#88: From Startup to Grown-Up: Eddie Kim, Co-founder and CTO of Gusto - Wearing different “hats” as a leader; learning to get his hands off the keyboard and enable others instead; and how to build a growth mindset
Mar 25, 2025
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Eddie Kim, Co-founder and CTO of Gusto, shares his inspiring journey of building a platform for small businesses. He discusses the nuances of co-founder dynamics and the importance of communication in leadership. Eddie reveals how he transitioned from a technical role to a leader, embracing a hands-off approach to enable his team. He also addresses the unique challenges faced by Asian founders and emphasizes a growth mindset. Bonding traditions among co-founders showcase how friendship fosters stronger professional relationships.
Thoughtfully documenting decision-making processes fosters transparency and promotes a culture of debate, ensuring team alignment and informed decisions.
Adopting a growth mindset by viewing challenges as learning opportunities enhances leadership capacity and inspires teams to embrace resilience.
Deep dives
Decision-Making Transparency
Making decisions thoughtfully is crucial in leadership, and expressing the rationale behind those decisions fosters transparency. One effective approach involves documenting the decision, articulating the reasoning, and addressing opposing viewpoints considered during the process. This not only demonstrates that various perspectives were taken into account but also reinforces to team members that their input is valued. Such a method promotes a culture of debate and reflection within the organization, ultimately leading to better-aligned teams and more informed decisions.
The Role of Luck in Career Growth
Luck plays a significant part in career paths and opportunities, often shaping pivotal moments that influence future success. For example, a chance encounter with a college roommate led to a collaborative venture that sparked the creation of Gusto. Furthermore, recognizing these moments of serendipity can deepen one's appreciation for the journey and emphasize the importance of remaining open to new experiences. Acknowledging that preparation and hard work complement these fortunate events encourages individuals to embrace their unique pathways.
Navigating Co-Founder Dynamics
Establishing clear roles among co-founders is essential for the cohesion and growth of a company. An impactful initial conversation about strengths, weaknesses, and desired responsibilities can lead to a well-defined structure that benefits the organization. This open communication helps to prevent misunderstandings and ensures that each founder can contribute effectively without ego overshadowing decisions. Over time, this practice nurtures a strong partnership built on trust and mutual respect, which is vital for long-term success.
The Impact of a Growth Mindset
Adopting a growth mindset is fundamental for effective leadership and personal development. Viewing challenges and failures as opportunities for learning can significantly enhance one's capacity to lead and innovate. For instance, engaging with mentors and consuming literature on management can provide invaluable insights and tools for navigating leadership roles. Such an approach not only benefits the leader personally but also inspires teams to embrace their own growth and resilience within the organization.
Eddie Kim is the CTO and cofounder of Gusto, which serves 400,000+ small and medium-sized businesses nationwide by helping them onboard, pay, insure, engage, and provide benefits for their teams, in one integrated, friendly, and easy-to-use platform. Eddie’s career has been shaped by chance encounters, a passion for software, and a deep commitment to growth. Before Gusto, he launched his first company—an experience that ultimately led him to reconnect with his future co-founder, Josh Reeves.
In this episode, Eddie opens up about co-founder dynamics, leadership struggles, scaling a company, and the surprising tools he uses to stay aligned with his team.
Episode Highlights & Timestamps
🔹 [00:00] - The Decision-Making Process of a Leader 🔹 [02:00] - The Origin Story of Gusto: A Half Marathon That Changed Everything 🔹 [06:00] - Co-Founder Dynamics: How Eddie, Josh, and Tomer Divided Leadership Roles 🔹 [10:00] - Managing Ego: Accepting the CTO Role Instead of CEO 🔹 [12:00] - Hands Off the Keyboard: How Eddie Transitioned from Engineer to Leader 🔹 [15:00] - The Role of Mentors: Lessons from Jeremy Stoppelman (Yelp) & Drew Houston (Dropbox) 🔹 [17:00] - Breaking Stereotypes: Being an Asian Founder of a Unicorn Startup 🔹 [20:00] - The Role of Company Values in Decision-Making & Hiring 🔹 [24:00] - Encouraging Debate in an Organization & Aligning the Team 🔹 [32:00] - Wearing Multiple Hats: The Skill Every Leader Must Master 🔹 [38:00] - The Highs and Lows of Hiring Executives 🔹 [40:00] - Gusto’s AI Initiatives: How AI is Revolutionizing Payroll & HR for Small Businesses 🔹 [45:00] - Eddie’s #1 Advice for Founders: The Power of a Growth Mindset