Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of humility and helpfulness, along with lessons he’s learned in hiring executives. We also explore the future of Gusto and the opportunities that lie ahead for the business.

(00:00 ) Intro

(00:36 ) Early Days and Product Market Fit

(01:02 ) Building a Scalable Business

(01:41 ) Gusto's Core Offerings and Customer Focus

(02:51 ) Challenges and Strategies in Payroll

(05:40 ) Expanding Gusto's Reach

(10:11 ) Customer Feedback and Product Development

(23:03 ) Hiring and Company Culture

(29:23 ) Values and Leadership at Gusto

(37:14 ) Sustaining Passion and Long-Term Vision

(43:27 ) Balancing Growth and Sustainability

(46:29 ) Balancing Competition and Kindness in Startups

(46:38 ) The Importance of Team Collaboration

(47:47 ) Navigating Feedback: Kindness vs. Niceness

(48:25 ) Hiring for Ambition and Humility

(49:57 ) Aligning Company Values with Success

(53:11 ) Work-Life Integration at Gusto

(56:11 ) Building a Long-Term Oriented Business

(57:15 ) Mentorship and Learning from Other Founders

(01:00:09 ) Structuring and Scaling Product Teams

(01:06:16 ) Organizational Design and Leadership

(01:08:31 ) Hiring Executives and Internal Growth

(01:13:13 ) The Journey of Rebranding to Gusto

(01:21:05 ) The Role of a CEO in a Growing Company

(01:28:39 ) Fundraising and Investor Relations

(01:33:14 ) Future Goals and Impact of Gusto

(01:35:48 ) Conclusion and Final Thoughts

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Sam Dewees and JR Bohannon

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.