Episode 46
I’ve had a lot of powerful conversations on the Successfully Unsuccessful podcast, but my recent sit-down with Jake Howes hit differently. This wasn’t just another business founder telling a story of launch and scale—this was a deep, real, and raw conversation with a man who dared to trade comfort for calling. Jake is the founder of Pioneer Golf Company, a custom golf simulator business, but more than that, he’s a guy who decided to chase something bigger than a paycheck. Watching Jake step out of the corporate safety net and into the unknown was like watching a modern-day David face down Goliath—armed not with stone, but with faith, grit, and relentless purpose.
What captivated me most was Jake’s clarity—not just in what he’s building, but why he’s building it. He’s not just selling simulators—he’s crafting custom experiences, leading with radical responsiveness, and embedding excellence in every install. I watched him go from pitching a nationwide video strategy at his W-2 job to criss-crossing the country filming facilities and putting his employer on the map—only to realize his ceiling was lower than his potential. That’s when he brought his business idea to our core council group. His plan? Launch in April 2025. Our feedback? Why wait? He left that meeting with courage in his pocket and launched months ahead of schedule. Since then, he’s not only been building a company—he’s been building a marriage, a brand, a life grounded in Christ. And let’s not forget—his wife’s starting a business too. That’s the kind of hustle that doesn’t just build companies. It builds legacies.
This conversation reminded me that freedom isn’t just financial—it’s spiritual, emotional, and deeply personal. Jake’s story is proof that when we stop waiting for perfect conditions and start obeying the call on our lives, amazing things happen. He didn’t have it all figured out. He still doesn’t. But he started. And in a world where so many play it safe, Jake’s leap is a wake-up call to all of us who have something burning inside. Whether you’re a CEO contemplating your next big move or a founder feeling the weight of the unknown, Jake’s journey will light a fire in you. Because if he can do it, you can too.
