His Wife Told Him to Go All In — So He Did | Bailey of GRAB Gear

In this episode of Give a Sit, Wes sits down with Bailey, co-founder of Grab Bags / GRAB Gear, a company he started with his brother. Bailey shares the story behind building the brand, what it’s like working alongside family, and how a practical idea turned into a business built around preparedness, confidence, and everyday carry. But Bailey’s story goes much deeper than business. He talks about growing up in a family rooted in civil service, with his dad working at the prison and his siblings following that same path as police officers, paramedics, and nurses. That foundation of service, sacrifice, and showing up for others shaped the way Bailey sees work, family, and responsibility. Bailey also opens up about the season when he was working two jobs while trying to build Grab Bags. One day, his wife told him to stop splitting his focus, trust himself, and give the business everything he had. That leap of faith changed everything. In one of the most personal parts of the conversation, Bailey shares the struggles he and his wife have faced on their journey to becoming parents, and the joy of expecting their first child through surrogacy. This episode is about entrepreneurship, family legacy, marriage, trust, resilience, and what can happen when the people closest to you believe in you before you fully believe in yourself.