Dear Portland,
You’ve been my home for nearly two decades.
I moved here when you were still a well-kept secret—a small city that felt like a big town. You had soul. You had charm. You had grit. You were a place where people from all walks of life lived side by side and still found common ground. A place where creativity, authenticity, and community thrived.
Here, I built a business that grew to employ over 500 people. I married my wife. We had three children. I poured everything I had into this city because Portland wasn’t just where I lived—it was part of who I was becoming. I believed in you. And for a long time, you made it easy to believe.
You were the envy of the country. The New York Times couldn’t stop writing about you. You were a beacon for the creative class—home to world-class design, food, art, music, independent business, and yes, sneakers. You were weird in the best possible way, full of character, full of life. You were the place people dreamed of moving to. The place people bragged about visiting. You were truly one-of-a-kind.
But like all great cities, you became a magnet.
First, the people came—from San Francisco, from Brooklyn, from Seattle and LA—seeking something more human-scaled, more affordable, more real. Then came the investment dollars, the developers, and the pressure that always follows. Rent doubled. Quirky storefronts became chain retailers. Iconic businesses closed. And slowly, the texture of Portland began to change. The authentic gave way to the expensive. The experimental gave way to the predictable.
Still, by 2019, we were hanging on—stronger than ever in some ways. Until the world stopped.
When the pandemic hit, Portlanders responded with care. We masked up, shut down, supported our neighbors. We did what was asked of us. And then, in the wake of George Floyd, we did something else—we took to the streets. We protested. We demanded justice. At first, it was peaceful. But eventually, things unraveled. What began as a noble cry for equity became something darker, more chaotic. Downtown fell into disrepair. Businesses shuttered. Families left. The combination of pandemic restrictions, economic strain, destructive protest activity, and longstanding policy failures around drugs and homelessness created the perfect storm.
And Portland? Portland began to spiral.
I don’t say that lightly. I’ve spent time in war-torn nations. There were moments in the aftermath of 2020 when parts of our city resembled those very places—abandoned, unsafe, and without direction.
Since then, the suburbs have recovered. But Portland proper continues to struggle. We are now a city with no clear plan, no shared vision, and very little momentum. We are trying to tax our way out of complex problems while watching high-earning households, small businesses, and cultural anchors walk out the door. Our commercial real estate market is collapsing—an estimated 38 more downtown buildings are expected to go into foreclosure this year alone.
We are, by any honest assessment, a city in freefall.
And yet, everywhere I go, I hear people putting on a brave face. "Portland is still special," they say. "We’ll figure it out. It’s just a phase." I understand the sentiment. I know the instinct. But here’s the uncomfortable truth: We won’t figure it out unless we act differently than we have.
Goodwill is not a strategy. Positivity is not a plan.
What we need now is courage—the kind of courage it takes to face hard truths, to confront uncomfortable realities, and to choose action over nostalgia. My greatest fear since the day I moved here has always been this: That when it mattered most, Portland would lack the political and civic will to save itself.
I have watched that fear be realized.
But I am not afraid. Not now. Not when it counts.
I’m not afraid to say that our current policies have failed. I’m not afraid to name the dysfunction or call out the drift. I’m not afraid to say that livability must come before ideology. That public safety, good schools, walkable neighborhoods, a thriving downtown, accessible mental health services, tourism, arts, business—all of it matters. And none of it is thriving right now.
I’m not going anywhere. But to stay, I must step forward. I must help lead. I must be part of the rebuild. Because I still believe in what Portland can be—not as a memory, but as a future.
We have the opportunity, right now, to reimagine what a modern American city can look like. One that is inclusive and thriving. One that respects its past without being bound by it. One that trades slogans for substance. One that attracts families, entrepreneurs, artists, and dreamers again—not with hype, but with a clear, compelling, and actionable vision.
That’s where I’m headed.
If this message resonates with you—if you share this urgency, this heartbreak, and this hope—then I invite you to join me. In the coming weeks, I’ll be sharing a bold, detailed vision for Portland’s future. A blueprint rooted in pragmatism, and in the belief that we are capable of far more than what we’ve settled for.
This is the moment to come together. To lead. To act. To stop hoping things get better, and to start making them better.
Let’s get to work.
If you’re in Portland, I hope this message lit a fire in you. And if you’re listening from somewhere else, I hope it made you think about your own city—what you love, what you’ve lost, and what’s worth fighting for.
The road back requires more than optimism. It requires leadership. It requires all of us.
In the coming weeks, I’ll be laying out a bold, pragmatic vision for Portland’s future. But the work doesn’t stop at the city limits. These conversations—about courage, unity, and rebuilding—are happening all across America.
So subscribe if you haven’t already, and share this episode with someone who cares deeply about where they live.
Until next time—stay principled, stay engaged, and remember: rebuilding starts when we decide to stop hoping and start acting.
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