Leap Academy with Ilana Golan
Episode 151: What It Takes to Scale a Company Without Breaking It | Mike Seckler, Justworks CEO
Date: March 24, 2026
Episode Overview
In this episode, Ilana Golan sits down with Mike Seckler, CEO of Justworks, to explore the candid realities of starting, scaling, and leading companies—without losing your way (or your sanity) during the journey. As a serial entrepreneur and longtime board member, Mike shares his hard-earned lessons from building teams, navigating crises, fostering resilience, and shaping company culture. The conversation delves into making tough decisions, transitioning leadership, avoiding self-inflicted wounds, and embracing change in a world upended by technology, especially AI.
Key Discussion Points & Insights
1. Early Influences and Starting Out (02:42 – 07:04)
- Non-linear Path: Mike studied geology and history in college, driven by curiosity rather than a set career plan. This broad education, while not directly related to tech, helped develop analytical thinking and communication.
- The Entrepreneurial Spark: Exposure to early internet use in college and close friendships led Mike to co-found his first company, inspired by the possibilities he saw ahead of the dot-com boom.
- Family Context: Mike grew up in a stable, supportive family, which instilled confidence but didn’t necessarily prepare him for the emotional complexity of entrepreneurship.
"I just was moved to wherever the energy felt real at the time."
— Mike Seckler (04:35)
2. Building and Surviving: First Company and the Dot-com Bust (07:04 – 14:46)
- Employees: Started in 1996, later acquired by ADP, now one of its largest divisions.
- Naivety and Growth: Early mistakes were mitigated by partnering with more experienced professionals.
- Dot-com Boom and Bust:
- The “oxygen” of capital vanished suddenly, forcing rapid, hard decisions—one-third of the team let go, pivoting to cash generation rather than “growth-at-all-costs.”
- Resilience and Perspective: The team learned that you often feel on top of the world just before disaster—and vice versa.
"We felt best right before things were about to be at their worst."
— Mike Seckler (11:49)
"As bad as that period was—I wouldn’t want to go through that again—there's a lot of good things that came... strength and confidence around actually how to run a business."
— Mike Seckler (14:34)
3. After the Exit: Building Again and Learning What Matters (15:06 – 19:13)
- Euclidean Technologies: Founded post-ADP; applied AI to public market investing. Enjoyed intellectual challenge but missed having a large team and meaningful leadership responsibilities.
- Timing & the Housing Crisis: Launching just before the financial crisis ultimately created strong early returns and learning opportunities.
4. The Justworks Journey: Board Member to CEO (19:13 – 25:53)
- Networking & Board Work: Mike got involved in the NYC tech scene, served on several boards—including as an early independent director of Justworks.
- Unique Founder-Operator Transition: After years on the board, Mike agreed to join Justworks as COO, then transitioned to CEO when founder Isaac Oates sought a change.
"I went from being his board member, to working for him. And then we did another... It became clear about a year in that Isaac had a two step transition in his mind—maybe you ought to do the CEO thing."
— Mike Seckler (24:03)
5. Leadership Lessons: Perspective, Roles, and Company Values (25:53 – 27:26)
- Multiple Angles: Board member, founder, executive—all offer different perspectives on creating great companies.
- Core Focus: Success comes down to taking care of customers and creating an environment for talented people to do their best work.
"If you can do those two things right, you're going to have a great company. The details on how to do that... there's a lot to it, but it all does come together at that level."
— Mike Seckler (27:15)
6. Patterns from Working with 14,000 Businesses (27:26 – 33:25)
- Beyond the Data: Real lessons come from the “psychological journey” of leaders, not just big data.
- Self-Inflicted Wounds:
- The biggest differentiator: minimize internal friction.
- Examples include bad co-founder dynamics, misaligned investors, and chasing early customers at the expense of strategic vision.
- Intentional Foundation: Mission, vision, and values must be more than slogans—they must be lived in the organization.
"The best ones have a low self inflicted wound quotient... Several years in you realize 20, 30% of your energy is just paying down these debts all the time."
— Mike Seckler (29:33)
- Go Slow to Go Fast: Invest in the right foundational decisions—be deliberate when it matters most; accelerate once the fundamentals are solid.
"Go slow to go fast later, I think, is a way to balance those two things."
