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The Stacking Benjamins Show

How to Save Your First $25,000 -- The Roadmap Most People Get Wrong (SB1838)

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Personal Finance, Financial Planning, Education, Retirement, Investing, Cfp, Business, Money

4.42K Ratings

🗓️ 6 May 2026

⏱️ 71 minutes

🧾️ Download transcript

Summary

Getting to your first $25,000 saved is harder than anything that comes after it. Not because the math is complicated -- because the habits aren't built yet, the fixed expenses are already set, and the standard advice about cutting small treats completely misses where the real leverage is. Scott Trench, VP of Operations at BiggerPockets and author of Set for Life, brings a roadmap that challenges almost everything you've heard about getting started -- and it begins with a decision most people aren't willing to make.

What You'll Walk Away With

  • Why the first $25,000 is the hardest milestone -- and why cutting lattes and happy hours won't get you there
  • The three budget categories that actually matter -- and why they account for two thirds of what most people spend
  • Why saving your next $1,000 is more valuable than earning your next $1,000 -- and the tax math that proves it
  • The house hacking strategy that can eliminate your largest monthly expense entirely -- even if you never want to be a full-time landlord
  • Why stocks are less risky than bonds for long-term investors -- and the age-based argument Scott makes that most people miss
  • The counterintuitive case for spending more on fun -- once you've handled the big fixed expenses first
  • Why developing a specialty may actually be riskier than being adaptable -- and what that means for your career strategy
  • The retirement account trap that catches early savers off guard -- and when maxing out isn't the right first move
  • How to actually vet a financial advisor before handing over your money -- and why the problem is often as much the client as the advisor
  • Why international stocks belong in your portfolio even when they've underperformed -- and the rebalancing math that changes the picture

Why This Matters Now

This conversation was originally recorded years ago, but it was pulled from the vault for a reason: saving that first $25,000 feels harder today than it did then. Costs are higher, decisions feel riskier, and it's easier than ever to feel stuck before you even get started. The core framework Scott lays out hasn't changed -- and if anything, it applies more directly now than when it was first recorded.

From the Basement

Scott Trench joins Joe and OG to walk through the early chapters of Set for Life -- the ones that challenge conventional saving wisdom before getting into the real estate strategy BiggerPockets is known for. The headline segment takes on a Bloomberg piece about bad financial advisors and a lawsuit against American Funds, and OG gets considerably more animated than usual about both. Doug arrives with muni bond trivia that turns out to be exactly as straightforward as it sounds -- which is either reassuring or anticlimactic depending on your expectations.

Resources Mentioned


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Transcript

Click on a timestamp to play from that location

0:00.0

Well, hey, there, Stacker. Today we're talking about one of the hardest things in personal finance, not investing, not retirement, not even figuring out what the heck the Fed's doing this week, just getting your first real pile of money saved, that first $25,000. Because once you've got momentum, you already know if you're somebody used on this.

0:21.9

Everything begins to change.

0:23.6

But before that, it can totally feel like you're stuck.

0:26.5

Like no matter how hard you try, something keeps pulling you back.

0:30.3

There's always, always another frustrating thing that happens as you try to get it rolling.

0:35.5

But man, when it does, it's so, so good. So today,

0:38.5

we're diving into a roadmap that challenges a lot of the advice you usually hear why cutting

0:43.2

small expenses isn't enough, why your biggest wins come from a handful of big decisions. And while,

0:48.3

quote, I'll save more when I make more is probably something that's holding you back. So we're also going to hit a couple

0:56.4

headlines that might get a little, let's say animated about financial advice and who should

1:02.2

you actually trust with your money. A topic that I think is important for every stacker who's

1:08.6

trying to grow their team put the right people on it. And here's the part

1:12.0

that surprised me coming back to this episode, which is this conversation originally happened

1:17.2

years ago. We just pulled it from the vault for Greatest Hits Week. And you know why? Because even

1:23.4

though you're going to hear a few references that are clearly from another moment in time.

1:28.2

Markets, news, maybe even a take or two that feels like a throwback.

1:31.5

Here's the thing.

1:32.5

These core ideas, I'd love to get your take.

1:35.8

But for me, the reason I wanted this one is because it holds up better now.

1:39.8

Because today, I feel like saving that first $25000 bucks actually feels harder than it did when we

1:46.2

produced it. Of course, it always feels harder, but cost or higher, decisions feel riskier,

1:50.9

and it's easier than ever because of all those things to feel stuck more before you even get

...

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