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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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.
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.
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. 🚀
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
Ross Overline retweeted
🎙️ New episode! Ross Overline sits down with Jennifer James, COO & Head of Investor Relations at Thoma Bravo, to explore how trust, transparency, and culture fueled the firm’s growth from $8B to $180B AUM.
🎧 Tune in now:
Spotify: bit.ly/3N8k7x2
Ross Overline retweeted
🎙️ New episode! @RossOverline sits down with Jonathan Weiss, former CEO of @WellsFargo Corporate & Investment Banking, to explore how integrity, trust, and leadership shape long-term success in finance.
🎧 Tune in now:
Spotify: bit.ly/4povMGz
Ross Overline retweeted
The populist left and populist right feed off of each other in a sick symbiosis.
Reject them both.
Ross Overline retweeted
My recent conversation on the Investing in Integrity podcast with @RossOverline, CEO of Scholars of Finance was a powerful reminder of why authentic leadership is so vital in today’s financial world.
We discussed how leaders must be guided by more than just quarterly results. Integrity, emotional intelligence, and a clear sense of purpose are the true drivers of sustainable, long-term value. In an era of increasing pressure, both from markets and new technologies like AI, it is imperative that we combat greed and ensure finance remains a force for good.
Listen to the full episode for more: bit.ly/3Kie6wr
#Leaders #Leadership #TrueNorth
Ross Overline retweeted
I always say OPM stands for “Other People’s Money.” So how are we incentivizing employees to find saving opportunities in the government? At @USOPM we have a program that solicits feedback and shares 5% of annual savings, up to $10k per award. Watch for more from my interview with the @RuthlessPodcast:
