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Aswand Cruickshank

Aswand Cruickshank

A six time published author, who teaches business owners how implement innovative teamwork.

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“Win”-Trapreneur Wednesday: How I First Learned to Proactively Solve Problems

4 min readApr 30, 2025

Featuring: Aswand Cruickshank

Welcome back to another “Win”-Trapreneur Wednesday, one of the many creative initiatives I’ve proudly built from the ground up.

Before we dive into today’s story, let’s quickly define the term:

“Win”-Trapreneur — A person who has an entrepreneurial vision for their life and business, yet had the good fortune of finding a job that aligns with that same vision.

This week, we’ve been focused on one core theme: Proactive Problem Solving. And today, I’m putting myself in the hot seat.

Yes, I’m the featured “Win”-Trapreneur this week. And I’m taking y’all back to the unexpected classroom that first taught me how to truly anticipate and solve problems before they blow up — my time at KinderCare Learning Center.

From Boxing Gloves to Baby Wipes

Let’s rewind.

About a year after the world flipped upside down during what some called the pandemic (and others called the scamdemic), I was growing increasingly frustrated with my job at a 9Round fitness gym. I was the head trainer — but it felt like I was running the whole operation.

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Aswand Cruickshank
Aswand Cruickshank

Written by Aswand Cruickshank

A six time published author, who teaches business owners how implement innovative teamwork.