In this episode, we sit down with Paige Hendrix Buckner to dive deeper into her journey leading mission-driven work across education, entrepreneurship, and venture. She shares the lessons she’s learned supporting underrepresented founders, how her leadership philosophy has evolved over time, and what it takes to build more inclusive systems that create opportunity for the next generation.

On episode 8 of High Leverage, Joe Ruscio sits down with Scott Hanselman for a conversation that goes far beyond prompts and productivity gains. They talk about craftsmanship, learning by doing, the long-term talent pipeline for engineering teams, and how AI could either free people to do more meaningful work or simply accelerate existing inefficiencies. From pair programming to Star Trek economics, this episode examines the bigger human questions behind the current AI boom.

For more, visit High Leverage.

GenAI is raising the stakes in managing a global workforce; trust and speed are emerging as decisive, EY research finds | EY – Global

72% of mobility teams are scaling GenAI and agentic AI to improve speed and consistency, but just 51% of functions trust that their data is accurate to move to the next phase.

Edtech’s pandemic boom is over as K-12 startup funding craters – Rest of World

Global edtech investment peaked at $16.7 billion in 2021, fueled by lockdowns that kept millions of children out of classrooms. By 2025, venture capital had plummeted to less than $3 billion, according to Tracxn, a Bengaluru-based platform that tracks global startup funding.

Why the Best Startups Look Stupid at First | by Gil Pignol | Mar, 2026 | Medium

The question that should haunt every founder and VC: how do you distinguish “stupid-good” from “stupid-stupid”?The difference isn’t boldness or contrarianism. Theranos was bold. WeWork was contrarian. Both destroyed capital. The difference lies in whether the obstacle blocking the idea is solvable through design or fundamental to physics and economics.

You probably wouldn’t notice if an AI chatbot slipped ads into its responses

We are computer scientists who have been tracking AI safety and privacy for several years. In a study we published in an Association for Computing Machinery journal, we found that chatbots trained to embed personalized product ads in replies to queries influenced people’s choices about products. And most participants didn’t recognize that they were being manipulated.

Agents can’t choose between structure and flexibility

I think it’s safe to say that when the LLM hype cycle started a few years ago, no one expected one of the great debates of our time would be between Python and Markdown as agent specification languages. But here we are, and this has quickly turned into one of the most consequential architectural questions in AI.

The IPO Pipeline Finally Gets Interesting

By this latter measure, the past few weeks have been pretty busy for venture-backed startups. Cerebras Systems, the designer of speedy AI inference chips, filed publicly last week for an offering expected to raise around $2 billion. The Silicon Valley company, which withdrew plans for an IPO last fall, is reportedly seeking a valuation upwards of $35 billion this time around. That alone would be enough to set IPO market watchers abuzz. Per Crunchbase data, it stands to be the largest initial share offering of a U.S. semiconductor company to date.

The Rise of the Probabilistic Founder – by Dan Nguyen-Huu

They are experimental by default. They are willing to abandon their priors. They’d rather run ten cheap experiments than commit to one expensive plan. Their iteration cycles are measured in days, not quarters. And (this is the part that would have been a red flag two years ago and is now a tell that they’ve read the environment correctly), their roadmaps are deliberately, almost defiantly, light.

Biamp turns 50

When bassist Norm Sundholm struggled to make his instrument heard over the roar of the crowd, his brother Conrad stepped in to help. The result was a hand-built amplifier powerful enough to fill the room — and the birth of a movement.

The Math on the Page – by Angel Medina – Between Courses

I built República the same way I built the coffee shops. And I built the coffee shops the same way I built this idea — long before it had a name. I built all of it as proof. Proof that I could build something real. Proof that I understood how this works.

High earners race ahead on AI as workplace divide widens

The highest-earning and most experienced workers are adopting AI in their jobs far faster than others, in a divide that risks widening inequality as the technology spreads through the workplace.

