Recently we were honored to welcome Bailey Pain, O’Fallon native and entrepreneur, to our Silver Creek Area CEO class! Bailey is the owner and creative force behind Piper & Finch Luxury Stationery, her custom wedding invitation and table card business, and Willa Street Stationery.

Bailey shared her entrepreneurial journey with honesty and heart. She began her Etsy shop in 2014, celebrating her first sale—only to wait more than a year before her second. Instead of becoming discouraged, she used that season to learn and grow. It was during this time that she realized the importance of branding—creating consistent colors, designs, and style that made her work recognizable and trustworthy. That lesson became a turning point in her business.

After graduating from Delta State University with a degree in CIS, Bailey was ready to climb the corporate ladder, make a lot of money, and become “the boss.” She worked in IT for many years with Panera and currently serves as a Project Manager for DraftKings, building an impressive professional career alongside her creative businesses.

She spoke openly with our students about how her definition of success has evolved over time. After marriage and starting a family, her priorities shifted. Today, she defines success as doing meaningful creative work, building real connections with her clients, and having more time with her family. She reminded our students that success doesn’t look the same for everyone—and that it’s okay for goals and priorities to change.

Bailey also spoke about the importance of building strong relationships, learning from others, and handling negative customer feedback with professionalism, emotional maturity, and grace.

Her message was especially impactful for our students as they prepare to launch their own businesses—many of whom plan to sell handcrafted products online. Understanding branding and online presence now will help them stand out, build credibility, and grow customer trust from the very beginning.

What stood out most was Bailey’s authenticity. Our students connected deeply with her honesty, her willingness to share both challenges and victories, and her encouragement to never stop learning and growing.

We are incredibly grateful to Bailey for investing in our students and reminding them that entrepreneurship is about more than profit—it’s about purpose, resilience, and relationships.

Thank you, Bailey, for inspiring the next generation of leaders and entrepreneurs. 💛