Weekender #181

📈 A new study shows more women are opening their own businesses than ever before.

💪 Should you sync your workouts to your menstrual cycle?

🖼️ Create visual impact at home with this guide on how to make a gallery wall.

✍️ Why writing letters to your future self might help you stay grounded in the present.

You’re taxed when you make money. You’re taxed when you spend money. You’re even taxed on things you’ve already paid taxes on.

So why are you handing over more money to the IRS than you need to?

Wealthy people and business owners don’t play by the same rules as W-2 employees—and it’s 100% legal. They use strategies baked into the tax code to reduce how much they owe (and sometimes walk away with big-time savings).

If you’re a founder, freelancer, or just someone tired of giving the government a fat cut of your earnings, it’s time to level up your tax game.

Here are 7 wildly underrated tax strategies most entrepreneurs completely miss—but the wealthy quietly swear by:

1. The Augusta Rule – Rent Your Own Home to Your Biz (Tax-Free)

This one sounds fake… but it’s IRS-approved.

If you own your home, you can rent it out to your own business for up to 14 days per year—and not pay a single cent in taxes on that income. It’s called the Augusta Rule (named after Augusta, GA, where residents used it to rent their homes during the Masters golf tournament).

Let’s say the market rate for renting your house is $1,500/day. That’s $21,000 per year of tax-free income. Your business gets a write-off. You get the cash. The IRS? Gets nothing.

👏 Chef’s kiss of a loophole.

2. Home Office Deduction—If You Zoom There, You Can Deduct It

Working from home? You could be sitting on literal deductions.

If you have a dedicated space in your home used exclusively for business (that means your dining table doesn’t count), you can deduct a portion of your:

• Rent or mortgage
• Utilities
• Internet
• Property taxes
• Home repairs + maintenance

This deduction isn’t just for full-time entrepreneurs either—if you freelance, consult, or side hustle, it might still apply.

Pro tip: Use the simplified method (up to $1,500) or calculate based on square footage for bigger savings.

3. Max Out Retirement Contributions—Let Your Money Grow (Without the Tax Man Watching)

Retirement accounts aren’t just for saving later. They’re a now-move to cut your tax bill today.

✅ Solo 401(k): Contribute up to $69,000 (as of 2024) if you’re self-employed. Tax-deferred, which means you don’t pay taxes on the money until you retire.
✅ SEP IRA: Easier to set up than a Solo 401(k), and great for freelancers or solopreneurs. Contributions are tax-deductible.
✅ HSA (Health Savings Account): Triple tax advantage: contributions are tax-deductible, growth is tax-free, and withdrawals for qualified medical expenses? Also tax-free.

Moral of the story: stash cash, cut taxes, and grow your future wealth.

4. Vehicle Deductions—Write Off That Boss Ride

Yes, your car could be a business expense—if you use it for biz purposes.

There are two big ways to take advantage:

• Standard mileage deduction: 67 cents per mile (2024 rate). Those client meetings, supply runs, and work trips? They add up.
• Bonus depreciation: Buy a car over 6,000 lbs (think Range Rover, Tesla Model X, or even a Ford F-150), and you may be able to write off the entire purchase price in year one.

Let that sink in: a $100K SUV could become a $100K deduction. The key? Use it primarily for business.

5. Invest in Real Estate—Make the IRS Work for You

Real estate = the tax strategist’s dream.

• Depreciation lets you reduce taxable rental income—even if you’re turning a profit.
• 1031 Exchanges allow you to sell a property and roll those profits into a new one without paying capital gains taxes.

Plus, real estate income is passive, and when structured right, can keep your effective tax rate shockingly low.

Real estate doesn’t just build wealth—it shields it.

6. Tax Bracket Planning—Split the Pie Strategically

If you’re in a high tax bracket (say, 35%+), consider shifting income to family members in lower brackets.

This could mean hiring your college-aged kid to help with marketing, admin, or customer support. They get work experience and a paycheck, and you get a deduction.

Even gifting appreciated assets (like shares in your company) to family in lower brackets can reduce your overall tax bill.

It’s not dodging. It’s delegating.

7. Down Years = Smart Tax Moves

Had a slow year? Before you wallow, know this: low-income years are a tax opportunity.

This is the perfect time to:

• Recognize deferred income (you’ll pay less tax on it now)
• Convert a traditional IRA to a Roth IRA (while in a lower bracket)
• Realize capital gains at a lower rate

Smart entrepreneurs plan for the long game—and that means knowing when to lean into the dips.

