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 process
Zero to One Is About Action – Stop overthinking and start moving
Don’t Spend Money Too Early – Cash preservation beats premature scaling
Hire for the Role, Not Potential – Designers ≠ operators
Never Burn Bridges – Integrity compounds over time
Your Network Is a Muscle – Make one reconnecting phone call per week
Resources & Links:
Connect with Jay!
Email: Jay@inkdstores.com
Linkedin: https://www.linkedin.com/in/jaysap/
Download the free Friday Habit Guide: https://thefridayhabit.com
01:32 Welcome to The Friday Habit
02:10 Meet Jay Sapovits: Serial Entrepreneur & Reinvention Expert
10:45 Authentic Personal Branding (White Glasses Story)
13:40 Losing Everything at 39: Hitting Rock Bottom
16:20 Early Success & the Confidence That Came With It
18:40 When Ego Meets the Financial Crisis
20:15 Starting Over: Rebuilding Confidence from Scratch
24:35 High-Stakes Negotiation & the St. Barts Pivot
29:10 Why You Should Never Burn Bridges
31:05 The Zero-to-One Playbook Every Founder Needs
37:50 The #1 Mistake New Entrepreneurs Make (Spending Too Early)
40:45 Why the First $1M Is the Hardest
43:50 Hiring the Right People Changed Everything
48:45 Pivoting Into the Merch Business & Finding Product-Market Fit
50:35 Jay’s Friday Habit: One Call That Changes Everything
52:30 Where to Connect With Jay & Final TakeawaysWhy Taking Action Beats Having The Perfect Plan