From baling straw as a teenager to running multiple companies and helping others grow theirs — today’s guest Jesse Bounds is a powerhouse entrepreneur. Based in Oregon, Jesse has built a trucking fleet, a global hay export business, and a business coaching platform that’s changing lives. We’ll hear how he scaled from humble beginnings to managing 20 employees and multiple ventures — and how you can apply his playbook to 10x your farm or business
Jesse Bounds — a farmer, hay exporter, trucking company owner, business coach, and content creator from Eugene, Oregon. Jesse’s story is one of grit, growth, and generosity. From his early days working on a grass seed farm at 16 after his parents divorced, to buying his first baler in high school, Jesse’s entrepreneurial journey is both inspiring and deeply practical.
We dive into the origin and expansion of Jesse Bounds Trucking, where every truck — including his iconic refurbished 1986 Peterbilt 259 shoot hood — is painted in classic Peterbilt orange. Jesse shares the story of restoring that first truck with a close friend who recently passed, a moment that shaped his approach to business and legacy.
His flagship venture, Bounds Hay Company, now includes massive storage barns, a hay bale press, hay squeezes, and a 110-foot scale — exporting hay daily to Korea and Japan. From farming and baling to international shipping logistics, Jesse breaks down the systems that keep the operation running 24/6.
He’s also the founder of Ten Four Coaching, a business training platform with workshops like Baler School and a Finance Workshop for entrepreneurs dealing with financial stress. Jesse provides listeners with practical, tactical strategies to identify growth opportunities, break through business plateaus, focus on revenue-driving activities, and craft a long-term vision.
As a bonus, we touch on Bounds Coffee, Jesse’s small-town coffee shop serving smoothies, espresso, and Lotus drinks in Junction City, Oregon — a reminder that passion projects and business can go hand in hand.
Whether you're a farmer, trucker, business owner, or dreamer, Jesse’s top five actionable tips and stories from the field offer a roadmap to turning hustle into success — with no excuses and no shortcuts.