i couldn't make the payments. >> hammitt was his third major investment.ony was determine thad this time he was going to do things right. this ohio native made his first fortune in the 1990s when he and a few friends founded a roofing company. >> things moved so fast and the money came in so quickly, i thought i could do no wrong. >> what motivated you in those days? >> money. >> he overindulged in all things fast and furious. >> a boat, ferrari. everything was red. a truck to pull it. >> so the company for you was sort of like an atm machine. and while he was a fantastic salesman his company bus not focused providing the best product or service. but instead of facing hard times, tony walked. >> why did you walk away? >> i wasn't happy. i lost my motivation and i was done. >> were you depressed? >> oh, yeah. i was. i was. >> he did a lot of soul searching. he went to a tony robbins event, a burning man event, things important to him, and tony decided he was ready to start fresh. >> went into the financial business right before the boom, early 2000, some de

he turned his love for creativity into hammitt. i love art, architecture design.'ve always enjoyed that. i thought i could put that into building a handbag brand. >> he partnered with an existing designer and eventually took over the whole company. >> what i came into this business, i had enough money, i thought, to build it. >> but he didn't. >> money is going fast, sales are not. i ran out of my money in a couple years. >> the situation was bad. he lost his home and spent nearly two years sleeping on friends' couches. >> does it feel shameful at all? >> there was a lot of shame around the wastefulness early in life. don't live backwards, right? i still had great things every day that i could focus on. that's what kept me going. >> losing his foundation didn't deter him from trying to save hammitt and become the effective leader that he wanted to be. >> even in the worst of times, you have to make sure everybody knows you're still going forward. >> was it easy to talk to people about it? >> not in the beginning. all of a sudden a light bulb went on. i don't give