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.