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Dave Says: How Big Is Your Why?
Dear Dave, I’m 26, and I graduated from college a few months ago. I was fortunate enough to have a job making $70,000 annually waiting for me. I don’t have any other debt, so my only real problem right now is about $5,000 in credit card debt. It doesn’t seem like a huge amount, but…
May 19, 2026
Dave Says: It’s a Hobby, Not an Investment
Dear Dave, I’m single, and I work with a well-known, high-end retail company. Over the years, I’ve noticed that certain models of some watch brands appreciate incredibly over time. I’ve seen a few that have doubled, tripled and even quadrupled in value over the years. With this in mind, what do you think about the idea…
March 16, 2026
Dave Says: The Healing Process Will Take Time
Dear Dave, I went through a divorce earlier this year, and I was granted custody of our children. They’re 13 and 18. The house we live in is paid for, and it’s worth about $450,000. I also don’t have any other debt. My ex-husband has been very good about paying child support, and I have…
December 18, 2025
Dave Says: Learning to Forgive Yourself
Dear Dave,  I started following your plan at the first of the year. It was one of my New Year’s resolutions. I even budgeted for Christmas each month. I’ve already gotten my holiday shopping done early, but in the process, I went a little crazy and overspent. Realistically, I know things will be okay. I…
December 16, 2025
Dave Says: Nothing can make you happier…or scare you more
Dear Dave, My wife and I recently learned she’s pregnant. She’s about to begin her second trimester, and we’re both really excited. There is a bit of concern, though. During a detailed ultrasound, the doctor found an issue that might mean our baby could need minor surgery soon after delivery. Financially, we’re in Baby Step…
October 15, 2025
Dave Says: Sometimes its lonely at the top
Dave, When I started my business, I never realized just how lonely leadership can feel. The weight of every decision, pressure to protect the culture and having very few peers who understand how heavy things can be is overwhelming sometimes. How did you stay grounded and connected during the early days of building your company?…
October 10, 2025
Dave Says: Big Inheritance Coming . . . Is a Prenup a Good Idea?
Dear Dave, What are your thoughts on prenuptial agreements? I’m a divorced single mom with two boys, and I’m their primary caregiver. I’d like to get married again one day if the right man comes along. The reason I ask about prenups is I’m expecting to receive an inheritance of about $5 million sometime in…
October 1, 2025
Dave Says: Giving is always in season
Dear Dave, My husband and I have already started putting money aside for Christmas. Recently, we were talking about what we might get our six-year-old twins, when we decided we want to make sure they experience the giving side of Christmas this year, rather than just receiving. What are some good ideas for making sure…
September 4, 2025
Dave Says: Focus on what’s important now
Dear Dave, I’m 22, working my way through college and I’ve already been able to start setting money for life after graduation. I had a talk with my parents recently about my plans once I get a real job and get out on my own. They seem to think I’ll be okay, but sometimes things…
July 30, 2025

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