John Ryu

Building access to institutional caliber investment strategies @SimplifyAsstMgt | Startup investing @hypothesisvc

[Garry Tan @garrytan]

Jo uses GBrain under the hood and this is one of the fastest ways to get a personal AI or company brain working for you

Personal AI is here

[Paul Graham @paulg]

No investor has any right to push you to get acquired if you don't want to. The company is your project, not theirs.

[Darren Rovell @darrenrovell]

Top 10 all time graduation speech by Eric Church at UNC.

[Jediwolf @Jediwolf]

What happens when you post a real Monet and say it’s AI? The coolest art social experiment I’ve seen in a while. Thank you @SHL0MS

[Aaron Levie @levie]

Forward deployed engineers, or equivalent, are about to become one of the most in-demand jobs in tech. And one of the most important functions for AI rollouts.

Deploying agents is far more technical of a task than most people realize, often far more involved than deploying software. Software generally works the same way every time, and generally for the past few decades has been updated versions of an existing technology or concept (which basically means easier for the enterprise to update their workflows on a newer system).

With agents, you’re actually deploying the equivalent of work output within the enterprise. The customer is effectively using you as a professional services provider for a task, which they expect to get solved nearly end-to-end now. This means you need to actually deeply understand the business process as a vendor, and get the customer from the current to the end state seamlessly.

Companies need help figuring out which models will work best for their workflows, they need extensive evals setup often, they need change management support for workflows, they need to get their data setup for the agents, and constant tuning of the agentic system for their process.

Massive role in tech now. And another example of the kind of highly technical work that AI is creating.

[Norgard @BrianNorgard]

If Anthropic starts invalidating layered SPVs and other “creative” financing structures, private markets are in for a reckoning. The SpaceX IPO will expose just how much synthetic ownership and outright fraud has accumulated in privates.

[spidey @lochan_twt]

The day a blind man sees. The first thing he throws away is the stick that has helped him all his life

[Elon Musk @elonmusk]

Accurate

[Raphael Schaad @raphaelschaad]

MIT student asked a question earlier today that a lot of young founders are quietly wondering about:

"Won’t the frontier labs just do everything?"

Yes it's true that OAI/Ant are shipping at incredible pace, but it's quite easy to avoid their blast radius and build amazing startups:

OpenAI is not going to build a cattle-herding drone, buy an old F-150 and drive from ranch to ranch like the founder of one of the fastest-growing YC W26 startups, Graze Mate.

Anthropic is not going to integrate with dental insurance verification systems (Lance).

Google is not going to navigate NATO procurement (Milliray).

The value is in the last mile, not the model. Sales cycles require humans who understand the customer. And most importantly, the market is expanding, not shrinking: AI isn't cannibalizing the existing 1% software spend — it's unlocking the other 5-6% that was going to humans. That's a much bigger market for startups yet-to-be-founded than the one the labs are playing in.

Now, what DOES seem risky?

A thin UI layer on top of ChatGPT with no domain expertise; a general-purpose chatbot or assistant; or a product that gets obsolete when model capabilities improve.

But — tools for specific industries; "full-stack" AI companies that actually are the service (AI law firm, AI accounting firm, AI uranium exploration company); or generally products where the customer doesn't want a tool but an outcome — are defensible ideas for startups.

[Nakul Mandan @nakul]

“Founders aren’t made when they start companies. They’re made when they interpret their market correctly.”

Episode 2 of @KnuckleUpHQ is live.

Qasar Younis (@qasar): Founder and CEO of Applied Intuition. One of the sharpest and most intentional operators you’ll ever meet on the craft of building a company.

Full episode ↓
--

00:00 Intro

01:19 What really makes someone a founder

05:26 The company that almost became Kickstarter

08:12 The most common misread on feedback

13:40 Why most founders don't end up with the best team

19:45 How to pick a co-founder

23:38 Your first 10 hires are really your first 100

28:21 The case for hiring slow and firing slow

33:22 Red, yellow, green: how Applied gives monthly feedback

35:00 The role that knows what’s actually going on in a company

40:01 How to operate with speed and intentionality

42:41 The three things Qasar spends time on

45:57 How Applied is driving AI adoption

52:06 The type of engineer Applied is now looking for

1:01:19 Why this could be the golden age of small companies

1:09:13 Quickfire: red flags, overrated advice, and superpowers

1:12:32 Qasar's advice to his 25-year-old self

[Paul Graham @paulg]

Hamming's talk is so important that I reproduced it on my site. It's one of the only things on my site written by someone else.

https://t.co/kWvKdwIiOm

[max @maxkolysh]

cursor’s long term viability was contingent on maintaining access to ant/oai models. both are actively building cursor competitors

that’s an existential platform risk

to survive they need their own foundation models. training frontier models requires deep pockets.. and they found the guy with the deepest pockets in the world

[John Ryu @john_ryu]

@kirbyman01 @a16z Bryan! Congrats-- so excited for you!

