Logan sits down with Bipul Sinha, CEO and co-founder of Rubrik and former VC at Lightspeed and Blumberg Capital. Bipul shares what he learned transitioning from investor to founder, why intuition beats expertise, and how he built Rubrik into a category-defining business by betting on uncool ideas. They talk product-market fit in the AI era, what most VCs get wrong today, and why the enterprise IT market is still just getting started. It’s a conversation packed with hard-earned wisdom and bold ta...
Jun 06, 2025•Ep. 146
Rick Smith (CEO, Axon) joined Logan to share the 30-year journey of building a nearly $50B public company behind the TASER, police body cameras, and now AI-powered tools like Draft One. He talks about taking Axon public in the early 2000s, navigating intense public scrutiny, and evolving from a controversial hardware startup into a software and AI pioneer. Rick also reflects on leadership lessons, regulatory battles, and his long-term mission to make the bullet obsolete. It’s a candid and compel...
May 30, 2025•Ep. 145
Logan sits down with Jeffrey Katzenberg, Hollywood legend and co-founder of DreamWorks, and Sujay Jaswa, former CFO of Dropbox - together, the duo behind WndrCo. They talk about building enduring companies, bridging tech and media, and what makes a great CEO partnership. The conversation also touches on storytelling as a business superpower and lessons from scaling at different stages. Whether you're a founder or a media nerd, there’s something here for you. (00:00) Intro (04:26) The Genesis of ...
May 23, 2025•1 hr 51 min•Ep. 144
In this episode, Logan is joined by Zach Weinberg (Co-Founder/CEO @ Curie.Bio) and Derek Thompson (writer at The Atlantic) for a candid discussion on the state of U.S. healthcare and scientific progress. They unpack what went right, and wrong, with COVID vaccine policy, the public backlash against mRNA technology, and the ripple effects on trust in science. The conversation also dives into the real reasons behind NIH budget cuts, the economics of drug discovery, and the business incentives in me...
May 13, 2025•Ep. 143
Yotam Segev is the co-founder and CEO of Cyera, one of the fastest-growing cybersecurity startups in the world. In this episode, he joins Logan to talk about scaling Cyera from 100 to 550 employees in under two years, what it takes to operate at that speed, and why going slow can actually be riskier. They cover lessons from a tough go-to-market year, the emotional conviction behind choosing data security, and how Yotam thinks about platform expansion, hiring, and staying close to customers. It’s...
May 09, 2025•Ep. 142
Ben Lamm, founder and CEO of Colossal Biosciences, joined the show to talk about the science (and business) of bringing extinct species back to life. Backed by top scientists and investors, Colossal is using advanced gene editing and synthetic biology to recreate animals like the woolly mammoth and dire wolf. Ben walks us through the technology, ethical considerations, and commercialization paths, including tech spinouts and conservation credits. It’s a wild conversation at the intersection of J...
May 02, 2025•1 hr 26 min•Ep. 141
Blake Scholl, founder and CEO of Boom Supersonic, is leading the boldest effort in decades to bring back commercial supersonic flight—this time with product-market fit. We talk about what went wrong with the world’s first try at supersonic commercial aircraft (launched in the 70s), why Boeing hasn’t introduced a new plane in over a decade, and how Blake’s startup is building a jet that flies 2x faster than today’s aircraft—without the sonic boom. This episode is a crash course in engineering amb...
Apr 25, 2025•1 hr 35 min•Ep. 140
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•1 hr 50 min•Season 139Ep. 139
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•1 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•1 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•1 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•1 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•1 hr 42 min•Ep. 117
