The BetterLife Letter
Ideas for a richer, freer life
Issue No. 013
OCT 12, 2026

The look my wife gave me when I told her we were broke :(

I still remember the look my wife gave me.

I was 24. I looked at Heather and said, "Honey, I don't know what to do. We are totally out of money. We don't have enough for groceries." 

We weren't partying. We weren't buying stupid stuff. We were both working hard. We were even starting to invest in real estate. But every month, the bank account dwindled until it was just... gone.

The look she gave me wasn't anger. It wasn't fear. 

It was trust.

It said, "Okay. What are we going to do?"

Not "what did you do" but "what are we going to do?" 

She was asking us. I was the one who owed her the answer.

Because I got us there.

It started when I was 18, buying a $50 pair of pants. The cashier said I could save 5% if I opened a store credit card. Two dollars and fifty cents! Sign me up.

That became a habit. If I wanted something I couldn't quite afford, no problem. I'd make payments. And I carried that habit straight into our marriage.

Heather was bringing home the steadiest paycheck we had: $9 an hour at Starbucks. I was the one who had no idea what to do with it.

When things went sideways in the very first marriage, Adam pointed at his wife: "The woman you put here with me..." (Genesis 3:12). I've done my share of that too.

Jocko Willink, the former Navy SEAL commander, built a whole book around the opposite instinct. His line: "There are no bad teams, only bad leaders."

That sounds harsh. I think it's good news. 

If it's my fault, it's my fix. 

(OH that line just hits, doesn't it!?) 

Whoever owns the problem gets to own the solution.

So we drew a line in the sand. No one was coming to save us. No raise. No rich relative. Just us.

I would fix this. 

And I did. 

I download 90 days of bank statements and categorize every transaction.  

What I discovered shocked me but... in hindsight, makes perfect sense:  We were losing $1,000 a month more than we were bringing in. 

Whoops. 

And I figured out I didn't have a money problem. I had a knowledge problem. 

Nobody had ever taught me this stuff. Not school, not my parents, not my job. So I started learning, beginning with Dave Ramsey's The Total Money Makeover.

The learning turned out to be the easy part. The hard part was deciding it was mine to fix.

I still see that look sometimes. On my team. On the investors who trust us with their money. It means the same thing it meant at 24.

"Okay. What are we going to do?"

It's still my job to answer.

And its still yours. 

Leadership (in business, in marriage, in parenting... all of it) isn't easy, but its required if you want to build a better life. 

Sometimes you just need to draw a line in the sand and say: 

 "No more. My new life begins now."

And then get to work. 

And hey - as always, if you’ve read this far, can you just hit the “REPLY” button on your email and send me a 1-3 sentence email on what stood out to you. I actually read these, and it helps me know what to create in the future for you. Thanks!

Brandon

P.S. If you have $13 to spare AND you want to draw that line in the sand regarding your future wealth and freedom from real estate investing, this is for you: On October 17, Ben Humble and I are kicking off the Best Deal Ever Challenge with a live workshop. I'd love to have you there. Sign up here

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