College sports are going through massive changes—from athlete pay drama to superconference realignment and transfer portal chaos, not to mention the giant class action lawsuit playing out now. Matt Brown, the publisher behind Extra Points and one of the top experts on the business of college athletics, joined the show to break it all down. We walked through the full history of college sports, the current money dynamics, and where things could be headed. (00:00) Meet Matt Brown: Expert in College...
Apr 18, 2025•2 hr 50 min
In this episode, Derek Thompson (Writer, The Atlantic) delves into the tumultuous nature of Trump’s trade policies, especially regarding tariffs, and how they impact American manufacturing and global markets. They discuss the constant changes in policy, the resulting uncertainty for industries like automotive and aerospace, and the mismatch between Trump’s ‘madman strategy’ and effective industrial policy. The conversation also explores the broader economic consequences, including stock market v...
Apr 11, 2025•1 hr 16 min•Ep. 138
Debate between Keith Rabois and Zach Weinberg on what tariffs are actually trying to accomplish. One core theme: Tariffs aren’t fully about “bringing back factories,” but rather a negotiation tool to eliminate foreign trade barriers - ultimately aiming to increase free trade, not restrict it. We also got into: - What each of them would do if they were in charge - Whether the trade deficit is a meaningful metric or just a misunderstood talking point - If tariffs could be part of an initiative to ...
Apr 09, 2025•52 min•Ep. 137
In this freeform episode, Logan sits down with Zach Weinberg (Co-Founder and CEO of Curie.Bio) to break down two of the biggest storylines in tech: tariffs and AI. They banter through the core arguments for and against tariffs, including national security, domestic employment, and negotiation power. Plus, they revisit what’s happened in past trade wars and share predictions on the real economic consequences this time around. Logan and Zach also discuss OpenAI’s $40B raise and the broader race fo...
Apr 02, 2025•1 hr 14 min•Ep. 136
Box CEO Aaron Levie joined the show to share his perspective on how AI is reshaping the enterprise landscape. He shared what his customers are actually thinking about when it comes to AI, the shift from closed to open-source models, and why the biggest opportunities might not be in flashy consumer tools but in workflow automation and data-rich enterprise applications. Aaron also shares his take on the changing business model dynamics in B2B, including the rise of usage-based pricing, and what it...
Mar 28, 2025•Ep. 135
After unveiling 45 new product announcements this week, Zoom CEO Eric Yuan joined the show to share how he’s thinking about the future of work. He shared how he prioritizes which features to build, his approach to rebuilding company culture, what he’d do differently if he were starting Zoom today, and much more. (00:00) Intro (01:14) Eric Yuan on Zoom's Recent Innovations (02:02) AI Companion and Its Capabilities (03:23) Zoom's Open Platform and AI Features (04:36) Customer-Centric AI Developmen...
Mar 21, 2025•Ep. 134
As tariff drama continues to heat up, Ryan Petersen, CEO of Flexport (one of the hottest freight forwarders in the world) came on the show to unpack the impact. Ryan also dives deep into the hidden world of US shipping, opportunities for AI automation in logistics, reflections on building Flexport, and some supply chain conspiracy theories. (00:00) Intro (01:16) Flexport's Mission and Operations (02:28) Impact of Tariffs on Businesses (05:15) Navigating New Duties and Regulations (09:19) Flexpor...
Mar 13, 2025•1 hr 19 min•Ep. 133
Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she’s mastered. She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-first businesses and what it takes to stay competitive in an evolving landscape. (00:00) Intro (00:56) Yamini Rangan's Background and Career Journey (...
Feb 21, 2025•1 hr 15 min•Ep. 132
Andy is the founder of Artisanal Ventures and Artisanal Talent, one of Silicon Valley’s top search firms. He’s helped build leadership teams at companies like Databricks, Snowflake, Confluent, Abnormal Security, AcuityMD, and many more. In this episode, he shares… - How founders can differentiate in the talent war today - Maximizing the success rate of executive hires - Why interviews are a waste of time - The best ways to do references - How to choose the right search firm & more (00:00) Intro ...
Feb 14, 2025•2 hr 31 min•Ep. 131
The recent controversy between WordPress and WP Engine put Matt Mullenweg (Co-Founder of WordPress, CEO of Automattic) under intense online scrutiny. In our conversation, he shared lessons from the controversy and managing through crisis, as well as this thoughts on the future of open source AI and more. (00:00) Intro (01:17) Controversy with WP Engine (03:36) Understanding Open Source and Trademarks (04:36) Automattic's Role and Contributions (08:26) Navigating Legal Battles and Community Relat...
Feb 07, 2025•1 hr 5 min•Ep. 130
Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I’ve been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to discuss what all founders and CEOs should consider when it comes to avoiding burnout and maximizing health and productivity. We covered his experiences wi...
Jan 24, 2025•1 hr 25 min•Ep. 129
Jay Chaudhry is the definition of a self-starter. Born in the Himalayas with no running water or electricity until high school, Jay has now scaled Zscaler to a $30B public company. He and his wife went all in many times over—betting their life savings and quitting their jobs to launch their first venture, Secure IT, which became a huge success. Jay then parlayed that into building multiple more self-funded, successful cybersecurity companies before founding Zscaler. In this episode, Jay shares h...
Jan 17, 2025•1 hr 2 min•Ep. 128
In this episode, Marc Benioff (CEO, Salesforce) responds to Satya Nadella’s recent predictions and shares his thoughts on the current reality of Agi. He dives into the rise of digital labor, the multi-trillion-dollar potential of agentic technology, and what the future split between software and agentic revenue might look like. Marc also discusses why CEOs need to stay grounded in delivering actionable solutions, and he emphasizes the moral obligation businesses have to retrain employees and inv...
