Jackson Miller

Jackson Miller – Leadership, Self-Discovery, and the Power of EO

Jackson Miller is the Founder and CEO of ResaleAI, a SaaS product used by over 700 retailers to simplify store operations. With over 15 years of experience as a tech entrepreneur, he launched L2M, LLC, which operated multiple Plato’s Closet stores; Bizen, a cloud analytics platform; and BorderJump, LLC, a startup providing integrated solutions for retailers. Jackson is also a keynote speaker in technology and a member of EO Nashville.

Here's a Glimpse of What You'll Learn

[2:42] Jackson Miller’s motivation to become an entrepreneur and his early triumphs and failures
[10:33] How an EO retreat helped Jackson reconsider leaving his marriage and gain deeper self-awareness
[16:09] EO’s role in Jackson’s leadership development
[20:45] The mindset shifts Jackson experienced from EO forums
[24:26] How Jackson discovered his core purpose
[29:12] Jackson shares his perspective on the future of AI in the workplace

In This Episode

Feeling stuck in both business and life can leave even the most driven entrepreneurs questioning their next move. It’s easy to get buried in daily operations or personal struggles and lose sight of what really matters. How can you create clarity and momentum when everything feels off track?

Seasoned entrepreneur and software developer Jackson Miller faced business friction and a strained marriage simultaneously. Through EO, he found structure, support, and space for self-reflection. A transformative forum retreat helped Jackson reconnect with his core purpose, save his marriage, and lead with greater empathy. By leaning into vulnerability and peer feedback, you can step back from control, embrace discomfort, and design a future rooted in clarity and intention.

In this episode of EO Nashville’s The Decision, Robert Hartline and Eric Jackson chat with Jackson Miller, Founder and CEO of ResaleAI, about how he navigated personal and professional turning points. Jackson talks about the mindset shifts he experienced during his EO forum, how he discovered his core purpose, and the future of AI in the workplace.

Quotable Moments:

“I’m highly competitive and generally discontent, and so that lended itself well to being an entrepreneur.”
“I like solutions that are obvious in hindsight but not obvious in foresight, right?”
“Sometimes you focus too much on the win-lose instead of the win-win.”
“I don’t have a lot of regard for the status quo… but I am also the status quo.”
“Let computers do what computers are good at so that people do what people are good at.”

Action Steps:

Embrace structured reflection through retreats or forums: Creating intentional space for introspection helps leaders reconnect with core values and long-term goals. It can also surface solutions to both personal and professional challenges that aren’t obvious in day-to-day operations.
Speak from personal experience, not advice: Sharing stories rather than prescribing solutions encourages empathy and trust among peers or team members. This method fosters deeper insights and more thoughtful leadership.
Identify and reduce friction in your processes: Pinpointing and removing minor obstacles can lead to smoother operations and better customer and employee experiences. Consistently improving workflows prevents burnout and boosts performance.
Acknowledge your evolving role as a leader: Recognizing when your business no longer needs your day-to-day involvement allows others to grow. Letting go of control can strengthen your team and free you to focus on future opportunities.
Align your actions with your core purpose: Understanding what truly drives you ensures that your decisions are both fulfilling and sustainable. This clarity helps guide strategic direction and personal satisfaction.