produced: Eco-Challenge, Rock Star, Contender, & The Biggest Loser.

Alex was the winner of The Amazing Race at age 24. He has hosted shows, created shows and produced shows for networks such as CBS, Travel Channel and VH1. He is most noted for the first of it’s kind interactive travel series called Around the World for Free– where he traveled the world relying on the kindness of strangers and his own intuitiveness.

Three years ago, these two innovators left the glamour of Hollywood behind to launch a tech start-up called DreamJobbing. In a nutshell, DreamJobbing helps guide students to their dream career by giving them the tools needed to brand themselves professionally using video, while offering them a solution to connect with virtual mentorships and companies for job shadowing experiences.

Since they are producers at their foundation what better way to explain what they do then with a video: DreamJobbing Overview Video.

Over the last 12 months, they have been working with thousands of students from an organization that needs to be on your radar, it’s called Jobs for America’s Graduates. JAG is a state-based national non-profit organization dedicated to preventing dropouts among young people who are most at-risk (Video: JAG). The directors, teachers and specialists in this organization work diligently with heart, passion, and purpose. These are the unsung heroes of America who dedicate their lives to help kids realize their potential and reach the American Dream.

I asked these two entrepreneurs about their journey and vision for DreamJobbing now and in the future. Here’s what they had to say:

Q. Alex, what inspired you to leave your dream job as a show creator behind and start DreamJobbing?

A: The answer is pretty simple. I am a blue collar kid from the north shore of Boston who has been blessed with many amazing opportunities that led to my dream career. I found myself thinking, how do I not take what I learned and pay it forward? This is my responsibility as a human. This was never a tough decision for Lisa and I…once the light bulb went off, there was no looking back.

Q. The DreamJobbing tagline is tell your story, share your story change your storywhat’s your story?

A: Flashback to 17 years ago: I was unhappy and feeling lost in my career. After spending four years in business school, I took a job in market analysis. Within the first week, I knew it wasn’t a fit for me. I remember asking myself the question, ”How did I get here? How could I have made such as mistake in my career path?”

Around that time, the reality TV genre was beginning to take shape in this country. I heard about a competition where you race around the world. It had yet to air, but it sounded incredible. To apply, I had to create a video of my teammate and I showing our passion and personality on camera. We shipped our video across the country to the casting people in Los Angeles. That one video changed everything; I was chosen to be on the show and eventually won. More importantly, while I was racing I became fascinated by the production crew. I knew in my soul after witnessing them work that it’s where I belonged. It took a lot of hard work and hustle to grow my career, but if I never made that first video, I might still be on the wrong path. It’s a rewarding feeling knowing that 17 years later, we are developing a way to pass what we learned on and give back.

Q. Can you tell me about more about the students DreamJobbing works with?

A: Most recently, we’ve been dedicating our time to JAG students. These students are typically at-risk youth who face multiple barriers to graduating high school. The national JAG Organization services these students by going into the classroom and giving them the hope, guidance and tangible skills needed to succeed. I could talk about how amazing they are for hours; it’s no wonder why eleven state governors sit on their board of directors. 

Q: How does DreamJobbing actually work?

A: Great question and a pretty easy answer. As soon as any organization working with students, high schools or universities wants to move forward, we build them out a page on It’s a branded page for the organization or school, but more importantly it’s the home base where all the students’ DreamJobbing video profiles from that school or organization will live. 

As soon as we set that up, we do a webinar where we walk all teachers through a video curriculum. Our video curriculum is a little piece of our magic- it’s a self directed, video based curriculum to teach the students about personal professional branding and creating opportunities. We make it easy: we do the heavy lifting of teaching and teachers tighten the screws through quality control and implementation.

Q. Lisa, you were a top network executive producer for years, what inspired you to leave that behind and start DreamJobbing?

A. I like being a pioneer. When I started working with Mark Burnett in 1995 – the term “reality TV” didn’t even exist. It was incredible to be part of something new, something innovative. I wanted to have that feeling again. I wanted to use the skills I have learned and connections I have made to create an innovative tech platform that would some day help millions. 

Q. So would you say DreamJobbing is kind of a cool boutique LinkedIn for students?

A. Yes. That’s a great way of putting it. We are a network for students – we help students create a video profile branding themselves professionally and then we teach them to use that profile to connect with professionals for mentorships and companies for job shadows. We give them unique tools to help them get started on their career path. Our hope is that students use this network to get many opportunities – basically career sampling. 

Q. Can you share some success stories?

A. I get excited every time I work with students, and when they succeed- it makes all the hard work worth it. There are so many different success stories, but here are two of my favorites:

We had a JAG high school senior from Florida make a DreamJobbing video profile explaining his goal was to be an engineer. Jacqueline Taylor, the communications coordinator, directly tweeted an engineering firm in Florida his profile video, which led to the company responding with a big YES- bring him in! I love stories like this- where social media is used as a tool to connect and create new experiences, rather than just views and likes.

On the opposite coast, two Los Angeles kids have really inspired me. Jazmyn & Noah, two high school seniors from King Drew High School in Compton, made awesome DreamJobbing video profiles which led them to a day job shadowing at McNulty Casting. The staff spent their time teaching students about entertainment, and the students had a blast. Both kids are on their way to college where they will continue studying entertainment. I cannot wait to see where these two end up.

As the world continues to rapidly change, it appears that DreamJobbing is using technology for good.

In addition to partnering with JAG, the DreamJobbing team is also working with a diverse range of nonprofits, high schools and colleges. Most recently, they traveled to Florida to work with Project Bridge of Eckerd Kids, a program that believes in second chances as they provide services to help youth achieve successful lives and avoid re-entry into the criminal justice system. These kids are talented, strong, and driven- but nobody knows their story. The team helped these students professionally brand themselves on camera to share their story and reach out to mentors. As producers, they want to help kids harness the power of video to grab attention and keep it.

Knowledge, education, and connection can change a person’s life forever. At its core, DreamJobbing’s purpose is to help others create extraordinary lives- whether that be as a mechanic, an engineer, a teacher, an underwater welder or a future Oscar-nominated director. Visual storytelling is the future of opportunity.

You can follow DreamJobbing at @dreamjobbing. If you would like more information, contact:

Author – Claire Marshall