The Leadership Podcast Podcast By Jan Rutherford and Jim Vaselopulos experts on leadership development cover art

The Leadership Podcast

The Leadership Podcast

By: Jan Rutherford and Jim Vaselopulos experts on leadership development
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We interview great leaders, review the books they read, and speak with highly influential authors who study them.Copyright © 2016-2025 Rafti Advisors, LLC & Self Reliant Leadership, LLC - All Rights Reserved. Economics Management Management & Leadership
Episodes
  • TLP491: Letting Go of Old Frameworks with Jack Swift

    TLP491: Letting Go of Old Frameworks with Jack Swift
    Dec 24 2025
    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
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    42 mins
  • TLP490: Reinventing Candy and Culture with Katie Lefkowitz

    TLP490: Reinventing Candy and Culture with Katie Lefkowitz
    Dec 17 2025
    Katie Lefkowitz is a neuroscience-trained entrepreneur and the founder and CEO of Harken Foods who's reinventing candy with gut health at its core. In this episode, Katie reveals how her neuroscience background taught her to demand feedback systematically and observe behavior over words—skills that proved universal across consulting, scaling, and founding companies. She shares why she chose measured growth at Harken after experiencing Caulipower's explosive trajectory. Katie explains how the "seven questions framework" helps teams navigate the market's rapid shifts by keeping core values fixed while pivoting operational tactics. Discover practical approaches to data-driven decision-making, building authentic workplace culture, and leading through uncertainty without losing sight of core values. Find The Leadership Podcast episode 490 on YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Katie Lefkowitz on Reinventing Candy and Culture https://bit.ly/TLP-490 Key Takeaways [03:03] Katie explains her neuroscience background taught her the scientific method, helping evaluate questions less emotionally and with reduced bias. [04:05] Katie describes how all decisions need to be based in data, seeking feedback from every person on the Harken team. [05:44] Katie shares Harken was created after a health scare related to colon cancer introduced her to food as medicine. [07:25] Katie explains Caulipower grew as the fastest growing brand in all of CPG, but for Harken she wants to be more measured. [09:03] Katie confirms the Caulipower success gave her confidence to go at it alone with Harken. [09:48] Katie reflects on trying to be what she thought a leader looked like, being insecure about her age and gender. [11:45] Katie explains there will always be some imposter syndrome, but having Harken within her control has helped relieve that feeling. [13:20] Katie recalls a pitch where the first person said her product doesn't taste good, leaving her crying in the cab to the airport. [15:25] Katie describes watching if people take a second bite during tastings because behavior tells more than words. [16:36] Katie emphasizes listening more than talking as the key leadership lesson. [17:29] Katie explains the company uses Southwest Airlines' seven questions framework where core values don't change but goals and focus do. [19:05] Katie notes that running decisions through core values becomes second nature and prevents losing time on wrong priorities. [20:18] Katie states at their early stage it's about hiring people who believe in what they're doing because culture is what happens when she's not in the room. [21:44] Katie explains parents understand prioritization better because anything to get more time with their kid is of high value. [23:40] Katie reflects that taking pauses to pick up her kid allows her to process things better and make better decisions. [24:46] Katie advises knowing what motivates you—autonomy, mastery, purpose or status, wealth, power—and making decisions based on who you actually are. [27:41] And remember... "If there is no struggle, there is no progress." – Frederick Douglass Quotable Quotes "If you're not telling me I'm doing something wrong or questioning what I'm doing, very frequently, I'm gonna have a problem with that because there's no way that I'm doing everything right." "Listen more than you talk. You will always get a lot more from really hearing people than you're ever going to get from talking at them." "When you're just yourself, it actually comes off much more authentic. And it's those relationships that you're holding yourself back from if you're not able to be your full self." "Have confidence in yourself, own who you are. And it'll actually take you much further than trying to fit into some old mold." "All decisions just need to be based in data and not necessarily, you know, stories." "It's about keeping your core values and making sure that runs through every decision that you're making." "My time is my most valuable resource, not only to myself personally, but to the company." "Taking that pause actually allows me to process things much better. And having that breathing room, I think I just make better decisions." "Know what motivates you... Not who you want people to think you are, but who you actually are." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Katie Lefkowitz Website | https://harkensweets.com Katie Lefkowitz Facebook | www.facebook.com/people/Harken-Sweets/61551227397377/?_rdr Katie Lefkowitz LinkedIn | www.linkedin.com/in/katielefkowitz Katie Lefkowitz Instagram | @harkensweets TLP478: The Consequences of Inaction with Nick Cooney TLP472: Embracing Uncertainty with Dr. Margaret Heffernan
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    28 mins
  • TLP489: Quitting – Knowing When to Walk Away

