From Jail Cell to Multi-Million Dollar Deals: Jay Siano's Incredible Journey Already prone to numbing out after a loss, Jay spiraled until a DUI landed him in jail. Here's how he recovered.
By Terry Rice Edited by Dan Bova
Opinions expressed by Entrepreneur contributors are their own.
Jay Siano is an accomplished entrepreneur who has made his name in commercial real estate and branding/marketing strategy here in New York City.
His influence and expertise have touched brands like Chipotle, Starbucks, Orangetheory Fitness, massage Envy, and Squeeze among others. Beyond his professional achievements, Jay is also a seasoned podcaster and health enthusiast who shares his knowledge with a dedicated audience on his show, the Live Better Podcast.
Already prone to numbing out after the death of a loved one, Jay continued down a self-destructive path until he got pulled over for a DUI and spent a couple of nights in jail. Today, Jay joins us to talk through his challenges in family life, how to change from self-destructive to self-disciplined tendencies, and finding purpose.
In today's episode, Jay shares:
- What he learned from his DUI wake-up call
- How to build momentum via small daily wins
- Finding purpose in fatherhood
I'll share a few of my favorite quotes from my conversation with Jay below.
Hitting Bottom Before Breakthrough
"I was arrested and spent two nights in jail. That rock-bottom moment became the turning point in my entrepreneurial journey. Sometimes, it takes a drastic wake-up call to push you towards your true path."
The Entrepreneurial Mindset Shift
"When I realized no one was coming to rescue me, that's when everything changed. As an entrepreneur, you have to understand that your success is entirely in your own hands. It's on you to decide what you're going to do with your life and your business."
Building Success, One Small Win at a Time
"For entrepreneurs, success is about stacking tiny wins every day. Each day brings its own challenges and opportunities. The key to building confidence and momentum in your business is to consistently do what you say you'll do, and push yourself to tackle things you're not sure you can handle."
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