30 Oct Built to Sell: Why Exited Founders Lose Money Investing – with Justin Donald, The Lifestyle Investor
Justin Donald has seen it happen to exited founders again and again. Justin built a mobile home park portfolio that covered his cost of living by 34, wrote the Wall Street Journal bestseller The Lifestyle Investor, and now studies how single family offices allocate serious money. He joins John Warrillow for the latest After the Deal episode of Built to Sell Radio, the series about making the most of life after a sale while avoiding the biggest mistakes founders make once the money lands.
John asks Justin what he’d tell a founder who has reinvested everything for twenty years and is about to get a $10 million check, and you discover how to:
– Catch the one habit that builds a business but wrecks an investor (Justin calls it starting from yes)
– Avoid the mistake that cost him $1 million in a deal his own lawyer told him to walk away from
– Write your investment criteria before the money lands, so decisions are easy when the pressure arrives
– Allocate like a billionaire’s family office, which typically holds only 15 to 30 percent in public stocks
– Understand why the wealthy make their money through concentration but keep it through diversification
– Compare a 20 percent return on a deal you run yourself against a 17 percent return where you’re not on the hook
– Recognize the single word in an investment pitch that should end the conversation
