Uprooted My Family for a Big Business Move… and Flopped Hard

In 2022, I moved my family from Canada to Colombia.

Why? Because I’d bet everything on a new venture.

I took a 50% stake in an enterprise-level cold-calling company. Convinced the CEO I had the answers to make their sister company a success.

The plan? Generate $30,000 in new revenue in the first month.

What Actually Happened

We launched the campaign.

The calls came flooding in.

But no one was closing.

It wasn’t the leads. It wasn’t the market.

The real problem? We weren’t Ahead of the Ask.

What Does “Ahead of the Ask” Mean?

Our prospects were curious, but they weren’t ready.

They didn’t have the proof, clarity, or confidence they needed to say yes.

Being Ahead of the Ask means making sure your prospects come to you already convinced:

• They know you’re the real deal.
• Their objections are handled before they even speak to you.
• Saying yes feels like a no-brainer.

Without that preparation? You’re just another voice in a crowded market.

How I Fixed It

After that month, I swore I’d never make the same mistake.

Now, every campaign I run is built to get Ahead of the Ask.

Here’s how it works:

1. Proof First. Before we talk, prospects know exactly what we can do and why we’re the best at it.
2. Objections Handled. We answer questions before they’re asked, eliminating hesitation.
3. Easy Wins. We make the next step clear, logical, and impossible to refuse.

The result? Deals close faster, easier, and without the guesswork.

If you’re chasing deals instead of closing them, you’re probably behind the ask.

Your job isn’t to convince someone on a call—it’s to make sure they’re ready to say yes before the call even happens.

What’s holding you back from being Ahead of the Ask?

Drop your thoughts below—I’d love to hear them.