When to pay estimated quarterly taxes

Let's be honest: taxes feel like that thing you're supposed to understand but somehow never learned, and now you're too embarrassed to ask.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Hannah Cole—artist-turned-tax-pro and author of the brand-new book Taxes for Humans—to finally explain taxes in language that doesn't require a CPA license to understand. Hannah's built her career translating tax code for freelancers, side hustlers, and small business owners who just want to know what they can deduct, what'll get them audited, and how to stop drowning in shoebox receipts.

She breaks down the real difference between a legitimate business expense and wishful thinking, how to track startup costs without losing your mind, and why the bookkeeping system that works is the one you'll actually use (spoiler: it doesn't have to be fancy). Whether you're launching a side gig, running a creative business, or just trying to keep the IRS from ruining your holiday season, Hannah's got the roadmap.

Then Joe and OG shift gears to tackle the "AI bubble" conversation everyone's having—is this tech hype justified, or are we watching 1999 all over again? They break down how to think about market froth without panicking, why smart investors don't build their strategy around TikTok prophets predicting doom, and how to prepare your portfolio for volatility without making fear-based moves.

Plus: Doug delivers trivia about Richard Pryor's Blazing Saddles days, because even tax talk deserves a palate cleanser.

What You'll Walk Away With:

• Tax basics explained in actual human language (finally)—what counts as a deduction and what's just wishful thinking

• How to set up simple, sustainable bookkeeping systems for side gigs or small businesses that you'll actually maintain

• The smartest way to track startup expenses without drowning in receipts or spreadsheets

• Why the IRS isn't as scary as you think when you've got your basics covered

• How to think about AI market hype without getting swept up in either the euphoria or the panic

• Smart strategies for preparing your portfolio for volatility without making emotion-driven decisions

• Why the right tax and investing systems buy you back time, creativity, and peace of mind

This Episode Is For You If:

• You've been winging it on taxes and know you're probably missing deductions (or making mistakes)

• You run a side hustle but have no idea what you can actually write off

• Tax season makes you anxious because you're never sure if you're doing it right

• You're hearing AI bubble talk everywhere and wondering if you should be worried about your investments

• You want systems that are simple enough to actually follow, not perfect enough to abandon by February

Before You Hit Play, Think About This:

What's the tax mistake you wish you could warn your younger self about? Drop it in the comments—we're all learning here, and sometimes the best lessons come from what we got wrong the first time.

FULL SHOW NOTES: https://www.stackingbenjamins.com/tax-basics-for-side-hustlers-ai-market-tips/

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