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Podcast Episode

Why Successful People Can't Find Love — with Matchmaker Siobhan Copland

The Entrepreneur’s Cut··1 August 2026·52 min

About this episode

She's helped countless professionals find lasting love — but what professional matchmaker and dating coach Siobhan Copland reveals in this conversation might surprise you. The biggest barrier to meaningful relationships isn't your schedule, your standards, or your success. It's your willingness to be seen. In this raw and eye-opening episode, Siobhan breaks down why high-achieving women often lead with masculine energy and push love away, why men inherently want to feel useful (and what happens when they don't), and the real meaning behind intimacy that most people get completely wrong. If you've ever wondered why you keep attracting the wrong person — or no one at all — this one's going to hit different.