Calacanis Told Geoff Jake Paul Would Ruin His Career — Then a16z Partners Wrote the First Checks

Source: a16z | Published: 2026-06-22T14:35:28Z

Jason Calacanis warned Geoff that partnering with Jake Paul would destroy his career, but a16z partners became the fund's first LPs anyway — committing on the very first call before Geoff even had his pitch ready.

Six years later, Jake and Geoff Woo — founder of Ketone IQ and former co-founder of HVMN — announced their growth fund on the American Optimist podcast. The portfolio includes Etched, Cognition, SpaceX, OpenAI, Anthropic, Saronic, and Modal. Marc Andreessen, Chris Dixon, and other a16z partners were their first LPs. Geoff recalls that after the very first pitch call, the other side said they were in — before he'd even finished the deck.

When Jason Calacanis heard about it, he told Geoff: you're making a huge mistake, Jake won't work, you're going to destroy your career.

That's now their favorite joke to tell.

Jake Has Always Been an Entrepreneur — He Just Operates in Unusual Arenas

Most people read Jake Paul as "influencer turned boxer turned investor." Geoff sees it differently: Jake has always been an entrepreneur. Content, boxing, investing are just the arenas he's chosen to compete in, one after another.

That framework explains a lot. When Jake came to Silicon Valley at 17, he wasn't there for a product launch — he wanted to understand how these companies actually worked. His first boxing match sold 30,000 tickets and drew the largest audience in amateur boxing history. His reaction wasn't "this is amazing, let's keep going." It was to step back from content entirely and put every resource toward becoming world champion.

His decision logic: double, triple, quadruple down on what works; sweep what doesn't work under the rug and pretend it never happened.

The host noted: that sounds exactly like a16z's playbook.

Attention and Capital Are Two Rare, Stackable Assets

Geoff's background is Stanford computer science. He built the biohacking company HVMN, then turned Ketone IQ into a real business — with Chris Dixon as an early investor. Throughout the conversation, he kept returning to one framework: what are the underlying principles? That question drives everything he does — optimizing individual cognitive performance, understanding how a company should be organized, how culture and society should evolve.

He used a clean analogy to explain why he does growth equity: managing $100 and managing $100 billion require roughly the same thing — one or two people with genuinely sharp judgment. The difference is only scale. This kind of work is ultimately about bet quality, not process complexity.

Then he said: but Jake can do something I can't.

His logic: in an era where capital is increasingly abundant and attention increasingly scarce, "deploying attention" and "deploying capital" are two rare, stackable assets. Jake can direct massive public attention without any external budget — that's an asset in itself. He framed it as a simple question: if one person can pull huge audiences just by living their life and picking up their phone, while another needs $100 million to achieve the same reach — which one do you want as a business partner?

Why Only Three Top Creators Are Left

Jake listed the people who've survived at the top of social media: himself, his brother Logan, and MrBeast. That's it.

He brought up Magcon as an example. In the early internet era, Magcon had the cultural weight of a Justin Bieber moment — an entire generation grew up following them. Shawn Mendes emerged from that group and became an international star, but Magcon as a collective has vanished. He's seen it too many times: the biggest names, and then silence.

His diagnosis: some burned out, some lost the daily motivation to make content, some couldn't navigate platform shifts. But the most critical factor — many never figured out how to convert influence into actual cash flow. A massive following with no money makes it very hard to keep doing this for 13, 14 years.

Geoff added a different angle: MrBeast is a highly engineered content machine. His judgment lies in topic selection and format, but if you swapped Jimmy out for a different host, the show could probably still run. Jake is different — his audience is following the story of a specific person. Nobody can replace his position in front of the camera. Both models work: one runs on systems, the other on narrative.

Pain Tolerance Is Their Core Criterion for Founders

Geoff distilled their investment judgment into two questions: does this person have a solid reason to believe they can reach the top of their field? And do they have enough pain tolerance to get there?

Jake's relationship with pain started early. In high school, the entire school turned on him online — classmates made anonymous accounts to attack him, teachers made snide remarks, even the principal got involved. He's never had a stretch of making content without being attacked. He says he just got used to it, because he grew up in that environment from day one.