    TLP489: Quitting – Knowing When to Walk Away
    Dec 10 2025
    Annie Duke is a three-time bestselling author, decision strategist, and former professional poker champion. She holds a PhD in cognitive psychology and is co-founder of the Alliance for Decision Education. Annie's latest best-selling book is "Quit: The Power of Knowing When to Walk Away." In this episode, Annie reveals why knowing when to walk away is the most underrated leadership skill. Drawing on cognitive psychology and real-world coaching with executives and venture capitalists, she breaks down why we're wired to stick with bad decisions, and more importantly, how to override that wiring. Annie explains how sunk costs, identity attachment, and status quo bias conspire to keep us committed past the point of reason. Listen now to stop grinding on goals that don't serve you, and start quitting your way to better outcomes. Find The Leadership Podcast episode 489 on YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Annie Duke on Quitting – Knowing When to Walk Away https://bit.ly/TLP-489 Key Takeaways [02:01] Annie reveals she's an avid tennis player and has a Bernadoodle dog not mentioned in her public bio. [02:54] Annie explains quitting is central to success because decisions are made under uncertainty and even perfect choices have bad outcomes 20% of the time. [06:25] Annie discusses how over-optimism harms decision-making by overestimating both likelihood and quality of good outcomes. [09:41] Annie describes Don Moore's research showing optimistic people just spend more time on unsolvable problems without performing better. [11:44] Annie clarifies that quitting feels too early in the moment but people looking back realize they quit too late. [14:27] Annie explains not quitting creates two problems: pursuing unhelpful goals plus losing opportunity cost of redirected resources. [15:03] Annie recommends using psychological distance through quitting coaches and kill criteria involving mental time travel. [16:19] Annie describes an exercise where executives set six-week benchmarks for underperforming employees, accelerating decisions. [19:38] Annie advises adding "unless" statements to goals since cost-benefit analyses change over time. [24:45] Annie addresses information paralysis by emphasizing the time-versus-accuracy trade-off in decisions. [30:49] Annie acknowledges self-knowledge matters but notes people have competing preferences between short-term wants and long-term values. [33:28] Annie explains how implicit decision-making allows bias to highlight factors supporting desired conclusions. [36:49] Annie explains explicit frameworks resolve short-term versus long-term conflicts by creating future accountability. [37:57] Annie tells negotiation clients every deal can be broken, paralleling keeping quitting as an option. [38:30] Annie addresses opportunity cost neglect where people focus on immediate goals without considering sacrifices. [44:32] Annie connects quitting to innovation since minimal starting information requires flexibility to pivot. [46:22] And remember…"If at first you don't succeed, try again, then quit, there's no point in being a damn fool about it." - W.C. fields. Quotable Quotes "When you make decisions to start things, you are making those decisions under conditions of uncertainty." "When you're thinking about quitting, it will generally feel like it's too early. But when you're looking at someone from the outside, if you're coaching, it'll feel like they're too late." "We quit way too late, as judged by our happiness." "When we don't quit something that we ought to quit, we have a double problem. One problem is that we're doing something that isn't helping us achieve our goals. And the other problem is an opportunity cost problem." "You don't want the goal itself to become an object because it is a representation of a cost benefit analysis." "In order to be a really good innovator, you have to build in this whole idea of quit." "Every deal can be broken, and even if you break it's not broken." These are the books mentioned in this episode Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Annie Duke Website | www.annieduke.com Annie Duke X | @annieduke Annie Duke Facebook | www.facebook.com/AnnieDukeAuthor Annie Duke LinkedIn | www.linkedin.com/in/annie-duke-30ab2b5/ Annie Duke Instagram | @_annieduke
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    47 mins
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I've been listening for 3 years and every time I listen to a show I feel like I can go apply the practices discussed in my personal life and lower to mid management career. I have 100% grown as a leader from listening to this show.

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