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When it comes to the extremes of the startup spectrum, three-time founder, investor and New York tech ecosystem advisor Jeff Wald has seen it all.

“I’ve counted Fred Wilson as an investor, raised over $60 million in funding and sold my startup WorkMarket to ADP,” says Wald. “But before all that, earlier on in my career, I had a startup implode, leaving me bankrupt, depressed, and on the verge of moving back in with my parents. And while I’m really proud of WorkMarket’s success, it wasn’t smooth sailing. At one point, the board forced me to get a leadership coach. After four years, my co-founder left the company.