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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Tech fails are never fun—and they never show up at a convenient time. In this episode, I’m pulling back the curtain on some of my worst tech disasters and what I’ve learned from each one. I’ll walk you through real-world examples—from broken payment automations to form fails and summit chaos—and how I kept my sanity and my customer relationships intact.
Whether you're in the middle of a launch, setting up automations, or just trying to get your stupid form to work, this episode will give you some perspective, a few laughs, and most importantly: a plan for what to do when the tech train derails.
Key Takeaways
- Tech fails are inevitable—but they don’t have to take you down with them
- Why how you respond matters more than whether you get it 100% right
- The reason I had to completely rebuild my website (and what I’d do differently now)
- A reminder that being “bad at tech” isn’t a character flaw—it’s an everyone problem
- Why the most important thing you can protect isn’t your funnel—it’s your reputation
Thrive in 5: What to Do When Tech Fails
- Have a backup plan
Know what your Plan B is if something critical crashes—especially during a launch or live promo window. - Spot-check your systems regularly
Just because it worked last month doesn’t mean it’s working now. Automations break—stay on top of them. - Make it right, fast
If something goes wrong for a customer, fix it and find a small way to go above and beyond. - Own it publicly, not perfectly
Your clients don’t need a tech explanation—they need clarity, resolution, and a little humanity. - Don’t DIY everything
You don’t have to be a tech genius. But you do need to understand how your systems work so you're not powerless when things go sideways.
At some point, your tech WILL fail. But that doesn’t mean you have to freak out or lose trust with your people. If you're tired of trying to figure it all out yourself or living in fear of the next platform crash, check out The Shortcut—my done-for-you setup that helps you build a business that works.
And if you’ve got a tech fail story of your own? Text the show or come say hi on my site—I’d love to hear it!
Loved this episode? Don’t miss out on more practical, no-nonsense advice to level up your life and business. Make sure to subscribe so you never miss an episode of Thriver's Ed! 🎙️
💡 Join the Conversation: Have questions, thoughts, or an "aha" moment you'd like to share? Text the show by clicking the link in the show notes or leave a review – I read every single one!
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Thanks for listening – your journey to thriving is just getting started!
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