Hey Reader,

For the first 6 months I posted content, nothing worked.

• Posts got no traction
• Engagement was flat
• And I seriously considered quitting more than once

At the time, there was no audience, no momentum, and no real signal that this was worth continuing.

Then one small decision changed everything.

I had commented on a post from another creator who was slightly ahead of me. He reached out and suggested we hop on a call. I almost ignored it. Spending 30 minutes with someone I didn’t know didn’t feel like a good use of time.

But I said yes.

At the end of that call, I asked if he’d ever considered coaching. He hadn’t. He said he’d do it for $1,000.

I wasn’t actively looking for a coach. And I wasn’t convinced it would work.

But I made the bet anyway.

That $1,000 bet ended up shaping everything that came after.

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Everyone wants a “great deal.”

Something that doesn’t just return your investment…but multiplies it.

But those opportunities rarely look obvious in the moment. If they did, everyone would take them.

The reality is, most great deals share three traits:

• They feel uncertain
  If there were no risk, the opportunity wouldn’t be mispriced
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• The upside is asymmetric​
  Limited downside, but a path to outsized returns
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• You can influence the outcome
  Not a passive bet…something you can actively improve

That’s where most people get it wrong.

They avoid opportunities with any downside, even when the upside is significantly larger.

Or they invest blindly without asking how they can tilt the odds in their favor.

The best decisions sit in the middle:

Small, calculated bets where the downside is manageable…and the upside can compound.

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There are three areas where you can place bets immediately, with meaningful upside and very manageable downside.

1. Talent

I’m not a fan of over-indexing on senior hires.

I’d much rather bet on junior talent… the ones who are hungry, resilient, and can figure things out.

They grow with you.

They build context inside your business.

And over time, they become far more valuable than what you could have bought upfront.

The best CEOs I work with don’t just hire… they develop and promote from within.

2. Coaches

This has been one of the highest ROI decisions I’ve made.

I look for people who are early… not fully “proven” yet… but clearly ahead of me in a specific area.

One of my favorite tactics is finding creators with small audiences… a few thousand subscribers or less.

These are the people who:

• are actively doing the work
• haven’t fully priced themselves yet
• and are still close to the learning curve

You get access to real, current insights… at a fraction of what it will cost later.

3. Yourself

This is the most overlooked one.

Starting something on the side… building an audience… going to an event… learning a new skill.

These are all small bets.

They don’t require massive capital… but they open doors that don’t exist yet.

Most won’t turn into anything meaningful.

But the ones that do… completely change your trajectory.

That one month with the coach changed everything.

He showed me how to package ideas… how to make content actually resonate… how to think like a creator, not just someone sharing information.

From there, things started to click.

3,000 followers turned into 10,000… then 20,000… then hundreds of thousands… faster than I ever expected.

It ended up being one of the highest ROI decisions I’ve ever made.

And what’s funny is… he never stopped being a few steps ahead.

Today, he’s one of the largest creators in finance and accounting. You may already know him.

​Nicolas Boucher​

We still talk all the time… sharing ideas, comparing notes, pushing each other forward.

What started as a small bet turned into something far more valuable than I could have expected.

Not just a great investment… but a great relationship.

Now I’m curious…

What’s a bet you made that paid off far more than you expected?
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Josh
Your CFO Guy