This day is always so odd for me. It’s August 7. And it’s the year 2026. Making this the 19th birthday of registering the domain for Silicon Florist. As of today, I have been doing this — whatever the fuck this actually is — for 6,940 days. Which is a genuinely strange way to spend a third of your life. ON A HOBBY. What exactly is wrong with me…? I swear. Every single year, it gets weirder and weirder to write this post.
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
Thoughts?
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Happy birthday to the Silicon Florist! 19 years… who even does that?!