AAR44 - Taxes Nobody Warns You About

The Investing for Beginners Podcast - Your Path to Financial Freedom

Andrew Sather

Investing, Business

4.1 • 1.5K Ratings

🗓️ 7 April 2026

⏱️ 43 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this episode of At Any Rate, Evan and Andrew break down the hidden tax traps that can catch even the most responsible investors off guard. From the brutal reality of self-employment taxes on your side hustle to the surprise tax bill hiding in your High-Yield Savings Account, they discuss the rules you need to know to protect your wealth. They also cover the "wash-sale rule," how 401K withdrawals can bump your tax bracket, and the massive benefits of utilizing a Roth IRA. Topics Covered: The Side Hustle Surprise: Being self-employed means paying both sides of the employment tax (around 15.3%) and requires filing quarterly estimated taxes. HYSA Tax Trap: The interest earned in a High-Yield Savings Account is taxed as ordinary income and is not automatically withheld. The Wash-Sale Rule: You cannot sell a stock for a loss to claim a tax deduction and then immediately buy it (or a similar asset) right back within a 61-day window. 401K Withdrawals: Every dollar pulled from a traditional 401K is taxed as ordinary income, which can unexpectedly push you into a higher tax bracket in retirement. The Roth Advantage: Roth IRAs offer incredible flexibility because you can pull out your contributions at any time without taxes or penalties. However, you must track those contributions yourself. Forgiven Debt is Income: If a loan is forgiven, that forgiven amount is often treated as taxable income by the IRS. Timestamps: 01:39 - Welcome and introduction to the "I did everything right" tax trap. 05:12 - Why Evan and Andrew both use professional tax advisors. 07:36 - Side gigs: Self-employment tax and the truth about deductions. 14:44 - The dirty secret of High-Yield Savings Accounts (HYSA). 19:00 - Taxable investing accounts and capital gains. 20:46 - Andrew explains the "wash-sale rule" for tax-loss harvesting. 27:26 - Why 401K withdrawals can push you into a higher tax bracket. 31:13 - Roth IRA rules: Why you must track your own contributions. 35:25 - 529 Plans and the penalties for non-education withdrawals. 37:52 - Quickfire tax traps: Social Security, unemployment, and forgiven debt. Resources Mentioned The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/ Free monthly budgeting spreadsheet: https://einvestingforbeginners.com/budget/ Email Evan: evan@einvestingforbeginners.com Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast! Remember, financial freedom is built one smart move at a time. Keep it simple, keep it steady, and at any rate, we’ll see you next time. Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Today’s show is sponsored by: Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠SHOPIFY.COM/beginners⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to start selling with Shopify today.⁠ ⁠⁠⁠⁠⁠https://www.shopify.com/beginners⁠⁠⁠⁠ Download the⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Plynk app⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ today to start building your investing confidence:⁠ ⁠⁠⁠⁠https://plynkinvest.app.link/IFB⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Upgrade your wardrobe with Quince to get high-quality, luxury essentials at a fraction of the cost by visiting ⁠https://quince.com/beginners⁠ Get your free quote and see how much you could save at⁠ ⁠⁠⁠⁠⁠⁠⁠⁠SelectQuote.com/beginners⁠⁠⁠⁠⁠⁠⁠⁠⁠ Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at ⁠https://whatnot.com/sell⁠ Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at ⁠https://notion.com/investing⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Interested in how your company sponsor the show? Reach us at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠equity@einvestingforbeginners.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠SUBSCRIBE TO THE SHOW ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Amazon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Tunein Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	I was like driving Uber and I was like, okay, the money from this and the money from that and I'm good.
0:05.2	And then I vividly remember sitting outside the Starbucks.
0:08.8	I remember the street I was on. I remember the almost down to the table I was sitting at and just that moment of realization.
0:15.2	Crap, I gotta go get a job.
0:17.7	Now all the traitors present, Let's get started, shall we?
0:21.6	From rags to riches.
0:23.6	I'm so sick of this.
0:24.6	Working like a dog and being treated worse.
0:26.6	Yorkshire to New York.
0:28.6	Or climbers, you and me.
0:29.6	A life dedicated to revenge.
0:31.6	Let's make this an occasion to remember.
0:34.6	A Woman of Substance on Channel 4, stream now.
0:38.0	The pace of change today can be overwhelming. What's most important to pay attention to
0:43.7	if you want to be creative, successful, innovative? I'm Bob Safian, host of Rapid Response.
0:50.5	Rapid Response is a podcast that cuts through the noise, featuring candid conversations twice a week with top business leaders navigating real-time challenges.
1:00.3	From the team behind the award-winning Masters of Scale podcast comes Rapid Response.
1:05.6	Search wherever you get your podcasts to listen and subscribe.
1:27.2	Good morning, everyone, and welcome back to at any rate.
1:32.0	My name is Evan Ray, and we are here to help you make sustainable financial changes without breaking a sweat.
1:39.0	And today I've got back my favorite co-host, Andrew Sather, the bullish investor, the bullishest, if that's a word, investor that I know.
1:40.1	How are you doing this morning, Andrew?
	...

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