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/

X (Twitter): https://x.com/TuliKrausInstagram: https://www.instagram.com/blackbird.recruiting/LinkedIn: https://www.linkedin.com/in/tuli-kraus/

Sponsored by Blackbird RecruitingTired 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.

In this episode of the What It Takes Podcast, we sit down with Avi Singer, Founder and CEO of Showd.me - a leader who hacked the corporate ladder from day one and later built a multi-million-dollar SaaS company without raising a single dollar of venture capital.

Avi breaks down his journey from a $65k entry-level role at DoubleClick (later acquired by Google) to bootstrapping and scaling a profitable, remote-first business. He shares the unfiltered reality of entrepreneurship: the moments he nearly quit, the pressure of making payroll, and the tough leadership decisions that come with being the one in charge.

This conversation is a masterclass in strategic career planning, sustainable company building, and rejecting Silicon Valley hype in favor of real, durable success. Whether you’re climbing the corporate ladder, building a startup, or trying to lead a team that actually cares, this episode delivers insights you won’t hear anywhere else.

💡 In This Episode, We Cover:

◼️ How Avi leveraged an Ivy League degree to land his first $65k job◼️ Adopting a “future VP” mindset from day one in corporate life◼️ Why he tells 99% of people not to start a tech startup◼️ The accidental pivot from a “nice-to-have” to a true “must-have” product◼️ Building a 50-person remote team across 13 states—with no office◼️ The hardest CEO skill: knowing when to walk away from easy money◼️ How to identify, promote, and retain rockstar employees—and when to let go◼️ The servant-leadership philosophy that creates real loyalty◼️ Navigating founder identity crises and near burnout◼️ Why most software companies fail—and how to avoid the same traps◼️ Avi’s non-negotiable advice for first-time founders

⏱️ Chapters

00:00 From Columbia to Corporate: Hacking the $65k Start

11:45 The Terminal Degree: Planning Your Career Like a Chess Game

14:27 Why I Left a $250k+ VP Job to Start From Scratch

21:42 The Pivot That Saved the Business

30:12 Hiring (and Firing) for a Team That Runs Without You

34:50 Building a Remote Culture That Actually Works

53:48 The Vacation Test: How to Know You’re a Good Leader

1:03:03 From Unicorn Dreams to Building a Real Business

🔗 Connect with Avi Singer

LinkedIn: https://www.linkedin.com/in/avisinger/Website: https://www.showd.me/

🔗 Connect with Tuli KrausX (Twitter): https://x.com/TuliKrausInstagram: 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.

In this powerful episode of the What It Takes Podcast, we sit down with Sam Shvarzblat, a contractor and entrepreneur who has lived both realities—being the boss and walking away from being the boss. Sam built a construction company from scratch in his early 20s, scaled it to multiple large projects, battled cash-flow pressure, burnout, family expectations, and eventually made the toughest decision an entrepreneur can make: closing his own company.

This conversation is brutally honest. Sam opens up about the identity crisis founders face, the ego tied to “being your own boss,” how cash flow really works behind the scenes in construction, and why moving his family to a new community changed everything. Whether you're an entrepreneur, contractor, or someone who’s ever wondered if stepping away is failure or growth—this episode will hit home.

This is a raw masterclass in humility, rebuilding, and what it really takes to balance business, family, faith, and your own well-being.

💡 In This Episode, We Discuss:

◼️ Sam’s early journey into construction and why he skipped working for others ◼️ The harsh truth about being a young business owner in the trades ◼️ Why most contractors struggle with cash flow—and how to fix it ◼️ The “friends & family discount” myth ◼️ The realities of managing 10+ simultaneous construction projects ◼️ Burnout, identity, and the moment Sam knew he had to step away ◼️ Moving from Lakewood to Monsey: lifestyle, community, and values ◼️ Economic slowdown, stalled projects, and clients pulling deposits ◼️ What it feels like to shut down your own company ◼️ How Sam rebuilt his life, career, and sense of direction ◼️ What every new entrepreneur should understand before starting

⏱️ Chapters

00:00 When the Dream of Being Your Own Boss Starts to Crack

2:19 Why I Refused to Become a Copy-Paste Contractor

6:19 Friends, Family & the Truth About ‘Discount Work’

7:06 Why Friends Should Pay MORE—Not Less

8:26 At My Peak: Running 10 Projects with a Tiny Team

10:25 The Cash-Flow Trap That Destroys Most Contractors

13:10 The Question I Never Wanted to Answer: Why I Closed My Company

16:46 The Commute That Broke Me: 4:30 AM Drives & Endless Inspections

17:55 When Clients Pump the Brakes & the Economy Turns on You

26:56 The Identity Shift of Going from a Boss to an Employee

34:49 Being an Employee vs Doing Your Own Thing

37:35 The Biggest Lessons I’ve Learned in These Chapters of My Life

🔗 Connect with Sam Shvarzblat: Instagram: https://www.instagram.com/samshvarzblat/?hl=en LinkedIn: https://www.linkedin.com/in/samshvarz/

🔗 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/

This episode is sponsored by Blackbird Recruiting. Tired of sifting through unqualified résumés? Let Blackbird Recruiting find you top talent so you can focus on growing your business. Visit blackbirdrecruiting.com to learn more.