How Gusto’s $10B founder raised $6M, built a team of 5—& hit $5M ARR in just 2 years. | Josh Reeves, Founder of Gusto
Jan 6, 2025
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Josh Reeves, Founder and CEO of Gusto, discusses his impressive journey in creating a payroll software giant now valued at $9.5B. He emphasizes the power of starting small, focusing on tech startups in California, and the value of iterating on product with a lean team. Reeves shares how customer interviews clarified their target market and the significance of addressing real pain points. He also reflects on the role of Y Combinator in accelerating their growth, highlighting the importance of maintaining a strong company mission and fostering customer loyalty.
Focusing on a niche pain point in payroll for small businesses allowed Gusto to build a meaningful and impactful product.
Maintaining a small team in the early stages facilitated faster decision-making and enabled effective iteration on the product.
Early customer feedback and insights directly shaped Gusto's offerings, ensuring they genuinely addressed user needs and promoted satisfaction.
Deep dives
Founding Vision and Early Days of Gusto
Josh Reeves emphasizes the initial challenges and motivations that drove the creation of Gusto, highlighting a focus on solving significant pain points for small businesses. The founding team, comprised of second-time entrepreneurs, intentionally targeted payroll as a critical area in which they could make a meaningful impact. Despite raising $6 million from notable investors, they operated frugally in the beginning, launching with just a five-person team and prioritizing the needs of small businesses over larger enterprise clients. This commitment to address a niche, albeit unexciting, service like payroll laid the foundation for their success, as they recognized the need for simpler, more accessible solutions.
The Power of Customer Feedback
Josh explains how understanding customer pain points played a significant role in refining Gusto's offerings. Early interactions with accountants and small business owners revealed a frustrating reality of manual payroll processes, motivating the team to innovate. This customer-driven approach led to insights that shaped their product, ensuring it was not only functional but also genuinely addressed the needs of users. They actively sought feedback through interviews and customer discussions, leading to a product design that prioritized ease of use and accessibility.
Building Trust Through Innovation
The podcast discusses Gusto's focus on creating a trustworthy product that simplifies payroll management for small businesses. Josh highlights that, despite the complexities involved in payroll, they aimed to streamline the process, reducing the manual effort required from business owners. Early adopters not only appreciated the modern approach but also expressed a sense of relief that they could finally rely on technology to manage payroll effectively. This resulted in strong word-of-mouth referrals, revealing that when products genuinely solve pressing issues, users readily share their positive experiences with others.
Significant Growth Milestones
Gusto's early growth trajectory was marked by significant milestones, reflecting their success in the market. Josh details how they scaled from 1,000 customers in their first year to 9,000 in the second, showcasing their ability to capture market demand. Recognizing the importance of expanding their geographical reach, Gusto dedicated efforts towards obtaining nationwide coverage, which required extensive research into local and state tax compliance. This strategy not only validated their initial business model but also positioned them as a reliable partner for small businesses across the country.
Maintaining Momentum and Focus
The conversation touches on the challenge of maintaining momentum while growing a startup, underscoring the importance of focusing on customer satisfaction and sustainable business practices. Josh reflects on how Gusto avoided the common pitfall of rapidly scaling without evaluating customer retention and satisfaction metrics. He underscores that while valuations and headcount are notable achievements, they are byproducts of creating genuine value for customers. By emphasizing a long-term vision and a mission-driven culture, Gusto has been able to support its growth without compromising its core values.
Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in California. It was exceptionally niche, and it worked.
After YC, he raised a $6M seed round from tier 1 angels, back when large seed rounds were not at all common. But, unlike others, he didn't spend the money. He kept his team small as they iterated on the product. By the time they raised their $20M Series A, they were only 10-15 people.
Here's the story of how they got started, gained initial traction, and took off.
Why you should listen:
Why starting super small can lead to massive outcomes.
Why you need a huge, no-brainer pain point to succeed.
How to use early customer interviews to deeply understand your ICP.
Why small teams allow for faster decision-making and execution.
Why deep passion about the problem set is so important.
Keywords Gusto, Josh Reeves, entrepreneurship, startup, payroll, small business, Y Combinator, business model, innovation, technology, fundraising, startup, product-market fit, team building, customer satisfaction, growth strategy, small business, Gusto, entrepreneurship, SaaS