Building a Better Dave – Details, episodes & analysis

This month has been a wild ride—I've spent a ton of money and even more energy waterproofing my basement, only to find out the pipes were completely clogged and needed major repairs. My childhood hangout is now a construction zone, and the work isn't over yet. But it's not all about the basement—this week I set out for what I thought would be a relaxing bike ride, only to end up carrying my bike up and down muddy stairs in pursuit of the elusive Brandywine Falls. Along the way, I found myself hot, sweaty, and covered in dust, whether I was cleaning at home or out on the trail. It got me thinking about attitude—how sometimes the work and the fun leave you feeling the same physically, but it's how you look at it that makes the difference. So join me as I share what I've learned about perseverance, getting older, and keeping your eye on the prize. Let's get better together, one adventure at a time!

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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.

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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.

This was recorded during my last few minutes of being 59. Life is dragging me kicking and screaming into my 60s. I'm not happy about it. 

Don't you get it? I'm 23 honest. I've been 23 my whole life? 

Have I made my last trip to Dairy Queen? It turns out everything I eat is poison. That's something you know but don't care, and it turns out you should've cared a little more than you did.

John Mayer has a great song called "Stop this Train" that has a line John 

Had a talk with my old man
Said, "Help me understand"
He said, "Turn 68"
"You renegotiate"

I was able to renew my drivers license for 8 years which means aside from a sticker (which I can get through the mail) I will be 68 the next time I renew my liscene.

WHen you go to the MBV you go in and get a number, and wait for your name to be called. I kind of feel like a 'This is not a drill" situation, and I'm waiting for my number to be called. UNlike the BMV, I'm hoping for a very long line.

You can buy me a coffee for my birthday using this link.

John Mayer - Stop This Train

No I'm not colorblind
I know the world is black and white
Try to keep an open mind but
I just can't sleep on this tonight
Stop this train
I wanna get off
And go home again
I can't take the speed
It's movin' in
I know I can't
But honestly
Won't someone stop this train?
Don't know how else to say it
Don't wanna see my parents go
One generation's length away
From fighting life out on my own   So scared of getting older
I'm only good at being young
So I play the numbers game
To find a way to say that Life has just begun
Had a talk with my old man
Said, "Help me understand"
He said, "Turn 68"
"You renegotiate"
"Don't stop this train"
"Don't for a minute change"
"The place you're in"
"And don't think I couldn't"
"Ever understand"
"I tried my hand"
"John, honestly"
"We'll never stop this train."   Once in a while
When its good
It'll feel like it should
And they're all still around And you're still safe and sound
And you don't miss a thing
Till you cry when you're drivin' away in the dark
Singing   Stop this train
I wanna get off
And go home again
I can't take the speed
It's movin in
I know I can't
'Cause now I see
I'll never stop this train

People are paying $80/hr to cuddle. What? You heard me. I did a google search and there are multiple companies. So I thought, "Well is that what the kids are calling sex today?"

One person on the "How to Cuddle" page stated, "If you feel sexual desires coming on, communicate them as soon as possible and probably stop cuddling."

Cuddle Buddy HR

What does the training manual for a cuddle buddy look like?

I love that one site states,  " No intentional genital stimulation of any kind." (but unintentional is allowed...")

The New Go-To Career For Every Guidance Counselor

I'm picturing the High School Guidance Counselor looking at a student with straight Ds.

Counselor: "Well Billy, I've looked at your grade."

Billy: "My family says I should apply to clown college."

Counselor: "I've got something different and it pays $40/hr. 

Full show notes and videos at http://betterdave.com/182

Today I talk about an interaction with Frederick Michael Plant which goes from zero fo FU in a very quick time

Marriage at First Sight - Horrible television that I could not stop watching

This one woman feels the word "husband" has magical powers and even though she just met her husband they are "soulmates." This could be a good show to watch with your significant other.

See https://youtu.be/soZf8jhcmus

Today it's 5 AM again, and I can't sleep. I'm slowly starting to work on my speech as on July 24th, 2018 I am being inducted into the Academy of Podcasters Hall of Fame.

It's really an honor and its humbling. Person and person have been leaving a message saying how it was, "Overdue," and "Well Deserved." They thank me for all the hard work. Hard work?

Somewhere I got a gene where I just love to help people. It makes me feel warm and fuzzy, so it really wasn't hard work

I got to be creative.

I got to play with technology

I got to help people. 

This wasn't hard work at all.

Thanks for listening

I had an epiphany and I'm not sure if I dreamed this, I don't know where it came from. I looked at the previous Mrs. Jacksons (since I have a matching set now) and I noticed that both of them were someone in a situation where I'm going to call it "Damsel in distress." When I met them, I saw them as a damsel in distress that I could come in on my white horse and save.

I was sitting in my bed and I wanted to think about how many women I had ever said the phrase, "I love you" to. I think this is spurred on this idea. Recently I've gone to two conferences in the past month and I'm starting to notice, where I thought my heart was just dead - for lack of a better phrase) I have met a few females that I would like to get to know you better. The bad news is they all live hundreds if not thousands of miles away and in some cases, are young enough to be my daughter, which makes me feel creepy.

