Values-Driven Leadership: Gusto’s Core Philosophy with Josh Reeves

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In this episode of The Startup CEO Show, host Mark MacLeod sits down with Josh Reeves, Co-founder and CEO of Gusto, to discuss Gusto’s values-driven approach, the intricacies of scaling an SMB, and the long-term vision for Gusto.

Josh delves into critical topics such as Gusto's UI simplicity, building a warm customer experience, and maintaining company culture. He shares his unique leadership style, the importance of aligning values in hiring, and how he promotes a culture of kindness and honest feedback at Gusto.
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Key highlights:
00:00: Hiking and Meeting
10:01: Gusto's YC Journey: Committed Co-founders and Community
13:25: Engineers Built Payroll System to Secure Funding
16:53: Why Early Founders Shouldn’t Obsess Over Competitors
21:44: Solving Accountants' Payroll Challenges at Gusto
31:42: From Humanities to Tech: My Entrepreneurial Journey
36:30: Hiring Kind, Competitive, and Ambitious Talent
38:30: Advancing Mission, Entrepreneurship, and Healthcare Through Challenges
46:40: Balancing Profit, Purpose, and Community at Gusto
52:20: How a Coach Boosts Personal and Professional Growth
55:44: Founders Must Grow to Stay Aligned
01:01:09: Timing and Strategy: Keys to Investor Success
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