Thought Leadership
Rajiv Rebello's writing on tax strategy, exit planning, and the quantitative side of private wealth — published on Substack.
Subscribe on Substack →
Elon Musk borrowed $44B against his Tesla stock to buy Twitter. He got a tax deduction for doing it. And he never had to sell a single Tesla share. You can use the same playbook.
Tax-aware investing combines tax planning and leverage to offset realized capital gains with portfolio deductions — turning a large, immediate tax bill into deferred, and ultimately eliminated, wealth
What happens when the escape from Corporate America turns into the same W2 income, work, and liability problem you were running from?
Most people don’t realize you can borrow against your stock portfolio in a similar way to how you can borrow against your real estate investments—but with better rates and payback provisions
A little planning can save tens to hundreds of millions of dollars.
Private Placement Life Insurance (PPLI) is a "Super Roth" for wealthy individuals that allows them to accumulate wealth free from income and estate taxes.
Like all things financial planning, being proactive in your thinking and planning with regards to your estate tax liabilities can save tens of millions in taxes
In 1999 Peter Thiel made a brilliant tactical decision with $2,000 that would end up saving him over $2 billion in income taxes
For those in high tax-brackets, the tax-savings alone more than makes up for the cost of the IUL wrapper
Giving up short-term return to reduce volatility and taxation ends up being a long-term win for clients in high tax brackets who know what they are doing
How my client saved $400k+ by diversifying their concentrated portfolio without taxation
How the Wealthy Use the Tax Code to Maximize After-Tax Growth
Schedule a no-obligation consultation to review your tax and financial picture.
Schedule a Consultation