The Entrepreneur Podcast · Eric Janssen and Eric Morse

64. Improving your luck with brand guru Shane Skillen

·28 min·1 clip

Jensen says high expectations can produce low resilience, and character comes from suffering.

Eric Morse introduces Shane Skillen as an Ivy HBA 2000 grad with a long career in market research. Skillen says the trip back to campus brought back memories, and that he now lives in Collingwood with his wife and three sons. He explains that his kids race skis competitively and that he once skied for Western. The episode quickly turns to the idea that entrepreneurial success often looks like luck from the outside. Skillen argues that luck can be influenced, rather than simply received. He frames it as something that can be improved through preparation and action. The discussion gives the idea a practical shape instead of leaving it as a slogan. Skillen draws on more than two decades at Hotspecs, where he has worked with international brands through major media shifts. He points to the changes brought by the internet, then social media, and now artificial intelligence. Those shifts form the backdrop for the episode’s larger argument about how businesses stay relevant. The conversation also makes room for a story about charitable work. Skillen describes helping SickKids with a campaign that needed to raise a huge amount of money for a new home. Research showed that many charities default to sadness and illness in their messaging. His team found a different strategic space. They helped shape an ad that framed disease as the enemy and children as fighters. The creative work, done with Cassette, gave the campaign a sharper emotional center. Skillen says the result was a major success. The effort raised far more than expected and became the most successful fundraising campaign in Canadian history. He also says it later won global ad campaign of the decade. From there, the episode returns to the central point: luck grows when people are prepared, open, and willing to act on the opportunities in front of them. Skillen treats chance as something you can position yourself for. He ties that back to entrepreneurship, where relationships and readiness often decide who gets noticed. The closing advice is blunt and social. Don’t sit alone. Talk to people. Build the relationships that make future openings easier to recognize. The episode ends with that idea of luck as something shaped by preparation and contact, not just fate.

As heard by us

A clear argument for preparing well enough to recognize luck when it shows up.

Shane Skillen makes a plain argument: luck is not purely random, and people can tilt it their way by preparing and staying open when chances appear.

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Why you'd press play

Hear how better preparation can turn chance into an advantage.

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