Founders Often Overestimate Early Risk

Mike Seckler entered entrepreneurship with no business background or playbook. When the dot-com crash hit, competitors disappeared overnight, capital vanished, and survival came down to making fast, uncomfortable decisions. In the middle of the chaos, Mike developed a skill most founders never build: intellectual stamina. The ability to absorb new information, pivot decisively, and rework a vision without panic or ego. Those lessons shaped the leader he is today as CEO of Justworks.In this episode, Mike shares how entrepreneurs can survive brutal business cycles, prepare for unforeseen moments, and build resilient, customer-obsessed companies that last.

In this episode, Hala and Mike will discuss:

(00:00) Introduction

(03:05) His Unlikely Path to Entrepreneurship

(09:20) Surviving the Dot-Com Market Crash

(12:50) Intellectual Stamina: The Pivoting Framework

(18:48) Joining Justworks and Leadership Approach

(23:44) Building Effective Advisory Boards for Entrepreneurs

(28:15) Customer Obsession as a Business Principle

(36:57) Mission, Values, and Culture at Justworks

(44:02) How Leaders Shape Employee Engagement

(49:57) Managing Risk During Rapid Business Growth

(53:57) Entrepreneurship Insights and Final Thoughts

Mike Seckler is the CEO of Justworks, a leading HR technology company dedicated to empowering small businesses. A seasoned entrepreneur, he has built and scaled multiple technology companies through volatile market cycles, including EmployeeEASE, which was acquired by ADP, and Euclidean Technologies, an investment management firm powered by machine learning. Mike also serves on multiple boards and is passionate about helping entrepreneurs build customer-obsessed, mission-driven companies.

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Resources Mentioned:

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

Justworks Website: justworks.com/

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Transcripts - youngandprofiting.com/episodes-new 

Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Startup, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Passive Income, Online Business, Solopreneur, Founder, Networking