Attorneys: Slow your horses! Don’t just download Claude!
I recently read Zack Shapiro’s incredible breakdown of the “Claude-Native Law Firm.” If you haven’t read it yet, go do that now! It is a masterclass in how legal professionals should be thinking about AI—using “Skills” to encode legal judgment and “Cowork” to turn the AI into a substantive partner. But while Zack gives us […]
I Chose AI Over Tradition
Nine months ago, I left the Department of Justice Tax Division. On the day I said goodbye, I didn’t have a job offer, or even a business plan. Despite that, I didn’t send out resumes or apply to any law firms. I didn’t consider other government positions. But I did receive one unsolicited job offer: […]
Year-End Tax Planning: Qualified Charitable Distributions (QCDs) from Your IRA
For clients with significant income and retirement savings, charitable giving can do more than advance the causes you care about — it can also be a valuable tax strategy. One powerful tool for this purpose is a Qualified Charitable Distribution (QCD) from an IRA. What is a QCD? A Qualified Charitable Distribution is a direct […]
Does the Failure to Use AI Constitute Legal Malpractice?
There’s a new standard of competent and diligent practice – and it requires using AI. AI is quickly defining a new standard for the competent and diligent practice of law. With the technology available to us today, the question is no longer whether a lawyer can or should use AI. Instead, it is whether the […]
The Future of Tax Enforcement
RIP, Tax Division. The new 2026 fiscal year is upon us – but the impact of the FY2026 budget on tax enforcement is still unknown. The FY26 budget introduces two seismic changes: the complete elimination of DOJ’s Tax Division and significant cutbacks in IRS enforcement funding. These changes signal a potential weakening of the federal […]
Qualified Small Business Stock (QSBS): A Powerful Tax Advantage for Founders and Early Investors
For founders and early investors, few tax incentives are as valuable as the Qualified Small Business Stock (QSBS) exclusion under Section 1202 of the Internal Revenue Code. If properly structured and documented, the QSBS rules can allow you to exclude up to 100% of the capital gains on the sale of qualifying stock. With the […]
Beyond the Balance Sheet: Building a Lasting Legacy
What truly sets Oakgrove apart is our dedication to your family as a whole. We understand that for families with an abundance mindset, wealth is a powerful tool for good. We specialize in structuring and advising on: At Oak Grove, we empower your family to not only navigate the complexities of wealth but to define […]
Trusted Tax Counsel for Generational Wealth
Welcome to Oakgrove Legal Strategies, where sophisticated legal expertise meets a profound commitment to your family’s enduring legacy. As a highly experienced tax attorney with 15 years in the field, I founded this firm specifically for families, founders, and fiduciaries who embrace an abundance mindset. You understand that true wealth extends beyond financial assets, encompassing […]
