How Compassion and Connection Built Two Businesses (with Windy Elstermeier)

Oct 22

If you’ve ever struggled with handing things off, trusting partners, or wondering if you’re the only one who truly gets what your business is about—this episode is for you.

On the latest episode of the TrustBuilt Podcast, I sat down with Windy Elstermeier, CEO of Pivotal Solutions and founder of Jane Wick, to talk about how connection and compassion have shaped every step of her entrepreneurial journey.

From training teams at Walmart to building a women-led gun range bag company (you read that right), Windy’s story is full of lessons on what happens when trust is your strategy, not your afterthought.

What Windy Taught Me About Leadership That Lasts

What struck me about Windy’s story wasn’t just her success—it was how deeply she leads from service.

She doesn’t manage people. She connects with them. Whether she’s building out a consulting team or launching a brand-new product line, her first question is never “How do I get what I want?” It’s “How do I help this person grow?”

And that posture—one of service and trust—has turned coworkers into long-term partners across multiple ventures.

We also talked about something many leaders are afraid to admit: that moment when imposter syndrome is screaming in your ear and you’re still supposed to show up with confidence. Windy’s been there. She knows what it’s like to stand on a stage or step into a boardroom and wonder, “Am I really the one for this job?” And she’s learned to lead anyway.

When she launched Jane Wick, it wasn’t some big brand play. It was a solution to a real, overlooked problem—every range bag on the market was designed by and for men. So she made one for women. Functional. Stylish. Thoughtful. Trusted.

And the way she launched it? Through story. Through conversation. Through the kind of genuine connection that makes people believe in your vision—because they believe in you.

There’s a pattern with Windy: when she leads with service, opportunity follows. Not always immediately. Not always predictably. But always in a way that builds something meaningful—and something that lasts.

My Favorite Takeaway

“You don’t have to have all the answers. You just have to be willing to ask the right questions and build with the right people.”

Too many entrepreneurs try to scale by doing more. Windy shows us how to scale by trusting more—through partnerships, through systems, and through people who share your vision.

If you’re tired of running a business that depends on you to do it all, Windy’s story is a reminder that trust isn’t just the outcome—it’s the engine.

Watch it on YouTube:
How Trust and Connection Built Two Thriving Businesses – with Windy Elstermeier