Josh Pittman is the Founder and CEO of Pip, which simplifies diabetes care through safe, painless, and easy-to-use lancets. Under his leadership, the company has grown its reach across the US and expanded distribution into DTC and retail channels.

Entrepreneurship is rarely a straight path. It's a journey defined by risks, resilience, and moments that test your conviction. How can you choose between safety and growth or between holding on and letting go?

From walking away from a secure accounting career to buying his first company with help from a mentor, diabetes care entrepreneur Josh Pittman learned the hard truths of business ownership. Through losing clients, managing debt, and navigating uncertainty, he discovered that confidence is built by persistence, not success. Josh advises entrepreneurs to embrace discomfort because it signals growth.

In this episode of The Decision, Robert Hartline and Eric Jackson sit down with Josh Pittman, Founder and CEO of Pip, to discuss how he built, scaled, and sold his company. Josh shares how a mentor's belief helped launch his career, how he rebuilt after losing a major client, and why selling his business led to personal clarity.