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September 16, 2025 27 mins

Watch the YouTube version of this episode HERE


Are you a law firm owner looking for advice on filing taxes? In this episode of the Maximum Lawyer Podcast, Jacqueline and Adam Williams, co-founders of Pennywise Tax Strategies, share their journey from traditional tax roles to building a firm focused on proactive, year-round tax planning for small businesses and law firms. 


Proactive tax planning for small businesses is so important and needs to be prioritized. Many small business owners react to their numbers and don't think ahead when it comes to taxes. Because of this, businesses are in a bad situation due to not knowing how to make the most of their money, where the money is going or how to proactively plan ahead. Jacqueline and Adam work to ensure small businesses are not left behind and succeed during this stressful time.


Jacqueline and Adam speak to the errors small businesses make during tax season. One of the biggest issues is a lack of communication between the tax preparer and the business owner. Most times, business owners hand accountants everything and call it a day. Sometimes, the business owner doesn't want to fill out the questionnaire, which means the dots are not connected. Big things can be missed, which can lead to issues after filing. Transparency between both parties is extremely important.

Listen in to learn more!


  • 03:21 Gap in Small Business Tax Planning 
  • 05:19 Trusted Advisor Model vs. Traditional Accounting 
  • 06:08 Proactive Tax Planning in Practice
  • 07:34 Monthly Client Check-ins and Accountability
  • 08:16 Common Mistakes by Law Firm Owners 
  • 09:36 Avoiding Numbers and Year-Round Tax Season 
  • 11:27 Regular Tax Planning Activities
  • 12:23 Understanding and Tracking Tax Liability 


Tune in to today’s episode and checkout the full show notes here


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