Christopher Lochhead Follow Your Different™

On this episode of Christopher Lochhead: Follow Your Different, we engage in a profound conversation with Command Sergeant Major Gretchen Evans, a decorated veteran who served 27 years in the U.S. Army. Gretchen shares her inspiring journey, from her motivations for joining the military to her experiences as one of the few women in a male-dominated environment. She discusses the challenges she faced, including injuries that led to her hearing loss, and her post-military work with Team Unbroken, an adaptive athletic team she founded. Gretchen Evans' story is one of resilience, leadership, and unwavering dedication to service. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Honoring Veterans and Their Service: Command Sergeant Major Gretchen Evans Christopher opens the episode by expressing his deep respect for veterans and the critical role they play in society. He then introduces Command Sergeant Major Gretchen Evans, highlighting her remarkable journey and the challenges she faced, including injuries sustained in combat that led to her hearing loss. Christopher emphasizes Gretchen’s role as an inspiration, both during her military career and in her life after service, particularly through her work with Team Unbroken, an adaptive athletic team for veterans and civilians who have faced life-altering injuries or trauma. Early Motivations and Joining the Military Gretchen shares her motivations for joining the military, which were born out of necessity. After losing her parents at a young age, her older brother became her guardian. Struggling to make ends meet while juggling college and work, she was inspired by her father, a World War II veteran, and the values instilled in her. She decided to enlist in the military, finding a welcoming environment in the Army after being turned away by other branches due to her height. Breaking Barriers as a Woman in the Military When Gretchen Evans enlisted in 1979, there were very few women in combat roles. She reflects on the challenges of being one of the few women in a male-dominated environment, particularly during basic training. Despite the tough leadership from Vietnam veterans who were not accustomed to training women, Evans expresses gratitude for the rigorous training she received, which prepared her for the realities of military life. She shares her first experience of being deployed to a combat zone in Grenada in 1983, describing the mix of nerves and excitement she felt. Despite her youth and inexperience, she relied on her training and the guidance of her leaders to navigate the chaotic environment. To hear more from Gretchen Evans and her inspiring story of never giving up, download and listen to this episode. Bio Command Sergeant Major Gretchen Evans is a highly decorated U.S. Army veteran, motivational speaker, and author. With over 27 years of service, she served as a senior intelligence analyst and paratrooper in multiple combat zones, including Afghanistan, where a mortar blast resulted in a traumatic brain injury and hearing loss. Despite her injury, Evans continues to inspire through her resilience, sharing her journey in overcoming adversity. She leads Team UNBROKEN, the first all-disabled team in the “World’s Toughest Race” on Amazon Prime, promoting awareness about disability and perseverance. Links Follow Command Sergeant Major Gretchen Evans! Team UNBROKEN | LinkedIn |  Instagram We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram, and subscribe on iTunes!

Christopher Lochhead, the renowned “Godfather of Category Design,” recently took the stage at the Constellations Connected Enterprise 2025 conference and delivered a blistering wake-up call to every business leader, entrepreneur, and innovator hoping to surf the current wave of AI disruption. Far from celebrating the AI gold rush, Lochhead warned that almost everyone is about to repeat the same mistakes of the past, chasing after existing markets, adding AI features like “copilots” or assistants, and calling it innovation. Drawing from his decades of expertise and path-breaking research, He then laid out a blueprint for actually leveraging AI for exponential value: it’s about category design, not incremental improvement. Here are three powerful takeaways from his masterclass that every forward-thinking leader needs to know. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Chasing “Better” Dooms You to Mediocrity Lochhead’s central thesis is as provocative as it is true: companies that use AI to make existing products just a little better are doomed to fail. He calls this the "existing market trap." Instead of designing the future, most businesses simply bolt AI onto their old offerings, thinking it will make them competitive. But "if your strategy involves simply bolting on an AI assistant or copilot, you're making a pussy move and you're fucked." Lochhead points out that companies making this mistake are chasing a market that’s already been designed by someone else. And in those markets, 76% of all the value goes to the category king (think OpenAI with ChatGPT). The rest fight for scraps, regardless of whether their AI copilot is a little nicer, faster, or more user-friendly.   