Six thousand three hundred and seventy one posts. If you’re keeping score. Even if you’re not. That’s what it is. (And if you need the lore about how all of this began, I’ll include it below. But I won’t force you to read through it now.) Fun fact: Six hundred seventy four of those posts have been written in the last twelve months. Which is like almost two posts a day. Every single day of the last year.

That means that roughly 10% of the posts over the last 19 years have been posted this year. “Why the sudden resurgence…?” you might ask. And rightly so. Well, because there is something happening in the Portland startup community that feels very familiar. And inspiring. And invigorating.

Honestly, I keep writing here because it’s my ongoing love letter to Portland. (A city I very much love and believe in.) And to Portland startups. And Portland founders. A testament to my belief in each and every person who calls Portland home. And a testament to the creative folks who delight and inspire us everyday. To the culture of craft that drives our community.

But this year. Looking back. It’s slightly different. Because it feels incredibly familiar. Something feels like I’ve been here multiple times before. Something feels like it’s the very same energy that inspired me to do this whole thing in the first place.

Like what…? Well, when I started this blog in 2007, there was…

• A new technology that was inspiring all sorts of folks to build apps and things (iPhone)
• Pockets — here and there — of super interesting startup activity but…
• No clear cohesive momentum across those startup pursuits
• Startups beginning to gravitate to a certain part of town (the Pearl)
• Community organizers working to bring people together in creative ways
• Pitch competitions highlighting innovative ideas (Bend Venture Conference and Venture NW)
• Very real venture scale startups being built
• A coworking space striving to be the center of the startup community (CubeSpace)

You know the old saying, “The more things change, the more they stay the same”…?

I think the Portland startup community has that saying tattooed on its proverbial ass.

Because I’ve been through this cycle at least three times in my 30 years working in, on, and around venture funded startups around here. There’s the naive optimism of the uprise, the heady peak of performance, and then — unfortunately and inevitably — the popping of one bubble or another that results in a downturn.

But Portland handles this differently than other places. And oddly. Whereas other communities seem to gather themselves, learn from previous mistakes, and begin to build again upon the remains of what could and should be salvaged, Portland does none of that. Instead, Portland decides to forget everything. Literally ev-ery-thing. (Best if you read that last part like Gary Oldman.) And start from scratch. All over again. Leveraging absolutely nothing from the previous generation. (Except for maybe some nostalgia for names and concepts, but let’s be honest: that’s just window dressing.)

Portland is forever recreating the wheel as it were. In spectacular Sisyphean fashion.

Kind of like it’s forever being subjected to that Men In Black flashy memory wipe thingamajig.

Which is why we’re always where we are. Because we’re always starting from scratch. Every decade or so.

I mean, it’s sort of charming. In a way. But it’s also somewhat frustrating after you’ve been through it a few times. And suddenly recognize that — holy shit — here we go again.

For me, personally, I was absolutely and utterly naive the first time I went through it. (“Up and to the right, forever!”) The next couple of times around, I learned. I observed. I tried shit. And I experimented.

And this time around…? I’m just like “Oh yeah. This again. Yeah, this thing. We always do this. Every. Single. Time.” I’m absolutely certain of where we are in the cycle. In almost a weirdly prescient way. (And yes, we’re continuing to recreate the wheel. Just like we have time and time again in the before times.)

It’s equal parts comforting and annoying. But it is what it is.

How long ago was 19 years ago…?

Now, I know some of you were not in a mode of paying attention or even realizing what the startup world was like when I started Silicon Florist.

I get it. I’m old.

But let me provide some broader context as to how long ago 2007 actually was. Using startups and notable figures to set the stage.

When I started blogging here…

• The iPhone was barely six weeks old
• Dropbox was still in Y Combinator
• Speaking of YC, they were still doing both Boston and Bay Area batches back then
• The Kindle didn’t exist
• Sam Altman was actively the founder and CEO of… Loopt
• Twitter was ~4 months old
• Facebook had only been open to the general public for ~11 months
• Netflix streaming was brand new
• Spotify had yet to launch

But maybe, even more importantly, there were tech industry uber unicorn companies did not even yet exist: Instagram (Fun fact: the original community manager was a Portland person so a lot of us had Burbn installed on our phones), Kickstarter, Slack, Square, Stripe… None of them were event a thing. Nor, of course, were any of these wackadoodle AI companies a glimmer in anyone’s eye.

