Episode 98: Master Tech Equity Divestiture: Insider Tax Strategies to Save Thousands with Greg O'Brien and John Malone

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Host: Christopher Nelson

Guests: Greg O'Brien & John Malone, Anomaly CPA

In this episode of Managing Tech Millions, Christopher Nelson is joined by certified tax planners Greg O'Brien and John Malone to break down essential tax strategies for managing tech equity. If you're a technology professional with stock options, RSUs, or other forms of equity compensation, this episode is packed with actionable insights to help you minimize taxes and maximize your wealth.

Discover how proactive tax planning can save you hundreds of thousands of dollars, why waiting until tax season is too late, and how to partner with the right professionals to optimize your financial future.

Highlights:

• Why Most People Overpay Taxes on Tech Equity: Common mistakes and how to avoid them.
• Proactive vs. Reactive Tax Planning: The key difference between tax strategists and traditional CPAs.
• Top 4 Fundamental Tax Strategies:
• Gradual Selling & Tax-Efficient Share Selection – Avoiding lump-sum tax shocks.
• Donating Appreciated Stock Instead of Cash – How to get a double tax benefit.
• Offsetting Gains with Tax Loss Harvesting – Leveraging losses to minimize tax exposure.
• Using Venture Capital & Capital Losses – Turning failed investments into tax-saving opportunities.
• Advanced Strategies for High-Net-Worth Individuals:
• Opportunity Zone Investing – Deferring and eliminating capital gains tax.
• Oil & Gas Investments – Leveraging tax incentives for high-income earners.
• Real Estate Tax Benefits – How short-term rentals and real estate professional status can offset income.
• Christopher’s Personal Journey: Lessons learned from tech IPO wealth and navigating tax pitfalls.

Episode Timeline:

• [00:00:30] The biggest tax mistakes tech employees make
• [00:05:45] Why CPAs aren’t enough – the value of a tax strategist
• [00:12:20] How tax planning can save millions over time
• [00:17:30] The power of gradual selling & tax-efficient share selection
• [00:26:15] Donating appreciated stock: A game-changer for charitable giving
• [00:32:40] Capital losses: How to turn failed investments into tax wins
• [00:40:20] Opportunity zone investing: What you need to know
• [00:47:15] Oil & gas tax incentives – a hidden gem for high earners
• [00:52:30] Real estate & depreciation strategies for tax savings
• [00:58:00] The long-term game: Why tax planning is a multi-year strategy