#971 What does it take to build a thriving matchmaking business while raising three kids and empowering others to find love? In this inspiring episode, host Brien Gearin sits down with Siobhan Copland, founder of Cupid in the City and Project 143, to hear how she transformed her side passion into a full-fledged career helping busy professionals find meaningful relationships. Siobhan shares her journey from getting laid off to becoming a sought-after “female Hitch,” the lessons she’s learned about knowing your worth and pricing accordingly, and how she balances entrepreneurship with motherhood. From the power of authentic connection to the freedom of working for yourself, this episode is a masterclass in following your passion and creating a life you love!

(Original Air Date - 10/30/25)

What we discuss with Siobhan:

+ Siobhan’s journey into matchmaking

+ Launching Cupid in the City after redundancy

+ Early success finding her first clients

+ Lessons from running London singles events

+ Transitioning from side hustle to full-time business

+ Balancing motherhood and entrepreneurship

+ The importance of self-awareness in dating

+ Coaching clients to become “ready for love”

+ Competing with dating apps through personal touch

+ Scaling her business and raising her prices

Thank you, Siobhan!

Check out Cupid in the City at ⁠CupidintheCity.com⁠.

Follow Siobhan on ⁠Instagram⁠.

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