Back then, we were all enamoured of the potential of “the cloud,” “the iPhone,” and the applications of open source code and languages as a potential means of building scalable pursuits.

But I digress. Let’s get back to the topic at hand…

Nineteen years in, I’m still not entirely sure what this even is. It’s not a news site. It’s not a publication. It’s not journalism. (Doubling down. This is absolutely for sure not journalism.) It’s a personal blog. It has always been a personal blog. It’s just a personal blog that got weirdly persistent. And habitual.

It’s a hobby. A bad habit, if I’m being honest. One I keep showing up to feed — day after day — for reasons I’ve never fully been able to articulate to anyone. Including myself.

Maybe I’m addicted…? But if so, I learned it from watching you.

But it’s still the same job it was on day one. Notice the thing. Recognize the effort. Write down the thing. Tell somebody about the thing. Hope that other people tell people about the thing. Repeat until dead, I guess…?

Because you’re the ones doing the actual work. I don’t build anything. I don’t hire anybody. I don’t make payroll or ship product. I don’t have the hard conversations where you tell your family you’re going to try this for another year.

You do that. All I do is watch you do it. And then I type about it. Poorly. And then I hit publish.

Nineteen years of that. Because you keep giving me things to write about.

So thank you. For building the stuff. For telling me about the stuff. For putting up with the headlines. And for continuing to take the enormous personal risk of starting something in a place that doesn’t always make it easy.

Crazy. Nineteen years ago. And still more to write.

Thank you so so very much for being here. For continuing to return. And for celebrating all of these courageous founders and builders who actually take the opportunity to put something out there. It’s really an amazing and beautiful thing that we have as a community.

So beautiful that I’ve probably got another nineteen years of content to vomit onto the Internet.

Happy birthday, Silicon Florist.

In lieu of gifts, maybe just watch one of my stupid YouTube videos. Or sign up for the newsletter.

Here’s to another year of being your most fervent hype man. Because that thing you’re working on…? It’s fucking awesome. More people should know about it.

Hang in there. And until we get a chance to chat again… keep up the good work.

Lore

On August 7, 2007, I sat bolt upright in bed at 2:00AM. (I mean, or around there.) With an idea I’d apparently been pontificating on for a while. Even without realizing it. Partially inspired by what I was experiencing in the tech community. Partially frustration that no one else seemed to be interested in celebrating it.

So I got up, wandered out to the computer, and went to go register “Silicon Forest.” Which was taken. (By a guy I went to college with. Oddly enough.)

So instead — with all of the sound judgment an early morning hour affords a person — I registered a pun. Silicon Florist. The combination of the Silicon Forest and the Rose City. Which was available. Even as a .com. Which probably should have told me something.

Then I spent a couple of days wrangling a WordPress install. Which was the only way to do WordPressy sorts of things back then. And then a day or two later, I actually worked up the nerve to hit publish on a post or two.

It wasn’t the blogging that intimidated me. The blogging part wasn’t new. I was used to writing stupid shit on the Internet. I mean, I’d been writing online since you had to write code to put words on the Internet. Like last century sort of stuff. The 1900s. It was a whole thing. Your HTML was handcrafted back then. Bespoke. Artisan.

But the motivation to blog was different this time.

It wasn’t about me having opinions at people. It was about the folks around me who were building things and not telling anybody about it. Developers shipping stuff on a weekend. Community organizers dragging people into the same room. A handful of people working on what we had just recently started calling “startups.”

All to a person with this underlying vibe of aggressive humility.

And that was my inspiration. My “this is fucking awesome and if you’re not going to tell people about it, then I am.” It was about me realizing the power and importance of the open source ethos and choosing to open source my marketing communications expertise. For the greater good.

I couldn’t be more proud of the work. And I can’t wait to hit publish again. Because you are building something amazing.

Happy birthday, Silicon Florist.

Previous Silicon Florist birthday posts

Birthdays make you nostalgic? Me too! So if you feel like wallowing in that nostalgia with me, please have at it. Here are a bunch of old birthday posts from yesteryear.