— Mike Seckler (32:31)
7. The Loneliness of Founders—and How to Fix It (33:25 – 37:55)
- Inevitable Isolation: Leadership, especially during hard times, can feel painfully lonely.
- Peer Groups: Mike’s solution—a group of founders who met monthly for over fifteen years, providing a safe space for vulnerability and advice (shared only through personal experience).
"The group... we met every month. And... once a year we'd go on a retreat together. ...To be able to benefit from their experience has been priceless."
— Mike Seckler (34:51)
- Group Structure: Initially rigorous—updates, timekeeping, presentations, sharing experiences (not direct advice). Evolved over time as trust deepened.
8. Navigating Change and Technological Disruption (37:55 – 43:22)
- AI and the Pace of Change: The whirlwind of AI is possibly the biggest dislocation Mike has seen in his career.
- Advice to Teams: Lean into change—don't cling to past practices. Ongoing adaptation and learning are essential to remain relevant.
"With AI, this is a time to like, lean into the change, be the change, manifest it, and not to like hold on tightly to the way things used to be."
— Mike Seckler (38:55)
- Justworks’ Three AI Impact Areas:
- Market: Anticipating new customer types and sectors.
- Customer Expectations: Predicting the shift toward conversational, instant insights over manual data wrangling.
- Internal Operations: Leveraging automation for operational efficiency while focusing human effort on high-touch, nuanced customer moments.
"I think the real area of differentiation is going to be in how we operate... your unique context, your data, your knowledge... manifesting in whole new ways."
— Mike Seckler (41:52)
9. What Makes Justworks Different? (43:29 – 45:33)
- Focuses squarely on small businesses—especially those with fewer than 100 employees—while competitors “move up-market.”
- Offers not just tools but full HR, compliance, and benefits coverage, freeing founders from regulatory headaches to concentrate on their core business.
"You can focus on what's really unique in your business. And that frees up entrepreneurs to do amazing things."
— Mike Seckler (45:13)
Notable Quotes & Memorable Moments
-
On Misreading the Future:
"We felt best right before things were about to be at their worst."
(11:49 — Mike Seckler) -
On Company “Injuries”:
"The best ones have a low self inflicted wound quotient."
(29:33 — Mike Seckler) -
On Peer Support:
"To be able to benefit from their experience has been priceless... you don't need to do it alone."
(34:51 — Mike Seckler) -
On Change:
“This is a time to lean into the change, be the change, manifest it and not to hold on tightly to the way things used to be."
(38:55 — Mike Seckler) -
On Leadership Simplicity (and complexity):
"Be the best for customers and create the best environment for incredible people to come and do their best work. It is that simple."
(27:14 — Mike Seckler)
Timestamps for Key Segments
- 02:42 — Mike’s unlikely college path and its impact
- 07:04–08:12 — Launching first company, early mistakes and team building
- 09:22–14:46 — Dot-com bust: Leading through crisis and layoffs
- 15:06 — Why start another company post-acquisition?
- 19:13–21:00 — Board work, NYC tech community, joining Justworks as an advisor
- 24:19–25:53 — Transitioning from COO to CEO
- 27:26 — Recurrent patterns among 14,000 small businesses
- 29:39–33:25 — Self-inflicted wounds and the importance of foundational decisions
- 33:25–37:55 — Combating founder loneliness through long-term peer groups
- 38:49 — Coping with tech and societal change at Justworks
- 43:50–45:33 — Who should choose Justworks VS other HR platforms?
Conclusion & Practical Takeaways
- Get Foundation Right: Don’t rush early crucial decisions (co-founders, investors, values). These choices have years-long implications.
- Remember You're Not Alone: Founder isolation is real but peer support is available—make building your peer group a priority.
- Embrace Relentless Change: Today’s market, especially with AI, will reward those who seek adaptation over nostalgia.
- Scale Deliberately: Go slow on mission-critical decisions, then accelerate when ready.
Connect with Mike Seckler:
- Justworks Website
- LinkedIn: [Mike Seckler, CEO of Justworks]
For More Leap Academy Resources:
This episode is a must-listen for founders, leaders, and anyone facing inflection points in their career or business journey, providing not just inspiration but concrete frameworks to scale—without breaking what matters most.