The Seattle Entrepreneur's Guide to Life, Love, Business and Cats

At 42, finally, I’ve reached that point where I can look back and actually reflect on the path that brought me here. I’ll admit, I thought I'd have "made it" by 17, but hey—every mistake along the way led to something bigger, each one a building block for what’s still unfolding. Right now, life’s good: I’m happily married to my fiercely independent college girlfriend, surrounded by a small, solid crew of friends, and co-running a successful tech company in downtown Seattle with my high school co-founder. But maybe you already knew that.

If you’re reading this, chances are we’ve crossed paths, or maybe you’ve heard about me through a mutual connection. Or maybe you’ve just stumbled across this by sheer chance, in which case, welcome. What happens next in your life could be pretty extraordinary, and maybe I’ll have something useful to share that helps you along the way.

This post is for you—whether you’re nearing 40 and looking for some guidance, reflecting on your own experiences, or just here to see what a Seattle entrepreneur has to say about life, business, and maybe even a cat or two. If you find a bit of insight or even a reason to smile while reading, then this will have been worth it.

Lesson 1: Life’s Better When You Care

Here’s the core of what I’ve learned: you can’t achieve anything alone, and the more you genuinely care about others, the greater your potential for success. It’s so easy to be a jerk, to dismiss people based on things like possessions or insecurities. But in reality, kindness and respect are the true keys to unlocking potential—both in business and in life.

In business, people are everything. Building something great takes bringing people together, and the secret sauce to that is real, heartfelt care. I’ll be the first to admit it took me a while to understand this. I had to hear the same message over and over before it clicked. This is for anyone out there who feels like they’re learning “too slow.” The truth is, everyone learns in their own way, and however you get there, it’s all good.

For those who think “caring” is just a strategy to get people to do what you want, that’s not it. Real caring is about asking questions, showing empathy, and being there to support others on their journey. It’s about helping people solve their problems when they want them solved, not just when it suits you. True connection happens when you genuinely want to help people achieve their own goals. As my dad always says, “You can’t fake chemistry.”

Most people you meet will click with you naturally, but those rare, 2% encounters where you don’t connect? That’s where the real growth happens. (I’ll share a story about that later on.)

Seattle, My Playground and My Mentor

Seattle has been more than just home; it’s been the backdrop to every twist and turn in my life. From blowing through millions of dollars to knowing Seattle’s restaurant and bar scenes inside out, this city has given me endless stories. Growing up as an immigrant kid from California’s Central Valley and then Tri-Cities, Washington, moving to Seattle was a game changer. From 90s TV like Boy Meets World and Dawson’s Creek to Cruel Intentions and Friends, the influences were real. If any of this rings a bell, this guide’s for you.

Seattle isn’t just for residents, either. I’ll share some travel tips for anyone planning a visit, plus some “what not to do” lessons learned through trial and plenty of error.

And by the way—this may be for public consumption, but if you don’t mind, keep what you read in confidence. Just joking (kind of).

See you at Assaggio’s.

From the series: The Seattle Entrepreneur's Guide to Life, Love, Business and Cats