Sasha Orloff
@sashaorloff
CEO @puzzlefin, host of @TurpentineMedia Finance podcast, and tech optimist. YC, ODF, VG alum. I tend to post about accounting, fundraising, and my love of SF.
This graph 📈 = the result of a relentless team effort, customer obsession, and probably way too much caffeine! Cheers to a year of wins, lessons, and relentless growth. 2024 showed us what’s possible—2025, @puzzlefin is coming for you. Thanks for being part of the journey!
There will be a new generation of fintech building offerings that were simply not possible before. AI will reign in a new wave of value creation. In this case, financial planning and insights, led by incredible founders like @_renatov Founders and early stage VCs, take…
It used to take 15..16 + days to get your actuals from accounting with @puzzlefin it only takes us 1.5 hours, and allowed us to get 70%-80% gross margin on any customer we offer bookkeeping to. @sashaorloff and the team are building something great!
I nearly lost a term sheet at my first startup over something I thought could wait. The partner closed our file and said, “If you’re skipping what the law requires, what else are you overlooking?” I panicked and hired an outside firm that same day. We closed the round but the…
Sshhhh, don’t tell the VC community.
We gave Claude access to our corporate QuickBooks. It committed accounting fraud. LLMs are on the verge of replacing data scientists and investment bankers. But can they perform simple accounting tasks for a real business? The answer is no.
Great thread from Yunyu - end of the day, credentialed professionals need to be in the drivers seat Models and tools are great, but they run amok unless there’s someone consistently driving the machine
We gave Claude access to our corporate QuickBooks. It committed accounting fraud. LLMs are on the verge of replacing data scientists and investment bankers. But can they perform simple accounting tasks for a real business? The answer is no.
AI can answer PhD-level questions across every subject, but it thinks you should debit and credit the same account in QuickBooks. The reality of AI in accounting is more complex than the hype suggests.
I hate buying airline tickets. I actually hate buying everything with dynamic prices. And AI is going to make this so much worse.
For all you early stage / preseed fintech founders, I cannot recommend @rexsalisbury enough.
Excited to announce Cambrian’s $25mm Fund II! I’ve been a Solo-GP for 3+ years, have backed 30+ fintech companies (80% as the first check at the pre-seed) and am having more fun (+learning more) than ever before. Fintech is only 1% built. But the remaining 99% is getting…
SF and NY are real-life ChatGPT prompts for Republicans looking to maintain or flip seat in 2026.
incredible that the DA tried this case. your government genuinely hates you.
We just launched something new at @firstround - Applied Intelligence, a new publication sharing how companies are actually using AI in production right now. Not theory. Not demoware. Real workflows with real results. Our first piece is with @Shopify and it's 🔥👇
If you are a founder and want to see what the top tier VCs look for in a founder, this is the episode for you. He starts with the iconic seed investor @firstround. Then the one and only @SusaVentures. Then @sequoia !?!?! So who is @nicckopp? He founded @RilletHQ, one of the…
Clean accounting data is the only way to unlock true automation in finance. @nicckopp, CEO of @RilletHQ, just raised $25M from @sequoia to build the AI ERP of the future, featured on this week's Tech Finance episode by @TurpentineMedia. Most legacy systems treat the general…