Todd McKinnon, Co-founder and CEO of Okta, shares insights from scaling his company to a $13B industry leader. He discusses the high-stakes decisions that shaped Okta, including the importance of market timing and building a strong team. Todd reflects on the psychological shifts in leadership and the critical relationship with board members. He also emphasizes the need for long-term thinking in investor relations and the challenges of innovation amidst growth, offering compelling anecdotes from his entrepreneurial journey.

Sridhar Ramaswamy, the innovative CEO of Snowflake and former leader at Google, shares insights from his transformative journey in tech. He discusses his vision for AI’s future, emphasizing Snowflake's unique AI integration and operational changes to enhance product development. Sridhar also reflects on the balance of passion and market needs in career choices, his leadership evolution, and the importance of accountability in teams. With bold predictions about AI's role in data solutions, he addresses challenges in the tech landscape and the need for competition amidst consolidation.

Evan Goldberg, Founder and EVP of Oracle NetSuite, reflects on over 26 years of leading the company. He shares invaluable insights on navigating economic crises and the importance of prioritizing existing customers. Goldberg discusses the evolution of NetSuite, the impact of AI on business software, and the role of customizability in their success. He emphasizes empathy in leadership, the challenges of hyper-growth, and his personal journey advocating for cancer awareness, inspired by his experiences. Humor and a strong company culture are central to his management philosophy.

Drew Houston, Co-founder and CEO of Dropbox, shares insights from his 17-year journey leading the company. He discusses the crucial leadership lessons learned while battling big tech rivals. The conversation dives into the transformative potential of AI, emphasizing tools like Dropbox Dash that enhance productivity and streamline tasks. Houston reflects on the company's 'memo first' culture, the challenges of early growth and competition, and the strategic decisions in navigating fundraising and infrastructure. A candid take on innovation and adapting to the future of work awaits!

Will Gaybrick, President of Stripe and former CFO with a rich background in finance and technology, shares his remarkable career journey from Yale Law to leading one of the largest private startups. He discusses the pivotal role of AI in payment systems and its ethical implications. Gaybrick also dives into the evolution of Stripe’s strategy towards stablecoins, the importance of effective capital allocation, and innovative organizational design. His insights on fostering a collaborative work culture and navigating the venture capital landscape are particularly compelling.

Parker Conrad, CEO of Rippling and a successful entrepreneur, shares insights from his journey building the $13B company. He discusses the concept of 'founder mode' and its practical application at Rippling, contrasting his experiences at Zenefits. Parker candidly addresses the complexities of investor relationships, noting that much of VC advice can be overrated. He also reflects on the dynamics of hiring, governance challenges, and the importance of anecdotal evidence in decision-making, all while emphasizing the value of speed and quality in execution.

Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ.Despite these challenges, John stepped up to rebuild the brand to the nearly $10B company it is today. We discuss how he shifted focus from weight loss to broad-based energy, secured key distribution deals, landed a major partnership with Pepsi, and much more. (00:00) Intro(01:34) The Origins of Celsius(03:30) Going Public: The Early Days(06:07) Challenges and Lawsuits(09:17) Rebuilding and Rebranding(13:18) Strategic Shifts and Market Positioning(30:40) The Role of Influencers and Social Media(32:03) John Fieldly's Leadership Journey(33:34) Reflecting on the Stock Price Journey(34:12) Navigating Public Company Challenges(35:25) Distribution Deals and Market Perception(38:00) Strategic Moves and Competitive Advantage(44:08) Marketing Strategies and Consumer Engagement(52:35) Leadership and Company Culture(01:02:01) International Expansion and Future Goals(01:06:01) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Sam Dewees and JR Bohannon 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/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google 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.

Josh Wolfe, Co-Founder of Lux Capital and a visionary in venture capital, dives into a whirlwind of topics. He discusses the necessity of monitoring news to spot hidden market opportunities and explores the delicate balance between investment risks and innovation. Josh sheds light on the geopolitical tensions surrounding Iran, societal happiness, and the future of AI technology. He also delves into ethical considerations in defense investments and the crucial role of storytelling in shaping investment narratives and building trust.

Emery Wells, co-founder and CEO of Frame.io, details his incredible journey from NYC bartender to startup founder, culminating in a $1.3 billion sale to Adobe. He shares insights from his work with SNL that ignited his entrepreneurial spirit. Discussing the importance of design and a unique company culture, he rejects the lean startup model and emphasizes maintaining high standards. Emery also navigates the intense processes of fundraising and acquisitions, along with the impact of AI on creativity—highlighting lessons learned along the way.

Dara Khosrowshahi, the CEO of Uber and a leader in transforming the company to profitability since 2017, shares insights into autonomous vehicles and consumer behavior shifts. He discusses overcoming challenges in AV strategy, emphasizing the societal importance of safety and user preferences. Dara also reflects on Uber's cultural reset, evolving company values, and the significance of operational efficiency. He highlights innovative adaptations in global markets and the vital role of transparent leadership in fostering trust and driving performance.