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Will it sell? Overcoming an artist's greatest worry

Despite her success, Caroline To, known professionally as Your Smith struggled to envision a secure financial future. After pursuing other business ventures, she found more freedom in her music.

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Caroline To is more than a musician, "I'm a small business owner, a restaurant owner, Airbnb manager, a business analyst, subcontractor," she said. "Oh, and I'm a mom."
Caroline To is more than a musician, "I'm a small business owner, a restaurant owner, Airbnb manager, a business analyst, subcontractor," she said. "Oh, and I'm a mom."
Graham Tolbert

Caroline To, professionally known as Your Smith, has been pursuing music for over two decades. But despite her success, she never felt financially secure.

“I didn't have health care, I didn't have any kind of retirement,” To said. “That felt so just unachievable based on, and I’m doing air quotes, like a middle-class artist income.”

In 2023, in pursuit of that security, To opened Howard’s Bar, in Stillwater, Minnesota, with the help of her chef husband.

To hear more of To’s story, click the audio player above.

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