Every now and then, you have a conversation that stays with you long after the mics are off. That’s exactly what happened when I sat down with Jen Livsey on the Exceptional Companies Podcast.
Jen is part of a fifth-generation ranching family in far eastern Colorado. She’s also the co-founder of EastCo Group, a rancher-led risk management business that’s deeply embedded in the ag world. But what made this episode so memorable wasn’t just the family business story or the entrepreneurial lessons—it was the clarity with which Jen talked about building something that actually lasts.
And the phrase that’s still echoing in my head? “Raise children worthy of empire.”
Lessons from a Ranch Built to Last
Jen’s family has been ranching for over 120 years. And while that kind of longevity is impressive on its own, what struck me was the intentionality behind it. Her parents never pressured her to come back home after school—but they did raise her to be someone who could thrive anywhere.
“You’re going to be a good, productive person,” they told her. “An asset to the world.” And by extension, an asset if she ever decided to come back.
That’s exactly what happened. After grad school, Jen eventually co-founded EastCo with her brother Charlie and sister-in-law Katie. Their business now provides risk management services to other ranchers—delivering analysis and insight in a space that can often feel like it’s drowning in complexity.
“We are the demographic we serve,” Jen told me. “We’re ranchers. We understand the business. And we’re simplifying the complex.”
What Makes a Family Enterprise Work
Coming from a family of eight siblings—five of whom are in business—I was curious to dig deeper into what makes a family business actually work.
Jen didn’t sugarcoat it: it’s not easy. But for their family, it comes down to a few key things—shared hardship, a deep respect for family heroes and traditions, and a business that’s exciting enough for future generations to want in.
“You’ve got to raise kids who are capable and independent,” she said, “but you’ve also got to build something worth working in.”
That landed hard. I’ve seen too many friends walk away from family operations not because they lacked love, but because the business lacked vision.
The Skill of Adjusting
Jen and I both come from industries—agriculture, oil and gas—that are notorious for being volatile. And this past year, EastCo got hit with a big regulatory curveball. Major compliance changes. More paperwork. More government oversight.
Instead of panicking, Jen and her team went to work.
“How can we be the best-positioned agency in the country to handle this?” they asked.
That’s the difference-maker. We don’t get to control the ocean, but we do have a boat and a rudder. We call it the “Act, Learn, Adjust” model in our world—and Jen’s team lives it.
Culture That’s Lived, Not Just Said
I asked her how she thinks about company culture, because that term gets thrown around a lot. Her answer was my favorite definition I’ve heard in a long time:
“Culture is just how we do things around here.”
At EastCo, that means EOS (Entrepreneurial Operating System), weekly leadership meetings, and clearly defined values: best in class, individual initiative, and professionalism. And here’s the key—those aren’t just slogans. They guide every hire, every decision, every client interaction.
One of the smartest moves they made? Bringing in two key employees, Olivia and Pete, to help lead.
“We don’t mind conflict—we’re family,” Jen laughed. “But having Olivia and Pete in the room balances us. I only wish we’d done it sooner.”
Faith, Family, and Focus
Jen’s perspective isn’t just shaped by business—it’s shaped by family and faith.
As a mom of four (ages nine to nine months), she knows what it means to focus. And after walking through a major health scare with one of her kids, she now sees life through a sharper lens.
“There are only a few real problems in life,” she said. “The rest? We can handle those.”
That really resonated with me. I’ve had my own moments—those nights early in parenting when you realize just how little control you actually have. That’s when faith becomes more than a concept. It becomes the foundation.
And honestly, it’s what allows us to run hard in our businesses without losing sight of what matters.
The Advice She’d Give Her Younger Self
As we wrapped up the conversation, I asked Jen what advice she’d give a younger version of herself stepping into today’s chaotic landscape—AI, political tension, market swings.
Her answer was simple but powerful: “Surround yourself with people you want to be like. Put yourself in rooms where you’re not the smartest. Be bold. Learn every day.”
That’s it. That’s the playbook.
Resources That Have Helped Jen Level Up
Because we both love talking shop, I also asked Jen what’s been shaping her thinking lately. She shared a few standouts:
- 📘 Book: Unreasonable Hospitality — “One of the best business books I’ve ever read.”
- 🎙️ Podcast: Invest Like the Best — especially the episode on Alpha School.
- 💡 Tech + AI: Every.to — “Takes you from dumb-dumb to slightly less dumb when it comes to AI.”
- 📖 Faith: BibleProject — a deep dive into scripture that’s felt like a college course for the soul.
Hope in the Chaos
We both felt the weight of recent national events when we recorded this episode. The Charlie Kirk tragedy was still fresh. But Jen offered a powerful reminder:
“Sometimes it takes something sad and profound to wake people up. Love your people. Be a light. Affect what you can.”
That’s the call.
And I’ll just add this: if we’re not doing this well in our families, our churches, our businesses—then we have no business talking about fixing the country. The change starts with us. Right here. Right now.
If you’re a business owner asking, “What’s my business worth?” or wondering when the right time to exit might be, visit us at excoadvisors.com to start the conversation.
We help exceptional people build exceptional businesses—and sell them when the time is right.
Thanks for reading. And thank you again to Jen Livsey for the rich, honest, and hope-filled conversation.
Let’s all keep building something worthy.
AND MORE TOPICS COVERED IN THE FULL INTERVIEW!!! You can check that out and subscribe to YouTube.
If you want to know more about Jen Livsey, you may reach out to her at:
- Website: eastcogroup.com
- Website: flyingdiamondcattleranch.com
Connect with Chris Seegers:
- Website: https://exceptionalcos.com/
- Email: Ch***@************OS.com
Other Resources:
- Books: Selling Main Street by Chris Seegers
