Building a Better Dave
Building a Better Dave

Building a Better Dave

Dave Jackson

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A funny look at relationships, marriage, divorce, love, sex, life, dating advice, and the weird thoughts that pop into Dave's head when he is sleep deprived. Guaranteed to make you laugh, cry, think, or groan. Life is too important to be taken seriously

Recent Episodes

The Kids are Going to Be Here
JUN 8, 2026
The Kids are Going to Be Here
I got a call from my sister-in-law as I was driving to get some pizza, and she invited me over to her house because the 3rd of April is my great nieces birthday. We were going to have a makeshift birthday party at the house, and she said all the kids are going to be here, meaning my niece and her three kids (my other niece lives out of state). I went over, and my great-niece has grown easily a foot and a half in the last three months. I can't remember the last time I saw her, but she's much taller. My great-nephew is taller than I am. It was one of those times when I knew to take a brain tattoo, meaning it's something that's not going to happen (so take a mental snap shot). I've been doing this a lot when the kids are together because the newphew is 18, and it's very weird that he's graduating from high school. It was kind of a slap in my face that, "Hey, if you wanted to watch this kid play high school sports, you missed it," and it made me very sad. My mom attended everything; now moms always do that, because they had to drive you there, probably, but nonetheless it was one of those where I think I saw him play sports three times. I thought, "You suck as an Uncle," but it was great to have them all together. It was really weird that the baby of the family is now a teenager. The middle great-niece will soon be driving, and the oldest Nephew is off to Myrtle Beach with his buddies. That phrase, "All the kids will be here," is something that, even before I got there, I realized is something that's going to be more and more special. Eventually we will blink, and someone will be married with a kid. The newphew has a girlfriend now who seems very sweet, and then the girls will go off. Who knows what will happen, right? Nonetheless, having everyone under the same roof will be harder and harder to do, because who knows, they might end up in other states, et cetera, et cetera. I actually got a little emotional because I was watching him leave. Here he is, this 18-year-old kid, and about six feet in front of him was my niece (his Mom). I remember vividly watching her on a blanket at my brother's house in North Hill. She occasionally would say "buh," and we all thought that was hilarious. Here was my little "buh" baby, and her first kid is now a high school graduate, and it just happened so incredibly fast. And faster it will go. If I'm going to see the great nieces, cheerleading or whatever they're doing, I'm going to have to step up my game as an Uncle. Check Your Calendar My niece had even sent a date and address to one of his last games. I remember thinking I need to check that and add it to my calendar, except he had already graduated and I had missed it. So check your calendar. I believe your calendar reflects your heart. Don't wait, as time is moving faster and faster. Get your prorities in place.
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10 MIN
And Then Life Pulled Me Back In
MAY 1, 2026
And Then Life Pulled Me Back In
On this episode of Building a Better Dave, I open up about a lifelong battle with debt, from childhood lessons learned at the family kitchen table to the hard realities of bankruptcy, divorce, and the ever-looming burden of credit cards. I share how persistent financial setbacks reshaped his perspective on money, hard work, and resilience. Just when he thought he had finally conquered debt, an unexpected basement flood pulled him back in, reminding him that life's challenges are never really finished. Join me as I explore what it means to keep pushing forward when setbacks strike, the value of perseverance, and how sometimes tearing things down is the first step to building something even better. Like the show? Wan to give some value back? Buy Dave a Coffee (or 10). Sequence of Topics Covered 1. Introduction & Theme of Debt Dave Jackson introduces debt as the main topic and his lifelong struggle with it 00:00. Show info and contact details are provided 00:08. 2. Early Lessons in Money and Debt Memories of his dad doing taxes and the tension around finances 00:36. The influence of the Lannister motto, "A Lannister always pays his debts," on his upbringing 01:22. Story of borrowing $300 from his grandfather to buy a car and the process of paying him back 01:28. Learning there are no "free lunches" and needing to earn money for things he wanted, such as music albums 01:47. 3. Family Finances & Value of Money Family's economic background (not rich, not poor, but frugal) 02:24. Use of coupons, hand-me-downs, and lessons in financial responsibility from his mother 02:33. 