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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
RESOURCES:
Visit our website: https://www.boxedbiz.us
Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/
Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163
Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/
If you enjoyed today’s podcast, don’t forget to subscribe, rate, and share the show! There’s more to come, so we hope to have you along with us on this journey!
Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700
Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa
Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified
By Boxed Business SolutionsYou’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
RESOURCES:
Visit our website: https://www.boxedbiz.us
Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/
Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163
Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/
If you enjoyed today’s podcast, don’t forget to subscribe, rate, and share the show! There’s more to come, so we hope to have you along with us on this journey!
Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700
Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa
Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified