Outthinkers

Robert E. Siegel is a lecturer in Management at the Stanford Graduate School of Business, where he has taught various courses ranging from Systems Leadership to Financial Management for Entrepreneurs to The Industrialist’s Dilemma to Corporations, Finance and Governance in the Global Economy. He is also a Venture Partner at Piva Capital and a General Partner at XSeed Capital, and sits on multiple Boards of Directors and has led investments in Zooz, Cirrosecure, and Lex Machina, among others. His multi-lens background and approach have afforded Robert a deep, intricate understanding into leadership in our constantly in flux world today, and how it requires an ever-more nuanced approach.  In this discussion, we dive into key insights from his most recent 2025 book, The Systems Leader: Mastering the Cross Pressures that Make or Break Today’s Companies, a perfect complement to his first book, The Brains and Brawn Company. We discuss the constant web of dualities that the modern systems leader confronts on an ongoing basis, as well as: How while our business frameworks have long been trending towards change-driven  frameworks with terms like “ambidextrous organization” and “exploitation vs. exploration,” world parameters have grown increasingly complex, requiring a different set of leadership skills The key characteristics of a systems leader, including the 5 cross-pressures that these leaders must learn to balance to be effective.  The four abilities that leaders must develop, including developing a product manager mindset—the ability to live at the intersection of customer needs, market demands, and the inner workings of your company  Episode Timeline:00:00—Highlight from today's episode01:30—Introducing Robert + the topic of today’s episode05:32—If you really know me, you know that...07:48—What is your definition of strategy?08:44—An overview of Robert's first book, The Brains and Brawn Company15:30—What are some key questions in your toolkit to become better at self-diagnostics17:50—Can you explain your quote: "leadership is ability to restrain in response to a certain stimulus"?21:30—Can you define a systems leader for us?23:42—What can we learn from the product manager's mindset?25:35—Can you give us an overview of the 5 cross-pressures leaders face?29:28—How is the landscape of investors changing under these pressures?32:25—The effect of AI on the workforce, and the role of leaders37:45—What is your advice to someone looking to shape strategy in light of these cross-pressures?40:39—How can people continue learning from you?______________________________________________________________Additional Resources:LinkedIn: https://www.linkedin.com/in/robertesiegel/Link to website: https://www.robertesiegel.com/the-systems-leaderThank you to our guests, thank you to our executive producer, Karina Reyes, our editor, Zach Ness, and the rest of the team. If you like what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.Follow us at outthinkernetworks.com/podcast

In this episode, we are joined by Brendan Rosseau and Matthew Weinzierl co-authors of Space to Grow: Unlocking the Final Economic Frontier. This episode is a journey, metaphorically speaking, into the beyond: outer space itself. Matthew is a Professor of Business Administration at Harvard Business School, and the Senior Associate Dean and Chair of the MBA program, where his award-winning research and teaching focus on economic policy and the business of space. He is the founder of the Economics of Space project at HBS and serves as an adviser on space to government agencies, companies, and investors. Brendan is a recognized leader in the space industry. He works in strategy at Blue Origin (the space company wholly owned by Jeff Bezos). He previously served as a teaching fellow and research associate at Harvard Business School and as a consultant to the U.S. Space Force. He is dedicated to using space technologies to bring about a more prosperous, peaceful, equitable and exciting future. In this episode, we explore the boundaries, and intersection, of fundamental laws of economics within the context of the rapidly developing space industry or market. We also glean insights on how other markets have and will evolve: the automobile industry, ecommerce, precision farming and potentially the economies around AI or blockchain. If we understand these underlying economic forces, we can more accurately anticipate when and how such new markets will emerge and, in the case of space, it may be coming much sooner than most of us outside of the space industry think. In this episode, we discuss: How the space industry and space technology have the potential to—and will—disrupt many business industries as we know them today The fascinating evolution of NASA as a government-funded R&D entity to a private sector ‘market creator’ acting as a “customer among many customers” so they can pave the way for space innovation The fundamental economic laws that govern how the space industry will evolve—and how markets here on earth will evolve as well The near-term financial opportunities you may not be thinking of that are providing a kind of economic bridge from private sector actors (who need near-term profit) and long-term players (like the government or large corporations who have the funding to pursue the opportunities offered by the moon and Mars) How the rapid formation of a space industry will directly impact companies in nearly every sector, even those with no obvious connection to space Episode Timeline:00:00—Highlight from today's episode01:28—Introducing Matthew and Brendan + the topic of today’s episode05:37—If you really know me, you know that...07:03—What is your definition of strategy?09:14—What are near-term opportunities the space industry will open?12:15—Some use cases of revenue opportunities from space17:39—Introducing the Evergreen '7 Ps'19:40—How has the role of NASA changed over time?29:26—What are things that need to be in place to realize the market of space?32:14—The governing laws of space 37:32—How will competition of the space markets unfold?40:17—What moThank you to our guests, thank you to our executive producer, Karina Reyes, our editor, Zach Ness, and the rest of the team. If you like what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.Follow us at outthinkernetworks.com/podcast

