744. 6 Smart Tax Moves Entrepreneurs Should Make Early in the Year

Feb 4, 2026

Timing matters: get tax moves done early in the year to avoid last-minute scrambling. Front-load retirement accounts and fully fund an HSA to extend compounding. Pay your children legitimately and build their Roth IRAs. Accelerate and time business expenses for strategic benefit. Revisit entity structure and depreciation choices with a calm, proactive plan.

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INSIGHT

Early-Year Timing Creates Leverage

Early-year tax moves create compounding benefits and more financial options than late-year scrambling.
Timing matters because acting sooner lets money work longer inside tax-advantaged accounts.

ADVICE

Front-Load Your 401(k) Contributions

Max out your 401(k) early in the year to reduce taxable income and capture more compound growth.
Automate contributions and stress-test cash flow so funding doesn't create financial pressure.

ADVICE

Max Out And Invest Your HSA Early

Fully fund your HSA early because it offers deductible contributions, tax-free growth, and tax-free qualified withdrawals.
Invest the HSA balance instead of leaving it in cash to let it grow over decades if you're healthy.

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Most entrepreneurs think tax strategy is a Q4 conversation. That's a mistake.

In this episode, Brian breaks down the smart tax moves that are best executed early in the year, when timing actually works in your favor. From front-loading your 401(k) and fully funding an HSA, to paying your kids, accelerating business expenses, revisiting entity structure, and maximizing depreciation - this isn't about loopholes. It's about fundamentals.

These strategies create leverage, extend compounding, and give you options instead of scrambling late in the year. Tax planning works best when it's calm, intentional, and proactive; not rushed and reactive.

If you want to keep more of what you earn and put your money to work longer, this episode is your early-year checklist.

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Brian Gubernick is a visionary leader with over 20 years of diverse business and life experience. Currently the Chief Real Estate Officer for PLACE Inc and Co-Founder of Metrix Masterminds, Brian has held numerous other significant roles in the real estate industry including property investor, Realtor, sales team owner, brokerage operating partner, title/escrow company investor, property management partner, and start-up executive. Brian has also trained and/or personally coached thousands of sales professionals on the tenants of business success, leadership, and personal development.

Brian's passion for excellence is matched only by his love for family. He resides in Scottsdale, Arizona, with his wife and two daughters. When he's not creating exceptional real estate experiences or nurturing his entrepreneurial ventures, Brian can be found enjoying quality time with his loved ones.

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