The Leadership Podcast

Oli Raison, co-founder of Safarini Leadership, designs immersive leadership expeditions in Kenya that combine cultural exchange with Samburu elders, wilderness trekking, and deep reflective coaching. In this conversation, Oli challenges one of leadership's most entrenched assumptions: that resilience is about individual grit and mental toughness. Drawing on the Samburu concept of naboisho—interdependence—he shows how real resilience is built through collective support, not solo endurance. He also names the single most important question leaders need to ask when entering any new culture or organization: What assumptions am I making? The catch? Most assumptions are invisible to us because they feel like "normal." Oli also explores why many wilderness and offsite leadership experiences fail to create lasting change, and shares his solution: a three-phase transformation framework—preparation, immersion, and integration—shaped by the work of past podcast guest, Joe Pine. This episode is an invitation to question your cultural defaults, rebuild genuine human connection, and develop a healthier relationship with time—so your leadership, and your team's resilience, can actually endure. Find episode 498 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Oli Raison on Why Grit Isn't Enough: Rethinking Resilience in Leadership https://bit.ly/TLP-498 Key Takeaways [04:12] Oli says the leadership assumption consistently dismantled his resilience—the Samburu are resilient through interdependence called "naboisho," not grit. [07:00] Oli identifies profound learning as the importance of having a shared sense of purpose and a very strong shared set of values. [08:31] Oli responds that people have very different expectations of leadership in different cultures around the world. [10:11] Oli reveals the Samburu doesn't have words for anxiety or depression and you'll certainly never meet somebody who knows somebody who committed suicide. Oli notes loneliness is now as damaging for your health as smoking 15 cigarettes a day. [12:00] Oli responds I think too much comfort can be a bad thing and people get discombobulated easily if things don't go quite to plan. [14:35] Oli answers the critical question leaders should ask: what assumptions am I making? Because we don't realize we're making assumptions. [17:07] Oli explains African societies have a fundamentally different understanding of time where there's always enough time. [20:10] Oli explains the Samburu are very spiritual people connected with their ancestors and you're also connected with your descendants. [22:30] Oli says mindset adjustment happens organically from just being offline during 10-day expeditions with six days of camel-supported trekking. [24:53] Oli describes their three-phase structure: preparation, immersion, and integration with coaching sessions at two, four, and six weeks after. [29:20] Oli responds his long-term impact is about flourishing, particularly helping men dealing with anxiety, depression, and suicidality. [31:43] Oli states his aspiration: how can we create workplaces, organizations and teams that flourish? Because that's when people really do their best work. [33:45] Jan shares his realization about keeping fingers on the keyboard versus closing the laptop because the most important thing is that person in front of you. [35:56] And remember..."One way to get the most out of life is to look upon it as an adventure." - William Feather Quotable Quotes "The Samburu, what makes them so resilient is this concept of interdependence, this reliance, this collective reliance on one another...if my cattle get wiped out because of a really challenging drought, I know that my neighbors are going to step in and they're going to give me some of their cattle." "Naboisho is a word in their language which kind of roughly translates to coming together or unity. And they often say things like 'we are because they are,' that we are all sort of in this together." "This is a society that doesn't have words for anxiety or depression. And you'll certainly never meet somebody who knows somebody who committed suicide...loneliness is now as damaging for your health as smoking 15 cigarettes a day." "In the west, we think of time as a commodity. We think of time as something that can be saved, it can be wasted, it can be lost. And as a result of that, I feel that time is the master of us and we are not the master of time." "The Samburu always say there's always enough time because they don't think of time as this continuous thing...time occurs when events happen, it's more relational and it's more eventful." "What assumptions am I making? And this is tricky, right, because a lot of the time we don't realize we're making assumptions." "We don't need to be experts, but we do need to be detectives...what assumptions am I making that might be getting in my way?" "All of this technology is actually causing our brains to operate on a frequency that is not conducive with creative thought at all. And by being in nature, just that alone creates an environment for people to have some really powerful insights." "I think one of the things that people come away with is I really need to take more time out to just contemplate and to think. You know, think about your business, think about your life. We don't take time to think anymore. We're just reacting." "This obsession with hyper productivity is actually just, again, it's all distraction, you know, it's taking us away from just being with ourselves in the moment or being with somebody else." "In 1990, the average man had five close friends and now he has one...every minute that we spend on a device, on a phone, on a laptop, thinking that we're connecting is a minute that we're not spending really connecting with somebody." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Oli Raison LinkedIn | www.linkedin.com/in/oli-raison-1107aa11/ Safarini Leadership Website | www.safarinileadership.com Safarini Leadership LinkedIn | www.linkedin.com/company/safarini-leadership Safarini Leadership Instagram | @safarinileadership

Geoff Woods, founder of AI Leadership and author of The AI Driven Leader, teaches leaders to use AI as a thinking partner. He explains the CRIT framework (Context, Role, Interview, Task). He shows how to make AI ask the right questions, collapse months of work into minutes, and focus on the 20% that drives most impact.

