Silly Money
Your Tax Return Isn't Going to File Itself
There's a specific kind of dread that only April 15th can produce.
You open up your computer, Google "how to file taxes before deadline," get served three ads, two of which have the word "FREE" in large letters, and click through a bunch of forms that ask for your SSN and AGI before they’ve even introduced themselves.
You end up on one of the big software options that seem trustworthy, but forty-five minutes in, something doesn't look right. Your estimated tax payment seems erroneously high. Your mind starts to stir.
Didn’t that get taken out of my income every month?
You open another tab to figure out what a 1099-DIV is. You go back to the form and find out that your session expired and you’ve lost all your progress. Time to start again…
But you can’t quite remember if you clicked the right box on that screen three minutes ago. And you're almost certain you entered the cost basis wrong on those RSU shares you sold.
And then somewhere in the back of your head you ask yourself:
Am I missing something?
The answer, more often than not, is yes.
(And not through any failure of your intelligence by the way.)
The tax code is genuinely complicated, and the standard deductions and credits many people qualify for are not obvious.
That’s why I started writing this newsletter, to give high earners a better sense of how to optimize their tax bill and grow their net worth.
Because that checkbox you skimmed past on page 12 of your return could have been worth $800.
And the cost basis error on your RSU sale might mean you overpaid by a few thousand dollars.
But nobody's going to flag it for you at this point.
If you haven't filed your personal return yet, here's what I'd actually do.
A few weeks ago, we profiled a handful of services for different tax situations and more readers reached out about one solution than anything else: Prime Meridian.
The response was so strong that we partnered with them for this tax season PSA because we think the offer is truly unbeatable.
Prime Meridian files your federal and state taxes for free.
Not free-with-an-asterisk, not free-for-simple-returns-then-pay-for-complexity.
Federal filing: $0. State filing: $0.
Okay, but why is it actually free?
This is the right question to ask, and it's the most common objection we heard after profiling them two months ago.
Free in taxes usually means you're getting upsold midway through. Free in tech usually means your data is getting sold.
Neither is true here. They don't sell your data and there's no paid tier waiting for you at the end of the flow.
And it’s that way by design because their mission is straightforward: tax prep should be free for everyone, the same way stock trading became free.
Can it actually handle my situation?
Here are a few examples of cases they've handled this season:
Exited founders with $1.3M+ AGI and 10+ K-1s across multiple states
Big tech employees with RSUs, crypto, and multiple rental properties
Bank MDs with complicated investment portfolios
Consulting firm partners with side consulting income and fund K-1s
LPs across multiple VC and private equity vehicles
And the reason they can handle all the complexity comes down to the team.
The team is former xAI, Google ML research, and General Catalyst. They are operators and engineers who have been at the frontier of AI and built and backed companies from zero. They even maxed out Tax Calc Bench, the primary academic benchmark for AI tax accuracy.
Most of the world's best AI engineers are working on AGI, biology foundation models, or the next big RL play. Almost none of them are doing this, which is precisely what makes this moment interesting.
If your situation looks like any of those examples above, you're in Prime Meridian’s wheelhouse. But honestly, the best thing you can do is pressure-test it yourself and see if they hold up.
Okay, but be real, who isn’t this for?
If you need your refund deposited in your bank account in the next two weeks, Prime Meridian isn't your best option right now.
You'll get a complete, accurate tax estimate before April 15 so you know exactly what you owe, but the full 1040 goes to the IRS by July 1.
That lag exists because they're being careful about accuracy, not cutting corners.
But if a fast refund is your primary need, it’s worth knowing upfront that this isn’t your best option right now.
What does the process actually look like?
Upload your documents: your prior return, W-2s, 1099s, K-1s, whatever applies to your situation.
Prime Meridian’s tax AI assistant walks you through follow-up questions, drafts your return with plain-English explanations of what it found, and you review before anything gets submitted.
The whole thing takes about 15 minutes.
So, if you've spent three hours fighting with TurboTax this week, it’s probably worth a few minutes right now.
See you next week,
— Ankur
P.S. Prime Meridian will stop taking new users for the personal tax filing deadline tomorrow evening, so today and tomorrow are your window!
Full disclosure: I'm an investor in Prime Meridian, and Silly Money has a partner relationship with them. I recommend them because I think they’re genuinely the best option at this price point, and arguably better than many CPA’s charging $3k-$5k for tax filing. Nothing here is tax, legal, or investment advice.
