Building a Better Dave

Dave Jackson

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

  1. And Then Life Pulled Me Back In

    3D AGO

    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.

    16 min
  2. Waterboarding for Fruit

    10/17/2025

    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.

    12 min
  3. Old Habits Die Hard

    10/09/2025

    Old Habits Die Hard

    In this episode, I open up about a recent experience I had on Reddit where, despite my own advice, I ended up feeding the trolls. I share how I got pulled into a frustrating back-and-forth with someone who just wasn't open to any input, and how that made me reflect on my own "educator mindset"—the urge to resolve every conflict or misunderstanding online. I talk about the importance of setting boundaries not just with online trolls, but also when inviting podcast guests onto your show. Remember: if someone really wants to be on your show, they'll usually find time that works for you. On the personal side, I give an update about being busier than ever at my church due to a colleague's health issues. I discuss how this has affected my routine, my stress levels (thanks for the heads up, Oura Ring!), and the push I'm giving myself to prioritize health and movement—even if it means just getting out to walk at my local park. Plus, I share a little inspiration from watching the Ozzy Osbourne documentary "Coming Home," which has me thinking about aging, health, and making time for what really matters. --- Key Takeaways: - Don't let internet trolls drain your energy—learn to recognize when to disengage (even if you think that last message might "fix" things). - When it comes to podcasting, don't be afraid to set your own boundaries around scheduling guests. - Some people just aren't open to feedback, and that's okay—sometimes it's best to step back. - Make sure your social profiles link to your website to help connect with people you actually can help. - Growth comes from noticing your own patterns—and learning from your mistakes. - Keep prioritizing your health and well-being, even when life gets busy. - Inspiration can come from unexpected places—even a documentary about Ozzy Osbourne. --- Links Mentioned: Coming Home -Ozzy Osbourne documentary  Connect with Me: betterdave.com Thanks for listening! If you enjoyed the episode, do consider buying me a coffee :)

    14 min

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About

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

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