How to retire with millions (and pay $0 taxes)

TL;DR

Anker (Teachable founder) shares tax optimization strategies—direct indexing and mega backdoor Roth IRA—to achieve tax-free retirement. He contrasts his own experience: Goldman Sachs returned ~6% vs S&P 13% due to high fees and poor asset allocation. The key insight is that tax savings, not investment selection, provide alpha for high earners.

Key insights

• Private banking (Goldman Sachs) underperforms simple S&P indexing after fees; Goldman averaged a 6% return while the S&P returned 13% over the same period. They charged 50–120 basis points and added b
• Direct indexing (e.g., via Freck) buys each S&P 500 stock individually. This allows tax-loss harvesting: Anker added $16,000 in usable tax losses on a $250,000 investment without changing the underlyi
• A mega backdoor Roth IRA lets you contribute up to $70,000/year into a Roth IRA via a 401(k). Combined with a backdoor Roth ($77,000/year total), modeled S&P indexing from age 21 yields ~$30 million t