Hour 2: Aired on Monday, June 13, 2016

 - Steve (Louisville, KY) needs to choose between aggressively funding his retirement or putting the extra money toward the mortgage.

- David (Orlando) says his disability payment decreased because the insurance company disputed the "own occupation" clause.

- Brandon (Pittsburgh) works with his dad, who isn't handling the finances of the business well.

- Evan (Seattle) asks if he should buy a foreclosure.

- Laura (Orlando) wonders if she should put Baby Step 6 on hold to focus on Baby Step 5.

- Marsha (Jacksonville, FL) wants to know how to leave her trucking company to her kids.

- Carey and Jon (Toledo, OH) ask how to sell their upside-down car.

- Dave further explains his reasoning after Carey and Jon are off the air.