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Jason Freedman
@jasonfreedman
GP Orange Collective - The YC Unc Fund | YC alum: S09 and W12 | Investor in Starcloud, Corgi, Mastra, Ironclad, Steadily, Browser-use and 100+ more
3.5K Following    12.2K Followers
I just gave my a Grokbot four years of past tax returns and financial files. Just a dump of folders and unlabled files. K-1s, 1099s, mortgage statements, HSA records, and every email with our CPA. 266 files. I just said, please double check my CPA's work. A few minutes later, it had found a lot of mistakes. Mortgage interest left off our 2022 return entirely. HSA payroll contributions counted twice, four years in a row, which created a penalty tax that never should have existed. A missing IRA form for Jen that would have cost us. On this year's return: home office errors, two K-1s missing, an outdated 1099, and startup losses we never claimed. And a retirement contribution the return already deducted...that we hadn't actually deposited. I sent it all to our CPA. They sent back an amended return. The bot reviewed that too. One fix went the wrong direction. The explanation had typos. Three versions later, all in one afternoon, it said ready to sign. Just a few hours start to finish. With about 90 seconds of my time and attention required. I was just the meat proxy hitting send as Grokbot watched the replies in my email. Our CPA is great and turned every fix around the same day. We chatted afterwards. He wanted to know what I was using - just normal ole' grokbot. I asked him what he was using? No AI tools. I set him up with @magnetictax for next season (we're an investor). All CPAs should be using Magnetic Tax or something like it. Every single one. All individuals should be double checking the work and past work with Grokbot or something like that. Want to copy the exact the prompt I used? it was just this: "Please do a thorough review of my taxes and help me understand if my CPA made any mistakes" "Think deeply" Or just tag your bot into this thread.
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Hey @united me and all the other Delta Diamonds are ready to switch. Do you have a one time status match to offer? Easiest market share move in history. Let us know.
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I’ve been investing in YC demo day companies for 16 years now as an angel, an LP and a VC. And I’ve been fortunate enough to have been invested during what many considered to be golden era for returns. We’ve invested $4 million so far into YC‘s summer 26 batch. These YC startups are stunningly underpriced. (Relative to future value) Keep this post. Happy to return back in the future with the receipts. I feel so lucky to be able to invest into the current golden era.
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Most people don't understand how uniquely powerful YC software is and why it matters so much for founders. It's not a fundraising CRM so that you don't have to buy their own CRM. It's a fundraising CRM that allows each YC founder's experience with a given investor be tracked, anonymized, and shared with other founders so that founders can spend more time with great investors that are likely to invest and less time with less-good investors who are less likely to invest. It's a not a custom built calendar-booking link so that you don't have to buy a calendar-booking app. It's a calendar booking app that imports YC data to help the founders understand the sort order they should meet with investors, based on their likelihood to invest based on many different factors. For instance, some investors are an 8/10 for value-add but write checks without social signal. Other investors are a 10/10 but never enter a round early. Sequence them accordingly. These innovations are not just technology. They are thoughtfully solving problems YC cares a ton about...AND they are examples of how YC startups should build features for their own customers.
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I am very supportive of everyone doing these types of split price rounds, at all stages. You should absolutely reward the investors that are willing to write the check without waiting to see who else is in the round. Venture is filled with maybe 5% of true independent thinkers, who write the check without hanging around the hoop. We get a dollar waited average of 1.5x step up on all our investments. Just from this dynamic.
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