In this episode of Business Owners Tell All: What It Takes, Jamie Seeker talks with Jonathan Raymond—CEO of Ren AI, based in San Diego, California. Jonathan is also the author of Good Authority, and he’s built a career around one thing: helping leaders show up with emotionally intelligent leadership.
If you’re a business owner, manager, or startup founder, this episode is a masterclass in how to lead with authenticity—and why your financial outcomes depend on it.
How a CEO Discovered Emotionally Intelligent Leadership
Jonathan started his career as a lawyer in Manhattan. Later, he moved into tech, clean energy, and nonprofit work. But it wasn’t until he became a CEO himself that he realized he had a serious problem. He could drive results, but he couldn’t develop people.
“I suck at this… and I think I’m a pretty well-intentioned person. Maybe this is a bigger problem than I think.”
—Jonathan Raymond
That realization led him to create the leadership development platform Ren AI, a coaching tech tool that guides leaders through conversations they’ve been avoiding.
Why Leaders Struggle With Being Real
Jamie asked:
“Why do you think so many leaders struggle with authenticity, even when they have the best intentions?”
Jonathan explains that most leaders have been taught that showing emotion is weak. But in reality, emotional intelligence is strength. When leaders talk openly about fear, stress, or mistakes, they actually build trust.
“We grow our businesses at the pace we grow our willingness to tell the truth.”
—Jonathan Raymond
How Emotionally Intelligent Leadership Drives Financial Results
This episode tackles a powerful question:
“How do you connect those dots between emotionally intelligent leadership and hard financial outcomes?”
—Jamie Seeker
Jonathan’s answer? It’s always behavioral. If you’re not hitting your KPIs, the real issue probably isn’t your sales tools or marketing budget. It’s how your team communicates, collaborates, and responds to feedback.
“The answer is always behavioral.”
—Jonathan Raymond
When leaders build emotionally intelligent teams, performance improves across the board—from retention and morale to revenue and project delivery.
The Financial Cost of Avoiding Hard Conversations
Jonathan highlights a painful truth: most leaders spend more time avoiding conversations than having them. And it’s expensive.
“You’re spending so much time not having those conversations—with all your workarounds and BS performance plans.”
—Jonathan Raymond
Instead of being direct with underperformers, leaders try to manage around them—costing time, money, and the trust of top performers.
Smart Financial Planning Starts With People
Jamie also asked:
“What are some strategies or principles that you advise your clients on with financial planning during early growth phases?”
Jonathan’s advice? Invest in connection. In-person gatherings, even without a business agenda, help build team trust and alignment. That’s how you prevent miscommunication, misalignment, and burnout down the road.
What It Takes to Be a Business Owner Today
Every episode ends with our signature question: What does it take to be a business owner?
“Blind faith and taking out the trash.”
—Jonathan Raymond
You need vision. You need grit. But most of all, you need to do the unglamorous stuff that keeps things moving—even when nobody’s watching.
Listen to the Episode
🎙 Episode Title: Emotionally Intelligent Leadership: What It Takes with Jonathan Raymond
👤 Guest: Jonathan Raymond, CEO of Ren AI
📍 Location: San Diego, California
📲 Website: tryren.com
📕 Book: Good Authority
Memorable Quotes
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“Leadership isn’t about being liked. It’s about being real—especially when it’s hard.”
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“Culture isn’t a perk. It’s how people feel between meetings.”
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“What it takes is whatever it takes.”
Final Thoughts
Emotionally intelligent leadership isn’t just good for your people—it’s good for business. This episode is a must-listen for anyone ready to lead with honesty, courage, and compassion.