Jan 10, 2025•41 min•Ep. 127
Eran Zinman entered a crowded category, out-executed everyone, and scaled monday.com into a $14B public company. In my latest conversation with him, he details their unique metric tracking system (dubbed Big Brain) that allows them to do the same amount of work with ½ the people, along with their relentless focus on cash over other metrics, and the little tactics that brought significant ROI (like sending everyone—including investors—a daily SMS with yesterday’s metrics). (00:00) Introduction to...
Dec 13, 2024•1 hr 12 min•Ep. 126
Glenn Fogel, CEO of Booking Holdings, has built a $170B travel empire that includes brands like http://Booking.com, Priceline, Kayak, and OpenTable. Glenn shares insights into how Booking has grown into a global powerhouse, weathering challenges like tsunamis, wars, 9/11, and the COVID-19 pandemic. We dive into the strategy behind the transformative acquisition of http://Booking.com, which now drives 90% of the company’s revenue, and the key lessons Glenn has learned about M&A success. Glenn als...
Dec 06, 2024•1 hr 18 min•Ep. 125
Ali Ghodsi, CEO of Databricks (now a $61B company), has become one of the top minds in AI, evolving from researcher to leading one of the biggest AI-centered private companies. In our conversation, he broke down the AI hype cycle in detail and made bold predictions for the future. He also shared his biggest operating lessons from scaling Databricks to a market leader and pivotal moments in his journey. (00:00) Introduction to AGI and AI Challenges (01:00) Ali Ghodsi's Journey in AI (01:38) The E...
Nov 22, 2024•1 hr 14 min•Ep. 124
Eoghan McCabe returned to the CEO seat at Intercom with a mission to shake things up. Over the past two years, he's been reinventing the company’s culture, leading with zero apologies, and transforming Intercom into an AI-driven powerhouse. In my latest conversation, we dive into Eoghan’s journey back to Intercom after a two-year break, his blueprint for turning a software company into an AI leader, and the tactics he uses to keep Intercom running like a high-intensity startup. Eoghan also share...
Nov 15, 2024•2 hr 36 min•Ep. 123
What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft. Todd also reflects on his journey to founding Okta, his bold choice to team up with a co-founder he hardly knew, and the motivations that have fueled him for over seven years as a public company CEO. Some key takeaways… [0:0...
Nov 08, 2024•1 hr 21 min•Ep. 122
Nine months into his role as Snowflake’s CEO, Sridhar Ramaswamy sat down for a candid discussion on the journey so far & what’s ahead. He uncovered details about his transition to Snowflake CEO, the operational changes he’s put in place to accelerate product development, and his bold predictions for AI’s future—along with how he’s guiding a vision for Snowflake to fit into that landscape. Sridhar also reflects on how his leadership has evolved, from leading a major Google unit to founding Neeva ...
Nov 01, 2024•51 min•Ep. 121
Evan Goldberg has been leading NetSuite for 26 years and counting. In this episode, Evan reflects on the journey of building NetSuite—from launching it with Larry Ellison’s support, to scaling through its IPO, and eventually being acquired by Oracle for $9.3B. He shares his leadership philosophies around humor and empathy, lessons learned from Larry Ellison and Marc Benioff, and why he still feels passionate about the business after all these years. [0:00] Intro [1:13] Lessons from Economic Cris...
Oct 25, 2024•1 hr 17 min•Ep. 120
Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work. [0:00] Intro [0:44] AI Opportunities for Dropbox [5:57] Dropbox's AI Principl...
Oct 18, 2024•2 hr 35 min•Ep. 119
Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadership role at Stripe. Will shares key insights on capital allocation, crypto, AI, investing, leadership, and more. Some takeaways: (00:00) Intro (01:09) ...
Sep 20, 2024•2 hr 42 min•Ep. 118
Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career, highlighting the differences in how he ran Zenefits compared to Rippling today. Additionally, Parker shared his candid views on the challenges of ha...
Sep 13, 2024•2 hr 42 min•Ep. 117
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, land...
Aug 30, 2024•1 hr 7 min•Ep. 116
Josh Wolfe , co-founder and managing partner at Lux Capital , is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today. (00:00) Intro (01:02) Daily News Routine (05:28) Geopolitical Insights (07:03) Competitiveness and Curiosity (11:01) Investment Strategies and Risks (26:07) The ...
Aug 23, 2024•2 hr 54 min•Ep. 115
Emery Wells is the co-founder and CEO of Frame.io , which he sold to Adobe in 2021 for nearly $1.3 billion. In our conversation, Emery shares his journey from NYC bartender to startup founder, including his agency work with Saturday Night Live that highlighted the pain points that led to Frame.io. We dive deep into his rejection of the lean startup concept, how he gets his team to obsess over design details, and the cultural reset at Frame.io that set the stage for its success. (00:00) Intro (01...
Aug 16, 2024•2 hr 42 min•Ep. 114
Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and some of the operating principles that have stuck with Dara since his days at Expedia. (00:00) Intro (01:49) Uber's Economic Resilience and Consumer T...
Aug 09, 2024•1 hr 9 min•Ep. 113
Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what the future of venture capital may look like over the next decade - here are a few favorite takeaways on what makes outstanding startups from one of the ...
Aug 02, 2024•2 hr 4 min•Ep. 112
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...
Jul 26, 2024•2 hr 34 min•Ep. 111
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. ...
Jul 12, 2024•2 hr 34 min•Ep. 110