Mark van Rijmenam is a futurist, award-winning keynote speaker globally ranked as number one in his field. Salesforce recognizes him as a leading voice in AI. His latest book, Now What: How to Ride the Tsunami of Change, is available now, and he's the founder of FutureWise. In this episode, Mark challenges the assumption that faster change requires faster action. He argues that organizations moving at breakneck speed with AI and emerging technologies often skip the critical step: pausing to think about consequences. Mark introduces his three E's framework—educate, experiment, execute—as a systematic approach for leaders navigating exponential technological convergence. He emphasizes that while root knowledge becomes obsolete, skills like adaptability, strategic foresight, digital literacy, and ethical grounding become essential for building resilience in uncertain futures. In this episode, you'll discover how to lead through exponential change without losing your humanity, your judgment, or your competitive edge. Find episode 496 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Mark van Rijmenam on Why Faster Change Doesn't Mean Faster Action https://bit.ly/TLP-496 Key Takeaways [02:14] Mark circumnavigated Australia on bicycle in 100 days, raising $25,000 for Dutch children's cancer fund. [04:19] Mark said the most important starting point is becoming aware and educating yourself on all emerging technologies, not just AI. [08:19] Mark explained we discover AI rather than invent it, so we need to slow down and think instead of rushing forward. [14:46] Mark's digital twin can be WhatsApp'd 24/7 in 29 languages to answer deeper questions about his book. [16:17] Mark hopes in 10 years leaders will ask "how could we have been so stupid to move so fast?" [19:42] Mark recommends the three E's framework: educate, experiment, then execute what works best. [21:52] Mark insists leaders must understand technology implications or they'll dismiss great ideas they don't understand. [25:15] Mark said we need authentic human leaders because a machine-run society would be efficient but unpleasant. [29:51] Mark hopes technology convergence will foster humility and help us live in tandem with nature. [36:58] Mark said focus on analytical skills, adaptability, foresight, digital literacy, ethics, creativity, and collaboration. [39:07] And remember..."Our intuition about the future is linear. But the reality of information technology is exponential, and that makes a profound difference. If I take 30 steps linearly, I get to 30. If I take 30 steps exponentially, I get to a billion." - Ray Kurzweil Quotable Quotes "Leadership today in this fast changing world is different from leadership yesterday. The world of yesterday is no longer." "We don't invent AI, we discover AI. And that is a completely different perspective that has a big effect on everything that we do." "A lot of the big tech companies don't even understand the LLMs that they're building. They don't understand how they operate, which is really problematic." "Critical thinking is under siege because of these large language models, but we still need to think ourselves." "It's a bit of a paradox. You think you need to move faster and faster because the world is changing faster and faster. But you also need to build in moments to pause and reflect." "It's nice to be the first to market, but often it also comes with all the R&D and all the problems. Sitting back a little bit longer will help you move faster in the end." "Static knowledge is sort of dead. We need to have dynamic interactions." "AI and capitalism is a perfect storm where they really feed into each other." "If we don't educate people how to leverage AI, how to deal with AI, they might think it cares about you." "If we're going to end up in a society that's run by machines, it will be a very not pleasant society to live in." "We are social animals. We need that social interaction." "History doesn't repeat itself, but it certainly rhymes." "Continually running faster and faster to grab more and more money might not be the best solution in the world where we built extremely powerful tools." "Root knowledge is sort of becoming out of date because you can just look up with the click of a button." "You're not going to have one career anymore. You're going to have multiple careers in your lifetime and potentially even have multiple careers at the same time." 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 Mark van Rijmenam website | www.thedigitalspeaker.com Mark van Rijmenam X | @vanrijmenam Mark van Rijmenam LinkedIn | http://linkedin.com/in/markvanrijmenam

