To Governor Kotek, Members of the Oregon Legislature, Mayor Wilson, and Multnomah County Chair Jessica Vega Pederson:
There is growing recognition that Portland — and Oregon — is overtaxed and underperforming. What’s missing isn’t awareness. What’s missing is urgency. There’s no vision to turn the tide. No coordinated strategy to stop the slow bleed of talent and investment. And we no longer have the luxury of time.
No loan program or task force will fix this. No economic development grant will outcompete the gravitational pull of low-tax states with open doors and open minds. Founders are leaving. Startups are relocating. Creativity is packing up — not because they’ve stopped believing in Portland, but because Portland has made it too hard to stay.
It’s time to make it easy again.
Over the past two decades, my partners and I have built businesses here that generated over $1 billion in taxable revenue. We hired locally. We leased space in Portland neighborhoods. We paid city, county, and state taxes — proudly, for years. We believed that building in Portland was good for business and good for the city.
But those kinds of opportunities are disappearing — not because the ambition is gone, but because the math no longer works.
Today, some of Oregon’s smartest, most driven entrepreneurs are quietly choosing other places to build. They’re not angry. They’re not shouting. They’re just leaving. And what they take with them isn’t just innovation — it’s future revenue, future jobs, and future civic contribution.
That’s what we’re losing. And once it’s gone, it doesn’t come back.
Here’s the core problem: too many of our local leaders are still trying to redistribute money we no longer attract. We create loan funds, grants, and incentives that tinker around the edges — while ignoring the fundamental reason businesses are leaving: unsustainable taxation in an open, competitive country.
You don’t revive a city by taxing its ambition. You revive it by unleashing it.
Let’s be clear about what founders are seeing when they compare Portland to places like Austin:
A business in Portland making $2 million in net income could owe more than $250,000 in combined state, county, and city taxes — before paying a dime to the IRS. That same business in Austin might pay under $10,000.
What makes this even more frustrating is how simple the fix could be. Instead of layering punitive taxes on the very people who drive the economy, we could build a model that rewards employment and long-term commitment. When people build companies and hire others, the tax base grows organically. Even with business tax relief, the downstream revenue from jobs, housing, consumption, and local spending would more than replace it.
But beyond the sheer amount, it’s the structure of our tax system that does the most damage. It’s layered, opaque, and punitive — hitting the same dollar multiple times and sending a clear message: success comes at a cost here. That message is driving away the very people we need to stay — the ones who create jobs, reinvest, and fuel long-term prosperity.
And tax policy is only half the story.
The other side of the coin is a lack of accountability and innovation in how government operates. For over a decade, state and local governments in Oregon have functioned in a relatively unconstrained, unaccountable environment. The result? Little innovation. Bloated systems. Diminishing outcomes. Residents and businesses are not getting the value they deserve. We’ve spent more and delivered less — and the forecasts only get worse from here. We cannot sustain more taxes. The answer isn’t to throw more money at broken systems. It’s to grow the base that funds them — and demand better outcomes from the public sector in return.
We need more than minor incentives — we need a strategic tax reset. That’s why I’m proposing a bold new approach: a comprehensive tax relief model, beginning with a five-year founders’ tax holiday.
No corporate income or excise tax. No Portland business license tax. No Multnomah County business income tax. No minimum business tax. No payroll tax on the first 25 hires. Let builders build — without extracting from them before they even get off the ground.
After five years, implement a simplified, competitive framework: a flat business tax not to exceed 2% combined city and county, no minimum tax on startups or low-margin companies, payroll tax waivers tied to local hiring and retention, and ten-year property tax abatements for qualifying companies. These are not giveaways. These are investments — in the people who create jobs, lease space, pay future taxes, and reinvest in their communities.
And I’m not asking the government to take the risk alone.
I’m ready to invest. In companies. In real estate. In people. In the city that shaped me. But I can’t — and won’t — do it if Portland continues to send the message that growth is something to be punished or extracted from.
Every time a founder leaves Portland, we lose decades of tax revenue. We lose the companies they would’ve built. The people they would’ve hired. The neighborhoods they would’ve helped transform. The city’s economic model is eating itself — short-term extraction at the cost of long-term prosperity.
Governor. Legislators. Mayor. Chair. If you want to compete with Austin, Salt Lake City, or even Vancouver, Washington — this is how. You lower the barriers for those already here who are ready to build. You don’t hand out grants — you create an environment where grants aren’t needed because success is viable on its own.
It’s time to lead with courage. To say what needs to be said: We will tax you less because we want you here more.
Portland’s future isn’t lost. But it is leaving — every month, one founder at a time.
Let’s change that — while we still can.
Justin M. Lewis
Entrepreneur, investor, Portland resident
If you care about Portland — if you want to see this city win again — I need your help.
Share this episode. Post it. Email it. Send it to someone in government. Share it with someone who’s thinking of leaving — or someone who still believes in this place.
We don’t have the luxury of waiting. Portland is bleeding talent, jobs, and investment — not because the ambition is gone, but because we’ve made it too hard to stay.
Let’s reverse that. Let’s build a city that welcomes risk-takers, builders, founders, and dreamers. Let’s build a city worth staying for.
I’ll be back tomorrow with another episode. Until then — stay kind, stay courageous, and stay in the fight for something better.
If you haven’t already, please subscribe on Substack, Apple Podcasts, or Spotify — and if today’s message moved you, leave a review or forward it to someone who needs to hear it.
This is how change starts — with people like you.
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