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 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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