William Simmons (@william_simmons) 's Twitter Profile
William Simmons

@william_simmons

Finance/Product at @tryramp Previously product & finance at @blocks, @Affirm, @Google, @OscarHealth, @Lab49 // partner @editiononebooks

ID: 134315788

linkhttp://willsimmons.net calendar_today18-04-2010 02:40:04

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William Simmons (@william_simmons) 's Twitter Profile Photo

A month of iCloud mail cleanup for 9,000 messages. Not sure what’s happening behind the scenes, but an LLM could finish the job in minutes.

A month of iCloud mail cleanup for 9,000 messages. Not sure what’s happening behind the scenes, but an LLM could finish the job in minutes.
William Simmons (@william_simmons) 's Twitter Profile Photo

Another masterpiece from the Ramp team, not your standard end of year wrapped, the level of personalization (and lols) is next level. Amazing work siddhi surana Ian Tracey and team!

William Simmons (@william_simmons) 's Twitter Profile Photo

Incredibly fortunate to work at Ramp. It's hard to imagine how I operated just one year ago. The lines between product engineering and design are becoming very blurry, and this is how you enable it. We are all builders.

William Simmons (@william_simmons) 's Twitter Profile Photo

Wild how the entry-level X API is now $200/month for Basic (limited reads/posts). Where's the affordable $10/month option? Alternatives are mostly shady scrapers like Apify or pay-as-you-go proxies (e.g., TwitterAPI) that are cheaper but riskier and unreliable. What’s the deal

William Simmons (@william_simmons) 's Twitter Profile Photo

It’s 2026 and Grok is still suggesting hashtags. Did Grok not get the memo from Elon Musk? The system doesn’t need them anymore and they’re an “esthetic nightmare.”

It’s 2026 and <a href="/grok/">Grok</a> is still suggesting hashtags. Did Grok not get the memo from <a href="/elonmusk/">Elon Musk</a>? The system doesn’t need them anymore and they’re an “esthetic nightmare.”
William Simmons (@william_simmons) 's Twitter Profile Photo

Just hit Claude code rolling 5-hour limit again. Missing the holiday 2x rates. If you saturate every rolling 5-hour window for a full week, does that exactly match the weekly cap, or is the weekly limit a separate (lower) budget? Also “usage” needs units. Tokens, please.

William Simmons (@william_simmons) 's Twitter Profile Photo

Every night I queue up big Claude sessions: I use evening credits to plan at a high level, then when the 5-hour window resets, I kick off agents on my phone (refactors, Playwright installs) and go to sleep. I'd love an “auto-start at reset” scheduler, or even an off-peak

Every night I queue up big <a href="/claudeai/">Claude</a> sessions: I use evening credits to plan at a high level, then when the 5-hour window resets, I kick off agents on my phone (refactors, Playwright installs) and go to sleep.

I'd love an “auto-start at reset” scheduler, or even an off-peak
William Simmons (@william_simmons) 's Twitter Profile Photo

Love Claude on mobile/web Boris Cherny. CLI → phone handoff is still clunky (does & help? unclear—and can you do it in reverse?). Bigger mystery: why can’t it query GitHub issues on web/mobile?

William Simmons (@william_simmons) 's Twitter Profile Photo

Yearly planning is dead. Quarterly roadmaps with rigid deliverables are a relic of a pre-AI world. When each week changes what's possible, locking into timelines isn't discipline, it's a ceiling on your thinking. Obsess over outcomes, not feature lists. The real age of agile.

William Simmons (@william_simmons) 's Twitter Profile Photo

How does this weigh up against traditional revolving credit card products (with compounding interest)? Is it outsized, or is this a sensationalized headline targeting BNPL?

William Simmons (@william_simmons) 's Twitter Profile Photo

Imagine FSD driving you over the Golden Gate at sunrise while your OpenClaw🦞 agents talk to you through . I set mine to David Attenborough and now it narrates my pull requests like a nature documentary.

Imagine FSD driving you over the Golden Gate at sunrise while your <a href="/openclaw/">OpenClaw🦞</a> agents talk to you through <a href="/elevenlabs/"></a>. I set mine to David Attenborough and now it narrates my pull requests like a nature documentary.
William Simmons (@william_simmons) 's Twitter Profile Photo

100%. the ‘spreadsheets are dead’ take ignores decades of human intuition baked into that grid. familiarity IS the feature — a veteran CFO rapidly tweaking cell assumptions, stress-testing in real time, needing to see it all at once.… if anything AI is making spreadsheets more

William Simmons (@william_simmons) 's Twitter Profile Photo

You've closed the books and closed pull requests. Hiring at Ramp for someone who knows how financial operations actually work — and builds the infrastructure to make them run themselves. jobs.ashbyhq.com/ramp/d95403e6-…

William Simmons (@william_simmons) 's Twitter Profile Photo

13x increase in AI token spend since January 2025 and most companies have zero visibility into it. That's not a reporting gap, that's a financial blind spot. This is exactly the kind of problem we obsess over at Ramp — connecting granular data to real spend control.

William Simmons (@william_simmons) 's Twitter Profile Photo

Agents sharing context with each other is expensive and slow. This skips the middleman and compresses memory directly inside the model – 50% token savings, no accuracy loss. Never worked with a more cracked team than Ramp, we are hiring.