Winning is About Creating the New, Not Improving the Old The path to massive value in the AI era lies in doing what legends like Sam Altman, Jensen Huang, and Steve Jobs did: creating entirely new categories that didn’t exist before. Lochhead illustrates this with both tech giants and quirky startups. He jokes about how Liquid Death became a force in the water business not by making better bottled water, but by launching “canned water”; an entirely new way to experience an old product with legendary branding and a distinct point of view. The same lesson holds for technology: “Different wins, better loses.” Lochhead encourages companies to listen to the language they use; calling your new AI product an “assistant” or “copilot” puts it in the sidecar, not the driver’s seat. In contrast, declaring your invention as a new category not only reframes the problem, but magnetizes the future (as when OpenAI refused to call its core product a database, instead introducing the “large language model”).   The Courage to Create: Why Category Design Demands Boldness Lochhead doesn’t sugarcoat the difficulty of this path. Category design requires courage: “Grow a set of balls,” he tells the audience when asked how to nurture a creator’s mindset. This isn’t reckless advice; it’s a recognition that in an AI-powered economy, the value of existing knowledge is collapsing toward zero. The knowledge worker, as Peter Drucker defined it, is being replaced by the knowledge contained within AI itself. The only safe (and rewarding) place is at the edge, inventing net new knowledge and value. In other words, creating the future instead of merely extending the present. Lochhead challenges all of us: “Do you really want to spend the last however many years of your career making the status quo incrementally better? Or do you want to spend whatever’s left of your work life making a massive material difference?” To hear the full episode from the man himself, download and listen to this episode.    We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners.

In this episode of Christopher Lochhead: Follow Your Different, we are treated to a rare dialogue with John Donovan, renowned technology executive and board member, whose career has spanned transformative eras at AT&T and who continues to shape the strategies of some of the world’s biggest companies. This conversation moves from leadership lessons around innovation and timing, through the current AI revolution and its economic implications, to personal reinvention in the face of relentless technological change. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Leading through Technology and Perfect Timing John Donovan shares candid insights about what it truly takes to lead technology for corporations at massive scale. He highlights that while choosing the right technology is challenging, selecting the right time to invest and deploy is even more crucial. Drawing from his stewardship of AT&T during pivotal events, including the company’s exclusive deal with Apple for the first iPhone, Donovan explains the delicate balance between being too early, which leads to overspending, and being too late, which risks losing market leadership. He stresses the necessity of a structured process and assembling trusted teams to ensure efficient and impactful execution. This approach, he maintains, applies as much to revolutionary events of the past like the smartphone era as it does to today’s accelerating world of artificial intelligence.   The New Industrial Revolution: AI’s Economic and Organizational Impact A major theme of the conversation revolves around the unprecedented buildout of infrastructure and investment occurring in AI. Donovan sees AI as the dawn of a new industrial age: one that, for the first time, is manufacturing intelligence itself. He explains that the billions being spent on infrastructure, real estate, and hardware underpin a transformation with no real historical precedent. With AI attributed to fueling a significant portion of current GDP growth, Donovan believes that while the hype is justified, it’s still early days. Like the early years of the iPhone, when supporting infrastructure lagged behind exponential demand, today’s rapid investment in AI is setting the groundwork for productivity and business model innovation across industries. The conversation touches on how traditional organizational roles and entire sectors are preparing for disruption; category leaders are poised to emerge quickly, and those companies that cannot adapt may not survive.   Reinventing Leadership and the Rise of the Creator Capitalist Donovan offers a personal take on how the pace of change is shifting what it takes to be a successful executive. He predicts that in the near future, the average age of top industry CEOs will drop significantly, as the new environment favors younger leaders who are native to emerging technologies. Experience, he suggests, is being surpassed in value by competency and the capacity to continually self-educate and reinvent oneself. Expanding on the evolution of work itself, Donovan aligns with Christopher's view that we are moving beyond the traditional "knowledge worker" into an era where net new knowledge creation and leveraging AI to build new value will define career success. This creator-driven approach requires not just technical skill, but also imagination and the courage to challenge existing processes. As AI increasingly automates repetitive and procedural tasks, human creativity in integrating and orchestrating these new tools will become the key differentiator across all fields. To hear more from John Donovan and the man who launched the iPhone, download and listen to this episode.    Bio Retired Chief Executive Officer of AT&T Communications, LLC, a wholly-owned subsidiary of AT&T Inc. John Donovan served as CEO from August 2017 until his retirement in ...

