What It Takes to Scale a Company Without Breaking It | Mike Seckler, Justworks CEO | E151

In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies.

Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management.

In this episode, Ilana and Mike will discuss:

(00:00) Introduction 

(02:42) From History and Geology Student to Entrepreneur

(07:05) The Early Days of Founding Employease

(09:08) Navigating the Dot Com Crash as a Founder

(14:53) Selling to ADP and Starting a New Venture

(17:23) Joining Justworks: From Board Member to COO

(24:37) Lessons from Transitioning to Justworks’ CEO

(26:00) The Biggest Blindspots for Small Businesses

(31:58) How to Beat Founder Loneliness

(36:34) Adapting to a Rapidly Evolving Market

(42:03) Justworks: Empowering Small Businesses for Growth

(44:49) Review and Q&A: BREAD Productivity Framework

Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams.

Connect with Mike:

Mike’s LinkedIn: linkedin.com/in/mikeseckler 

Resources Mentioned:

Justworks Website: https://www.justworks.com 

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