When Opportunities Start Punching Back
☕ Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #16: Opportunity —> Problem —> Repeat
I laughed when I pulled this issue from the archive because it’s one of those “oh cool, we’re doing this again” themes, and apparently, my business heard me and said, “Bet.”
Bernie and I swap stories on the funniest “opportunities turned problems” experiences (someone offered to book me private jets…I don’t think my LinkedIn profile makes me look that successful!), and we talk about what to do when people interrupt your day with a cold pitch. I tend to Uno-reverse them, but Bernie has a mischievous approach, of course.
Then we get into the less-funny part of growth: when the role that helped you build the business isn’t the role you need now, and we wrap by normalizing the cycle: bigger problems usually mean you’re playing a bigger game, but repeating the same problems might mean you’re the problem you keep having!
Give it a listen, and if you’re in the trenches, fighting business battles right now too, just know you’re not alone… we’re in it with you!
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
thecaffeinatedentrepreneur.com 