If you’ve ever wondered why so many high school graduates seem ill-prepared for life in the real world, you aren’t alone. On this episode of Christopher Lochhead: Follow Your Different, we have a powerful conversation with education innovator Ted Dintersmith where the broken state of America’s education system is laid bare, and a refreshingly practical vision for the future is explored. The discussion, centered on Ted's new documentary “Multiple Choice,” makes a compelling case for reimagining high schools as launchpads for life, not just college admissions. As Ted puts it, “Imagine if the purpose of school were to prepare kids for life instead of standardized tests.” It’s a simple idea with revolutionary implications. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Ted Dintersmith on the Cost of Standardization In today’s high-pressure academic environment, schools have become laser-focused on standardized testing and college prep at the expense of real-world readiness. Ted Dintersmith is unflinching in his critique: “You hold people accountable to test scores. What are they going to do? They’re going to do test prep. And I think it’s damaging the futures of millions and millions of kids.” The impact is startling. Curiosity, creativity, and a sense of purpose are “crushed”, replaced by a relentless treadmill of test drills and application padding. What’s more, society has paradoxically managed to “make people less capable at older and older ages.” Where previous generations might have been working, serving in the military, or starting their own ventures in their teens, many of today’s young adults struggle to launch. The root, according to Ted , is a model of schooling stuck in the late 19th century, one designed for a world of rote tasks, not the dynamic, creative economy of today. “We’ve gone from 99% of the jobs being ‘here’s your assignment, do it’ jobs to basically close to 0%. Now we need people to create and invent their path forward,” Ted explains. But our schools, he laments, “put that into a meat grinder” that discourages independent thought and problem-solving.   Winchester’s Innovation Center: Real-World Learning for Every Student Perhaps the most hopeful moment in the conversation is Ted Dintersmith’s description of the Innovation Center in Winchester, Virginia: a school that’s rewriting the rules. There, every student, regardless of their academic track, participates in hands-on, career-oriented learning. From carpentry and welding to health care and artificial intelligence, the center offers a real taste of practical skills and modern technologies. What sets Winchester apart is that this isn’t a program for a select few. “Every kid is spending healthy amounts of their high school time in there, in the Innovation Center,” Ted shares, highlighting how this all-in approach bridges the gap between vocational and academic pathways. Importantly, college-bound students benefit, developing resilient, adaptable skills alongside their career-focused peers. “If a kid was at a school and they optionally took welding instead of AP chemistry, an elite college would turn them down… But here, because that’s what all the kids do, they say, ‘Oh, well, they kind of had to do it. I can’t really ding them for that,’” - Ted Dintersmith The results are telling. Students who might have once been written off as “suboptimal” are thriving. College applicants stand out with compelling stories of real achievement. And, perhaps most importantly, the community is united in supporting all students, regardless of their background or political leanings. “The school sends a message to the community that we respect all paths, and the community comes together irrespective of where they are in a very broken country, politically. Those political views don’t matter. It’s like,

The business world rewards those bold enough to bet on seismic shifts; those who don’t just ride the wave, but fundamentally reshape the tide. In a fascinating conversation with Tien Tzuo, legendary founder of Zoura, we get a rare look into category design, entrepreneurial persistence, and the mindset required to rewire an entire industry, as Tzuo did for the subscription economy. As technology continues to accelerate, with AI now setting the stage for yet another major leap, this dialogue holds powerful lessons for anyone seeking to lead, not follow. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Building Enduring Category Leaders: Evangelism and Timing Legendary startups aren’t created by chance. As Tien Tzuo describes, successful category creation starts with seeing a shift others overlook, then boldly evangelizing that vision. "Part of the category is to say, okay, there's a shift that's happening with this new technology. It's a significant, meaningful, profound shift." - Tien Tzuo Tien Tzuo’s journey with Zoura began well before “subscription” was a buzzword; when Netflix mailed DVDs and Wall Street scoffed at recurring revenue. He and his team endured blank stares and skepticism, proving that timing, storytelling, and the relentless ability to communicate the new reality separates mere participants from true category leaders.   