Just make sure you’re working with a CPA who gets business owners and freelancers and is fluent in strategy—not just spreadsheets.

To learn more about maximizing these tax-saving strategies, read more here.

YYou don’t need another motivational quote about time. You need to stop managing tasks like it’s 2013.

If your day feels like a swirl of Post-its, rogue Slack threads, and “just circling back” emails, it’s not because you’re unproductive. It’s because you’re under-supported.

Task management isn’t about crossing things off a list—it’s about clearing mental space, reducing decision fatigue, and making your team (and yourself) way less stressed.

Here’s how to do it better:

✅ 1. Visualize Everything

Overwhelm thrives in ambiguity. Use Wrike to break projects into timelines, dependencies, and dashboards you can actually read. It’s like giving your brain a visual roadmap.

🧠 2. Centralize or Suffer

If you’re toggling between 6 apps to finish one task, it’s a no. Zoho Projects keeps convos, docs, tasks, and time tracking in one place. Clean. Clear. No more tab scavenger hunts.

🧘‍♀️ 3. Respect Your Bandwidth

Overcommitment is a system failure, not a character flaw. Resource Guru lets you see team availability in real time—so you stop double-booking and start planning like a pro.

📈 4. Automate the Follow-Up

Reminders shouldn’t be your full-time job. Smartsheet sets recurring tasks, approvals, and updates so you can stop micromanaging and start focusing.

The truth? Task management done right makes you look effortlessly on top of it. And that’s what we like to call main character energy ✨.

📚 Read: Hello Beautiful by Ann Napolitano

If Little Women had a modern-day makeover—with messier emotions and more therapy—Hello Beautiful would be it. A sweeping, sisterhood-heavy saga that’ll wreck you in the best way. BYO tissues.

📺 Watch: Reacher

Season 3 is here and it’s still serving big biceps, bigger brains, and even bigger beatdowns. Reacher doesn’t just walk into trouble, he solves it with fists, facts, and no time for BS.

🎧 Listen: The Giver by Chappell Roan

Country twang, queer joy, and a chorus that knows what it’s doing. Chappell Roan’s The Giver flips the cowboy fantasy on its head in this flirty, fiddle-laced anthem about giving women what country boys…often don’t. A little subversive, a lot seductive.

If you’ve ever stared at your screen trying to remember if a client paid you, or cried inside at tax time (no judgment), your accounting system is failing you.

And no, the answer isn’t another spreadsheet. It’s about using the right tool for the way you work.

✨ If You’re Freelance, Creative, or Wearing 12 Hats:

FreshBooks is your finance fairy godmother.

It’s built for people who didn’t major in accounting but still want to get paid, stay legit, and look pro doing it.

• Send polished invoices in under a minute
• Track time + expenses automatically (no more mental math)
• Auto-remind clients to pay you (so you don’t have to)

Use FreshBooks if you want to look like you have a CFO—without needing one.

💼 If You’re Running a Real Operation (Team, Payroll, Growth Mode):

Xero is your power tool.

It’s robust without being overwhelming, and perfect for business owners who need real insight—not just a “finance folder.”

• Connect your bank, Stripe, Gusto—you name it
• Run payroll, track inventory, and get real-time reporting
• Invite your accountant in (without giving up control)

Use Xero if you’re building a business that’s built to last.

Bottom line: You’re not failing at finances. Your system just hasn’t caught up to you.

Fix that—and start feeling the peace of knowing your money’s handled.

Meet Stormi! This pint-sized Pomsky packs a punch of personality into her 11 pounds. Get ready for an energetic and loving companion who’s as smart as she is determined. Don’t let her size fool you—this little firecracker can hold her own, even against her much larger “sister”! Be prepared for adorable “conversations” and toys that may not last long. Despite her playful destruction, Stormi is absolutely irreplaceable.

🐾 Got a cute fur baby? Submit them to be our pet of the week in an upcoming issue.

• Orora Packaging Solutions is hiring for an Account Executive (Hybrid).
• Great Gums is hiring for a Vice President Marketing/Brand (Sonoma, CA).
• That’s it. is hiring for a Social Media Manager (Los Angeles, CA).
• Future Electronics is hiring for a Strategic Account Manager (Detroit, MI).
• CONMED Corporation is hiring for a Human Resources Coordinator (Largo, FL).

⭐ View more jobs here >

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