Taxes in The Self-Employed Man

Only Taxes: the latest headlines first, then BRO’s own Taxes stories and video. All of Self-Employed Men →

Latest news · Taxes

New York Post9m ago · 3:58 PM ET
California just voted to give two billionaires $4 billion in taxpayer money so they can do obscure research
Washington Examiner16m ago · 3:51 PM ET
Lisa McClain wins GOP conference chair election
The Gateway Pundit22m ago · 3:45 PM ET
BREAKING: RINO Senator John Thune Reelected as GOP Leader
The Western Journal24m ago · 3:43 PM ET
ICYMI Watch: Crowd of 100,000 NCAA Football Fans Roars When Melania Shows up on Stadium Jumbotron
LifeZette27m ago · 3:40 PM ET
Billy Joel Announces Stunning Stage Return Despite Doctors’ Warning
The New American1h ago · 3:01 PM ET
Trump Agrees With Democratic Officials and Operatives on Vote Fraud
The American Conservative · Opinion1h ago · 3:00 PM ET
October Inflation Hotter Than Expected, Setting Up A Rate Hike
Washington Times1h ago · 2:53 PM ET
California rejects pioneering wealth tax
Conservative Treehouse · Opinion1h ago · 2:47 PM ET
Incoming House Oversight Chairman Robert Garcia Names His Targets from Trump Administration
Breitbart1h ago · 2:46 PM ET
Rep. Lauren Boebert Refuses to Concede as Colorado House Race Remains Uncalled by AP
Rebel News1h ago · 2:41 PM ET
Lawyer preps class action over Veterans Affairs MAID offers as more veterans come forward
The Gateway Pundit1h ago · 2:40 PM ET
BREAKING: Jim Jordan Elected House Minority Leader After Historic Midterm Upset

GuideRay OkonkwoNov 5, 20265 min

One business account and a Friday habit beat any software

Most guys don't need an app to fix their books. They need to stop paying for diesel with the same card they use at the grocery store.

Hire the second guy when the first one can run a job alone

GuideMarcus ValeSep 25, 20266 min

Your first helper is probably an employee, not a 1099 guy

GuideRay OkonkwoSep 24, 20266 min

Quarterly taxes and the one rule that ends the April ambush

Price the breakdown, not the machine

GuideMoneyRay OkonkwoNov 8, 20265 min

The $669 rental that actually loses $173 a month

Taxes on video

Worth an hour of your evening

From channels we rate. Plays on YouTube.

Michael Ruger - Greenbush Financial GroupSep 22

Understanding Self-Employment Tax: A Guide for the Newly Self-Employed

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Self Employed Taxes Explained & Tax Tips

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How to File Self Employed Taxes - First Time Self Employed Tax Return, LLC, Sole Proprietor

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Filing Taxes for Self-Employed 2026 [Beginner Guide 2026]

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Self-Employed Taxes: What Freelancers NEED to Know

Jackson HewittAug 18

Self-employment taxes explained

The FuturDec 26

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How to Price Your Service as An Entrepreneur | Self-Employed or Freelancer

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Sell your handwriting by the envelope, not the design

Addressing wedding envelopes and lettering shop signs can pay well per hour, if you stay out of design work. Here's the math, the costs, and when to skip it.

GuideRetirementRay OkonkwoNov 7, 20266 min

A Roth ladder pays tax early so you can retire early

A Roth conversion ladder can fund a retirement before 59½ without the 10 percent penalty. The catch is the five-year wait nobody puts in the brochure.

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GuideMoneyRay OkonkwoNov 7, 20266 min

The tax bill that ambushes self-employed men every April

Nobody withholds for you when you work for yourself. Here's the arithmetic on quarterly payments, the safe harbor, and a separate account that does the work.

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Side Hustles6 min read

Gutter cleaning pays twice a year if you build a route

One cleaning earns you a Saturday's wage. A route of repeat customers earns you a second income. Here's the math, the risks, and when to pass.

Poll

When did you last ask for a raise?

GuideSkillsWes DunbarNov 7, 20266 min

Fix the fuel first, then adjust the carburetor

Most small engines that won't start or run right don't need a screw turned. They need clean fuel. Here's the order to work in, and how to set the screws when they do.

GuideTradesAde FisherNov 6, 20266 min

Live on Year-One Pay and Finish the Apprenticeship

Apprentice wages start low and climb on a schedule. Housing is what decides whether you're still around when they do.

Dude.com — 16 AI advisers who listen, talk and are here with you

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GuideSelf-Employed WomenNina CastellanNov 6, 20265 min

Hire help when you can write the job on one page

The right moment to bring on your first contractor has little to do with how busy you feel. It has to do with what you can hand over in writing.

Quiz

Is your money actually in order?

Six questions. No email required, no sales pitch at the end.

GuideCorporate MenMarcus ValeNov 5, 20265 min

Hand off the work you're best at first

You keep the work because you're good at it, and that's exactly why it should go first. A way to let go without dropping the ball.

NewsNewsBRO DeskNov 5, 20261 min

California Voters Reject Prop. 40 Billionaire Tax, Approve Bond Measures

Voters turned down several propositions, including a proposed one-time tax on billionaires, while backing a number of bond measures.

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Rewrite my CV so it actually gets read

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GuideCouples in BusinessCal BrennanNov 4, 20266 min

You both sign the return, so you both sit in the meeting

A joint return makes you both liable. Bring these questions to your accountant in October, while there's still time to act.

Shirts.com — Design it with AI. Wear it this week.

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BRO TakeCorporate MenMarcus ValeNov 4, 20265 min

Loud orders get managed around. Quiet ones get followed.

The tyrant and the pushover make the same mistake. Real authority is built from decisions made on time, reasons given plainly, and misses owned first.

Poll

Where does your phone charge overnight?

GuideStartupsRay OkonkwoNov 4, 20265 min

Stop running your business through your checking account

Mixing business and personal money feels harmless all year. Then March shows up, and you pay somebody by the hour to sort it out.

GuideRetirementRay OkonkwoNov 3, 20265 min

The IRS gives you an extra lane at fifty. Use it.

Catch-up contributions let you save more once you turn fifty. Who qualifies, what changed for the early sixties, and how to fund it without wrecking your budget.