Every entrepreneur has been there—you invest in a shiny new tool or launch what feels like a brilliant idea, only to watch it backfire in real time. In this episode of Mike and Blaine, we dive into the unpredictable world of digital transformation and explore how even the smartest business upgrades can cause unexpected chaos. From software updates that crash your website to marketing campaigns that miss the mark, we unpack the unintended consequences of decisions that were supposed to make things better.
Mike shares a personal story about rolling out an AI-powered SEO tool to level up his website—only to discover it locked everyone out of the content during a live event. It’s a perfect example of how small businesses can get caught off guard by technology that promises efficiency but delivers headaches instead.
We explore the bigger picture of why digital tools fail, how to prepare for the unexpected, and why flexibility and resilience are critical when things go sideways. Along the way, Mike and Blaine share stories of business leaders who survived digital disasters, lessons learned from tech fails, and practical advice for making smarter choices in an age where every upgrade comes with risks.
Whether you’re an entrepreneur, small business owner, or part of a growing company experimenting with new technology, this episode gives you insights on balancing innovation with caution—and a reminder that even the best-laid plans sometimes blow up.
#DigitalTransformation #BusinessTechnology #TechFails #EntrepreneurshipPodcast #MikeAndBlaine
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Featured Beer: @ShinerBeer @omenbrewingyeg
Mike: Shiner Shandy
Blaine: Cabin, Last Best & Bale Breaker Collaboration - Border Hop West Coast Pale Ale
Watch on YouTube: https://youtu.be/CXwU1tvQPps
Thanks to our Beer Sponsors:
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• Karen Hairston from 3S Smart Consulting: 3ssmartconsulting.com
• Larry Weinstein, the Cash Flow Cowboy in Houston Texas!
• Neighbor Pat
• Devin
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