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I Stayed Too Long
A conversation over sushi changed how I think about capability. Recorded version inside.

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🎧️ Prefer to listen? I recorded this week’s newsletter for you.
Jon and I went out to omakase last week in the West Village. Date nights are hard to schedule with a toddler, but we make time to be together, just the two of us. Late into the meal, a man in his 50’s sitting alone at the bar struck up a conversation with us.
We started chatting and learned that he had recently started writing on Substack after shutting down his hedge fund. Although he spent his whole career in finance and had access to both the capital and connections to keep growing his fund, he retired.
When pressed about it he said: “I learned I was a great manager. I was a great leader. But I wasn’t a great capital allocator.”
He explained that being mid-career and closing down a hedge fund with over a billion dollars under management was tough. It was difficult to explain to his investors that the investing game just wasn’t for him. And he didn’t want to spend the rest of his life being mediocre at something, even if he was widely perceived as successful.

Recognizing that something impressive to others is not your particular strength is an important form of self-awareness.
Staying with something just because you’re capable of doing it can become a trap, especially when the work sounds elite and pays well. But the opportunity cost of staying in a role you are merely good at is never discovering what you could be exceptional at.
This conversation resonated with me because I’ve often approached work asking the question, “Can I do this?” And, as it turns out, I can do a lot of things. But most capable people can do a lot of things. Just because you can do it doesn’t mean you should.
I’ve stuck out many jobs longer than I wanted to just because I could do them, or even do them well.
The harder and more honest question to ask is, “Am I unusually suited to this?”
That requires a deeper level of introspection that notices what work you feel at ease with. It’s the work where your particular combination of skills, experiences and intuitions give you an edge.
If you’re unsure, ask: What work do people come to me for again and again? What is the thing people recommend me for when I’m not in the room? What type of work is easeful and joyful?
At the end of the evening when we said goodbye to our sushi friend, I didn’t find it impressive that he was a former hedge fund manager. But I did find it impressive that he had the courage to leave in pursuit of discovering what he thought might be his life mission.
Instead of asking, “Can I do this?” ask, “Am I unusually suited to do this?”
That’s where you’ll find your edge.
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Frontier Tech Roundup — SheFi Edition 🏇
Claude Opus 5.5 is here
Anthropic released Claude Opus 5.5, which it says performs at the level of Fable 5.1 on most work while costing 40% less to run than Opus 5. It also comes with stronger safeguards meant to stop it from doing things like trying to escape its testing environment. Anthropic says external groups including METR and Frontier Design tested the model before release.
AI is helping build AI
This one is worth paying attention to. OpenAI says it has reached its goal of an "automated research intern", with coding agents now doing meaningful work inside its research process. Anthropic says Claude now leads 26% of its AI R&D work, and is collaborating on more than 90% of it. We are moving into a period where AI is participating directly in the research that produces future AI systems.Meta's Muse is taking off, and Amazon blocked it
Meta's new personal AI agent Muse climbed to the top of the U.S. App Store. It can do things on your behalf instead of simply answering questions, including researching, filling out forms and making purchases. Then Amazon blocked Muse from shopping on Amazon.com, saying unauthorized AI-agent access violates its terms. This is an early look at a question we're going to see much more often: when your AI acts for you online, which companies will let it through the door?An AI error almost led the U.S. military to board a Chinese ship
This story is wild. According to reporting based on people familiar with the incident, a U.S. military intelligence report created with help from AI incorrectly identified cargo on a Chinese ship as components related to a nuclear weapons program. Armed personnel were preparing to board the ship and military aircraft were already in the air before officials caught the error. It is a stark example of why verification matters when AI is being used in high-stakes environments.AI got financial questions wrong 57% of the time in one benchmark
A study from fintech company Saturn tested 18 AI models across more than 10,000 responses to personal-finance questions. The models gave incorrect answers 57% of the time on average, with the error rate rising to 88% on harder questions. Even the best-performing model in the study, Claude Opus 5 in reasoning mode, still failed 39% of the answers. Saturn sells AI software to financial advisers, so that context is worth knowing, but the results are a useful reminder to verify anything consequential before moving money.A fake "Claude trading bot" scam took more than $517,000
TRM Labs found a coordinated scam using YouTube tutorials that promised to teach people how to build a crypto arbitrage bot with Claude. The tutorials instead walked victims into deploying and funding malicious smart contracts. TRM traced about $517,205 in losses across 224 victim wallets. Claude was only used as branding for the scam, not in the actual contracts. What makes this one especially nasty is that the victims themselves deploy and fund the contracts, so many of the usual phishing and wallet warnings never appear.The SEC created a five-year pathway for tokenized U.S. stocks
The SEC issued a temporary five-year "Innovation Exemption" that allows qualifying venues to facilitate onchain trading of tokenized U.S.-listed stocks using permissioned automated market makers and liquidity pools without registering as national securities exchanges under the usual framework. The tokenized shares have to carry the same rights as the underlying shares, including voting and dividends, and issuers can object to having their stock traded this way. The exemption is conditional and temporary while the SEC considers longer-term rules.The most AI-exposed jobs are seeing faster advertised-pay growth
Indeed Hiring Lab found that advertised salaries in the most AI-exposed occupations have risen about 46% since 2021, compared with 25% in the least-exposed occupations. The pay difference is much more pronounced in senior roles and basically disappears at entry level. That doesn't tell us what happens to every individual job as AI adoption grows, but it is an interesting counterpoint to the idea that AI exposure automatically means lower pay.
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SheFi Global Events + Opportunities 🌎
Stay connected with SheFi around the world. From meetups and summits to workshops and special partner events, this is where you’ll find the can’t-miss gatherings happening across our global community.
09/23-30 Sicily: Roots & ReFi: RSVP here
Our global ambassador Julia is hosting a retreat in Sicily for women in the blockchain and AI space this September. We’ll spend 4 days in the picturesque fishing village of Scopello, on the edge of the Zingaro nature reserve, and 3 in Ragusa, the southeast tip of the island. We’ll visit the olive groves on the land GrowFi and RiFai Sicilia have purchased for regenerative farming funded by regenerative finance, and spend long days exploring Sicily, eating well, swimming, sailing and plenty of other activities.
The retreat will have a positive sum effect on both the participants and the environment! Find the information here and reach out to Jul directly if you’re interested.
Telegram group: https://t.me/+ao2ltFamsgRmMjVi

