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

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

🎙 Listen to the show

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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.

Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful discussions about hiring, motivations, and success I've ever had on the podcast. It was truly enjoyable to sit down with a seasoned portfolio founder.

(00:00) Introduction and Episode Overview

(01:03) Market Reflections and Ramp's Growth

(04:01) Artificial Intelligence in Business

(10:09) Ramp's AI Implementation: Toby the Slack Bot

(16:49) AI's Impact on Business Models and Hiring

(31:15) The Future of Organizational Structure

(31:36) The Evolution of Bookkeeping

(33:49) The Impact of Automation on Bookkeeping Jobs

(35:31) Streamlining Expense Management with Ramp

(37:00) The Concept of Self-Driving Money

(38:09) AI Integration in Ramp's Services

(39:38) Zero Touch AI and Customer Experience

(40:54) Agentic AI and Practical Applications

(49:15) Balancing Autonomy and Centralization in Organizations

(56:09) Developing New Products at Ramp

(01:04:01) Resource Allocation in Organizations

(01:05:00) Creating Conditions for Success

(01:08:37) Balancing Existing and New Products

(01:11:02) Hiring for Curiosity

(01:16:09) The Pursuit of Perfection

(01:21:21) The Joy of the Process

(01:24:37) Building a Timeless Product

(01:33:15) Conclusion and Reflections

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

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

🎙 Listen to the show

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

Follow on Socials

📸 Instagram - https://www.instagram.com/theloganbartlettshow

🐦 Twitter - https://twitter.com/loganbartshow

🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow

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.

Klarna CEO Sebastian Siemiatkowski led the rise from a profitable business to their peak $50 billion valuation, in which they were burning $150 million a month. In my latest episode, Sebastian shares how he turned Klarna back to profitability and discusses Klarna’s ongoing pursuit of creating a digital financial assistant. He also reflects on their recent boardroom drama with Sequoia and outlines the operating principles and the repaired mistakes that have made Klarna the company it is today.

(00:00) Intro

(01:45) Personal Reflections on Alcohol and Family

(03:03) The Journey to Sobriety

(05:57) Milestones and Achievements

(07:59) Understanding Company Success

(10:54) Challenges and Pivots in Business

(16:50) Building and Maintaining Company Culture

(26:16) Leadership and Motivation

(32:42) What Klarna Does

(41:33) Reflecting on Leadership and Self-Development

(41:48) Promoting Young Talent and Internal Growth

(44:52) Balancing Autonomy and Standardization

(46:29) Adopting Agile and Toyota's Influence

(55:05) Navigating Regulatory Challenges

(01:00:11) Klarna's Financial Journey and Market Expansion

(01:10:38) Handling Valuation Resets and Layoffs

(01:23:57) Evaluating Individuals in Business Relationships

(01:24:22) Stability of Institutions and Individuals

(01:25:40) Perverse Incentives in VC Firms

(01:26:50) Hands-On Leadership in VC Firms

(01:28:54) The Impact of Michael Moritz

(01:34:52) Leadership Evolution and Self-Reflection

(01:39:11) Facing Challenges and Finding Solitude

(01:42:19) AI Integration at Klarna

(01:52:03) Balancing Capitalism and Societal Impact

(02:00:53) Creativity and Constraints in Problem Solving

(02:05:41) Conclusion and Final Thoughts

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

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

🎙 Listen to the show

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

Follow on Socials

📸 Instagram - https://www.instagram.com/theloganbartlettshow

🐦 Twitter - https://twitter.com/loganbartshow

🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow

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.