Our Story
Chapter 1: There Has to Be a Better Way
After years of growing a successful business, including ranking on the Inc 5000 list, and creating a lifestyle they once could only dream of, 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.
Chapter 2: Enough's Enough
Jackie (a licensed CPA) and Adam (a licensed attorney), had finally had enough. They 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, when their (prior) tax preparer wouldn’t do much more than calculate the estimated taxes they needed to pay (which, by the way, he got wrong).
Chapter 3: Proving It
Through Adam’s law firm, the team helped its clients receive over $80 million of benefits from the various pandemic-related programs that were created. Throughout that process, 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.
Pennywise Tax Strategies was formed to help entrepreneuers write a different story, with a commitment to foresightedness and full-sightedness.
Who We Help (And Who We Don't Help)
You're a good fit for us if:
- You believe that your business should work for you, instead of the other way around.
- Your bookkeeping is solid, your tax returns are filed on time, but you’re frustrated by the amount you’re paying.
- You are decisive. When an expert gives you advice, you can weigh the pros and cons, make a decision, and move onto the next thing.
- You’re sick of your accountant not bringing any good ideas to save you on your taxes, and/or they tend to shoot down any ideas you bring to them.
- You like being told the truth, regardless of how difficult it is, so you can make better decisions.
- When you are presented with a variety of options, you don’t get FOMO. You make the best decision based on the information you have.
- You may be aware of some strategies that are out there (thanks, TikTok), but don’t know how to implement them, or whether they will even work for your business.
- Maybe you think that taxation is theft, or that we should defund the IRS.
You're not a good fit for us if:
- You’re making less than $100,000 per year, consistently, with no real growth plans.
- You’re several years behind on filing your taxes.
- Your bookkeeping is bad enough that you can’t get within 10% of knowing your business revenue.
- You bury your head in the sand and avoid problems instead of facing them head on.
- You think that because you have heard of a strategy, you can probably figure it out on your own instead of working with an expert who can move faster, and know what landmines may await you.
- You are a help-rejecting complainer.
- You want to commit tax fraud, tax evasion, or just in general be sleazy about things.
