If you’ve ever stared at an open email thread and thought, “Okay, is this quality follow up, or did I just turn into a teenie bopper waiting on a text back from their crush?”… this one’s for you. We talk about the moment a warm lead turns weird, and how fast your confidence can leak out when you start trying to interpret someone’s silence instead of responding to it.

In this episode, Bernie and I get honest about where that line actually is between professional persistence and straight-up chasing. We unpack the subtle signals people give (and the ones they don’t), what it looks like to close the loop without burning the bridge, and why “fortune is in the follow-up” doesn’t mean you need to keep knocking on a door that’s clearly not opening.

You’ll walk away with a clearer gut-check for your next follow-up, a better way to stay in your CEO energy when someone’s dragging their feet, and a little permission to stop making excuses for prospects who won’t decide.

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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/

Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #19: When “Under Construction” is an Understatement

What does it actually looks like when your business is “under construction” for real? Not just a cute rebrand season, but the kind where the platform shifts under your feet and the systems you built on suddenly stop cooperating.

In this episode, Bernie and I get into the very specific pain of rebuilding while you’re still delivering, still selling, still trying to act like you’re totally fine… while your brain is quietly running a demolition crew in the background.

We also pull apart that tricky question: is this broken, or is this just growth? And what do you hang onto as non-negotiable so you don’t rebuild the wrong thing.

And yes, we’ve both had a moments where we discovered “if the detour is better, you have to make that the main route” which is annoyingly true, but also kind of relieving if you’re in a season where the best next step isn’t the one you planned.

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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/

☕ 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.

🌐 www.leadsmarterco.com

✉️ alison@leadsmarterco.com

🤝 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/

✉️ bernie@insigniatraining.com

🤝 https://www.linkedin.com/in/badiii/