Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hybrid world, and why mission-driven support for small businesses matters now more than ever.

What You’ll Learn:

How Mike evolved from first-time founder to CEO of Justworks
The “self-inflicted wound quotient” every founder faces—and how to reduce it
How values shape Justworks’ culture and decision-making
The impact of structured, intentional board leadership
Why Justworks pulled its IPO and why it was the right call
Lessons from integrating a remote team post-acquisition
How to stay adaptable without losing momentum
Why stepping back (even for vacation) makes you a stronger leader
Balancing in-person U.S. operations with global remote teams
The importance of staying close to your end user

Key Takeaways:

➡️ Minimize your “self-inflicted wounds”: Founders often make early decisions—co-founder choices, board composition, capital structure—that can hinder growth. Mike calls this your “self-inflicted wound quotient.” Keep it low.

➡️ Good governance starts with leadership: Don’t wait for your board to self-organize. Set norms, prep materials early, and lead it the way you’d lead your exec team.

➡️ Clarity beats comfort: From acquisitions to layoffs, Mike emphasizes over-communicating the why and making decisions that would “look good on the front page of the Wall Street Journal.”

➡️ Culture isn’t what you say—it’s what you do: Values like “comradery” and “grit” must be defined through behavior and reinforced through recognition, awards, and storytelling.

➡️ Board building is strategic: Justworks’ board includes domain-specific experts—from healthcare to global payments. Choose members like you’d build your C-suite.

➡️ Hard decisions made early pay off later: Fix the roof when it’s sunny. The cost of delay is always higher.

➡️ Remote vs. in-person is not either/or: Justworks combines in-office culture in the U.S. with distributed international teams, intentionally designing for both.

➡️ Real leadership means managing your energy: Mike learned from parenting that being the calmest person in the room is often your superpower.

➡️ Mission attracts the right people: Employees at Justworks are deeply motivated by its purpose—to serve small businesses as heroes of the economy.

Where to find Mike Seckler:

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Ep. 109 - EotW Ch.9: Tellings of the Wheel & Ch. 10: Leavetaking