Opportunity: BITCOIN TREASURIES - Delegate Application: Apply here
30 women. 30 sponsored seats. One seat at the table.
Applications are now open for the Women in Bitcoin Delegate Program at Bitcoin Treasuries Conference 2026 in New York City.
We’re selecting 30 women working across Digital Assets/Crypto, TradFi and FinTech for fully sponsored conference seats and dedicated Women in Bitcoin cohort programming.
📍 SECOND, New York City
📅 September 28, 2026
⏰ Applications close September 18

✨💫✨
Crypto Events 🌎
Going to ETHCC, Token2049 or Devcon? Join our Global Events Telegram Chat: https://t.me/shefisummit
09/23 Munich: Ethereum Munich #7 🥨: RSVP here
09/25 London: Coffee & Breakfast, with STUK and Altitude: RSVP here
09/26 Chicago: LOVABLE × KARAOKE: Build the future of karaoke…. Then sing with it!: RSVP here
09/26 Istanbul: Monad Blitz İstanbul v2: RSVP here
09/28 Zurich: Blockstories Horizon 2026: Zurich Summit: RSVP here
09/29-10/02 Washington DC/NYC: The Future of Money, Governance, and the Law: RSVP here
09/29 Turkey: Grok Bot Meetup Istanbul w/ Neon Apps & RevenueCat: RSVP here
10/06 Singapore: OKX Now, Singapore: RSVP here
10/06 Singapore: SH3 Connects Coffee Meetup Singapore Edition Token2049 💫: RSVP here
10/08 San Francisco: InTheRoom: Trust, Presence & Connection - #SFTechWeek: RSVP here
10/16 Washington: Groundwork: RSVP here
10/19 Florianópolis: IslandDAO v5: Florianópolis Brazil: RSVP here
11/17-18 Florida: EthWomen Florida: RSVP here
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