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

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

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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

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🎬 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

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🐦 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.

Olivier Pomel built Datadog into a $40B company while burning only $25M in capital. In our conversation, he shares the fundraising lessons, operating principles, and core insights that made this possible. He also discusses the pros and cons of building a tech company in NYC, how early-career professionals should approach learning AI tools, how Datadog is building a trusted relationship with their users around AI features, and much more

(00:00) Intro

(01:30) Datadog's Early Challenges and Lessons

(04:32) The Core Insight Behind Datadog

(05:20) Building the Right Product

(07:46) Transitioning to Open Beta

(09:38) Expanding Datadog's Product Line

(11:26) Platform Vision and Modular Products

(18:12) Empowering Product Teams

(22:14) Acquisitions and Integration Strategy

(33:18) Customer-Centric Approach

(36:39) Bottom-Up Sales Strategy

(46:04) Navigating Founder Challenges

(46:37) Building a Collaborative Management Team

(48:32) Staying Close to Customers

(51:36) Maintaining a Culture of Discipline and Efficiency

(56:26) Pricing Strategy and Market Positioning

(01:01:24) Fostering a Low-Ego, High-Performance Culture

(01:06:32) Hiring and Promoting for Long-Term Success

(01:12:21) Fundraising and Investor Relations

(01:16:03) Deciding Whether to Sell or Scale

(01:18:26) The Impact of AI on Software Development

(01:23:24) Choosing New York Over Silicon Valley

(01:28:04) Final Thoughts 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.

Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path.

(00:00) Intro

(01:00) Steve Kaufer's Journey with Tripadvisor

(03:18) Handling Negative Reviews and Legal Issues

(05:24) Psychology of Reviews and User Behavior

(10:01) Impact of AI on Review Platforms

(15:02) Graduation Speech and Key Lessons

(16:33) Speed Wins: The Importance of Agility

(22:46) Measuring Success and Embracing Change

(28:40) Hard Work and Personal Growth

(36:20) Management and Leadership Insights

(40:23) Setting Company Culture

(48:00) Adapting to Market Changes

(51:45) Hiring the Right People

(53:27) Identifying Red Flags in Interviews

(54:51) The Importance of Self-Improvement

(55:29) Curiosity and Adaptability in Candidates

(56:36) Managing Through Crises: 9/11 and COVID-19

(01:02:12) Lessons from Early Career and Centerline Software

(01:05:02) Founding Tripadvisor and Its Growth

(01:18:03) Tripadvisor's Acquisition and Integration with IAC

(01:25:23) Transitioning from Tripadvisor to Give Freely

(01:27:26) The Vision and Impact of Give Freely

(01:37:10) Conclusion and Final Thoughts

Show Notes:

https://givefreely.com/

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

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🐦 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.

Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand, push past rejection, and redefine the non-alcoholic beer industry.

(00:00) Introduction to Athletic Brewing

(00:52) The Early Days and Breakthrough Moments

(01:15) Celebrity Partnerships and Brand Building

(03:16) The Philosophy of Brand and Movement

(07:33) The Non-Alcoholic Beer Market

(10:46) The Entrepreneurial Journey and Personal Sacrifices

(18:22) Scaling the Business and Marketing Strategies

(28:20) Navigating Regulations and Health Trends

(39:07) The Importance of a Tech Co-Founder

(39:31) Home Brewing Beginnings

(40:13) Innovative Brewing Process

(41:13) Food Safety Challenges

(43:24) Raising Funds and Building a Brewery

(44:24) Vertical Integration Benefits

(45:33) Early Sales Efforts

(46:56) Investor Relations and Accountability

(51:14) Long-Term Vision and Focus

(01:00:10) Cultural Differences in Non-Alcoholic Beer

(01:02:35) Health Considerations and Alcohol

(01:10:38) The Sensation of Drinking

(01:12:50) Reflections on the Entrepreneurial Journey

(01:14:46) 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

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🐦 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.

In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood’s new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more.

(00:00) Intro

(03:27) The Origin of the Name 'Robinhood'

(08:43) Navigating the GameStop and Meme Stock Saga

(10:52) Rebuilding Trust and Brand Impact

(19:10) Crisis Communication and Leadership Lessons

(23:54) Industry Insights and Future of Trading

(31:00) AI and Financial Services

(33:34) Crypto and Regulatory Challenges

(40:14) The Viral Launch of Robinhood

(47:01) The Gold Card Launch and Customer Strategy

(50:08) The Vision Behind Robinhood's Credit Card

(53:50) Building vs. Buying: The X1 Acquisition

(56:12) Integrating X1 into Robinhood

(57:11) The GM Structure and Its Benefits

(58:42) Challenges and Trade-offs of Decentralization

(01:01:08) Financial Modeling and Customer Economics

(01:04:48) Navigating Remote Work and Returning to the Office

(01:09:14) Managing Stock Price Expectations

(01:13:23) Hiring and Retaining Talent

(01:17:11) Fundraising and Investor Relations

(01:31:09) Launching Sherwood Media

(01:38:56) Reflections and Future Aspirations

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

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📸 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.

On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI personal assistants, highlights the biggest opportunities and risks in the AI landscape today, and much more.

(00:00) Intro

(00:50) The Personal Impact of Leading OpenAI

(01:44) Unveiling Multimodal AI: A Leap in Technology

(02:47) The Surprising Use Cases and Benefits of Multimodal AI

(03:23) Behind the Scenes: Making Multimodal AI Possible

(08:36) Envisioning the Future of AI in Communication and Creativity

(10:21) The Business of AI: Monetization, Open Source, and Future Directions

(16:42) AI's Role in Shaping Future Jobs and Experiences

(20:29) Debunking AGI: A Continuous Journey Towards Advanced AI

(24:04) Exploring the Pace of Scientific and Technological Progress

(24:18) The Importance of Interpretability in AI

(25:11) Navigating AI Ethics and Regulation

(27:26) The Safety Paradigm in AI and Beyond

(28:55) Personal Reflections and the Impact of AI on Society

(29:11) The Future of AI: Fast Takeoff Scenarios and Societal Changes

(30:59) Navigating Personal and Professional Challenges

(40:21) The Role of AI in Creative and Personal Identity

(43:09) Educational System Adaptations for the AI Era

(44:30) Contemplating the Future with Advanced AI

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.