[nihal @nihalmehta]

New York is about to make a massive mistake. The NY State Senate is advancing a proposal to decouple from federal QSBS (Section 1202) — the tax provision that lets startup founders exclude gains on qualifying exits. If this passes, founders would owe 10-13% in combined state and city tax on exits that are tax-free at the federal level and in nearly every other major tech state. Even worse: it's retroactive to January 1, 2025. This comes right as the federal government just expanded QSBS benefits and New Jersey moved to full conformity. New York wants to go in the opposite direction.

As a seed investor in NYC who has backed hundreds of companies, I can tell you: founders are mobile. If New York becomes one of the most punitive states for startup exits, the best founders will simply build somewhere else — and the jobs, tax revenue, and innovation will follow. NYC has built something special over the last two decades. This proposal puts it all at risk for a short-sighted revenue grab.

If you're a founder, investor, or anyone who cares about the NYC tech ecosystem — please sign the TechNYC open letter before Monday below 👇🏾👇🏾👇🏾

Keep building, NYC 🗽

[pradeep @pradeep24]

Announcing jo 1.0 - rebuilt from scratch!

Two years ago we launched a macOS productivity sidekick.

Today it's something different: a personal AI that actually knows your life.

Your Mac. Your dedicated cloud machine. Your data stays yours.

https://t.co/gJbSvP6b9N

[Larry Cheng @larryvc]

In capital rotations, industry-leading companies are not spared. In 2006-2009, example peak to trough declines:
- Amazon (-61%)
- eBay (-78%)
- Apple (-61%)
- Salesforce (-71%)
- VMWare (-88%)
- EMC (-65%)
- etc...

Therein lies the opportunity with hard capital rotations.

[David Marcus @davidmarcus]

A few thoughts about PayPal, nearly 12 years after I left.

I woke up this morning to dozens of messages from former PayPal colleagues. It pushed me to finally speak up.

I never spoke publicly about the company after I left. Part of that was loyalty to John Donahoe, who gave me an unlikely opportunity, handing the reins of PayPal to a startup guy who, on paper, had no business running a then 15,000-person organization. But part of it was something else: I had left. I chose not to stay and fight for the changes I believed in. Speaking from the sidelines felt like armchair commentary. Easy opinions without the burden of execution. So I stayed quiet.

But twelve years of silence is long enough. And today's news makes it clear the pattern I've watched unfold isn't self-correcting.

I left PayPal in 2014 because I was deeply frustrated. We had executed a silent turnaround of a company that had lost its soul. We brought back engineering talent, shipped good products quickly, and acquired Braintree and Venmo. The company was on a tear. So much so that Carl Icahn felt compelled to accumulate a position in eBay and push for a PayPal spinoff. At the time, eBay decided to fight Icahn.

It was a difficult period for me, caught between what I felt was right for PayPal and my loyalty to the eBay team.

This is when Mark Zuckerberg approached me to join Facebook. The combination of his conviction that messaging would become foundational, the appeal of going back to building products at scale, and my growing exhaustion with the internal politics at PayPal and eBay eventually convinced me to leave and join one of the best teams in the world, one I had admired for a long time.

In the summer of 2014, I met John in a café in Portola Valley and told him I had decided to leave. During that conversation, he told me that Icahn had effectively won the fight, that PayPal was going to become an independent company, and he tried to convince me to stay on as CEO, but I had already said yes to Mark, and my word is my bond. There was no turning back.

After my departure, the board scrambled to find a replacement, and it took a few months for them to land on Dan Schulman. The leadership style shifted from product-led to financially-led. Over time, product conviction gave way to financial optimization.

Much of the momentum we had created still persisted and carried the company forward, mainly driven by Bill Ready, who came over in the Braintree acquisition and rose to COO. Under his leadership, Venmo grew exponentially, and total payment volume (TPV) accelerated quickly. But the shift under Schulman became more pronounced after Bill's departure at the end of 2019. With him went the product conviction that had defined the post-spinoff momentum. Then, for a period, COVID-fueled online shopping hid a lot of the company's new weaknesses.

