Buying A Business Back Again | My First Million Podcast

TL;DR

A founder sold Webshots for $80 million, bought it back for pennies, resold for $20–30 million, then bought it back again. This inspired the idea of an “undertaker” service that winds down dying tech companies for a fee, handling fire sales of talent, hardware, and assets, plus official closure to avoid tax issues and maximize investor value.

Key insights

• The same company (Webshots) was sold, bought back cheaply, resold at a smaller multiple, then repurchased a second time.
• An “undertaker” service could specialize in winding down tech companies, handling both physical assets (hardware) and human assets (talent) via fire sale, plus all administrative closure tasks.
• Investors want the shutdown process done cleanly to maximize residual value and avoid future tax liabilities.