Welcome to the space between

Melissa Kwan is a 3x bootstrapper who's built a successful software business that's designed specifically for her lifestyle. Melissa talks about her founder journey and the transition from trying to build a $100M business to building a company that suites her as a person. Melissa also produces fire LinkedIn content about what it's really like to build a company and has fascinating ideas for her next chapter. Other topics include non negotiables, the tradeoffs of building big, being surrounded by unicorn porn and the fulfillment of building a community outside of work.

Ryan Vaughn on basketball, the drive for validation and achievement, sabbaticals, surrendering to win, fulfillment, coaching, working with founders and how to build a different type of organization - letting it unfold. Plus, how to make meaningful changes and not end up "in a van down by the river."‍

Chris Gillette on fishing and nature, surviving cancer, what's next, what game are you playing and how do you know if you're winning, stress being a killer, making it ugly, Leader Standard Work, quasars vs. blackholes, success vs. fulfillment, staying calm under pressure, and thinking intentionally.

After reflecting on a conversation with two young, career-focused friends, I thought about my own journey from 30 to 47. I penned some advice to my younger self. While age brings it's own set of challenges, it also offers clarity and devotion to being true to yourself. You too will one day be 48.

Wade sits down with Raj, a programmer, turned attorney, turned entrepreneur. From his programming days on a 1979 Apple II Plus to riding the wild internet 1.0 wave in Silicon Valley, Raj shares his experiences growing up in a household influenced by post-war survival, his transition from computer science to law, and the pivotal moments that led him to finding his own unique path.

Lesson, lessons everywhere -- even during math homework. Plotting joy and hustle. The further left on the graph, the more joy; the further right, the more hustle. It’s about recognizing where you are on the plot line—like when the ever-delightful eye twitch resurfaces—and then finding ways to course correct.

In my recent meditation, the topic of discipline resurfaced, and my perspective on it has shifted. I’ve always considered myself disciplined, but as life got busier, I let key habits slip. Taking time off this summer, I realized that busyness isn’t discipline—without my usual structure, my mind ran wild. I now see discipline as essential for creating mental space and focus. It’s not just another task; it’s a tool that helps me stay centered and in control.

In this episode of Emberterra, I sit down with my longtime friend and entrepreneur, Dan Reilly, for a deep conversation about life, business, and personal growth. Dan shares his journey from tech sales to real estate investing, discussing the challenges of balancing ambition with contentment, and the importance of living within "concentric circles" in relationships. We explore navigating life’s ups and downs, maintaining an open heart, and aligning actions with values for a fulfilling life.

In "Embracing the Unknown: A Modern Pilgrimage," I reflect on a passage from “Build the Life You Want” that resonates deeply with me. After 19 years of chasing clearly defined business goals, I’ve stepped away, now facing the unknown and exploring new paths. Despite the anxiety of not having a specific plan, I find excitement in the freedom to explore and embrace the unknown. Inspired by the monk's pilgrimage, I realize that maybe not knowing is the best part.

Deciding when to move on from a business, job, relationship, or any situation is tough. Even when things look good externally, your inner voice might suggest a change. I've asked and heard this question many times without finding a great answer. After years of thought, I've landed on three key questions to guide this decision: Why are you doing it? What is it costing you? How long has it been unbearable? These questions help clarify whether it's time to move on and embrace new opportunities.

Welcome to Emberterra, a podcast exploring life's transitional spaces. Emberterra represents the land between who you are and who you want to be, illuminating the path through change. After selling my second business, I'm taking a rare break from constant work to explore new interests without financial pressure. Despite feeling exhausted from years of misalignment, I’m grateful for this opportunity to reflect and share insights on navigating the unknown. Join me as we find our way through the dimly lit path of life's journey.