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

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? 🔗 Connect with Hershy Goldstein LinkedIn: https://www.linkedin.com/in/hershey-goldstein/ Website: https://fridayapp.com/ https://www.youtube.com/@UCBesHuegt2AQ1NmBjq-SHeQ 🔗 Connect with Tuli Kraus X (Twitter): https://x.com/TuliKraus Instagram: https://www.instagram.com/blackbird.recruiting/ LinkedIn: https://www.linkedin.com/in/tuli-kraus/ Sponsored by Blackbird Recruiting Tired of sorting through unqualified résumés? Blackbird Recruiting helps you hire top talent—so you can focus on growing your business. Visit blackbirdrecruiting.com to learn more.