Tim DraperFounder and Managing Partne, Draper Associate · I back the ideas that look crazy first

Wealthy People NEVER Sell Their Assets — Here's What They Do Instead

11 Aug 2026 · 1 min

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In a brief dialogue, the speakers explain a wealth‑preservation strategy used by affluent investors. Rather than selling appreciated assets, they borrow against them, allowing them to retain ownership while avoiding capital‑gains taxes. The example given is a $100 million real‑estate project funded with $30 million of equity; after seven years the equity is returned, the asset remains, and no tax is paid on the return. The speakers then combine this low‑risk, cash‑flowing real‑estate exposure with a high‑growth Bitcoin position that historically yields 30‑40 % CAGR. Every seven years the real‑estate cash flow can fund the Bitcoin investment, providing both steady income, tax write‑offs, and the upside of a volatile asset. The overall message is that wealthy individuals preserve and grow wealth by retaining assets, leveraging debt, and pairing stable and high‑growth investments.

Let's say I had a $100 million project. I had $30 million in. 7 years, I get my $30 million back, but I still keep the asset. This is how the wealthy— this is how it works. Wealthy people do not sell their assets.
No, they never sell. They borrow against them.
They borrow against them. So I still have my asset. I have my $30 million and I pay no taxes on my $30 million. Okay. Now put the two together. Now I have real estate banging, slow, stable. And I have Bitcoin doing its freaking thing, but a CAGR of 30 to 40% a year. Every 7 years, I don't end up with a real estate project. I end up with a real estate project that paid for a Bitcoin project, and I got cash flow, and I got write-offs. I get the best of 2 animals, 2 beasts, 2 like super Marvel action heroes joined together.