Our newsroom AI policy – Ars Technica

Our approach comes from two convictions: that AI cannot replace human insight, creativity, and ingenuity, and that these tools, used well, can help professionals do better work. From those starting points, it was always clear what we wouldn’t allow. AI would not become the author, the illustrator, or the videographer. These tools are best used by professionals in the service of their profession, not as a clever end run around it, and certainly not as a path to eventually replacing it.

Fragments: April 2

As we see LLMs churn out scads of code, folks have increasingly turned to Cognitive Debt as a metaphor for capturing how a team can lose understanding of what a system does. Margaret-Anne Storey thinks a good way of thinking about these problems is to consider three layers of system health…

What we lose when artificial intelligence does our shopping

As scholars studying the intersection of law and technology, we have watched AI-assisted commerce expand rapidly. Our research finds that without updated legal measures, this shift toward automated commerce could quietly erode the economic, psychological and social benefits that people receive from shopping on their own terms.

The Writer-Researcher’s Guide to Claude Code

Over the past few months, I have been using Claude Code to explore these questions for myself. The result is a full-stack knowledge management system spanning multiple software products, internal systems, and a local model.

Raising a Series A in 2026. I have now gone through a proper… | by Daniel Aisen | Proof Reading | Mar, 2026 | Medium

I had fairly optimistic expectations from the onset, and both times we pretty much hit our targets on the nose, but both experiences were intense, challenging, and a rollercoaster of emotions.

A good AGENTS.md is a model upgrade. A bad one is worse than no docs at all. | Augment Code

We pulled dozens of AGENTS.md files from across our monorepo and measured their effect on code generation. The best ones gave our coding agent a quality jump equivalent to upgrading from Haiku to Opus. The worst ones made the output worse than having no AGENTS.md at all.

When LLMs Get Personal – by Joshua Budman

The more interesting question is whether the space of materially distinct answers is much smaller – and whether answers to the same question, across different users, tend to share a stable common core with variation concentrated more at the margins.

Business Insider Email Newsletters: Subscribe Now – Business Insider

That number has been notching up in recent years. As of October 2024, around a quarter of the company’s code was AI-generated, Google said at the time. Last fall, it said the number had risen to 50%.

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

Claude Code’s Head of Product on how AI is changing the PM role, building products before the model is ready, inside Claude Code’s launch room process, and why speed matters more than strategy now

World’s first 50 MW superhot geothermal plant eyes 2030 launch

Quaise Energy said it is moving ahead with plans to build what it describes as the world’s first power plant using superhot geothermal energy, with an initial 50-megawatt facility planned in Oregon.

UO’s Knight Campus fosters startup incubation, biomaterial printing

The newest addition to the University of Oregon will see labs refine bioengineered 3D printed biomedical tissue, serve as an incubator for startups and support the next generation of researchers.

Startup World Cup is a series of global startup conferences and competitions, powered by Pegasus Tech Ventures, consisting of 100+ regional startup competitions across six continents, leading up to the Grand Finale in Silicon Valley.

That Grand Finale is November 18-20, 2026, in San Francisco. And the grand prize? $1,000,000, awarded as a direct equity investment or convertible note depending on company size. That’s not a trophy. That’s not a handshake and a “congratulations, here’s some cloud credits.” That’s a million dollar check.

The Portland Regional judges include Dave Barcos of North Bank Innovations, Josh Carter of Upstart Collective, Chris Magaña of Pinnacle Wealth Advisors, Yalda Moshiri from OEN’s Angel Oregon program, Nick Triska of Greater Portland Inc, and Shanbo Zhang from Oregon Angel Partners, among others.

Interested in competing…? Cool. Applications close May 8, 2026. That gives you two weeks to procrastinate.

For more information, visit Startup World Cup Portland.

Eight. Thousand. Folks.

Now look. Are all 8000 of those people active on the Slack…? Ha. No. No they are not. Not even close. The word “zombie.” A staggering understatement. In fact, if you’re anything like many “members,” you signed up years ago, checked in once or twice, and haven’t opened it since.

