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#91: From Startup to Grown-up: Mike Seckler, CEO of Justworks — how to run a great board process, how to avoid self-inflicted wounds, and the value of taking big risks early in your career

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Manage episode 480855765 series 2991408
Content provided by Alisa Cohn. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Alisa Cohn or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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:

Connect with Alisa!

Follow Alisa Cohn on

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

  continue reading

92 episodes

Artwork
iconShare
 
Manage episode 480855765 series 2991408
Content provided by Alisa Cohn. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Alisa Cohn or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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:

Connect with Alisa!

Follow Alisa Cohn on

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

  continue reading

92 episodes

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