Chairman & CEO @SOF_National // Former @Piper_Sandler @X @SoFi // +1 for @DrMaiaMosse // "If not us, who? If not now, when?" - JFK
San Francisco, CA
Joined October 2011
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Had the opportunity to sit down with @Ripple Co-Founder and Executive Chairman, @chrislarsensf, to talk about crypto, climate, and the future of finance. His insights are a must listen 👇 anchor.fm/scholars-of-financ…
Ross Overline retweeted
Three facts about life I want you to learn now.
1. Nobody cares about you and what other people think of you is none of your business.
People aren’t thinking about you anyway so f*ck em.
2. No one is coming to save you.
Not your parents or your friends. Parents might want what’s best for you, but they worked in a different economy and a different era, so they can’t fully understand the dilemmas you’re facing right now.
3. It’s not one big thing that makes you special.
Most people work their 9 to 5, but they’re thinking about getting home to watch a game or tv show.
Take the next hour and go through your contacts, call 20 people, rebuild a relationship or start a new one.
You’re now ahead of the average person.
In life and business you can’t be 50% in, you can’t even be 90% in. You have to be all in.
Whatever it is, your business, your health, your craft, go the extra mile.
Partial commitment isn’t differentiating enough.
Nobody is coming. Go get it yourself.
Ross Overline retweeted
The reports about the events at Cornell—and the lack of accountability for the perpetrators—are sickening. So is the victim blaming in response.
Victim blaming: “If you don’t want to be raped, don’t go to a frat party.”
Responsibility: Don’t. Rape. Women.
The right focus is not on teaching girls and women to avoid harm. It’s on raising boys and men who don’t commit it in the first place.
👏
Today at Hello America, we witnessed history in the making.
For almost 50 years, I've dedicated my life to helping people improve the quality of their lives, and I've worked with presidents on both sides of the aisle for more than 35 years.
I'm truly grateful to have been here to kick off the launch of America.gov, and to introduce the President of the United States and my friend of 15 years, @jgebbia. Joe is the co-founder of Airbnb and America's first Chief Design Officer, and he led the world-class team that built America.gov.
America.gov is a brand-new website built for one purpose: a government that truly SERVES its people.
Our government, sometimes with the best of intentions, has made it very difficult to get the help you've been promised.
Today that changes: 29,000 government websites are now ONE, using AI to answer your questions, and soon it will do the work for you. It's one website, one place, all the answers. It's simple, easy, and there for you whenever you need it.
You can even speak in three languages, with more to come. You have to check it out!
People right, left, and center came together to make this happen. Built by Americans, for Americans, to change the quality of your life. 🇺🇸🤝
Ross Overline retweeted
Thiel on Trump:
“There are a lot of things I got wrong... was crazier than I thought. It was more dangerous than I thought.”
“You wish they’d appointed more competent people.”
“administration is… staffed by not very smart but very loyal people”
Ross Overline retweeted
A core focus of the @POTUS Admin is to create a high performance culture in which government delivers for the American people. That means accountability + disproportionately rewarding truly outstanding performance. @USOPM is proud to support.
Federal Agencies can now award up to $25,000 cash to an employee who is "highly exceptional and unusually outstanding.”
It’s seems @DavidSacks is so suspicious of liberals that he’s not actually listening to @AnthropicAI and @OpenAI… even @elonmusk said he agrees with @DarioAmodei’s letter… he doesn’t trust the people who know more about AI than he does? When they’re saying humanity itself is at stake?
A dead giveaway that someone doesn't understand what we do is "financial literacy." The person has done no research.
Ross Overline retweeted
I've spent the last decade getting deals done.
I’m now going to do them at one of the most important AI companies in the game. I am joining @cognition as VP of Global Partnerships.
Eight years at Brex taught me how to sprint at what I do best. Grateful to the team that bet on me.
Cognition’s insane talent density and ambition made it the obvious next move. The dealmaking opportunity is real. Time to get back in the arena. 🚀
I was in the top 1% of all ChatGPT users globally last year... and I will boycott the company if they do what they say they're going to do...
If @OpenAI bets on ads as a revenue stream, I'm going to cancel my accounts, delete the app everywhere, and actively encourage everyone I know to stop using the platform.
It's now widely understood that the ad model creates perverse incentives. It incentivizes you to spend more and more time in the apps — this is what led social media companies to addict people to their phones.
Charging subscriptions for value delivered and building useful products that people are willing to pay for is the path that's both good for their business and good for humanity.
Grateful to @MikeNietzel with @Forbes sharing the story of Scholars of Finance. @SOF_National team is working hard to make a stronger financial system.