But that’s okay. You’re still one of us.

And for those of you who ARE lurking around in there…? It’s kinda working right? Kinda keeping you connected? And engaged? Or something? And stuff?

If you haven’t joined yet, it’s free. It costs you nothing but a few minutes of your time. Come hang out with 8000 of your new best friends. Introduce yourself in #001_intro. And follow the Code of Conduct. Or just lurk. We’re not judging.

Much.

And while I’ve rattled off this answer in any number of ways, I’ve never really taken the time to write it down.

Until now.

Why now…? Well for one, I’m tired of repeating myself. But I’m also motivated to capture this because I’m fairly certain that this isn’t a problem that is unique to Portland. Or Oregon. I’m sure it’s similar in any number of other communities. And so I’m capturing it with the hopes that it does two things: 1) I hope it puts a finer point on the early stage capital dynamics around here for local founders and 2) I hope it helps other communities recognize that their early stage financing challenges are not unique.

Long story short, I’m hopeful that by committing this to a digital page, it at least gives us a starting point to discuss it, highlight opportunities to fix it, and look for ways to improve things around here. Rising water and all that.

(Maybe cue up The Downward Spiral by Nine Inch Nails. This could take a minute.)

Let’s get into it…

Local early stage funding is trapped in a vicious cycle. And you’re soaking in it.

tl;dr

Let’s start with the obvious: There isn’t a lot of — if any — local, risk-tolerant capital in Oregon. Never has been.

So when you start a company here — at the exact moment you’re most energized and passionate about what you’re building — you’re not building. You’re gallivanting. You’re tincupping around Seattle and the Bay Area, pitching investors who have never been to Portland. Trying to sell them on both the vision for your company as well as the reasoning as to why you’re building in Oregon.

You’re spending your best “early stage startup founder” energy and excitement on planes and in lobbies talking to potential investors instead of talking to potentiaal customers and building your product.

By the time you actually raise — if you raise — you’ve already lost some of that early founder energy. Some of that momentum. All of that time on the road. All of that searching and scraping together checks. The fire is most definitely dimmer than it was six months ago — or worse yet, a year ago — when you started looking for capital. And you’ve just signed up for another marathon sprint. Even though you’re still trying to catch your breath.

Even worse…? That slower start compounds. You grow more slowly. You hire more slowly. You get to market more slowly. It takes you much much longer to hit that inflection point. And to raise follow on.

Lather. Rinse. Repeat.

Which means a liquidity event — if it happens at all — takes a lot longer too. We’re not talking five or seven years. We’re talking twelve to fifteen.

And here’s another wrinkle. Those exits? They’re usually acquisitions — not IPOs. Which means the capital gets distributed to a very limited group of folks — like founders and investors — rather than every employee. And most of those investors…? They’re out of state. They’re in Bay Area. They’re in Seattle. They’re back east.

The liquified capital doesn’t impact us here, by and large. It lands wherever the people writing the checks are sitting. It goes back to where that risk tolerant capital came from. Rather than recycling through our community.

And the founders? After fifteen years or more of grinding? They’re exhausted. They’re not looking at the ecosystem thinking “I can’t wait to do that again!” Instead, they’re questioning their role as a founder, “I don’t know if I have another fifteen years in me to do that again ”

So when they finally have wealth of their own — capital that could theoretically flow back into the ecosystem and fund the next generation of startups — they get extremely careful with it. They get risk averse. Some folks might say, “Stingy,” even. (I mean, I wouldn’t. But some folks might.) And honestly, who can blame them? The system nearly broke them. Why would they put their hard-won capital back into the machine that made it so difficult for them to succeed in the first place?

So they don’t invest in the next generation. Which means that generation of startups still doesn’t have early local capital. Which means the next founder is right back where the last one started — full of energy, no local capital, booking a flight to San Francisco.

Return capital doesn’t come back because exits are rare. Exits are rare because companies are underfunded. Companies are underfunded because return capital doesn’t come back.

