One Take with Phillip Oakley

Published on 24 February 2026 at 11:31

Disrupting the disruptors


How being in retail contributed to branding - Click on the picture to watch

👉 The Scoop – Phillip Oakley has been in advertising for almost 3 decades. He is a true fan of branding, not in the superficial “logo and colors” way but in the deeper sense that branding is what tells a consumer why to buy that product.

👉 Decisive Moment #1 – Was working in retail, saw the movie “What Women Want”, decided advertising was for him, quit retail, became a bartender, went back to school and started freelancing.

👉 Unexpected change or event – Fiverr. Talented people doing great work, but not living in our own ecosystem.

👉 What did he do? – Realized Fiverr would disrupt his world, doubled down on providing enough value so he would not be disrupted. “For me, it was more, how do we add more layers of expertise, training, experience?” Basically, disrupting the disruptor.

👉 About older workers – I think bringing someone in who can teach you something outside your industry is really important but relate it back to your business. Someone who can come in and actually teach them something that they may otherwise learn the hard way. It just takes experience to do that. And it takes different life experiences and business experiences to recognize the financial or business impact or cultural impact of those things as well.

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