Josh Pittman

Josh Pittman – The Decisions That Define Entrepreneurs

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.

Here's a Glimpse of What You'll Learn

[3:23] How an accounting career led Josh Pittman to discover his entrepreneurial drive
[9:12] Josh talks about purchasing his first company at age 27 with the help of a mentor
[11:05] What Josh learned from losing a major client after purchasing his first business
[16:56] How joining EO gave Josh guidance and confidence through tough decisions
[19:39] Josh’s decision to restructure ownership and buy out investors
[27:06] How launching Pip led Josh to sell his first company
[32:19] The emotions of selling a company after 12 years
[38:35] Josh explains the role of therapy in his sobriety journey

In This Episode

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.

Quotable Moments:

“Not only is where we are in life a result of our own decisions, but other people’s decisions.”
“I wanted to be a part of something bigger than myself, something we were building.”
“You find the confidence within yourself to just do whatever it takes to overcome the challenge.”
“You want to sell your business when it’s on the way up, not when it’s on the way down.”
“I might give up, but not today. Today, I’m going to focus on being better.”

Action Steps:

Embrace discomfort as growth: When challenges feel overwhelming, it’s often a sign you’re growing. Facing discomfort head-on builds resilience and confidence that outlasts short-term wins.
Seek mentors who believe in you: Having someone willing to invest time or resources in your vision can change your trajectory. Their faith provides accountability and courage when self-doubt sets in.
Prepare for the worst-case scenario: Clearly defining the downside of a decision helps neutralize fear. When risk becomes measurable, it becomes manageable.
Build peer support through community: Joining entrepreneurial groups like EO gives founders a network of people who understand their struggles. Sharing openly with peers creates perspective and strength in isolation.
Prioritize personal well-being over performance: Success means little without mental clarity and balance. Reassessing habits — like Josh’s journey toward sobriety — creates the space to lead with focus and purpose.