How do you go from being "stuck" at $2M in revenue for years to crossing the $100M threshold?

In this episode of the Fearless Founders Club, we sit down with Carson Popinjay, CEO of Squeeze Media. Carson shares the raw, unfiltered journey of his 17-year entrepreneurial career—specifically the 11-year "grind" where growth remained flat, and the pivotal changes in 2019 that led to doubling the business year-over-year.

In this episode, we discuss:

• The "Found Revenue" Strategy: How marketing automation and mining old data can create instant growth.

• The Scaling Pivot: Why Carson moved from working in the business to working on the business.

• The Capital Dilemma: When to take on a partner and why having enough funding is the fuel for product-market fit.

• Leadership & Integrity: Managing over 6,000 employees without a single legal subpoena.

• Direct Feedback: Why "niceness" can be a silent killer for small businesses and how to implement radical transparency.

In this episode, we sit down with Ben Clark — former Amazon and KPMG leader, and recently exited founder — to break down how he built a fast-growing tech company with zero outside investment.

Ben shares the real strategy behind scaling through frugality, strong foundations, and hiring the best people, even when resources are limited. He talks about facing “cliff moments,” managing engineers, and making smart decisions when your needs grow faster than your team.

If you’re a founder trying to grow without funding, struggling with talent allocation, or navigating the early-stage grind, this episode gives you the mindset and tools to move forward with clarity.

In this episode of Fearless Founders, Ike returns to share what he learned building his second startup — and why the journey wasn’t any easier the second time around.

He breaks down the right time to raise funding, how early-stage founders can avoid common mistakes, and why managing engineers is more about clarity and communication than technical expertise.

From navigating the psychology of a second-time founder to building culture, dealing with stress, and staying focused on customer value, this conversation is packed with practical insights for anyone growing a startup.

Tune in for a candid breakdown of funding, leadership, engineering management, and the realities of building in the AI era.