Building a Startup Nearly Broke Me | What It Takes to Leave a Secure Career

YV
3 hours ago
2 min read

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