Entrepreneurship Simplified

Why Your ‘Successful’ Business is Secretly Failing (The Harsh Reality)


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You’ve hit your revenue targets. Your team seems productive. On paper, everything’s working... So why does it feel like the wheels are about to fall off? Let me tell you, I’ve been there. I’ve sat in that CEO chair, patting myself on the back for “crushing it,” only to realize later I was inches away from disaster. And honestly? It’s terrifying how easy it is to miss the cracks until they swallow you whole.

I’ll never forget the day I hired a consultant who ripped off the blindfold. I thought I ran a tight ship: great culture, clear goals, everyone aligned. Turns out? My employees were frustrated, my mid-level managers were borderline toxic, and half the processes I bragged about? Pure fiction. It was embarrassing. But here’s the kicker: every entrepreneur does this. We get so obsessed with looking successful that we stop asking the hard questions. We ignore the whispers (or outright warnings) from our teams. We confuse motion for progress.

But here’s what I learned the hard way: “success” is a trap if you’re not willing to get real. In this episode, I’m spilling the unfiltered truth about the red flags I missed, the ego that nearly sank me, and the moment I had to admit, “Man, I don’t have a clue.” I’ll walk you through the exact steps I took to rebuild trust, fix my leadership blind spots, and turn a stagnant business into one that actually thrives.

Spoiler: It starts with swallowing your pride. If you’re ready to stop pretending and start growing, this one’s for you.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:52 - Why people dread starting businesses

02:37 - Keith’s personal experiences with coaching and consulting

04:58 - The impact of coaching and consulting on business growth

07:30 - The common misconception that big businesses have everything figured out

09:17 - Let’s talk about company culture and employee engagement

11:12 - The role of coaching and consulting in personal and professional development

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Entrepreneurship SimplifiedBy Boxed Business Solutions