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Josh Reeves

CEO of Gusto. Discusses the company's acquisition of Guideline to enhance services for small businesses.

Top 10 podcasts with Josh Reeves

Ranked by the Snipd community
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74 snips
Mar 18, 2025 • 25min

Customer Obsession Made Gusto A $9.6 Billion Company

Josh Reeves, Co-founder and CEO of Gusto, takes us through the journey of building a $9.6 billion payroll and HR company tailored for small businesses. He discusses the challenges entrepreneurs face with outdated payroll systems and the shift from a marketplace model to user-friendly payroll solutions. Josh emphasizes the importance of customer obsession and agility in scaling a startup, while also revealing how Gusto leverages AI to enhance support for small businesses and navigate operational hurdles.
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19 snips
Jan 15, 2025 • 1h 14min

Gusto Co-Founders: Josh Reeves, Edward Kim & Tomer London

Josh Reeves, Co-founder and CEO of Gusto, along with fellow co-founders Eddie Kim and Tomer London, share their inspiring entrepreneurial journey. They reflect on their early startup ideas, including a memorable photo-sharing venture. The founders discuss the evolution of Gusto's payroll solutions, emphasizing their commitment to customer feedback and creating a positive experience for small businesses. They also touch on navigating challenges during the COVID-19 pandemic, showcasing their dedication to supporting clients through turbulent times.
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11 snips
Jan 6, 2025 • 57min

How Gusto’s $10B founder raised $6M, built a team of 5—& hit $5M ARR in just 2 years. | Josh Reeves, Founder of Gusto

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.
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10 snips
Aug 27, 2025 • 3h 4min

SpaceX Launch: Deep Dive & Reactions | Josh Reeves, Keller Cliffton, Will Brown, Julia Steinberg, Olivia Moore, Flo Crivello

Join Will Brown, a researcher at Prime Intellect, as he unveils their new Environment Hub for reinforcement learning. Josh Reeves, CEO of Gusto, dives into his company's acquisition of Guideline to streamline small business retirement solutions. Keller Cliffton, co-founder of Zipline, shares stunning growth in drone deliveries, revealing a commitment to safety. Julia Steinberg, GM at Arena Magazine, contrasts California's infrastructure woes with China’s development prowess. Lastly, Olivia Moore from Andreessen Horowitz discusses the Consumer AI Top 100 and its insights on innovative companies.
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4 snips
Aug 2, 2024 • 1h 5min

Overcoming SMB Roadblocks: Expert tips from Gusto's Josh Reeves | Episode 1988

Josh Reeves, Co-founder and CEO of Gusto, shares insights from his entrepreneurial journey, emphasizing the importance of building products that resonate with users, particularly in the SMB sector. He discusses overcoming challenges like compliance and cybersecurity in small businesses, as well as effective growth strategies and metrics. Reeves also highlights unique marketing tactics, such as word-of-mouth referrals, and the significance of fostering deep customer connections to drive retention and satisfaction in today’s competitive landscape.
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Jun 4, 2025 • 26min

Early days building a decacorn

Josh Reeves, co-founder and CEO of Gusto, shares insights from his journey of building a multibillion-dollar people platform. He discusses the challenges of launching Gusto, particularly in payroll processing and understanding customer needs. Reeves emphasizes the importance of organic growth strategies over paid marketing, sharing a humorous anecdote about unique advertising tactics. The conversation also highlights milestones in creating a scalable payroll system tailored for small businesses, providing valuable lessons for aspiring entrepreneurs.
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May 23, 2025 • 49min

The Great Financial Services Debate

Josh Reeves, CEO of Gusto, shares insights on providing tailored payroll solutions for small businesses. Gabriel Stengel of Rogo discusses training AI for investment firms, raising debates on the trustworthiness of tech in finance. Jeff Seibert from Digits dives into the automation of bookkeeping and the challenges of merging software with financial services. Together, they explore the balance between innovation, user experience, and the evolving landscape of financial technology amidst shifting economic dynamics.
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Dec 16, 2024 • 39min

Josh Reeves: How Gusto Took The Pain Out Of Payroll

Josh Reeves, co-founder and CEO of Gusto, shares insights on revolutionizing payroll for small businesses. He discusses the founding challenges faced by Gusto's team, emphasizing the impact of simplifying payroll from a burden into a valuable tool for entrepreneurs. Reeves highlights the importance of early customer feedback and innovative team dynamics in their growth. He also addresses effective board management strategies and the essence of entrepreneurship, focusing on real-world problem-solving as a guiding principle.
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Dec 3, 2024 • 49min

Josh Reeves, CEO of Gusto – Building a $9.6 Billion Company to Serve Small Businesses

Josh Reeves, CEO and Co-founder of Gusto, leads one of the largest HR and payroll companies dedicated to small businesses. He shares insights on finding product-market fit in a complex sector and building Gusto’s embedded fintech strategy. The discussion emphasizes the evolving role of a CEO, focusing on strategic leadership and talent management. Reeves also highlights the importance of partnerships and customer feedback in enhancing services, as well as the story behind Gusto’s piggy mascot, Penny, which symbolizes reliability and support.
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Oct 18, 2024 • 1h 35min

Bloomberg Businessweek Weekend - October 18th, 2024

Ed Price, a former British trade official and geopolitical analyst, provides sharp insights on the upcoming U.S. elections and their impact on global relations. Harmit Singh, CFO of Levi Strauss & Co., discusses the evolution of denim in a casual fashion landscape. Josh Reeves, CEO of Gusto, addresses the challenges and opportunities for small businesses in today's economy. Camilla Marcus, a chef, explores the benefits of regenerative farming and sustainable practices, while Marianne Franks highlights the complexities of free speech in modern discourse.

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