• Silicon Florist is two today. What a short strange trip it’s been.
• Time for big kid pants: Silicon Florist is three years old
• Four years and seven hours ago… Silicon Florist is four
• Half a decade later: Thank you for putting up with bad grammar, ridiculously long headlines, haphazard posting schedules, and an all too rosy view of the Portland startup scene
• Six years of Silicon Florist (or How a poorly written blog with ridiculously long headlines somehow spawns awesome things like PIE, TechFestNW, and Oregon Story Board)
• Golden birthday: It’s August 7 and Silicon Florist turned seven years old today
• Silicon Florist is eight. And eight is great. Or something. And stuff.
• Nine years of nonsense: Silicon Florist completes another year of assaulting the English language
• The more things change, the more they stay the same: 10 years of Silicon Florist babbling about the Portland startup community
• It goes to 11: Silicon Florist is officially a tween (Fair warning: This one is really really dark. But you can skim past that if you want some interesting historical context.)
• A dozen long stemmed Rose City years: Silicon Florist is 12 years old
• Officially a teenager: Silicon Florist turns 13 years old
• Another year older, none the wiser: Silicon Florist is 14 years old
• Silicon Florist is 15 years old… so I’m taking a sabbatical from it. It’s old enough to stay by itself for a bit.
• Old enough to drive: Silicon Florist is 16 years old
• Wondering when the whole “wiser” part happens: Silicon Florist is 17 years old
• Old enough to vote: Silicon Florist is 18 years old

OpenAI’s new AI smart speaker will reportedly sell for between $300 and $400 | TechCrunch

Bloomberg now reports that the device will be “donut-shaped,” designed thusly to allow users to carry it around their home and place it in different locations, like a bedside table or a kitchen counter.

Former A16z partner to raise $100m for new venture firm debut

As first reported by the Wall Street Journal (WSJ), former partner at Andreessen Horowitz (A16z) Bryan Kim plans to raise roughly $100m for the debut fund of his new venture, Mido Capital.

99% of My Website Traffic Is Bots | PatronView

I’ve spent a year fighting bots on my philanthropy donor database, PatronView. Nobody teaches you this stuff when you’re vibe coding, so I’ll share what I’ve learned.

July jobs report: US economy shed 23,000 jobs, a sudden reversal

The U.S. economy shed 23,000 jobs in July, a sign that the labor market had not stabilized after four months of positive growth.

Taste Is All That’s Left

You had an idea, and between the idea and the working program stood hours— sometimes weeks—of typing, of reading manuals, of misunderstanding an API and slowly grinding the wrong version into a slightly less wrong one. Production was the wall. Everyone hit it. It was the thing that separated the people who could from the people who could only talk about it. That wall is gone.

Christine Drazan releases first TV ad in Oregon general election against Gov. Tina Kotek – oregonlive.com

Neither Kotek nor Drazan, who has served in the Legislature for much of the past seven years, have focused their campaigns on their legislative achievements or policy agenda. Instead, Kotek has sought to portray Drazan as a Trump loyalist, while Drazan has focused on criticizing the state’s lack of progress on education, homelessness and other issues.

16 Democratic Lawmakers Press Treasurer Steiner for a Full Audit of Retirement Fund Risks — Oregon Journalism Project

Sixteen Democratic lawmakers want Oregon State Treasurer Elizabeth Steiner to conduct what they say is a long overdue comprehensive audit of the Oregon Public Employees Retirement Fund.

Knowing When to Stop: The Art of Making a Loop Converge | Andreessen Horowitz

“Done” is rarely a property of the work itself. It is a judgment produced by the system around the work. Humans do not possess a universal detector for “done”. We rely on a patchwork of signals like tests, specifications, precedent, approval, deadlines, risk, and finding that point of diminishing returns. In each case, completion comes from outside the work itself.

No Summer Doldrums For Active Startup Investors In July

Among lead investors, Khosla Ventures topped the ranks last month, while Y Combinator was by far the busiest backer by deal count. The highest-spending investors for the period, meanwhile, appear to be Coatue and Nvidia.

Should Investors Always Follow On? Here’s the Real Math

This matters because founders waste weeks stressing about investor decisions that have nothing to do with their company’s potential. Worse, some founders avoid great early investors because they heard “you should only work with investors who promise to follow on.”

Agent Plugins

Agent Plugins is an open, vendor-neutral standard for packaging reusable components into portable plugins. Its version 1.0.0 specification defines a shared format for Agent Skills and MCP servers that compatible clients can discover and load consistently.

Why Open-Source Models Haven’t Killed the Big Dogs

If model quality is becoming commoditized, why are OpenAI and Anthropic still making ungodly amounts of money while charging more for their best models?