Patrick Veroneau is CEO of Emery Leadership Group and author of The Leadership Bridge: How to engage your employees and drive organizational excellence and The Missing Piece: What Great Teams Do That Others Overlook. In this episode, Patrick explains why organizations' increasing focus on accountability systems over the past five years has coincided with employee engagement hitting a 10-year low. He reveals the accountability paradox: the harder you push for accountability, the further you get from ownership. Patrick discusses why leaders fall short in closing the gap between intention and impact—we intellectually understand leadership concepts, but fail to apply them consistently. Patrick explains the sequence that moves teams from compliance to genuine commitment (support → celebrate → own), reveals the invisible habit great teams practice (recognizing progress along the journey, not just outcomes). If you're tired of accountability systems that aren't working and want to build real ownership on your team, this episode will change how you lead. Find episode 495 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Patrick Veroneau on The Accountability Paradox https://bit.ly/TLP-495 Key Takeaways [02:57] Patrick said growing up in a large family made him more intuitive because he was always around older people having adult conversations. [04:43] Patrick explained that leaders fall short because they intellectually understand concepts but don't apply them consistently or model the behaviors they expect. [06:58] Patrick shared that social exclusion triggers the same brain response as physical pain, and unexpected recognition spikes dopamine while unrecognized effort decreases it. [11:47] Patrick revealed the accountability paradox: average teams focus on accountability first, but great teams support and celebrate first to create ownership. [14:25] Patrick shared Stephen Covey's insight that leaders need to trust other people first, not wait for others to trust them. [17:32] Patrick said the invisible habit of great teams is celebrating progress along the way, not just the final outcome. [21:34] Patrick said companies that aren't flexible on remote work will be at a disadvantage, but connection must be intentional and meaningful. [26:49] Patrick shared that Rear Admiral Cutler Dawson's success came from "walking the deck plates"—connecting with people at all levels, not his authority. [33:24] And remember..."Leadership is not about a title or a designation. It's about impact, influence and inspiration. Impact involves getting results, influence is about spreading the passion you have for your work, and you have to inspire teammates and customers." - Robin S. Sharma Quotable Quotes "Don't settle for accountability. It's the low bar. Shoot for ownership." "To be on a great team, you have to first commit to being a great teammate." "Average organizations focus on accountability first. Great teams support and celebrate first, then create ownership." "We need to trust other people first. You need to give before you get." "When people feel they should be recognized and aren't, their dopamine levels go down. That's what we experience as disengagement." "Accountability is included in ownership. But not the reverse." "Humility is the circuit breaker on overconfidence." "Walking the deck plates—connecting with people at all levels. We've overcomplicated what it means to lead." "If you don't commit first to being a great teammate, you absolutely won't be part of a great team because you're the weakest link." "Look for work, look for stuff to do, look where you can help." 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 Emery Leadership Group Website | www.emeryleadershipgroup.com Emery Leadership Group Facebook | www.facebook.com/profile.php?id=100063653920372 Patrick Veroneau LinkedIn | www.linkedin.com/in/patrick-veroneau Patrick Veroneau Instagram | @patrickveroneau

