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/
🔗 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/
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