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

Calling him a contractor doesn't make him one. How to hire your first set of hands without handing the IRS and your insurer a reason to come knocking.

GuideStartupsRay Okonkwo23 Sept 20265 min

Pick the day you don't answer the phone

You'll lose a few jobs closing one day a week. You'll keep your head, your marriage and a business you can still stand in five years.

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GuideMoneyRay Okonkwo23 Sept 20266 min

The side income tax bill nobody sets money aside for

You cleared $11,000 detailing cars on Saturdays. Roughly a third of it was never yours. Do the arithmetic now, not in April.

Delicious.com — Nine thousand recipes and a plan for tonight

PartnerDelicious.com

Self-Employed Men6 min read

Before you pay for leads, call the people who already paid you

When the phone goes quiet, the cheapest work you'll find is sitting in your old invoices. Most guys skip straight to buying leads instead.

Poll

How many days a week are you actually training?

GuideStartupsRay Okonkwo23 Sept 20265 min

The food truck costs that aren't on anybody's spreadsheet

The truck is the cheap part. It's the commissary, the generator hours and the days you don't sell that decide whether you're still open in year two.

GuideMoneyRay Okonkwo23 Sept 20265 min

When to do your own taxes and when to pay somebody

The test isn't how smart you are. It's whether your return contains judgment calls, and how many Saturdays you're willing to burn finding out.

Names.com — The name is the first thing you sell

PartnerNames.com

GuideSelf-Employed MenRay Okonkwo24 Sept 20266 min

Quarterly taxes and the one rule that ends the April ambush

Four payments, one safe harbor rule and a second bank account. That's the whole system, and it keeps April from eating your truck payment.

Quiz

Does your wardrobe actually fit you?

Five questions, honestly answered, and a plan for the next fortnight.

GuideStartupsRay Okonkwo23 Sept 20265 min

Buy the tool before you hire the person

A second set of hands costs a lot more than the paycheck. Run the payback math on the machine first, and be honest about what it can't do.

GuideSide HustlesWes Dunbar23 Sept 20266 min

Sharpening Blades for the Neighborhood Without Ruining Anybody's Knives

Mower blades, kitchen knives and chainsaw chains pay real money on a Saturday, but only if you batch the work and know what to turn away.

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Rehearse the raise conversation with me

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GuideSelf-Employed MenRay Okonkwo24 Sept 20266 min

Why $45 an hour is a pay cut when it's your own truck

The rate that feels rich the day you go out on your own can leave you broke by April. Do this math before you quote another job.

CancerDefying.com — The research, protocols and reading in one place

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GuideStartupsRay Okonkwo23 Sept 20265 min

A five-page website is all a local business needs

Your site has one job: make the phone ring. Most of what agencies sell you actively gets in the way of that.

Poll

What was your first ever job?

GuideSide HustlesNina Castellan23 Sept 20266 min

What Sells at the Farmers Market and What Just Sits There

Cottage food law, a 30-inch home oven, and the honest math on an 18-hour week spent behind a folding table.

GuideTradesRay Okonkwo23 Sept 20266 min

Licensing, Insurance and Your First Ten Customers

You can be running your own trade business a year from now. The order you do things in decides whether you make money or just make noise.

Coconut.com — Tell us when. We find where the sun is.

PartnerCoconut.com

GuideStartupsRay Okonkwo23 Sept 20266 min

Your Farmers Market Stand Isn't a Hobby, It's a Business

The Saturday math that decides whether the market pays you or quietly bills you, and why half the stands are gone by September.

Quiz

Is your money actually in order?

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

Side Hustles6 min

Don't Lose Your Day Job Building Your Side Hustle

Trades6 min

Price the Job So You Actually Keep the Money

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Rehearse the raise conversation with me

Ask it

GuideStartupsRay Okonkwo23 Sept 20266 min

One Hour on Friday Is All Your Books Need

Do your bookkeeping in a fixed weekly hour and you'll always know three numbers that decide whether your business lives.

Ivermectin.com — Tracked USPS delivery, no clinic visit

PartnerIvermectin.com

Side Hustles6 min read

What Moving Help and Junk Hauling Really Pay on a Saturday

Your truck can make money on weekends, but the dump scale and your insurance agent get a vote before you do.

Poll

How often do you see your closest friends?

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