Startup Spotlight: HitchPiggy wants to turn empty car seats into a new rideshare marketplace – GeekWire

The bootstrapped startup is small, with a little more than 100 registered users signing up for Pacific Northwest trips since its launch on June 1. No rides have been completed through the platform just yet, but Windham is looking to grow college ridership this fall through a partnership with the Portland State Business Accelerator.

Autodesk appears to be moving Portland office to Slabtown – Portland Business Journal

Autodesk is moving into a new space at 2151 N.W. Savier St., according to building permits filed with the city. Its current offices are in the Towne Storage Building on the east side of the Burnside Bridge.

(2019) Adding to the local startup accelerator ledger: Oregon Enterprise Blockchain Venture Studio announces inaugural class

There’s a new class of startups in a new accelerator. The Oregon Enterprise Blockchain Venture Studio housed at R/GA in Portland has announced their first class of companies. 

Empowering Main Street by Unlocking Access to Capital

THE COMMITTEE ON BANKING, HOUSING, AND URBAN AFFAIRS will meet in OPEN SESSION, HYBRID FORMAT to conduct a hearing entitled, “Empowering Main Street by Unlocking Access to Capital.” The witnesses will be: Ms. Dalia Blass, Senior Investment Management Partner, Sullivan & Cromwell; The Honorable Kenneth Bentsen, President and CEO, SIFMA; Mr. Mike Flood, Senior Vice President, Center for Capital Markets Competitiveness, U.S. Chamber of Commerce; and Mr. Cantrell Dumas, Senior Researcher for Financial Regulation and Policy, Joint Center for Political and Economic Studies.

How to Support Rural Oregon Businesses Affected by Wildfire

Rural communities are built on the belief that people show up for each other. A business that survives a fire season because its neighbors kept ordering, kept buying gift cards, kept showing up is proof of the resilience that drives rural economic development.

Say goodbye to Lloyd Center at these 8 wild last-day mall events – Here is Oregon – hereisoregon.com

Saturday, Aug. 8, is the official last day of Lloyd Center, and it’s going to be a party.

We just gave you a lot of options. Pick one reasonable item you can complete this week that is accessible for you.

These are small actions, but they add up. Rural communities have always run on people choosing to invest in each other, in ordinary ways, over and over, especially when it’s hard.

If you know someone who feels helpless watching this fire season unfold, send them this. Show them they’re not.

For the list of actions, visit “How to support rural Oregon businesses affected by wildfire.”

Panthalassa, a 10-year old startup making technology that aims to generate electricity from the movement of waves and use it to run graphics processing units, is raising $225 million at a nearly $2 billion valuation after the investment, according to two people with direct knowledge of the deal. The fundraise will double Panthalassa’s valuation from just three months ago, when it raised $140 million at a roughly $1 billion valuation after the investment

According to Interesting Engineering, their latest model Ocean-3 is planned to be launched in the North Pacific in 2026. With commercial deployments in 2027.

Here’s a look at Ocean-2.

Obviously, I’m keeping my eye on the — ahem — ball with this one. So I’ll make sure to report back with any updates.

For more information, visit Panthalassa.

Why I’m leaving OpenAI to build telepathy

On Thursday, July 23rd, I resigned from OpenAI. On the 24th, I started as a Founding Researcher at Conduit. We’re building telepathy: thought-to-text models, trained on non-invasive neural data.

(2016) Easily the most overlooked and most successful content startup in Portland: Digital Trends turns 10

Every once in a while it comes up in conversation. “What’s the most overlooked company in town? Or the company that no one knows is here?” For a time, a good answer was Survey Monkey. Or MetaFilter. Or maybe deflecting with a regional office, like Pinterest or Yahoo! or Yieldbot. But time and time again, one of my favorite go to answers has been a homegrown startup here in town, Digital Trends. Yes, that Digital Trends.

OpenAI Didn’t Notice Its AI Agents Using a Message Board to Plan Their Hacking Spree | WIRED

At the Black Hat security conference, the AI giant revealed new details about how its agents went rogue, hacked several other companies—and did it all right under the company’s nose.

Sequoia doubles down on AI with $10B fund under new leadership  — TFN

Sequoia Capital plans to raise about $10 billion in new capital, which would be its biggest commitment in 54 years, according to Bloomberg.