How Scholars Of Finance Is Transforming The Education Of Financial Leaders forbes.com/sites/michaeltnie…
Ross Overline retweeted
I wrote this early this morning and I wasn't sure if I would actually publish it, but here it is:
blog.samaltman.com/2279512
Ross Overline retweeted
BREAKING: WHOOP RAISES $575M AT $10.1B VALUATION
I am pleased to announce that we’ve raised $575M at a $10.1B valuation to accelerate our mission of unlocking human performance and healthspan globally.
This round was led by Collaborative Fund with participation from 2PointZero Group, Qatar Investment Authority (QIA), Mubadala Investment Company, Abbott, Mayo Clinic, Macquarie Capital, Glade Brook, B-Flexion, IVP, Foundry, Accomplice, Affinity Partners, Promus Ventures, and Bullhound Capital alongside a group of individual investors including Cristiano Ronaldo, LeBron James, Rory McIlroy, Virgil van Dijk, and Mathieu van der Poel.
This investor group and this moment reflect a powerful evolution underway for Whoop and the broader healthcare market.
Whoop was born in performance - trusted by the best athletes in the world to train, recover, and compete at the highest level. That foundation remains core to who we are. You see that in the iconic athlete investors joining this round.
But it also represents our push into broader health.
In the past 12 months, WHOOP has received medical clearances, launched blood testing, and created a platform that has saved lives. Abbott and Mayo Clinic - two of the most respected and influential institutions in global healthcare - are now investors in Whoop. These are organizations that have shaped modern medicine. Their decision to partner with us is a clear validation of where our technology is headed.
Healthcare systems around the world are reactive. For too long, they have waited for people to get sick, then intervene. Chronic disease is rising and costs continue to climb.
At Whoop, we believe the future looks fundamentally different. We are building the most powerful, personal, preventive health platform in the world - powered by continuous biometric data, advanced analytics, and AI to help people understand their bodies and improve their health in real time.
I am grateful to our team, our members, and our partners for believing in this vision. I’ve been building this company for 14 years and I’ve never been more excited for the future.
Ross Overline retweeted
🎙️ New episode: @RossOverline x Ben Choi (Managing Partner, @NextLegacy_ )
Ben helps oversee $3.5B+ invested across VC firms + early-stage startups—and shares how Next Legacy’s flagship model has driven $3B+ distributed to charity.
Spotify: bit.ly/4upndhB
Ross Overline retweeted
Best of 2025 & 2024 is here! We’ve distilled 30+ hours of wisdom into one powerhouse episode of Investing in Integrity. Hear @HowardMarksBook, @traestephens, and other top leaders share how they’re transforming finance for the better.
🎧 Tune in now: bit.ly/4prYGot
Ross Overline retweeted
Major preprint just out!
We compare how humans and LLMs form judgments across seven epistemological stages.
We highlight seven fault lines, points at which humans and LLMs fundamentally diverge:
The Grounding fault: Humans anchor judgment in perceptual, embodied, and social experience, whereas LLMs begin from text alone, reconstructing meaning indirectly from symbols.
The Parsing fault: Humans parse situations through integrated perceptual and conceptual processes; LLMs perform mechanical tokenization that yields a structurally convenient but semantically thin representation.
The Experience fault: Humans rely on episodic memory, intuitive physics and psychology, and learned concepts; LLMs rely solely on statistical associations encoded in embeddings.
The Motivation fault: Human judgment is guided by emotions, goals, values, and evolutionarily shaped motivations; LLMs have no intrinsic preferences, aims, or affective significance.
The Causality fault: Humans reason using causal models, counterfactuals, and principled evaluation; LLMs integrate textual context without constructing causal explanations, depending instead on surface correlations.
The Metacognitive fault: Humans monitor uncertainty, detect errors, and can suspend judgment; LLMs lack metacognition and must always produce an output, making hallucinations structurally unavoidable.
The Value fault: Human judgments reflect identity, morality, and real-world stakes; LLM "judgments" are probabilistic next-token predictions without intrinsic valuation or accountability.
Despite these fault lines, humans systematically over-believe LLM outputs, because fluent and confident language produce a credibility bias.
We argue that this creates a structural condition, Epistemia:
linguistic plausibility substitutes for epistemic evaluation, producing the feeling of knowing without actually knowing.
To address Epistemia, we propose three complementary strategies: epistemic evaluation, epistemic governance, and epistemic literacy.
Full paper in the first reply.
Joint with @Walter4C & @matjazperc
