In this episode of Business Owners Tell All: What It Takes, host Jamie Seeker sits down with Jonathan Raymond, the founder and CEO of Ren AI, a coaching technology company based in San Diego, California. With a background that spans law, tech entrepreneurship, and nonprofit leadership, Jonathan shares how he discovered the missing link in leadership: authentic, emotionally intelligent conversations.

We dig into:

• Why leaders struggle with hard feedback
• How personal development collides with business results
• The myth of “soft skills” in the workplace
• Why culture is the biggest driver of financial outcomes
• Common financial missteps leaders make while scaling

Plus, Jonathan delivers a powerful answer to our signature question—what it really takes to be a business owner in today’s world.

🧠 Key Themes & Takeaways

🧭 Origin Story

• Jonathan realized in his first CEO role that driving results wasn’t enough—he lacked the ability to develop people.
• Despite personal training in therapy and mindfulness, he couldn’t translate those skills into the workplace. That gap sparked the creation of Good Authority and eventually Ren AI.

"I suck at this… and I think I'm a pretty well-intentioned person. Maybe this is a bigger problem than I think."

🧠 Emotional Intelligence is a Business Strategy

• Leaders often confuse vulnerability with weakness. In fact, acknowledging fear or anxiety fosters trust and deepens engagement.
• Authenticity is not a luxury—it’s a productivity tool.

“We grow our businesses at the pace we grow our willingness to tell the truth.”

💸 Financial Planning & Leadership Behavior

• The disconnect between culture and financial outcomes is a major issue in growth-stage businesses.
• Jonathan breaks it down: poor metrics aren’t a product problem—they’re a people and behavior problem.

“The answer is always behavioral.”

• Leaders often spend most of their time on the bottom 20% of performers, neglecting the team’s top talent.

“You're spending so much time not having those conversations—with all your workarounds and BS performance plans.”

🏗 Strategic Leadership Advice

• Get your team in person. Even just to connect, no agenda. Building context and relationship improves team alignment and reduces friction.
• Ask deeper questions: “Who was your first boss?” “What did authority look like growing up?”

“In the absence of personal glue, small problems become massive.”

🔥 Memorable Quotes

“Leadership isn't about being liked or being right. It’s about being real—especially when it’s hard.”

—Jonathan Raymond

“Blind faith and taking out the trash. That’s what it takes.”

—Jonathan Raymond on what it takes to be a business owner

“It’s not that you don’t have time to have the conversation—you’re already spending more time not having it.”

—Jonathan Raymond

“Your mother doesn’t work here. You're not special. You're not better than anyone. Do what it takes.”

—Jonathan Raymond

📍 Guest Info

Jonathan Raymond

Founder & CEO, Ren AI

Author of Good Authority

Personal site: jonathanraymond.com

Location: San Diego, CA

Social: LinkedIn