You're Not Behind — You're Just in the Hard Market with Jesse Cruz

Jesse Cruz has been building Brightway Insurance, The Cruz Agency, in the middle of one of the hardest markets the industry has seen — and he didn't just survive it, he pivoted, stayed all in, and started winning.In this conversation, William sits down with his friend, fellow veteran, and mastermind group member Jesse Cruz to talk about what it really takes to build a family business from scratch. From drawing on his 401k to keep the lights on, to flipping vintage cast irons on eBay just to stay afloat — Jesse's story is raw, real, and full of the kind of grit that doesn't make it into highlight reels.But this episode goes deeper than business. Jesse opens up about a year that tested him on every front — growing a business, navigating personal loss, and finally receiving the news he and his wife had been praying for: baby Noah is on the way. What you'll hear is a man who kept driving when it would have been easier to quit — and who credits community, faith, and a good mastermind group for helping him turn the corner.Key Highlights[00:02:30] — From corporate America to Brightway: how COVID changed Jesse's trajectory and why insurance made sense for a 20-year sales veteran.[00:06:30] — What happened when his wife joined the business full-time — the clash, the growth, and why it made the whole operation sharper.[00:07:00] — Drawing from the 401k, pivoting to commercial lines, and reselling on eBay: how Jesse kept the business alive during the hard market.[00:10:30] — Why business insurance isn't one-size-fits-all — and the questions most owners never think to ask until it's too late.[00:16:30] — A year and a half in the mastermind group: how community contributed to 25% revenue growth and a mindset shift.[00:20:30] — How to actually work a Chamber of Commerce — not to get clients, but to become a people connector.[00:28:00] — A year of personal trials, grief, and the news that changed everything: baby Noah is coming.[00:31:00] — Jesse's framework for getting through the hard seasons: control the controllables, invest in yourself, and don't you dare quit.Jesse's 3 Life Lessons:Don't be afraid of challenges. Reinvest in yourself and go all in. And find a support system that believes in you — because no one builds anything great alone.Ready to connect with Jesse?Search Brightway Cruz on Facebook or Google, or give the Cruz Agency a call at (346) 355-6611. Veteran-owned, family-operated, and right here in Pearland.And if this conversation hit home, share it with a business owner who's in the middle of a hard season — they need to hear it. Subscribe to Business Coffee Hour so you never miss a conversation that reminds you leadership, resilience, and community are what actually build businesses worth having.You are loved. You are enough. And you are stronger than the problems you face.