Mark Steffe is President and CEO of First Command Financial Services, bringing over 30 years of financial services leadership. In this episode, Mark explains why he left his dream job working with ultra-high-net-worth families to serve military members who truly need financial guidance. He shares how military families face unique challenges including frequent relocations, spouse underemployment, and modest pay, requiring advisors who understand their sacrifices. Mark demonstrates how building trust and psychological safety enables difficult financial conversations, comparing financial advisors to doctors who need honest patient information. He outlines his quality control approach for serving the tight-knit military community, emphasizing mission alignment, compliance-first culture, and protecting reputation. Discover practical strategies for leading with mission over metrics, building trust for difficult conversations, and coaching teams to improve rather than simply demanding better results. Find episode 494 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Mark Steffe on When Leadership Is About Who You Serve https://bit.ly/TLP-494 Key Takeaways [04:06] Mark explains he left ultra-high-net-worth services because he wanted to change lives, not just help wealthy people get wealthier. [07:26] Mark reveals how much military families sacrifice, putting our interests and safety ahead of their own. [11:34] Mark notes COVID year one was easier as crisis mode, but year two's transition back proved harder. [14:34] Mark explains First Command uses AI for exponential growth without adding employees, upskilling workers instead. [17:27] Mark credits Simon Sinek's "Start with Why" for emphasizing communicating the why, not just what and how. [21:54] Mark reframes the financial mess as reflecting "how busy you've been taking care of everybody else," not personal failure. [27:42] Mark outlines quality control requires mission-aligned hiring and rejecting the false choice between profitability and compliance. [33:13] Mark tells his "throw strikes" story: His son didn't need parents yelling commands, he needed a coach to fix his mechanics. [38:52] And remember..."Knowledge will forever govern ignorance; and a people who mean to be their own governors must arm themselves with the power which knowledge gives." - James Madison Quotable Quotes "Our job was to help wealthy people get wealthier. I wanted to change lives instead." "If Jack's not throwing strikes, he doesn't need someone to yell at him to throw strikes. He needs the coach to walk out to the mound and help him adjust his mechanics." "If employees aren't performing at the level you need, it's not because they don't want to. They don't know how yet." "What became an accommodation for concern of people's health and safety became an entitlement." "We can either be profitable or we can be compliant. The answer is always AND—we have to be profitable AND we have to be compliant." "Early in your career you get promoted for what you do. Later, it's how you lead, how you communicate, how you paint a vision." "Your messy finances are a reflection of how busy you've been taking care of everybody else, not personal failure." "If you take care of your clients and do the right thing for them, the profits will show up." 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 Mark Steffe Website | www.firstcommand.com Mark Steffe LinkedIn | www.linkedin.com/in/mark-steffe Below are two articles from Mark about his leadership philosophy and communication strategies and the financial challenges facing military families and the importance of financial advisors. ● https://medium.com/authority-magazine/impactful-communication-mark-steffe-of-first-command-financial-services-inc-on-5-essential-e60d3e4855f7 ● https://usveteransmagazine.com/usvm/helping-military-families-overcome-historic-money-struggles/

Jim and Jan tackle the uncomfortable truth about "sand people," those team members who grind everything to a halt, and why even your best glue guy can't overcome the friction they create. Drawing from their coaching experience, Jim and Jan reveal how to identify and deal with sand people before they destroy your team. They explore the telltale signs—projecting, hoarding resources, passive-aggressive behavior—and explain why leaders consistently wait too long to act. They also share the harsh truth that someone who is not performing well is costing more than they produce, and costing opportunities and damaging team morale in ways that are difficult to quantify. In this episode, you'll learn how sand people self-identify through their behavior, the specific ways they inhibit high performance, and most importantly, why it's critical to move quickly.. Find episode 493 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Jim and Jan on "Sand People" - The Hidden Drag on Your Team's Performance https://bit.ly/tlp-493 Key Takeaways [01:35] Jim coined the term "sand people" to describe team members who act as sand in the gears, preventing smooth team operation. [03:05] Jan noted that 60% of people in the U.S. are not in high-value jobs with only 31% engagement, creating a disconnect between economic growth and worker fulfillment. [05:12] Sand people often project by complaining about what others aren't doing, which is exactly what they themselves aren't doing. [07:34] Jan confirmed that one bad person on a team poisons everything, making it impossible to have a successful team experience. [12:33] A-players immediately avoid sand people and start looking for better teams because they expect leaders to uphold standards. [16:04] Jim witnessed Larry Yost pick up a cigarette butt when no one was watching, demonstrating how modeling behavior matters more than words. [19:17] Jan admitted being a sand person as a young cynical military officer, making wisecracks without anyone coaching her on the impact. [21:05] Jim acknowledged being too harsh early in his management career and emphasized the importance of learning from mistakes. [22:06] Jan's biggest business mistake was bragging about new hires then keeping them too long trying to fix them instead of recognizing sunk costs. [23:49] Jim advocated hiring for unteachable qualities like curiosity in salespeople rather than skills you can train. [26:34] Jan recommended "Top Grading" by Brad Smart for distinguishing between easy-to-change skills and hard-to-change qualities like energy and passion. [33:36] Leaders must be attracted to friction to identify where to remove resistance and lubricate the machine for team effectiveness. [29:57] Jan identified two coaching buckets: helping people prioritize time strategically and having difficult conversations about performance expectations. [33:21] And remember… "The path of least resistance is the path of the loser." - H. G. Well Quotable Quotes "If getting rid of people is easy for you and you don't lose sleep over it, you're probably a sociopath." "The day it gets easy for you is the day you've kind of lost your soul." - "We've got to have good friction. Friction that produces traction, not friction that produces drag." "Your culture becomes the worst behavior you tolerate." "One bad person, even if they're a little bad, is way more powerful than the best person for a team." "Look for work, look for things to do, and give more than you take." - "Sand people are limiting your culture. They are in effect a toleration of sub optimal performance of weakness." "If we pay people that aren't getting the job done, then they're either a charity case or they are a thief." "As a leader, I think we need to be attracted to friction." "People are not fine wine." 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 Jan Rutherford LinkedIn | www.linkedin.com/in/janrutherford Jan Rutherford X | @JanRutherford Jim Vaselopulos LinkedIn | www.linkedin.com/in/jimvaselopulos Jim Vaselopulos xX | @jim_va

