Author: Sam DeMaio

Big Dan is the kind of entrepreneur who makes quitting look impossible — because for him, it never was an option. On Episode 20 of The Relentless Podcast, Sam DeMaio brings Dan on to talk about the journey of building a business that was meant to last. From the early days of figuring it out to the hard-won lessons of scaling, Dan’s story is a reminder that resilience is the most valuable asset any business owner can have.

Why Quitting Was Never an Option for Big Dan

Dan does not romanticize entrepreneurship. He is honest about the moments when things were falling apart — when cash was tight, when deals fell through, when the weight of running a business felt unbearable. But quitting was never in the conversation. Dan explains the mindset that kept him going through the hardest times and why that refusal to quit is what separates the entrepreneurs who make it from those who do not.

Building Something Meant to Last

Dan is not interested in building something fast and fragile. He is building for the long haul — a business with strong foundations, loyal customers, and a reputation that grows with every project. Sam and Dan discuss the decisions that create lasting businesses versus those that create short-lived hustle machines. The conversation covers everything from hiring to culture to the daily habits that compound over years into massive results.

Grit, Growth, and the Long Game

At its core, this episode is about playing the long game. Dan and Sam talk about delayed gratification, the power of consistency, and why the operators who show up every single day — even when it is hard — are the ones who eventually break through. For anyone in the early stages of building a business or going through a rough patch, this conversation is the motivation you need to keep going.

Related Episodes

• Drew Farnese on the Grind of Entrepreneurship and Staying Hungry — Relentless Podcast Episode 13
• Jay Doran on Navigating Business Challenges and the Power of Adaptability — Episode 9
• W-2 to 8 Figures: How Sam DeMaio Built Showcase Remodels from Nothing

About The Relentless Podcast

The Relentless Podcast is hosted by Sam DeMaio. Subscribe on YouTube to catch every new episode.