The Logan Bartlett Show

EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses

Jul 26, 2024

Josh Reeves, Founder and CEO of Gusto, discusses the early days and strategic growth of Gusto, highlighting the importance of proving product viability before scaling. He emphasizes building a culture aligned with company values, work-life balance, long-term success, and empowering teams for efficient product development. Reeves also shares insights on hiring executives, company growth, and Gusto's vision to become an entrepreneurship platform.

01:34:05

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Episode guests

Josh Reeves

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Podcast summary created with Snipd AI

Quick takeaways

Gusto's success lies in targeting small businesses, aiding entrepreneurs with simplicity and accessibility.

Strategic growth includes geographic expansion, unit economics focus, and intentional hiring practices.

Cultivating a cohesive team through values alignment and work-life balance fosters long-term success.

Diversifying product offerings, focusing on customer needs, and simplifying processes drive Gusto's evolution.

Deep dives

Gusto's Founding Principles and Journey

Gusto's co-founder and CEO, Josh, discusses Gusto's evolution from its founding in 2011 to becoming a multi-billion dollar business. The podcast explores Gusto's early days, focusing on finding product-market fit in a narrow market segment. It delves into the company culture, executive hiring, and their journey to scale into the thriving business it is today.

Gusto Took Years to Build 50-State Coverage

01:03

Gusto Has Pods

01:02

Work: More Than Just a Paycheck

00:28

Intro

2min

Building Gusto: From Founding to Strategic Expansion

17min

Building a Business and Navigating Challenges

10min

Emphasizing Company Values and Ownership Mentality

24min

Exploring Work-Life Balance and Long-Term Success at Gusto

4min

Exploring Influential Figures and Building a Leadership Team

3min

Evolution of Product Structure and Team Empowerment

8min

Founder Advice on Hiring Executives and Company Growth

25min

Long-term vision and impact goals for Gusto

2min

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: Justin Hrabovsky

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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 of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.

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The Logan Bartlett Show

EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

Gusto's Founding Principles and Journey

Gusto's Customer Focus and Market Range

Building a Scalable Business Model

Cultivating Values and Company Culture

Focus on Work-Life Balance and Sustainable Growth

Reframing the Concept of Work-Life Balance

Strategic Evolution of Product Offerings and Market Expansion

Gusto Took Years to Build 50-State Coverage

Gusto Has Pods

Work: More Than Just a Paycheck

Remember Everything You Learn from Podcasts