Some moments in business quietly reveal what truly matters, and this was one of them.

A pushy sales rep walked into a bowling center expecting a transaction—but what he really demonstrated was the cost of ignoring context, cues, and basic humanity.

This short story unpacks why curiosity, kindness, and awareness matter far more than any binder full of features. You’ll hear how showing up misaligned with the room can shut doors—and how leading with relationship can open many more. A small moment, a big reminder: your presence is part of your pitch.

Sometimes the thing we wished someone would give us becomes the thing we’re meant to build ourselves. In this episode, Jason reflects on the early dreams, detours, and small-town influences that shaped his relationship with entrepreneurship. He shares how a long-held fantasy of being “chosen” by a seasoned business owner eventually transformed into becoming that stabilizing presence for others.

Along the way, he explores the real work behind growth—systems, scaffolding, and sustained intention—and how supporting emerging entrepreneurs has become one of the most meaningful parts of his career. Listeners are invited to consider where they’ve already become what their younger selves were waiting for.

 When things in business finally feel steady, it’s tempting to coast — but that’s often the moment when fresh creativity matters most.

In this episode, Jason shares how launching the micropod rekindled a sense of possibility, reopened old creative muscles, and sparked entirely new projects, including a tactile mailer rooted in community and connection. He reflects on why small experiments can revive momentum and how following a creative spark can reshape the work in surprising ways.

This short reflection invites you to consider where something new might reawaken energy in your own business and life. Try one small creative shift this week and see what it unlocks.

In this episode, we explore how quiet mentors shape us long before we realize we’re being influenced.

Jason shares the story of Keith, a colleague who modeled a simple, consistent habit of planting possibilities in every interaction.
Through his example, we see how gentle prompts, generous ideas, and low-pressure invitations can open meaningful doors in business and relationships.

The episode also highlights how seed planting shows up in Jason’s own work today, including a recent video collaboration that grew from a single, thoughtful outreach. It’s a reminder that clarity and opportunity often begin with small, intentional gestures. Try planting some seeds this week.

In this episode, Jason reframes one of sales culture’s most famous lines by showing why the real work isn’t in closing fast—it’s in opening with intention. He shares early memories from his staffing days, where discovery meetings taught him that trust creates more momentum than pressure ever could. We hear how an old client relationship unexpectedly grew into his biggest project of the year, and why small acts of service compound over time. Through stories of colleagues, friendships, and slow, steady connection-building, this episode invites us to rethink what sustainable growth really looks like. The reminder is simple: open the relationship first, and the right opportunities will follow.

unforgettable in business and life.

Show Notes:

People do business with people, not brands. Be human, be creative, be real - and you’ll stand out.

Key Ideas: Authenticity, vulnerability, humor, connection.

Quote: “People don’t remember boring.”

Jason tells the story of his first big sales mistake and how one small slip almost cost him the deal, and what it taught him about knowing when to stop talking.

Show Notes: After closing a deal, Jason made a rookie mistake: he kept talking. The lesson stuck. Learning when to stop talking is important for sales.

Key Ideas: Listening, confidence, communication.

Quote: “Once they say yes - stop selling.”

Jason shares the story behind the 100 Cups MicroPod name - and a key leadership principle: protect your focus by limiting who gets a say in your vision.

Show Notes:From a coach’s advice to a designer’s insight, Jason learned that too many voices can dilute clarity.

Key Ideas: Focus, decision making, leadership, brand alignment.

Quote: “Protect your focus by limiting the inputs around you.”

A true story from Jason’s staffing days - when a baseball bat, a bad deal, and karma taught a lasting lesson about integrity and relationships.

Show Notes:

A client once strong-armed Jason out of a fee. Later, the tables turned. Integrity wins every time.

Key Ideas: Integrity, reputation, long-term thinking, relationships.

Quote: “Never burn bridges - and definitely don’t smash them with a bat.”

Jason reflects on a coffee shop encounter that revealed a truth about success - it doesn’t show up all at once; it leaks out slowly through rhythm and daily habits.

Show Notes:

From drummers to writers to leaders - those who love their craft keep the beat, every day.

Key Ideas: Consistency, purpose, daily rhythm, mastery.

Quote: “Success leaks out slowly from daily habits.”