Round and round and round.

Every once in a while, there’s a glimmer of hope

In December 2014, Tripwire got acquired for $710 million and New Relic went public — in the same week. I wrote at the time with hope that “maybe, just maybe, we’ll see a little bit of this wealth reinvested in the Portland startup scene.”

I was so hopeful. It felt like the cycle might actually break. New money, new talent, new ideas on the streets. That’s what’s supposed to happen after a liquidity event. That’s how the flywheel spins in the other direction.

And some of it did happen. But not enough. Not nearly enough to shift the structural reality. Because one week of exits — even a historic one — doesn’t fix a pipeline problem that’s been building for decades.

And then we took the opportunity to make the vicious cycle even more vicious

Which brings us to SB 1507 and the QSBS mess. You’ve heard me on this. At length. (At significant length. Ad nauseam. I know.) The governor signed it on April 9 — and yes, she said something that matters, so read that post — but the signing doesn’t fix the cycle.

But here’s the thing I didn’t say clearly enough in those posts: QSBS taxation doesn’t just add a new problem. It accelerates the vicious cycle. It takes the one remaining incentive for local investors to reinvest locally — the tax exclusion on gains from holding small business stock for five or more years — and removes it. But not for outside capital. Just for us. Just for Oregonians.

Talk about exacerbation. The vicious cycle isn’t just continuing. It got a legislative turbo boost.

But it has worked here. Once.

You know what’s even more maddening? We have proof that the cycle can break.

Oregon Venture Fund invested in a little company called Jama Software. Jama bootstrapped. They took about $1 million in angel funding, largely from OVF. They built. They were patient. And in March 2024, they were valued at $1.2 billion. A 60x return for OVF.

That’s what local, patient, long-horizon capital can produce. That’s the cycle running in reverse — local investment creates a local success, which generates returns, which can fund the next round of local companies.

It happened.

But it happened once. And once isn’t a pattern. Once is an anecdote. We need it to happen again and again and again until the cycle flips — until there’s enough local capital cycling back into the ecosystem that a founder starting a company in Portland has the same shot at early-stage funding as a founder in Seattle or Salt Lake or wherever.

But it’s going to take some pretty courageous investors to do that. And to break us out of this vicious cycle. For good.

Portland Surges to No. 1 in America’s Factory Startup Boom

Portland has quietly grabbed the top spot in a new national look at manufacturing startups, edging out both old-school industrial hubs and glossy tech metros. An analysis of five years of firm formation data shows the Portland metro logged about 2.47 manufacturing firms younger than five years per 10,000 residents, which works out to roughly 250 more new manufacturing firms than the national average would predict over the same period.

Cloudability Founder Mat Ellis Opens Fractional Executive Practice for Pacific Northwest SaaS and AI Companies

Mat Ellis, founder of Cloudability and Managing Partner of Sunny Ventures, has opened a fractional executive practice focused on Pacific Northwest SaaS, AI and infrastructure companies. Engagements include fractional CEO, fractional CxO and strategic advisory roles, with inquiries open through matellis.com.

Cascade Seed Fund rebrands to Long Way Ventures – Portland Business Journal

Long Way Ventures consists of Pease and venture partners Milena Morris, who is based in Bend, and Jim Clifton, who is based in Nashville. Clifton is the point person for potential deals in the Eastern U.S.

“Semiconductor Startups Head to Silicon Forest”… Gyeonggi Innovation Center Begins Full-Scale Expansion into Portland, U.S. – 벤처스퀘어

The Gyeonggi Center for Creative Economy and Innovation announced that it has selected nine semiconductor startups to participate in the ‘2026 Portland, USA Expansion Program’ and has commenced full-scale support for their global expansion, starting with an orientation. This program is operated in cooperation with Greater Portland Inc. (GPI), an economic promotion agency in Portland, Oregon, and aims to go beyond simple market exploration to facilitate practical business connections with local companies and investors.

