Five Questions with Crackle Plus Redbox’s Darren Olive

Darren Olive
President, Advertising Sales
Crackle Plus Redbox


What are three attributes that got you where you are now?

1) Believing in yourself (but surround yourself with people who know what you don’t). 2) Being able to adapt, evolve and change. 3) Being persistent – but not obsessed.


What advice would you give to someone who is looking to enter the market?

Talk to as many people about the roles in media – all sides – and what purpose they serve. And ask a ton of questions.


Pre-workday, what is your morning ritual?

I’d love to say it’s 20 minutes on my Peloton and meditating…but it’s more like getting a 3 year old out to daycare and coffee. A lot of coffee.


What about your job keeps you up at night?

The pace that it moves at. Once you think you’ve figured things out, they change and you need to shift on the fly. And learning that you simply cannot get through your to-do list every day.


In an industry brimming with information, what isn’t talked about enough?

The role the viewer plays in any decision making at a company. We sometimes forget that we succeed (or fail) based on what a potential customer does. What they want, when and where they want it, and how they get it. Fill a need, big or small, and you have a better chance to succeed. And don’t overthink things.

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