Mike Seckler: How to Build a Business That Thrives When Others Fail | Entrepreneurship | E384 - Young and Profiting with Hala Taha Recap

Podcast: Young and Profiting with Hala Taha

Published: 2026-02-02

Duration: 1 hr 4 min

Guests: Mike Seckler

Summary

Mike Seckler shares his journey from a liberal arts background to becoming a successful entrepreneur, emphasizing the importance of intellectual stamina and customer obsession in building resilient businesses like Justworks.

What Happened

Mike Seckler entered entrepreneurship without a formal business education, yet he successfully navigated his first company, EmployeeEASE, through the dot-com crash, a period when 80-90% of similar companies failed. He attributes this success to making fast, uncomfortable decisions and reducing team size by a third to ensure survival. This experience taught him the importance of intellectual stamina - a concept introduced to him by Ann Winblad, which involves adapting to new information and pivoting decisively without ego.

After EmployeeEASE was acquired by ADP, Seckler joined Justworks, initially as a board member, then COO, and eventually CEO. This leadership transition was initiated smoothly by founder Isaac Oates, highlighting the company's commitment to strong internal governance. Seckler emphasizes the role of effective advisory boards in guiding long-term company success, especially for businesses with distributed shareholder bases.

Seckler discusses the importance of staying close to customers, meeting with 10 CEOs daily to maintain a deep understanding of market needs. He believes that senior leaders should engage directly with customers to prevent poor decision-making and outcomes for the company. Justworks, under his leadership, focuses on being mission-driven, aiming to empower small businesses and make entrepreneurship more accessible.

The company values camaraderie, openness, grit, integrity, and simplicity, using these as a North Star for decision-making. They reinforce these values through awards and storytelling, ensuring that they remain deeply ingrained in the company culture. This approach helps the company stay resilient and maintain a strong culture, even during challenging times.

Seckler also highlights the importance of managing risk during periods of rapid business growth. He warns against over-reliance on a single large customer, which can narrow a company's market focus and lead to vulnerability. Instead, he advocates for a diversified customer base to ensure stability and growth.

In conclusion, Seckler reflects on the entrepreneurial journey, noting that many overestimate the risks of starting a business, especially early in their careers. He argues that entrepreneurship offers more control over one's environment and that starting a business in one's 20s presents a high upside with minimal downside, providing valuable experience.

Key Insights