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May 28, 2025 62 mins

"Shoot For The Moon. Even If You Miss, You'll Land Among The Stars." ~ Norman Vincent Peale

 

Our guest this week is a WSET level 3 sommelier, who has a passion for attending to tables and connecting her patrons with new wines and dishes that have the potential of expanding their enjoyment of life.

Maddie Wadman is no stranger to trying new things, she’s been doing it her whole life.  Her parents must have had some sense of hope for this when they named her Madison after Daryl Hannah’s mermaid in the movie Splash.  A fish out of water tale of a mermaid trying to live in the human world.  Her parents recount a child who could not sit still, always curious and engaging in things that interested her.  Once, at a restaurant when she was three years old, Madison insisted on being let out of her highchair and went around the restaurant with her napkin to wipe off the tables she noticed were dirty.  The first steps into a career she would later pursue. 

In grade school, Madison wanted a name that wasn’t so plain sounding, something with a unique spelling that better fit her personality, and so it was that she became Maddie.

When she was 18 years old, Maddie set out on her own and made a big move from Indiana to Seattle, where she started working in restaurants.  It was at one of these jobs where she served a man on a rooftop bar who was in town on a business trip from Portland, Oregon.  He seemed a little quiet, so she invited him to hang out a month later.  Maddie discovered that he was a great listener and an amazing conversationalist.  At the end of their evening together, Maddie went against first date conventions and said, “I don’t even know if I’ll ever see you again, but I think I’m going to be married to you.” 

She was right.  She moved down to Portland to begin building a life with her husband.

All was well, until Covid happened and Portland felt increasingly unsafe.  Unable to work in restaurants, Maddie pursued a brief career as a mortgage broker.   Maddie soon found the experience lived up to its Latin translation, “mortgage” means “death pledge”, so she quit and moved on. 

Then she moved with her husband to Sioux Falls, South Dakota for his job.  On their first day living in Sioux Falls, before their moving van was even unloaded, she met her future employer who was excited to have her work at his family’s Italian Restaurant, Mirabella. 

And so goes the amazing story of Maddie’s life.  She’s confident.  She tries things out.  She is successful.  

When I playfully asked her where she sees herself in 5 years, I wasn’t surprised that she had an answer ready to go, “I hope to have some sort of supplemental import business specializing in Australian wine that hosts a big annual event”.

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**Video broadcast available** on YouTube @imperfectbest

**Learn more about Jason Freeman** at AwkwardlyAwesome.com

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