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Smart Strategies for Preparing for Tax Season Without the Stress

1d ago 19:25

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Tax stress doesn’t start in April—it starts when we ignore the basics. We sit down with Rose, best-selling author of Add a Zero, to turn anxiety into a simple, repeatable system that keeps your books clean and your tax bill smaller. From hiring an affordable bookkeeper to building monthly routines, we walk through the exact steps that make compliance easy and strategy possible.
We dig into the power of clean data: connecting your accounts to QuickBooks, letting a pro categorize your transactions, and answering a short monthly list of questions so your P&L stays accurate. Then we layer in automation using project tools like Asana—recurring tasks for contractor 1099s, retirement contributions before the cutoff, and a post-filing strategy session with your CPA. The result is less guesswork, fewer surprises, and more time to focus on work that grows the business.
Rose breaks down the tax-savvy retirement options many entrepreneurs skip. Learn how a solo 401k can combine employee and profit-sharing contributions toward a high annual limit, why a SEP IRA might fit certain team setups, and how a defined benefit pension plan can unlock six-figure, tax-deductible contributions for high earners. We also cover structure choices, salary versus distributions, and the low-hanging savings a good accountant will spot when you bring organized numbers and smart questions.
If you’re ready to stop scrambling and start saving, this conversation gives you the playbook: simple systems, clear roles for your bookkeeper and CPA, and proven strategies to keep more of what you earn. Subscribe, share with a founder friend, and leave a review with the tax question you want us to tackle next.

Chapters

1. Meet Rose And Her Money Mission (00:00:00)

2. From Debt To Millionaire Mindset (00:00:58)

3. First Move: Hire A Bookkeeper (00:02:15)

4. Setting Up Software And Categories (00:04:29)

5. Monthly Systems That Reduce Stress (00:06:13)

6. Recurring Checklists And Compliance (00:08:10)

7. Solo 401k And SEP Basics (00:10:16)

8. Defined Benefit Plans Explained (00:12:11)

9. Prepping For Your CPA Meeting (00:14:09)

10. Questions To Ask Your Accountant (00:15:35)

11. Biggest Mistakes And Final Takeaways (00:17:10)

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