September 16, 2026 · 47 min · Episode 778
Beyond Automation: Joshua Evarts on Relational Leadership and Human Connection
About this episode
Anika sat down with Joshua Evarts to explore how the rapid acceleration of artificial intelligence and digital communication impacts the fundamental engine of every business: human relationships. Drawing from a diverse career leading national security software companies, managing historic building restorations, running a community cigar lounge, and parenting a son working at OpenAI, Joshua offered practical insights into balancing technological automation with authentic connection, intentional culture building, and genuine curiosity.
In This Episode
- Transitioning from early software programming on a Commodore 64 to leading national security tech companies
- The accidental pivot from accounting to building Easy Street Draw for automobile accident and homicide investigations
- Deploying to Iraq and working with New Scotland Yard on post-blast investigations
- Surviving stage 3 pancreatic lymphoma in 2020 and how facing mortality reshaped his perspective on presence
- Opening a historic cigar lounge and discovering that authentic generosity is contagious
- The reality of parenting an OpenAI employee and navigating generative AI at the dinner table
- Why genuine relationships and curiosity remain the ultimate competitive advantages in an automated world
- The philosophy behind his book series, starting with If Jesus Smoked Cigars: Eight Lessons in Relational Leadership
Timestamps
- 00:03 Introduction: Balancing AI integration with thoughtful, ethical, and strategic human guidance
- 02:54 Early programming roots on a Commodore 64 and leaving accounting for tech entrepreneurship
- 07:15 The three sentinel shifts: accelerating communication speed, COVID-19 distancing, and the advent of AI
- 09:12 Battling stage 3 pancreatic lymphoma during 2020 and choosing gratitude as a daily mindset
- 10:14 Choosing presence over devices: leaving phones behind and prioritizing real human interaction
- 14:38 Writing If Jesus Smoked Cigars: using cheeky titles and obscure historical stories to teach relational leadership
- 26:45 Navigating generative AI slop, social media echo chambers, and the obsession with capturing digital data
- 29:21 Advice for the next generation: pursuing math, logic, and curiosity rather than fearing replacement
- 41:47 Recognizing that relationships are hard work and require intentional daily effort
Key Insights & Takeaways
Insight 1: Relationships Cannot Be Outsourced to AI
While generative AI automates routine tasks and text generation, it cannot replace genuine human connection. In an increasingly automated business world, the ability to build trust, listen deeply, and maintain authentic relationships serves as an irreplaceable discriminator.
Insight 2: Reckless Generosity Builds Thriving Communities
Treating business relationships purely as transactions limits growth. True generosity is contagious; when business owners genuinely support their peers and foster inclusive environments, the entire community benefits and rises together.
Insight 3: Focus on Culture and Process Over Outcomes
Founders and leaders cannot control external market conditions or outcomes—they can only control their attitude and actions. Prioritizing a healthy, people-first culture and mastering daily processes naturally attracts top talent and loyal customers.
Insight 4: Curiosity Outweighs Perfection
Entering unfamiliar rooms and asking genuine questions creates unexpected opportunities. Being infinitely curious and willing to admit what you do not understand allows professionals to successfully navigate major career pivots across entirely different industries.
Insight 5: Avoid Confusing Market Velocity with Productivity
The rapid speed of technological advancement often tricks organizations into measuring activity rather than true business impact. Leaders must evaluate whether new tools genuinely serve their mission or create unnecessary friction for human users.
Resources & Links Mentioned
- IfJesus.com (Joshua's official website for workshops, book info, and direct contact)
- If Jesus Smoked Cigars: Eight Lessons in Relational Leadership by Joshua Evarts
About Joshua Evarts
Joshua Evarts is an author, entrepreneur and former technology executive with more than 30 years of experience building businesses in technology. He is the author of If Jesus Smokes Cigars: Eight Lessons in Relational Leadership, a book exploring how leaders and professionals can build stronger relationships in a tech-saturated world. After decades in tech, Joshua opened a cigar lounge built around conversation, storytelling and authentic connection, which became a real-world expression of his belief that innovation matters, but people still come first. As the father of a son who works at OpenAI, Joshua brings both personal and professional perspective to conversations about AI, the future of work and the human skills that technology cannot replace.
Connect with Joshua
- Website: https://ifjesus.com/
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Article
Joshua Evarts on Relational Leadership and Human Connection in the Age of AI
Joshua Evarts is an author, entrepreneur and former technology executive with more than 30 years of experience building technology businesses. In this episode of Your Brand Amplified, he talks with Anika Jackson about balancing automation with human connection, intentional culture and curiosity. His core point: AI can take on routine work, but trust and relationships cannot be outsourced.
Joshua Evarts is the author of If Jesus Smoked Cigars: Eight Lessons in Relational Leadership, the first book in a series on how leaders can build stronger relationships in a tech-saturated world. His workshops, book information and contact details are at IfJesus.com.
How did curiosity shape Joshua Evarts's career?
Curiosity is the thread that runs through every turn of his career. Joshua Evarts started programming on a Commodore 64. An accidental pivot away from accounting led him to build Easy Street Draw, software used in automobile accident and homicide investigations. That work took him to Iraq and to collaborating with New Scotland Yard on post-blast investigations. He went on to lead national security technology companies and, along the way, managed historic building restorations.
His view is that walking into unfamiliar rooms, asking real questions and admitting what you don't understand opens doors that perfectionism keeps shut. That willingness is what let him move between very different industries.
What changed after his cancer diagnosis?
In 2020, Joshua Evarts was diagnosed with stage 3 pancreatic lymphoma. Facing his own mortality changed how he thinks about being present with the people around him.
It also shaped his next chapter. After decades in tech, he opened a cigar lounge in a historic setting, built around conversation and storytelling. There he found that generosity spreads. When business owners support their peers and make inclusive spaces, the whole community benefits. He calls it reckless generosity, the opposite of treating relationships as transactions.
Why can't relationships be outsourced to AI?
Because tools can automate tasks but not trust. Joshua Evarts has a close view of the technology: his son works at OpenAI, so generative AI comes up regularly at the family dinner table. He sees clear value in automating routine tasks and text generation. He is equally clear that AI cannot replace deep listening and real relationships, and that in an automated business world those human skills become a differentiator. His cautions for leaders:
- Do not confuse velocity with productivity. Fast technology can push teams to measure activity instead of impact. Ask whether a new tool serves the mission or adds friction for people.
- Focus on culture and process, not outcomes. Leaders cannot control the market, only their attitude and actions. A healthy, people-first culture attracts strong talent and loyal customers.
- Stay curious. Genuine questions create opportunities that polished answers rarely do.
Key takeaways
- Use technology to support relationships, not replace them.
- Measure impact, not activity; speed is not the same as productivity.
- Culture and process are within a leader's control; market outcomes are not.
- Generosity among business owners strengthens the whole community.
- Asking questions and admitting what you don't know opens doors across industries.
Listen to Anika Jackson's full conversation with Joshua Evarts on Your Brand Amplified.
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