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Dave Says: Where did the money go?
Dear Dave,  I have a roommate, and we’ve shared the same two-bedroom apartment for about three years. During that time, we’ve always had an agreement that we would split the bills fifty-fifty. But for the last several months, he’s been very late paying his half of the bills. There have even been a few times…
Dave Says: Plug in or promote from within?
Dave, I own a small business with about 20 team members, and we’re doing pretty well. Last year, we had revenues of about $1.2 million and profits of $250,000. How do I find leadership within my company that cares about the vision and value of my company enough to help me grow it to the…
Dave Says: A safety net, not a hammock
Dear Dave, My husband and I are in a bad situation, and we’re thinking about taking my parents up on their offer to move in with them. We both work two jobs. I’m a medical transcriptionist with a small business on the side, and he’s a warehouse clerk who is also trying to get a…
Dave Says: You’re being a good big brother
Dear Dave, My mother died about a year and a half ago, and she left me and my younger sister $75,000 each. My sister is 16, and she plans on enlisting in the military after high school, then using the G.I. Bill to pay for college afterward. She won’t receive the inheritance money until she’s…
Dave Says: You’re playing with fire
Dear Dave, My wife and I owe about $40,000 on our mortgage. My father-in-law, who is a very nice and generous man, said he wants to pay off the house for us, then let us pay him back over time. We’ve borrowed much smaller amounts of money from him in the past, and we were…
Dave Says: My wife thinks she owes me money
Dear Dave, My wife and I have been married for nine months, and we’ve been following your Baby Steps plan for three months. We have about $50,000 in debt, and I recently cashed out an old whole life policy that enabled us to pay off $22,000 of our debt. My wife still feels weird about…
Dave Says: Increase Expectations Gradually
Dear Dave, I’m getting married this summer and about to become a stepmom. To be honest, I’m a little worried about the family dynamic. My fiancé’s daughter from an earlier marriage seems a bit irresponsible. She’s 23, has trouble holding a job and still lives at home. She seems to expect her dad to step…
Dave Says: If you’re not going all in, stay out
Dave,  I have an idea for a small business I think would be a huge success in my area. How do you feel about me keeping my current day job, and hiring a full-time manager for the business to handle the day-to-day operations, while I do the accounting and oversee things? If it doesn’t break…
Dave Says: A big mess
Dear Dave, I’m a single mom, and I opened my own small business last year. The business isn’t growing at all, and my mom and dad are helping me with the bills. On top of all this, I don’t receive any child support payments from my ex-husband. But my biggest concern is our home. I…

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