Jinky Panganiban serves as Professor of Practice at the University of Oregon's Sports Product Management Program, founder of 1969Blue Consulting, and founding member of Oregon Sports Angels. She is a former Vice President and General Manager at Nike with over 20 years of global executive experience. She led multibillion-dollar businesses across Asia Pacific, North America, Latin America, and Europe. In this episode, Jinky reveals why "fitting in" kills leadership potential and how your cultural background becomes your superpower in global business. Jinky explains how the sports product industry has built intentional leadership development by translating a shared mission to fit local cultures instead of forcing one uniform way while maintaining a unified mission. She addresses the volatile state of global trade by emphasizing curiosity and critical thinking as essential skills for the next generation. Jinky argues that despite rising nationalism and tariff threats, consumers are already voting for a borderless world through their digital behavior and content consumption. In this episode, you'll discover how to leverage your cultural background as a superpower, build high-performing global teams, and lead with authenticity in an increasingly connected world. Find The Leadership Podcast episode 492 on YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Jinky Panganiban on Stop Fitting In https://bit.ly/TLP-492 Key Takeaways [04:09] Jinky describes how she started at Nike through a blind ad in Manila and was handpicked to help build Southeast Asia operations. [06:26] Jinky reveals how three white male mentors helped her realize her cultural background was her superpower. [09:47] Jinky explains that great leadership starts with being—knowing who you are and what you stand for—not just the doing of checking off deliverables and performance goals. [12:51] Jinky distinguishes influence from selling. [13:42] Jinky describes how SPM deliberately keeps students in the same project teams for 18 months because leadership is formed in the messy middle when deadlines are tight and not everybody agrees. [17:12] Jinky explains the collective industry commitment to raising next-generation leaders who will progress the culture. [20:32] Jinky demonstrates how global brands must translate their message locally. [25:17] Jinky shares how mentor Kate Delhagen gave her courage to leave corporate and explore angel investing. [28:58] Jinky describes her current advisory work with startup brands where she's both business advisor and biggest cheerleader, modeling what Kate did for her. [31:04] Jinky argues that despite borders and tariffs, the next generation of consumers already thinks globally through social media and digital platforms, celebrating differences rather than fearing them. [34:09] Jinky emphasizes that curiosity combined with critical thinking—vetting sources and asking why—is essential for navigating today's information-saturated world. [37:26] Jinky encourages everyone to celebrate where they've come from because there's only one of you, and you can't be more original than that—your background is your competitive advantage. [ ] And remember… "To be one, to be united, is a great thing, but to respect the right to be different is maybe even greater." – Bono Quotable Quotes "There's only one of you, so you can't be more original than that." "My cultural background and where I came from and all of my lived experience actually isn't something that I should shy away from or even be embarrassed about, but actually use it to my advantage and actually leverage it." "Great leadership starts with being. It's knowing who you are, what you stand for, and how you show up, especially when no one's watching." "We believe that leadership is formed in the messy middle. You know, when the deadlines are tight, the tempers are like rising and then not everybody's agreeing, but then you still have a deadline to hit." "Global doesn't mean uniform. The best teams share common purpose but express it in ways that feel very local." "Even if we put borders around things, the consumers will vote anyway to go beyond borders. Ideas, innovation, their talent, creativity, I don't think it carries a passport." "Human leadership never goes out of style." "Learn to lead yourself first. Build credibility, make sure that you practice empathy, and then lead through action and not titles." "If you don't know how to work in teams, you cannot work in the industry." "It's not so much exporting the culture, it's about translating it so that it works for everybody." "Cultural intelligence or cultural fluency is really critical because I've seen how that has become the one skill that could bridge global teams and communicate even beyond language." "Making sure that you find sources that are credible. Not just take things face value. Critical thinking is also something that's really important to ask the question why." "Culture, whether that's country culture or community culture, it's something to leverage, and it could always be a superpower for you." "We want to make sure that we leave this place better than we found it." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Jinky Panganiban LinkedIn | http://linkedin.com/in/jinky-panganiban

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

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

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