In this episode of The Friday Habit, host Mark Labriola II sits down with serial entrepreneur Jay Sapovits, a builder who knows firsthand how to turn setbacks into springboards.Jay shares his raw journey—from early success in sports media and private aviation, to losing everything during the financial crisis, to rebuilding and scaling Inked, a custom merch company on track to surpass $5M in revenue.🧠 Key Takeaways Entrepreneurship Isn’t a Straight Line – Success, failure, and reinvention are all part of the processZero to One Is About Action – Stop overthinking and start movingDon’t Spend Money Too Early – Cash preservation beats premature scalingHire for the Role, Not Potential – Designers ≠ operatorsNever Burn Bridges – Integrity compounds over timeYour Network Is a Muscle – Make one reconnecting phone call per weekResources & Links:Connect with Jay!Email: [email protected]: https://www.linkedin.com/in/jaysap/ Download the free Friday Habit Guide: https://thefridayhabit.com01:32 Welcome to The Friday Habit02:10 Meet Jay Sapovits: Serial Entrepreneur & Reinvention Expert10:45 Authentic Personal Branding (White Glasses Story)13:40 Losing Everything at 39: Hitting Rock Bottom16:20 Early Success & the Confidence That Came With It18:40 When Ego Meets the Financial Crisis20:15 Starting Over: Rebuilding Confidence from Scratch24:35 High-Stakes Negotiation & the St. Barts Pivot29:10 Why You Should Never Burn Bridges31:05 The Zero-to-One Playbook Every Founder Needs37:50 The #1 Mistake New Entrepreneurs Make (Spending Too Early)40:45 Why the First $1M Is the Hardest43:50 Hiring the Right People Changed Everything48:45 Pivoting Into the Merch Business & Finding Product-Market Fit50:35 Jay’s Friday Habit: One Call That Changes Everything52:30 Where to Connect With Jay & Final TakeawaysWhy Taking Action Beats Having The Perfect Plan