4. Adult Experiences with Debt First marriage: fertility challenges lead to substantial credit card debt for treatments 02:41. Living paycheck to paycheck and discussing bankruptcy, which conflicted with his "pay your debts" values 03:30. After 9/11, wife's hours were cut, leading them to file for bankruptcy reluctantly 03:40. 5. Struggles with Debt in Later Life Marriage to a partner with poor credit and inheriting someone else's credit card debt after divorce 04:17. Failed attempts at debt consolidation and the difficulty of accessing better loan rates 05:09. Gradual process of securing slightly better loans and working towards being debt-free 05:25. 6. The Turning Point: Selling the School of Podcasting Conversation with his boss about potential for the School of Podcasting 05:42. Decision to sell the business for enough money to pay off debt, while maintaining a professional relationship 06:23. Finishing 2025 debt-free and entering the new year with a clean slate 07:07. Enjoying financial freedom and considering future opportunities and contributions to family 07:38. 7. Setbacks: Home Flooding and New Debt Feeling of finally catching up to peers in life after years of feeling behind 08:03. Discovery of water damage and mold in the basement after heavy rain 09:18. Realization of the high cost involved in repairs and choosing to finance the repairs rather than deplete savings 10:30. Resuming strategies from earlier years to manage debt and expenses 11:05. 8. Mindset and Coping Strategies Acceptance of debt as a temporary setback and readiness to cut corners and reduce expenses (e.g., fewer streaming services, no fast food) 11:48. Reflecting on the possibility of being in debt into old age and the impact on personal plans 12:22. 9. Tackling Change and Optimism Clearing out the workshop and preparing for basement renovations 12:51. Parallel between demolishing basement parts and the demolition of his childhood schools 13:31. Considering new configurations for the basement, such as moving down his podcasting studio, and seeking hidden benefits 14:05. Drawing inspiration from his grandmother's longevity supported by daily movement 14:18. 10. It is What It is Paying for repairs and looking forward with optimism, knowing things will improve 14:46. Mention of listener support through "buy me a coffee" on the website to help with expenses 14:58. Closing wishes for the audience and a tease for the next episode 15:19.
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15 MIN
Waterboarding for Fruit
OCT 17, 2025
Waterboarding for Fruit
Hey, it's Dave—and on this episode of Building a Better Dave, I talk all about the weirdness that is Halloween in my neighborhood lately. As October rolls in, I've noticed a crazy escalation in skeleton yard decorations. What used to be simple six-foot skeletons have turned into these massive twelve-foot giants. I can't help but wonder if this is just the middle-aged version of keeping up with the Joneses. Halloween itself has always struck me as strange, especially when you factor in how expensive candy has gotten (seriously, $15 a bag now?!) and how we've all just accepted feeding our kids mountains of sugar as tradition. Confession: If I buy a bunch of candy, I'm probably just going to eat it myself, which is why I might skip handing it out altogether and let myself get "tricked" this year. This episode, I also reminisce about the good old days of Halloween pranks—TPing houses, knocking and running, and my brother's infamous police escort home after getting caught. My dad was definitely not amused. It feels like those harmless pranks just don't happen anymore—probably because today's doorbell cameras have killed the fun. Of course, I have to mention bobbing for apples, which, looking back, is basically waterboarding with fruit. Pump enough apple cider into a kid and you end up with what I like to call the "Runs" (and I list every synonym I can think of—because why not?). And what's up with every costume needing to be "slutty" these days? Slutty nurse, slutty librarian, even slutty Daffy Duck! Not sure when that trend started, but it seems to get more out there every year. I wrap up by admitting I bought a new Christmas tree—when all I intended was a little four-foot tree, I walked out with a seven-and-a-half foot beauty. Honestly, I think I'm trying to recapture one of my favorite childhood memories: coming in from the snow, curling up in front of the tree with a thick blanket and some hot chocolate from my mom. That feeling of safety just sticks with me, especially as the holidays get closer. Hope you enjoy my holiday ramblings, stories of waterboarding for fruit, and my skepticism about modern Halloween. Until next time, hang in there—it's going to get better. Highlights: Giant skeletons and the one-upmanship of Halloween decorations The economics—and temptations—of Halloween candy How doorbell cameras ruined classic Halloween pranks Bobbing for apples: my take on this bizarre tradition The rise of "slutty" costumes and my bewilderment Reflecting on the holidays and chasing those cozy, safe memories Did this episode make you laugh,cry, think, or groan? Consider buying Dave a coffee.
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12 MIN