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.

Get the full show notes here - https://bit.ly/TLP-491

Key Takeaways
[02:04] Jack shares that stopping drinking a few years ago has been "incredibly clarifying" for his decision making and presence as a leader.
[05:20] Jack shares how his perspective on leadership has evolved from military to entrepreneurship to board service.
[10:42] 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.
[16:03] Jack identifies the biggest blind spot for larger companies and the biggest blind spot for early-stage companies and founders.
[20:51] Jack reflects on how his experiences as an entrepreneur shaped how he evaluates opportunities and risks.
[23:35] Jack reflects on something 18 years ago that helped him learn without screwing up.
[25:07] Jack discusses the role of ego versus intuition in leadership.
[27:53] Jack defines governance in highly regulated industries like insurance and financial services versus the AI space.
[32:54] 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."
[36:48] Jack describes how Boulder's ecosystem has influenced his approach to leadership and growth.
[40:30] 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."
[41:48] Jack says one piece of advice for leaders navigating uncertainty today. He explains why whole-body listening matters for the future of leadership.
[45:40] 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

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 491 on YouTube, or wherever you get your podcasts!