Member Spotlight: Katharine Reinhold, Executive Director of Built Oregon

From food and beverage to apparel and outdoor gear, Built Oregon connects, amplifies, and accelerates the companies that define Oregon’s product culture, helping founders access mentorship, retail opportunities, educational programs, and a supportive community.

“Hello, Computer.”

2026 feels pretty key for all of this. The models have to be refined and perfected for voice. In some cases, perhaps even shrunken down to perform in real-time on-device. Then we need to figure out the right form-factors for said devices. Sure, the smartphone will remain key, and will probably serve as the connection for most companion tech, but we’re going to get a range of purpose-built hardware for AI out in the wild which will be predominantly controlled via voice.

The Title Cards in Blade Runner Are Fucking Amazing – Rands in Repose

Appreciating typography is a study in paradox. The primary goal of well-designed typography is to help you read the words, not appreciate how the words are composed of letters and how each of those individual letters has been designed to convey a small bit of meaning. If you see the typography rather than read the words, the typography has failed in its job, right? You should be reading, not staring at the shape of that uppercase A.

I Think I’ve Been Building RuntimeWire Since I Was 13 | by Ryan Merket | Aug, 2026 | Medium

Looking back, I had accidentally built a tiny publishing system: a CMS, a reader app and a distribution model. On floppy disks. For middle school news.

NVIDIA’s Vera Whitepaper Has a Thread Loose

The frustrating part is that Vera does not need this help, with early independent testing suggesting Olympus is genuinely formidable. The whitepaper’s strongest case is the hardware; its weakest case is the story wrapped around it, so let’s pull that story apart.

Trail Blazers could face hefty NBA relocation fee if team leaves Portland – oregonlive.com

Two weeks ago, a Trail Blazers official suggested the team’s new owners might have to pay the NBA a $1 billion relocation fee if they decide to move the team out of Portland.

Having fun is the new moat. — Justin Welsh

Michael’s self-created job was born out of his love for this little corner of the world. And his whole mission is to help other people love it too. He’s the man about town, promoting small businesses, connecting this person to that person, and throwing events so that good people can get together and meet each other the old-fashioned way, over a beer.

The Return Of The Repeat Founder: Inside YC’s Growing Class Of Second-Timers

What we found is that repeat participation to date has mostly been a two-chapter journey: 428 founders (94%) went through YC exactly twice, while only 25 appeared three times. Twitch and Stash co-founder Justin Kan was the sole four-time founder.

AI’s architects say the next era of human history is here

If these moguls are right, we may be entering the most consequential technological transition in human history — the opening stages of an “intelligence explosion” that transforms civilization faster than humanity can understand or control.

I grew up in Portland hearing that we’re “overdue for The Big One.” As an adult that pushed me to get my own household ready, and then to help friends and neighbors do the same.

Building a proper emergency kit is something anyone can do. Helping others taught me that it’s also something very few people want to do. Researching every item, reading reviews, comparing prices, and actually buying it all can add up to a lot of time and headache. I built this business for everyone who doesn’t want to make “prepping” their latest hobby.

We research and source everything, buying in bulk to keep prices as low as possible. Spreading out the purchase over six months turns one overwhelming project into six easy steps. We’d love to get this off your to-do list.

One person can get all of the prep materials for less than $1000 at $150/mo. Packages are available for up to four people. And the best part…? It shows up once a month. In six separate shipments. So you’re not having to deal a bunch of stuff. (You can also go pick stuff up, if you prefer.)

For more information or to sign up, visit PDX Quake Prep.

Those 4 million domains are held across roughly 750,000 active customers at roughly five domains each. A whole lot of individual people — quite possibly including you — picking up a handful of names and actually putting them to use.

Porkbun is an amazingly awesome ICANN accredited domain name registrar based out of the Pacific Northwest. It offers a refreshingly easy and affordable approach to domain registration, as well as web and email hosting. Porkbun was the first registrar to offer free SSL Certificates via Let’s Encrypt and is widely recognized for its value-driven and security-first offerings, backed by live, human customer support 365 days a year via phone and chat, and 24/7 email coverage.

After taking seven years to reach its first million domains, Porkbun added its second million in two years, its third in roughly 15 months, and its fourth in under a year.

“Every million comes faster than the last, and that’s because our customers keep telling their friends,” said Ray. “We celebrate each million not because it’s a big number, but because it’s real: developers and small businesses actually using their domains.”

For more, read the full announcement or go shop local for that perfect domain at Porkbun.