In this episode of the What It Takes Podcast, we sit down with Hershy Goldstein, CEO and Co-Founder of FRIDAY—a SaaS founder who went from unemployment to building a thriving tech startup serving over 1,200 customers.

Hershy breaks down his journey from leaving a secure career to bootstrapping and scaling a profitable, remote-first business. He shares the unfiltered reality of entrepreneurship: the moments he almost shut everything down, the pressure of scaling fast, and the leadership decisions that come with being the one in charge.

This conversation is a masterclass in career decisions, startup growth, and building a sustainable business. Whether you’re considering leaving a corporate job, building a startup, or leading a remote team, this episode delivers insights you won’t hear anywhere else.

💡 In This Episode, We Cover:

◼️ How Hershy turned unemployment into a SaaS startup success story ◼️ The pivotal moment that almost ended the company ◼️ Scaling to 1,200 customers without investors or venture capital ◼️ Building a fully remote team across multiple states ◼️ Recognizing when to leave a secure career to pursue entrepreneurship ◼️ Handling founder burnout and mental pressure while growing a company ◼️ How to identify, retain, and lead high-performing employees ◼️ Lessons from the accidental product pivots that saved the business ◼️ Hershy’s non-negotiable advice for first-time founders

⏱️ Chapters:

0:00 Intro - The $250k Question

11:54 The Breakthrough: Conquering Imposter Syndrome at Fingercheck

19:24 The 9-Year Grind: From Support to Manager to $250k

22:30 The Coaching Epiphany: Discovering a Hidden Superpower

37:19 The Final Straw: Why I Quit My Cushy Job

42:09 The Wilderness: Depression, COVID, and Consulting

54:10 Startup Nightmare: The Week Our Bank Vanished

1:02:55 Founder Truths: Surrender, Hiring, & The Fear of Content

1:20:38 Final Advice: Should You Leave Your Safe Job?

LinkedIn: https://www.linkedin.com/in/hershey-goldstein/Website: https://fridayapp.com/

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