Entrepreneurship can feel like you’re building something important while the street stays weirdly empty, no water cooler, no built-in coworkers, and not always a clear place to put the hard stuff (or the good stuff) when it happens.

In this episode, Bernie and I talk about what that loneliness actually looks like in “real life business” and the difference between needing someone for the tough days versus the wins you’re scared to say out loud, the way we each spiral (or shut down) when it’s an “empty parade” season, and why oversharing with the wrong people can cost you more than staying quiet.

We also get practical about the kind of support that actually helps from your “Core 4” and how a relationship-first networking culture can quietly become the bench you lean on when you need perspective, encouragement, or someone to talk you off the ledge.

If you’ve ever felt like your “parade crowd” looked more like an empty street, this one’s for 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/