Ross Overline

Chairman & CEO @SOF_National // Former @Piper_Sandler @X @SoFi // +1 for @DrMaiaMosse // Romans 5:3-4 // Om Mani Padme Hum

[Ross Overline @RossOverline]

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 👇 https://t.co/HVWF0Wq4dL

[Ross Overline @RossOverline]

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.

[Ross Overline @RossOverline]

@mansourtarek_ @a16z This is horrible for society.

[Ryan Petersen @typesfast]

Financial Times perfectly illustrates our possible futures

[Ross Overline @RossOverline]

Grateful to @MikeNietzel with @Forbes sharing the story of Scholars of Finance. @SOF_National team is working hard to make a stronger financial system.

[Mike Nietzel @MikeNietzel]

How Scholars Of Finance Is Transforming The Education Of Financial Leaders https://t.co/qm6J7xQYv8

[Ross Overline @RossOverline]

@chamath Warren Buffet would say that financial engineering is misguided and dangerous. Compensation is a cost!

[Sam Altman @sama]

I wrote this early this morning and I wasn't sure if I would actually publish it, but here it is:

https://t.co/7Dw9UFpeep

[Ross Overline @RossOverline]

@willahmed @WHOOP Congrats! Have been and will remain a port user and promoter for life. My NPS is 100!

[Will Ahmed @willahmed]

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.

[Scholars of Finance @SOF_National]

🎙️ 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: https://t.co/AIusNSVDji

[Scholars of Finance @SOF_National]

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: https://t.co/yAOAY5mTij

[Valerio Capraro @ValerioCapraro]

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

[Scholars of Finance @SOF_National]

🎙️ 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: https://t.co/iwffEQnavs

[Ross Overline @RossOverline]

@SOF_National @WellsFargo Jon Weiss was great!

[Scholars of Finance @SOF_National]

🎙️ 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: https://t.co/bR9yBp58nc

[Dave Hale - Concerned Republican @CountryFirstRep]

The populist left and populist right feed off of each other in a sick symbiosis.

Reject them both.

[Ross Overline @RossOverline]

The ultimate test of a secure sense of self is not feeling any type of way when someone calls you "bud" or "buddy".

[Ross Overline @RossOverline]

@Bill_George Thank you for joining us Bill!

[Bill George @Bill_George]

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: https://t.co/9KEXINmRbV

#Leaders #Leadership #TrueNorth

[Ross Overline @RossOverline]

@LionPhlox @NCDude80 @JTLonsdale I'm with you. What happened was tragic and deplorable.

[Ross Overline @RossOverline]

@NCDude80 @JTLonsdale I fully agree that people on the extreme/far left celebrated murder, and that's horrible. Like, dispicable. 100% aligned with you there. That said, we can also agree that hatred isn't what builds a democratic nation -- but what can pull it apart (study the Civil War).