During that period, the company made a fundamental miscalculation: it optimized for payment volume instead of margin and differentiation. It leaned into unbranded checkout, where PayPal had the least leverage, instead of branded checkout, where the margin, data, and customer relationship actually lived.

Visa masterfully structured a deal that effectively ended PayPal's ability to steer customers toward bank-funded transactions, which had been a core driver of PayPal's economics. Not long after, PayPal lost a significant portion of eBay's volume. Over time, it saw its share of checkout among its most profitable customers steadily erode as Apple Pay and others continued to execute well.

The same pattern repeated itself across lending, buy-now-pay-later (BNPL), and new rails.

On lending, PayPal missed the opportunity to turn it into a platform weapon. Products like Working Capital were conservative, short-duration, and optimized for loss minimization. Lending never became programmable, never became identity-driven, and never became a reason for merchants or consumers to choose PayPal over something else.

The missed opportunity in BNPL was even more striking. Klarna, Affirm, and Afterpay didn't just offer installment payments, they built consumer finance brands, persistent credit identities, and new shopping behaviors. PayPal saw the BNPL turn, entered the market, and had every advantage: distribution, trust, and merchant relationships. But BNPL was treated as a defensive checkout feature rather than an offensive category. There was no attempt to turn it into a core consumer relationship, no super-app behavior, and no meaningful differentiation for merchants. Others built platforms, PayPal added a feature.

The failure to lean into building and owning new rails followed the same logic. After the spinoff, PayPal had a once-in-a-generation opportunity to build a global, at scale payment network. Instead, the company focused on building on top of existing networks and third-party rails.

More recently, that mindset carried over to PYUSD. Technically, the product was sound. Strategically, it launched without a compelling transactional reason to exist. PYUSD had distribution, but no organic demand. It was not embedded deeply enough into flows to become a true settlement layer, a cross-border merchant rail, or a programmable money primitive. It sat adjacent to the product instead of inside the core of it.

Acquisitions during this period followed a similar pattern. Honey was not a strategic acquisition for PayPal. It added activity, but not leverage. It lived outside the transaction, monetized affiliate economics rather than payment economics, and never meaningfully strengthened PayPal's control of the customer or the checkout moment. Xoom solved a real problem in remittances, but it never compounded PayPal's advantage. It scaled volume without changing the underlying rails, identity graph, or settlement model, and as importantly, it didn’t cater to a high-value, high-margin customer archetype.

None of these were bad companies. They were just a wrong fit for PayPal and became unnecessary distractions.

The board eventually recognized the problem. In 2023, they brought in Alex Chriss, an Intuit veteran with a strong product background, explicitly to restore product conviction. It was the right instinct.

But Alex came from software, not payments. He understood SMB product development. He didn't have the muscle memory for transaction economics, network effects, or settlement infrastructure.

In hindsight, he also made an error: clearing out much of the leadership team that understood payments deeply. Executives with years of institutional knowledge departed within his first year.

This morning, Alex was removed as CEO. Branded checkout grew 1% last quarter. The board tapped another operator, Enrique Lores, the former HP CEO who's been on the PayPal board for five years.

I don’t know Enrique. And he might be a great leader, but on paper at least, he’s a hardware executive. For a payments company.

The common thread through all of this is incentive design. Once PayPal became independent, short/medium-term predictability beat long-term vision and ambition. Stock performance mattered more than platform risk and network opportunity. Financial optimization replaced product conviction.

I'm not claiming I would have made every call differently. Running a public company at scale involves tradeoffs I didn't have to make after I left. But the pattern, choosing predictability over platform risk, again and again, was a choice, not an inevitability.

Over time, the company that had every advantage and could’ve become the most consequential and relevant payments company of our time, lost its mojo, its product edge, and its ability to compete in a market that’s being rewired and reinvented in front of our eyes.

That's the part that's hardest to watch for a company I care so deeply about.

[John Ryu @john_ryu]

@JBaksht @AlexHormozi Cosigned!

[Alex Hormozi @AlexHormozi]

The world will reward you in proportion to your courage, not your intellect.

[John Ryu @john_ryu]

Convinced that this winter storm forecast was manufactured by Big Ag (and Big Toilet Paper) to sell more stuff.