Benjamin Plesser

Person in the arena. Eng ~5 at two unicorns and founded 8 figure ARR payments startup.

[Benjamin Plesser @bjpless]

LLM tip for the hacks @NewYorker . Run your content through ChatGPT with more opinionated system prompts to better disguise your bias:

“The day that Altman was fired, he flew back to his twenty-seven-million-dollar mansion in San Francisco, which has panoramic views of the bay and once featured a cantilevered infinity pool…”

Your credibility would shoot way up if you just added the following:

> Don’t reveal our low IQ, populist agenda with content that otherwise adds zero value.

[Benjamin Plesser @bjpless]

@daltonc @paulg Every message from a non-decision making associate is a waste of time for founders, regardless of how it is derived.

[Benjamin Plesser @bjpless]

@SMB_Attorney You think, due to your educational background and perceived IQ, that you'll be less replaceable in 5 years than a truck driver. You are not. Neither liability ambiguity nor regulatory capture will help you. It's going to com for all of us.

[Benjamin Plesser @bjpless]

@sweatystartup @grok how does a guy with this stupid a take -- he has never employed > D level tech talent in his life -- get 177k views and accumulate 400k followers? I'm not mad, I want to study at his feet.

[Benjamin Plesser @bjpless]

X would be 10x more interesting if opinions were verifiably backed up with prediction market positions. With X Money launching, you should be able to click a button in an X post to place a Polymarket bet -- if an associated market exists. That would give me a reason to fund my X account @nikitabier @elonmusk

[Benjamin Plesser @bjpless]

@AnthropicAI , in the wake of you nuking your government contracts AND winning respect of millions of end users, open up the #Claude connector marketplace to consumer apps!

Your connector experience is comparatively magical for consumer apps -- it's much more powerful today than ChatGPT app APIs -- but marketplace access is hidden behind a Google Form.

Let consumers enjoy artifacts that connect to external, deterministic data models. It's truly wonderful.

[Benjamin Plesser @bjpless]

Post-AI, there’s a PE arbitrage opportunity to takeover corporates like JetBlue, fire their entire IT teams, and compensate outlier talented (YC-style) founders like professional athletes with millions in annual cash comp.

JetBlue’s technology, as just one corporate example, is objectively an abomination. Historically, this makes sense — they structurally can only hire C-D tech talent. Their CTO seemingly has never coded, based on their resume.

Hiring a small seal team to overhaul their entire system pre-LLM wouldn’t have been technically viable.

Soon, however, (if not right now) they will be able to acquihire a seed or series A team that failed to hit PMF to replace their army of iemployees and contractors. They’d 10x their tech while cutting their IT budget.

At that level of cash comp, you could overcome opportunity cost and find enough highly motivated / competent people.

PE fund cares less about optics / politics of paying outlier engineers 10x VPs.

With LLMs, getting up to speed with legacy systems would be less problematic.

Frontier labs are actively compensating the most talented researchers 8-9 figures. Smart corporates (likely PE takeovers) need to start paying hyper talented founding engineers mid 7.

Until that happens, YC, VCs, and major tech companies are arbitraging this talent pool.

[Benjamin Plesser @bjpless]

@Claude When you mean to @claudeai but accidentally @ mention a random man named Claude...

[Benjamin Plesser @bjpless]

Passage Money is the first way to talk to your money inside your favorite LLM.

We counterintuitively chose to start with @Claude instead of ChatGPT due to the massive difference in integration quality as a third-party developer.

1) When you ask a complex question like "how much car down payment can I afford this month?", Claude agentically tries multiple tool calls to answer that question -- retrieve account balances, retrieve monthly spend, retrieve income, etc. -- whereas ChatGPT just tries to pick a single "best guess". The result quality is massive.

2) ChatGPT also does not let users "allow-all" for write MCP tools which is subtle but critical for decent UX. The user has to constantly dismiss annoying alerts.

3) Claude artifacts are insanely powerful for consumer experiences, even though their UX is not dialed in yet -- @AnthropicAI needs to work on making publishing and sharing affordance more visible.

@xai @nikitabier add MCP support so we can embed deterministic experiences for personal finance...

[Benjamin Plesser @bjpless]

@Claude https://t.co/o7PRM0BAYq

[Benjamin Plesser @bjpless]

@Claude We're early @Plaid engineers backed by the VC fund of the Plaid CEO and Max Altman.

[Benjamin Plesser @bjpless]

@claudeai @AnthropicAI We are a team of early Plaid engineers who wanted to see if we could make a personal finance app live 100% inside Claude conversationally as a connector. The experience is 10X+ any other fintech app. Live now -- https://t.co/o7PRM0BAYq.

[Benjamin Plesser @bjpless]

@UberEats @DoorDash I'm verifiably a delivery food addict who spends $2k+ per year. Right now I'm verifiably splitting it down the middle -- proof here: https://t.co/Pvr1Eo9uEC). Can one of you DM me with some sort of loyalty offer so I can have a reason to stick to one?

[Benjamin Plesser @bjpless]

@tenobrus 1) Two-sided marketplaces with humans are not fucked -- just low growth. 2) Regulated industries with extremely high correctness thresholds like fintech seem less fucked.