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3x Y Combinator alum launches program to enable the next generation of YC founders

While the term “unicorn” might seem a little overused in the startup world — given the number of billion dollar companies continuing to ascend the ranks — the term is a good description for founders who have been through the venerable Y Combinator accelerator program more than once. Two times in interesting. Three times is a metric that only belongs to a handful of folks. And one of them is Portland’s Darius Monsef.

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Silicon Florist links arrangement for August 14, 2025

Here’s a roundup of interesting startup links I came across today:

The End of Buy-and-Hold: Why Venture Capital Needs Portfolio Liquidity Management by @ttunguz

But the investment landscape has fundamentally shifted beneath our feet. Time to IPO has tripled from four years two decades ago to 12-13 years today. M&A exits, once a reliable four-year path to liquidity, now stretch seven to eight years on average. The math has become untenable for traditional fund models.

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Oregon is the bestest most wonderfulest place to be the most amazingest awesomest entrepreneur ever

If social media is to be believed, Oregon is the best place in the universe to be an entrepreneur. Every few weeks, a new “report” comes out that ranks Oregon or Portland among the top places for entrepreneurship. And then those stories get shared ad nauseam on social media, aggregating thousands of likes and comments and reshares. And then, once that tempest in a teapot starts to die down, another “ranking” comes out. And it starts all over again.

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Portland’s Paige Hendrix Buckner sits down with TechCrunch

I’m always amazed at the level of talent that calls Portland home. Quietly. Like we don’t make a big deal about it. We just have incredible folks in our midst. And one of those folks is Paige Hendrix Buckner, the CEO of All Raise. Recently, Paige got the chance to sit down with TechCrunch to talk about her organization and their comprehensive annual report on VC in 2024.

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Silicon Florist links arrangement for August 12, 2025

Here’s a roundup of interesting startup links I came across today:

Trump’s ‘Big Beautiful Bill’ will slash $15 billion in federal money to Oregon, Kotek says – OPB

Oregon stands to lose more than $15 billion in federal funding for health care, food assistance and other purposes in coming years, under the sweeping spending bill congressional Republicans passed earlier this year.

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Business Oregon continues “Innovation Hub” investments to the tune of ~$3.8M

One of the things you learn in working with the Oregon state government is that things are funded in bienniums — two year tranches of funding — based on the available state budget coming out of the long session. So if you’re applying for funding, it’s a nailbiter to find out how much your org is going to get over the next two years — if at all. So I’m happy to report that the state will continue to fund the “Innovation Hub” activity it started last biennium by providing ~$3.8 million of operating capital to innovation hubs around Oregon.

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Silicon Florist links arrangement for August 11, 2025

Here’s a roundup of interesting startup links I came across today:

How I chat with my notes | Marshall Kirkpatrick

I’ve been experimenting lately with a workflow and tech combination that is SO EXCITING to me that I wanted to write a blog post about it. And incidentally, when I work with organizations I always bring years of knowledge and experience to the table – but this feels like a big step up in how powerfully I’m able to do that.

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