Dave Whorton is a tech investor and founder who spent 20 years of his career at the highest levels of Silicon Valley venture capital and tech startups. At the preeminent tech venture capital firm Kleiner Perkins, he worked directly with John Doerr for several years. He cofounded four companies, including drugstore.com and Good Technology.  This episode is longer than our usual shorter format—and with good reason. It's about companies that last longer. We dive deep into the world of evergreen businesses—those built to adapt and grow profitably for 100 years and more. Think of these as the direct juxtaposition to venture capital-funded enterprises—where those are built with the sole intention of selling, going public or shutting down if not performing, evergreen businesses are built to endure.  In 2013, Dave founded Tugboat Institute to connect, support, and inspire purpose-driven leaders of these businesses, and this upcoming May 2025, Dave, with Bo Burlingham, releases Another Way: Building Companies that Last...and Last...and Last. In this episode, we uncover some of the most profound insights from his book, so many of which fly in the face of current, common, dogmas around innovation and entrepreneurship, including: Why the companies VCs most often tout today as exemplars of greatness (Google, Microsoft) took very little VC funding—and why you should probably avoid VC investors as well The fact that the size of venture capital market has exploded multifold since 1999 and what that means for nature of how businesses are built and operate today The “Evergreen 7Ps” that characterize these companies, and specific case studies and examples of companies that live these values. Two of my favorites:  They pace their growth—and avoid hyperscaling They pursue pragmatic innovation, rather than radical breakthrough innovation __________________________________________________________________________Episode Timeline:00:00—Highlight from today's episode01:02—Introducing Dave + the topic of today’s episode03:19—If you really know me, you know that...06:23—What is your definition of strategy?09:00—Explaining the evolution of venture capital in the past 50 years 12:02—The pitfalls of taking venture capital 17:39—Introducing the Evergreen '7 Ps'24:12—How to know if a business' pace of growth is healthy 26:50—People as a critical part of your strategy 33:58—Pragmatic innovation in evergreen businesses38:53—What public companies could adopt from the 7 Ps to behave more like evergreen businesses45:00—How can people can keep learning from you?______________________________________________________________Additional Resources:LinkedIn: https://www.linkedin.com/in/davewhorton/Link to book: https://www.tugboatinstitute.com/anotherway/The Tugboat Institute: https://www.tugboatinstitute.com/Thank you to our guests, thank you to our executive producer, Karina Reyes, our editor, Zach Ness, and the rest of the team. If you like what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.Follow us at outthinkernetworks.com/podcast

Cindy Anderson, Chief Marketing Officer at the IBM Institute for Business Value, shares her insights on quantifying the ROI of thought leadership. She discusses vital metrics that demonstrate the effectiveness of thought leadership in enhancing organizational credibility. The conversation highlights the delicate balance between innovation and consistency in messaging. Cindy also explores how generative AI is shaping thought leadership while emphasizing the necessity of a human touch. Tune in for valuable strategies to elevate your brand's authority!

Faisal Hoque, an award-winning entrepreneur and bestselling author, discusses the evolution of AI from a mere tool to a strategic partner for humanity. He introduces his complementary frameworks, OPEN and CARE, designed to guide the safe adoption of AI while emphasizing ethical considerations. The conversation delves into the challenges and risks of integrating AI into society, urging a balance between optimism and caution. Faisal also highlights how individual actions can collectively shape our future, inspiring listeners to engage thoughtfully with technology.

JoAnn Garbin, a sustainability and technology innovator with 25 years of experience, shares insights from her career, including her work at Microsoft. She discusses the parallels between innovation cycles and nature’s adaptive processes, emphasizing the necessity for businesses to continuously innovate. Garbin breaks down four distinct innovation patterns, showcasing how innovation extends beyond technology to encompass business models and customer experience. The importance of collaboration and a holistic approach to sustainability in innovation also takes center stage.

Peter Compo, author of The Emergent Approach to Strategy and former DuPont leader, shares his unique perspective on strategy, likening it to evolution and music. He discusses how strategy should be agile and adaptive, debunking the top-down approach. With insights from creative processes related to Marie Curie and jazz legend Charlie Parker, Compo emphasizes mastering fundamentals before innovation. He also highlights the dangers of disconnected execution and the need for cohesive strategies, urging leaders to embrace continuous refinement and discard outdated beliefs.

Antonio Nieto-Rodriguez, a leading thinker on project management and author of 'Powered by Projects', dives into the transformative shift towards a project economy. He discusses how AI and digitalization are reshaping work, predicting that by 2030, 70% of jobs will be project-based. The episode emphasizes the decline of traditional hierarchies in favor of nimble, project-driven teams. Nieto also shares insights on the importance of effective leadership in aligning strategy with execution amidst this changing landscape, and the rise of new consulting models that empower clients.

Devin DeCiantis, co-author of "The Enduring Enterprise" and Managing Partner at Lansberg Gersick Advisors, shares insights on the distinct strengths of family businesses. He discusses their resilience and unique long-term strategies that allow them to thrive even during economic turbulence. The conversation highlights how family enterprises can teach traditional corporations about planning for the future and adapting to challenges. DeCiantis also delves into the critical role of redundancy and community commitment in ensuring stability and success.

In this conversation, Sandra Matz, an expert in human behavior and AI from Columbia Business School, discusses her groundbreaking research on "psychological targeting." She highlights how digital footprints reveal personal psychology and can influence decisions, from purchases to voting. The podcast explores the balance between hyper-personalization and ethical concerns about privacy. Additionally, Matz touches on the dynamics of human identity and the evolving role of AI in organizational strategies, stressing the importance of integrating ethical practices in tech-driven environments.