Hour 2: Aired on Monday, May 23, 2016

- Jess (New Haven, CT) wonders if she should open a private law practice.

- Evan and Catherine (Spokane, WA) are excited to shout that they've paid off $260,000 in two and a half years and are now debt-free!

- Dave reads the Blinds.com question of the day from Nicole, who asks if she should cash in a thrift savings plan to pay off debt.

- Teresa (Boise, ID) says her in-laws are being told not to buy long-term care insurance.

- Ben (Phoenix) is going into the Air Force to be dentist.

- Jay (Manhattan, KS) asks how much to spend on a car while he's in college.

- Ben (Manitoba, Canada) wants to know how to grow a small business.

- Mandy (Dallas) has $18,000 in credit card debt, and a judgment wiped out her bank account.

- Cathy (St. Joseph, MI) is moving out of state and wonders how to get rid of her house.