The fall of the theorem economy – David Bessis

In the past few months, as I was grappling with the rapidly changing situation around AI and mathematics, I found myself more troubled than I ever expected to be. In theory, I should feel vindicated and happy. In practice, I am also puzzled, worried, and sad.

Startups Brag They Spend More Money on AI Than Human Employees

A new class of AI startups say they are taking money that would normally be used to hire people and are spending it on AI compute instead.

A Better Way To Fail: How This Platform Aims To Turn Startup Shutdowns Into Something Salvageable

Founder and CEO Dori Yona came up with the concept while building his previous company, after a board member asked him to produce a “shutdown analysis.” The process proved so complex and time-consuming that it sparked the idea for a software platform to automate and streamline company closures.

Software Eats Its Own – On my Om

Despite all the hoopla about AGI, and changing the course of human history (and it will), the fact remains that most of these big boys know one thing. Money is in automating software. Money gets the valuations. And valuations get the money.

Great companies are built in hackathons – by Ian Vanagas

When you think about hackathons, you picture a bunch of engineers huddled around laptops, coding up a storm. This is mostly what our hackathons look like with one difference: they’re not just for engineers.

I am an idiot – by Julie Zhuo – The Looking Glass

Surely there is a difference between an accomplished person saying they are an idiot, and actually being an idiot. After all, if you are accomplished, you must not be an idiot. But what is idiocy, really?

Agents with Taste

With enough experience, you can not only tell what feels better, but also why. By then you’ve not only built your taste, but also the ability to articulate it.

How personal finance advice is getting political, thanks to ‘finfluencers’

While most Americans over 64 say they turn to professional financial planners for guidance, a 2025 Gallup poll found that 42% of 18- to 29-year-olds seek financial advice on social media. That’s almost double the share among those ages 30 to 49.

How data centers could play a role in the midterm elections : NPR

“It has become a kitchen table issue, and it has become a very relevant political issue,” said Christabel Randolph, associate director of the Center for AI and Digital Policy, a technology nonprofit that promotes fairness and accountability.

Market of Choice Celebrates 10 Years of Powering Food Innovation

Long before “local” became a trend, Oregon’s largest independent, family-owned grocer Market of Choice opened doors and cleared pathways for emerging Oregon makers through collaborative relationships with influential incubators and its signature MOJO program. Celebrating its 10th anniversary, Market of Choice’s MOJO program has provided hundreds of local makers and thousands of products with a critical path to market, addressing historical barriers for small businesses and guiding them to success with product development consulting, distribution support, and promotions.

Bootstrapped Startups Don’t Win More Often; You’re Reading the Data Wrong | by Paul O’Brien | Apr, 2026 | Medium

Let me encourage you look at three reasons that no one articulates; this is the difference between giving a founder useful capital strategy advice and dooming them to a slow death because their advisor confused ideology with math.

Cascade Seed Fund rebrands to Long Way Ventures – Portland Business Journal

The newest iteration further reflects the shifting investment landscape where the definition of seed round has grown to include bigger checks and more mature companies, Pease said.

A More Intuitive OURA App | The Webby Awards

Portland digital agency Instrument won three Webbys for their work on the Oura app. 

Expensify shareholders evaluate stock split amid Nasdaq warning – Portland Business Journal

In addition to the building in downtown Portland, the company has also invested in an extensive remodel of a nearby food cart pod. The company leased the space where the Midtown Beer Garden is located, 431 S.W. Harvey Milk St., through 2030, according to its annual report. The company works with the ChefStable restaurant group to manage the pod.

The most interesting startups showcased at Google Cloud Next 2026 | TechCrunch

The most significant is that the tech giant has earmarked a new $750 million budget to help its Cloud partners sell more AI agents to enterprises. This funding is available to partners ranging from startups to the big consulting firms. It can be used for costs like Gemini proof-of-concept projects, Google forward-deployed engineers, cloud credits, and deployment rebates.