In this episode of the What It Takes Podcast, we sit down with Abe Breuer, CEO of John To Go—a self-made entrepreneur who built a multi-million-dollar empire in an essential but often overlooked industry and achieved a successful private equity exit.

Abe breaks down his 20-year journey from selling his first computer company as a teenager to scaling a portable sanitation business into a $50M national leader. He shares the unfiltered reality of entrepreneurship: the partner who quit during the first brutal winter, near-death cash flow moments, and the unconventional employee strategy that turned a secretary into a $280k-a-year partner.

This conversation is a masterclass in resilience, operational scaling, and leadership mindset. Whether you’re starting a service business, struggling to scale, or curious about exits and life after selling, this episode delivers hard-earned lessons you won’t find in textbooks.

💡 In This Episode, We Cover:

◼️ How Abe built his first company at 16 and sold it for $25k◼️ The “walk between the drops” philosophy learned from his parents◼️ Scaling revenue to $50M without losing control◼️ The partner who walked away—and the brother who stayed to build a legacy◼️ Managing ADHD as a superpower using pen, paper, and ruthless systems◼️ Why Abe never gives raises—and the bonus system that creates extreme loyalty◼️ The New Yorker article that changed everything and attracted private equity◼️ The harsh reality of scaling too fast and running out of cash◼️ Selling the business: identity loss, regret, and what comes next◼️ His current venture in the challenging world of assisted living (ALFs)

⏱️ Chapters:

0:00 Intro – Meeting in the Shul & the Founder of John To Go10:11 Early Hustle – Selling a Computer Company at 1616:11 First Major Bet – Buying a 24-Unit Building with $400k20:20 The Birth of John To Go – A Partner, a Stick Shift Truck & the First Winter23:02 The Pivot – Bringing His Brother in as the Right Partner32:20 Scaling Secrets – From $400k to $50M in Revenue39:45 The New Yorker Call That Changed Everything

57:32 The $280k Employee – A Bonus System That Creates Partners1:04:14 Life After the Exit – Identity, Travel & Starting Over1:07:37 Final Advice – Would He Do It All Again?

🔗 Connect with Abe BreuerInstagram: https://www.instagram.com/breuerabe/LinkedIn: https://www.linkedin.com/in/abe-breuer-a339725/

🔗 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 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.