The Most Valuable Things I Learned From Building and Selling 4 Companies

In this episode of the What It Takes Podcast, host Tuli Kraus sits down with Shai Stern — entrepreneur, investor, and advisor — to talk about building multiple companies from scratch, what separates great employees from mediocre ones, and what 30 years in business actually teaches you about people, sales, and showing up. Shai Stern didn't come from money. He grew up in Teaneck, New Jersey, dropped out of YU, got married young, and needed parnassah fast. What followed was four companies built with his partner Seth Farman — starting with a conversation over vintage seltzer on Pesach — that spanned SEC filings, business formations, background checks, and payment processing. He sold them all. And then started again. Along the way, Shai learned things no business school teaches: how to close your first client when your father's chavrusa thinks you're a fool, how to handle a valued employee who gets poached, why firing people is one of the hardest things he's never gotten good at, and what makes someone like Michelle — his chief of staff for 13-plus years — genuinely irreplaceable. He's also brutally honest about what he got wrong. Waiting too long to let people go. Trusting people who weren't honest. Letting ambition outrun organizational discipline. This episode is one of the most real, wisdom-packed conversations we've had on this podcast — and it applies whether you're a W-2 employee trying to level up or a founder building something from nothing. If you're trying to figure out what it actually takes to grow in your career or your business, this one is for you. 💡 In This Episode, We Cover: ◼️ How Shai went from a W-2 employee to building four companies with one partner and zero partnership agreements ◼️ The Pesach conversation over vintage seltzer that launched Vintage Filings ◼️ What his father taught him about learning before work — and why it stuck for 30 years ◼️ The first client rejection that drove him harder than any yes ever could ◼️ How he expanded a business to all 50 states in under 60 days using Chabad ◼️ What makes Michelle McClosky the best hire he ever made — and what made his worst hire so painful ◼️ How COVID nearly destroyed V-Check Global and what saved it ◼️ The right way to ask for a raise, handle rejection, and set yourself up for a yes ◼️ What separates salespeople who crush it from those who plateau ◼️ Why fear has no place in sales — and how to actually get it out of your system ⏱️ Chapters 0:00 Teaneck to Teaneck: Shai's Background, Family & Early Influences 7:58 The Pesach Handshake: How Vintage Filings Was Born Over Seltzer 15:02 Getting the First Client: Rejection, Persistence & Humble Confidence 23:03 Selling Vintage Filings, Building V-Corp & Expanding to All 50 States With Chabad 28:30 V-Check Global, COVID & What Happens When Your Business Falls Off a Cliff 40:17 Best Hire, Worst Hire & What Loyalty Actually Looks Like in Business 55:14 How to Ask for a Raise, Handle Rejection & Make Yourself More Valuable 1:09:08 Sales Without Fear: What 30 Years Taught Shai About Relationships & Parnassah 🔗 Connect with Shai Stern LinkedIn: https://www.linkedin.com/in/shaistern1 Phone: 917-579-3107 Email: stern@gotavi.co Website: gotavi.co 🔗 Connect with the Host — Tuli Kraus Instagram: https://www.instagram.com/blackbird.recruiting/ LinkedIn: https://www.linkedin.com/in/tuli-kraus/ Blackbird Recruiting Hiring the wrong person is expensive — not just financially, but culturally. Blackbird Recruiting helps growing companies hire people who actually perform, so you can spend less time filtering résumés and more time building your business.