Let's start off with the very first person I said I love you to. I was 16 years old, does that really count? Well, yeah, it did at the time. And I thought of the very first time I found myself attracted to this person. My very first memory is she was a flag girl. What else do you have to say? She was a flag girl in the marching band and I gave her a ride home after a football game because she was wasted. I remember her passing out. We'll kind of in her head hitting the passenger side window. And I thought, oh my God, she's going to break the window. But what is that? You guessed it.

Damsel in distress.

The second girl was a very, very brief dating period, but very intense. And you'll notice a pattern here. She was dating somebody who lived far away. It was a long-distance relationship. Which is hilarious when you're all of 16, 17 and I was the friend that she talked to deal with the fact that her boyfriend was far, far away. Yeah, you guessed it. Damsel in distress.

The third one I was a late teen now and we worked together. Again, I am the friend that she talks about her boyfriend who lives far, far away.

Damsel in distress

Number four turned into ex-wife number one who I would like to interview. I think it would be interesting 20 years out now too, to talk about our area of life. Let's just kick back and, and what do you think of if you were to describe Dave Jackson? That's the key. I think these people at one point did know me at one point. Anyway, when I first met her, she had a horrible living situation. Her mom was dating gigantic losers. And she lived in the hood:

Damsel in distress.

Damsel number five was the nurse (if you're a regular listener to the show you've met her as she became wife #2). When I met the nurse, she explained to me how she had been dating a guy who had cheated on her seven times.

Damsel in distress.

But when I look back at these women that I said, "I love you" to, I was like, oh my God, they were all damsels in distress. And that's amazing to me, and that's why I'm podcasting in fie in the morning as I can't sleep.

So if you looked up the word Gullible it says, "easily persuaded to believe something; credulous." So I looked up credulous and it said, "having or showing too great a readiness to believe things." 

I had an interesting conversation today and we were talking about these places that appear to prey on the Gullible. You know the drill.

You get dragged to a meeting where you hear a pitch.

Everyone can benefit from the product. It's super easy to join. It's even free.

You are encouraged to bring your friends.

If you want to become a member there are fees based on your level of dedication. 

There are weekly meetings to attend and in some cases twice a week. 

There are brainstorming session on how you can get the word out there and raise more money for the company.

If you are active enough and demonstrate dedication, you may get an advisory board.

Some people show up and swear the product works, while others don't attend weekly meetings and don't seem to be getting any results

Some people think the whole thing is a scam. The people pushing the product are just a bunch of snake oil salesmen trying to brainwash people

What company do you think I'm talking about?

So I'm watching Jerry's Seinfeld's Comedians in Cars Getting Coffee on Netflix.  It's amusing. He gets these obscure cars and picks up celebrities and talks with them over coffee. He gets paid a lot of money for this.  They aren't earth shattering interviews, but the show is cool. I was watching trying to figure out what it was that made this show cool. Then it came to me.

There was jazz music in the background. Now watching a toothless waitress in some strange dinner is cool. Look! it's coffee in slow motion put to jazz! I've never seen coffee poured like this. It's like seeing coffee for the first time. Holy Cow. 

Now when Jerry pulls up in a 1972 VW Van with rust to pick up Kramer, it's cool. 

Then I thought about the Charlie Brown Christmas Special. Here is this boy face male pattern baldness at a very early age, being bullied by his friends, and disrespected by his dog. There isn't much of a story, then get him involved with a bizarre play that also has no story. Then Linus just takes control and start blurting out random scripture like a long lost Osteen and the Christmas Special comes to an end. Why do we watch every year? Becuase it's got one of the coolest soundtracks ever. Filled with some really cool jazz. I don't even like jazz.

It makes anything cool. I recently started using Advocare products (which have boosted my weight loss efforts) and while they have great products let's not kid ourselves they are a multilevel marketing business. It's Amway for fat people. So I signed up so I can discount on the products and I'm reading some really boring stuff. 

Now lately I'm stuck. I keep throwing out my back, and that makes it hard to exercise. I'm losing weight (down 3 lbs in the last 30 days) but I keep throwing out my back from sneezing. Then when my back is out, it's hard to exercise. The lack of exercises makes me less healthy, which leaves me open to getting sick, which leads to me sneezing more. You see where this is headed. You know what makes exercising in your living room better? You guessed it. 

Mentioned in This Episode

Advocare

I have some friends who have giant TVs. Two years ago I bought a 32" flat screen. Now when I go to their house and come home, my 32" looks like a toy. So I decided to buy a bigger 1080 TV.

This lead to me asking about what is the difference between 1080 and 4K, then what was the difference between 4k and HDR?

Then the guy at Best Buy gave me a demo of both, and I could feel myself getting sucked in. I had found a cheaper TV but now I could feel myself talking myself into grabbing the credit card.

I ended up with a 55" 4K HDR tv.

Then I brought it home. Uh Oh.

Then I went to plug it into my soundbar. Uh Oh.

Through the process of carrying these items from store to trunk to apartment, I pulled muscles in my back.

When I watch the Tonight Show, it feels like Jimmy Fallon is in my living room. My TV is just about the size of my couch.