Unlock Hidden Tax Strategies Most Business Owners Never Hear About
Free Tax Savings Toolkit for "Entrepreneurs on Fire" Listeners
You work hard to grow your business — don’t let the IRS take more than its fair share. These free resources are designed to help entrepreneurs like you keep more of your money and make smarter tax moves all year long.
↓ Click the button to get your free resources↓
📦 Here's What You'll Get Instantly When You Opt In:
✅ 151 Tax Strategies, Deductions & Credits
Our giant list of overlooked deductions, income-shifting tactics, and year-end plays, all well organized so you can immediately spot what you’re missing.
✅ 7 Tax Strategies You Must Ask Your Tax Preparer About
Your current accountant might be costing you thousands. Use this checklist to find out how, and at the very least know what you could be missing.
✅ Turn Your Tax Return Into a Treasure Map
Stop guessing about where savings could be and spot money you're legally leaving on the table. We'll show you where 'X' marks the spot.
✅ Know What Questions to Ask
Never feel unsure in a tax meeting again. Show up informed, empowered, and ready to take action.
✅ Stay Ahead of the IRS
Learn how the wealthy and well-advised use the tax code to grow their wealth—without raising red flags.
What Others Are Saying About Pennywise Tax Strategies
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As a small business owner transitioning into the retirement stage of life, tax planning is essential. The initial meetings for the tax plan have been great, and Pennywise has been very responsive given that we started a bit late for the current tax year. I look forward to having the entire next year to take the best advantage of tax strategies in 2025!
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~ Claudine Thiem
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Nice, thoughtful, knowledgeable professionals. Unique blend of legal and accounting tax advice and strategies for people who are looking for new tax savings ideas as well as help with the execution of those ideas. Highly recommended.
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~ John Reh
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Jackie is an exceptional professional whose expertise in tax strategies surpasses that of any accountant I have previously worked with. Collaborating with her has been a true pleasure, and I highly recommend Pennywise for anyone seeking top-tier financial guidance.
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~ Daniel Merck
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Jackie and the team at Pennywise are rock stars! They have been helping me with tax strategy in my local business, Keystone Detail, for a little over a year now and making a big impact. They will also be doing my taxes soon which I am looking forward to.
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~ Cody Brace
Meet Jackie and Adam Williams
Pennywise Tax Strategies was formed to help entrepreneurs write a different story, with a commitment to foresightedness and full-sightedness.
After years of growing a successful business, including ranking on the Inc 5000 list, Jackie and Adam Williams grew tired of the annual meeting with the tax preparer where a surprisingly large tax bill was met with a “Congratulations” from the accountant.
There had to be a better way.
Jackie (a licensed CPA) and Adam (a licensed attorney) began sharpening their skills, digging into the tax code, obtaining further certifications, and using their own business as an “alpha test” for a tax strategy business. In that first year, they reduced their own tax bill by over $250,000.
Through Adam’s law firm, they learned that most small businesses were getting similar treatment by their tax preparers: meeting once during tax season, having their forms completed at the last minute, and essentially making charitable contributions to the IRS.
They offer something different: An approach to meaningfully reducing your taxes.
Too many people think that there is a "right" answer when it comes to their taxes. Others have heard of some strategies, but don't think they apply to their business. Others believe that tax planning is only for the wealthy.
We are here to set the record straight: if you are a business owner who believes you pay too much in taxes, you have options available.
The resources you can get on this page will help you keep more of your hard-earned money. This is possible for you.