The Entrepreneur’s Guide to Failing Upward

5 min read

It’s where you land that counts. I’ve failed at several businesses in multiple industries: academia, advertising, real estate, as co-founder of an online ID verification startup, and as an angel investor in ten early-stage startups. If degrees, diplomas, or certificates for failure existed, I’d have a framed Ph.D. for failure hanging on my wall. So how does an expert in entrepreneurial failure end up as a financially unstressed retired b-school prof living on a beach outside Riga, Latvia? The answer: by failing upwards resiliently. Each failure seeded its opposite….and vice versa. Success Hubris, Or Why Nothing Fails Like Success Easy…...

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RigaWriter I\'m a NYer living in Latvia since 2005, after living in Italy from 1989-2005, Spain and Catalonia in 1976, 1980-81 and 1986-87, southern France the summers of 1985 & 1986 and Portugal in the Carnation Revolution summer of 1974. Conversational Russian and Latvian are my 6th and 7th languages. I did channel check research for one hedge fund and a Wall St research firm from 2009-12 and taught Behavioral Investing, Entrepreneurship and History at Riga Business School from 2012-16. Title of my investments course: The History of Human Financial Stupidity--Including Mine. From 1998-2007 I invested in real estate in Latvia and Estonia. Since 2015 I\'ve invested 7 early stage startups, none of which have yet failed, but some of which inevitably will. Best trade: shorting 20m JPY with spot and options trades on FXY in early 2013 Worst trade: long yield-trap MLPs in 2015 My wrestling match with The Great Humiliator: ongoing.