TLP491: Letting Go of Old Frameworks with Jack Swift

Jack Swift is a West Point graduate, former CEO of TIFIN and Liminal Collective, and co-founder of Pacific Current Group and Sangha. He now advises frontier AI ventures, including Vantage Discovery (sold to Shopify), Brightwave, and Grid Aero, and co-founded Sangha, a community for conscious leadership. In this episode, Jack explains why the biggest threat to your organization isn't outside pressure. It's your need to be right. He shows why old leadership habits—command and control, chasing quarterly targets, and relying only on past wins—no longer work. He offers a different approach built on deep listening, less ego, and faster instincts. Jack talks about the blind spots he sees on boards, from big companies ignoring rapid change to startups burning cash to prove a point. He also shares how to spot the moment when governance stops supporting durability and starts blocking innovation—and what to do before bureaucracy kills your edge. Listen to this episode to learn how to drop old frameworks, trust your gut, and build a learning culture that works with AI instead of fighting it. Find The Leadership Podcast episode 490 on YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Jack Swift on Letting Go of Old Frameworks https://bit.ly/TLP-491 Key Takeaways [02:28] Jack shares that stopping drinking a few years ago has been "incredibly clarifying" for his decision making and presence as a leader. [05:19] Jack shares how his perspective on leadership has evolved from military to entrepreneurship to board service. [10:11] Jack emphasizes three critical elements that make an effective independent board director: maintaining independence to evaluate organizational health, stepping into conflict early, and the ability to "look around corners" and anticipate future disruption. [15:07] Jack identifies the biggest blind spot for larger companies and the biggest blind spot for early-stage companies and founders. [19:26] Jack reflects on how his experiences as an entrepreneur shaped how he evaluates opportunities and risks. [21:48] Jack reflects on something 18 years ago that helped him learn without screwing up. [23:00] Jack discusses the role of ego versus intuition in leadership. [25:34] Jack defines governance in highly regulated industries like insurance and financial services versus the AI space. [29:56] Jack agrees AI works best in regulated spaces because "machine based learning and models work really well in systems, rules based systems" where regulatory review "may have taken humans six months to do, it can be done in like six minutes." [33:16] Jack describes how Boulder's ecosystem has influenced his approach to leadership and growth. [36:35] Jack advises traditional industry leaders to "let go of old frameworks" and "be open to how it might be done" because entrenched industries are "specifically ripe for innovation and disruption." [37:36] Jack says one piece of advice for leaders navigating uncertainty today. He explains why whole-body listening matters for the future of leadership. [41:19] And remember..."I know of no more encouraging fact than the unquestionable ability of man to elevate his life by conscious endeavor." - Henry David Thoreau Quotable Quotes "Leaders make decisions and they look for and create alignment within an organization." "The need to be right is the biggest blind spot. Taking the position that I want to be right, I'm gonna burn capital to show the world that I'm right is a very risky way to go about your business." "I made a lot of mistakes. I screwed a lot of things up. Sometimes because I didn't know any better, sometimes because I let my ego make decisions, and sometimes because I was relying on old frameworks that just wouldn't work anymore." "Your go mind shouldn't always drive the car. Sometimes you need to put instinct in the driver's seat and let your brain be the passenger." "Let go of old frameworks. Don't think you know better. Work on self awareness, work on your personal growth edges. Better at you is better at what you do." "Listen with your whole body. Your body knows—that's your gut, your instinct, your intuition. The faster you can listen, receive, and act, the faster you'll be able to go." "Human beings are the only species that can imagine infinite future potentials and bring them into reality. That creative capability is uniquely human and incredibly special." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Jack Swift Website | www.jackcswift.com Jack Swift LinkedIn | www.linkedin.com/in/jack-c-swift