There are two kinds of lottery winners: Those who grow their wealth, invest in the future, and help people and organizations dear to them, leaving enough to pass on to their heirs—and the kind of people who blow it and lose it all within a few years. Hopefully, last night’s three Powerball winners will use their money wisely. Whether you play weekly, join the office pool, or swear off gambling entirely, everyone can learn a little something from those hapless souls whose lives took a turn for the worse when their lottery dreams came true.

1. Carefully vet your financial advisors: Abraham Shakespeare pocketed $17 million of a $30 million jackpot in 2006. He befriended a woman, DeeDee Moore, who said she’d help “protect” his money from friends and family who were asking for handouts. She’d convinced him to transfer his money to her account, and then killed him. She was sentenced to life in prison without parole.

2. Update your estate plan regularly: A Chicago dry cleaner, Urooj Khan won $1 million in a lottery and the next day, was poisoned by cyanide. The family grappled over his winnings, which were ultimately doled out to his widow and daughter.

3. Get the best insurance you can afford: Suzanne Mullins of Virginia won $4.2 million in 1993 and took her winnings in annual payments instead of a lump sum. Her son, who was very ill, amassed $1 million in medical bills., which Mullins paid. When Susan’s money ran low, she borrowed from a special lottery-winners foundation, but didn’t pay it back. She cashed out the rest of her winnings, and ended up broke and owing more than $150,000 to the foundation after she was sued for not repaying the loan.

4. Pay your taxes: Alex and Rhoda Toth of Florida won $13 million and lived like, well, millionaires, staying in expensive Las Vegas hotel rooms and gambling the night away. In addition to squabbling over money with family members, they filed false tax returns for three years in a row, and lied in court documents about their assets. Alex died just before their 2008 trial; Rhoda went to jail, penniless.

5. Practice saying “no”: Billie Bob Harrell, a churchgoing man, won a $31 million jackpot and dished out money to anyone who asked, as was his nature. He soon went broke and confessed to his financial advisor that winning was the worst thing that ever happened. Shortly after, he killed himself.