He offered a counterintuitive take: most people never get "canceled" because their presence is too small to register. So for most people, the real question isn't how to handle criticism — it's whether you've ever done anything worth criticizing. His words:

You have to do something first before you can be talked about. If you're nothing, you don't even qualify to be canceled.

Geoff connected this directly to founders: someone who gets physically hit every day in training, simultaneously attacked online, and still manages to grow through all of it — their pain threshold is extraordinarily rare in the startup world. That's why they believe Jake's experience can transfer directly to portfolio company founders — not through advice, but through real examples and real conversations.

"AI Maxing" and "Looks Maxing"

Geoff wrote a blog post arguing that in an era approaching AGI, only two things are truly worth maximizing: mastery of AI tools (AI maxing) and social charisma and influence (looks maxing). He described these as more culturally resonant reframings of "IQ maxing" and "EQ maxing."

He then turned the frame on a16z's media strategy: you've built your own propaganda machine, constantly publishing your worldview — that's looks-maxing for the VC world.

Someone asked what he'd do if he were a 22-year-old graduating in 2026. His answer was surprisingly traditional: get the math and computer science fundamentals solid. He believes that people who genuinely understand how large language models work are better positioned to use them well. He pointed out that the people leading the industry — people like Scott Wu — are all serious mathematicians. Understanding the structure of a system is what lets you actually command it, rather than just navigate its interface.

Badges, Stanford, and the NFL

Geoff offered a precise correction to Peter Thiel's "don't go to college" argument: Thiel himself has a Stanford undergraduate degree and a Stanford law degree. He collected every badge first, then declared badges useless.

His logic: if you have no other way to signal your abilities to the world, credentials are a valuable form of external validation — not because the education itself is worth that much, but because it gives you a starting point, a reason for others to believe you've reached the top of something. What actually matters, he argued, is that everyone should work to become the best in the world at something — violin, boxing, making videos — and then consider whether educational credentials can help you get there.

In this episode, Jake publicly said for the first time that he's seriously considering Stanford. He visited the campus that day and thought it was beautiful. But he added that he has NFL ambitions — he wants to play slot receiver, and figures that building experience on the Stanford football team before approaching the Cleveland Browns or the Dallas Cowboys is the more rational path.

The host and Geoff's reaction: the Cleveland Browns — are you serious?

He said yes.

Streaming Culture Has Peaked

When Jake turned to current streaming culture, he pointed to a controversial male streamer as a case study. He said the logic of that person's success isn't complicated: did something no one had done before, genuinely didn't care, said a lot of things that were true, and exposed himself completely.

People want to see things they've never seen before.

That's the underlying principle Jake uses to explain a lot of content success.

Then he said something candid: he thinks what he was doing on YouTube back in the day was the previous iteration of this culture. Streamers now work multiple hours every day just to hold attention, constantly escalating the stakes — and he has some complicated feelings about whether he bears any responsibility for that.

But he also thinks the playbook is approaching its ceiling. Platforms have started clamping down on extreme content, and some streamers have been banned as a result. The room to push further is shrinking.

Geoff's frame was more structural: in an era of AI-generated content flooding every feed, real people with actual histories and specific stories will become more valuable. What audiences ultimately care about is the handful of people they genuinely grew up following. This is a celebrity survival race, and most have already been eliminated. The ones still standing will become scarcer as the noise gets louder.

The Education System, and What They Actually Care About in Policy

Jake's most definitive political opinion landed on education reform. He believes the American education system has barely changed since the 1920s and '30s, while the world has become completely different. He mentioned Alpha School as an example of the kind of new educational model he finds interesting.

His criticism was specific: schools teach the Pythagorean theorem, but not how to file taxes, not how to understand compound growth. If young people left school knowing how money worked, he said, the whole economy would be in better shape. Changing the education system is like planting a fruit tree — you wait 30 or 40 years to see results, but those results shape an entire generation.

Geoff added a concrete policy example — the Trump accounts plan, which would give every American child a stock account from birth, so they could watch compound interest work with their own eyes. He thinks financial literacy matters as much as mathematical literacy — maybe more than most of the formulas he memorized and never actually used.

Jake said that if he ever decides to enter politics, the biggest driver would be exactly this kind of long-term, generational work — not because he's necessarily the most qualified person, but because he thinks he has clear enough judgment and enough courage to say it out loud.