The Relentless Power of Story and Persistence Distilling complex ideas into a market-moving narrative is as important as technical innovation. Tzuo credits much of Zoura’s momentum to persistent storytelling: on stage, in books, and across every communication platform available. “What I saw was good storytellers…talk about a big, big trend that’s happening all around us…the market, the world.” Writing a book, he admits, was hard but necessary. "The only person that can tell your company story is you. Right, because it’s your idea, it’s your vision." For founders, being ignored or doubted isn’t a sign to pivot away; it’s a signal to refine and hammer home the message until the world is ready to hear it.   Tien Tzuo's Advice for Category Creators in the AI Era Today, the pace of change is faster than ever. Yet the recipe for winning new categories remains strikingly consistent. Tzuo counsels entrepreneurs to begin with their unique insight into a megatrend, not with the category label itself: “Don’t start with a category. Start with…what gives you a right to exist?” - Tien Tzuo The logic applies in AI as much as SaaS: massive investments will be lost by those chasing what’s already established, while the next category-defining companies will stay close to their customers, listen relentlessly, and focus on the transformation they alone can catalyze. As Tzuo puts it, “With every new technology shift, there's an opportunity to displace an incumbent.;” if you have the courage to shape, not just surf, the future. To hear more from Tien Tzuo on the art of Category Making, download and listen to this episode.    Bio ChatGPT said: Tien Tzuo, acclaimed author of Founders, Keepers, is a visionary entrepreneur and respected thought leader in the subscription economy. Best known as the founder and CEO of Zuora, he has helped redefine how companies build recurring revenue models, drawing on decades of experience at the forefront of technology and innovation. In Founders, Keepers, Tien shares powerful insights on leadership, culture, and the enduring commitment required to build companies that last. His writing blends practical guidance with stories from his own journey scaling global businesses. A sought-after speaker and mentor, Tien inspires founders to stay true to their mission while adapting to change, fostering organizations that thrive for generations.   Links Connect with Tien Tzuo! Zuora Website | LinkedIn | Medium

When it comes to startup success, few voices are as insightful as Rich Hagberg and Tien Tzuo. On this episode of “Christopher Lochhead: Follow Your Different,” these two innovators unveiled the complex tapestry of traits, behaviors, and pitfalls that define great founders. With decades of psychological research and hands-on experience in the tech ecosystem, they’ve distilled their findings in their new book, Founders, Keepers: Why Founders Are Built to Fail and What It Takes to Succeed. This lively, honest conversation goes far beyond the usual business platitudes, aiming to equip listeners, whether aspiring entrepreneurs, seasoned founders, or investors, with tools for self-awareness, adaptability, and ultimately, building companies that last. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   The Double-Edged Sword of Founders: Why Strengths Can Be Weaknesses One of the core insights that Hagberg and Tzuo bring forward is the “double-edged sword” nature of founder psychology. Successful founders often possess massive vision and creative drive, seeing the future before others do and inspiring teams with almost evangelical zeal. Yet, these very strengths can morph into ticking time bombs as companies grow. Founders are frequently high in vision but far less gifted in execution or relationship building. Hagberg’s decades of data, including 50+ measured personality elements and 46 leadership competencies, reveal consistent patterns: founders often struggle to manage and scale companies beyond their own shadow. As Hagberg observes, those strong on visionary skills can be “allergic to structure,” resisting the very systems and processes that enable growth and stability. Tien Tzuo, drawing on his own journey as a founder, recounts the moment when his company started unraveling as it outgrew his initial hands-on approach. The culture suffered, teams fragmented, and productivity declined. Only by honestly confronting his own leadership shortcomings and seeking help from coaches like Hagberg, was he able to pivot and build an organization beyond himself. The lesson is clear: self-awareness is not optional; it’s the foundation for sustainable success.   The Critical Role of Self-Awareness, Adaptability, and “Recovering Founders” Delving deeper, Lochhead, Hagberg, and Tzuo discuss a trait that repeatedly separates successful founders from those destined to “blow up”: brutal, reflective self-awareness. Hagberg’s research shows that founders who actively seek feedback, reflect on both successes and failures, and are open to learning are dramatically more successful than their peers. It’s not just about innate curiosity; it’s about the willingness to recognize weakness, hire complementary strengths, and genuinely adapt as the organization matures. This journey often requires what the guests jokingly call becoming a “recovering founder,” someone who learns the hard way that vision alone won’t scale an enterprise. The most successful founders are those who create adaptable organizations, listen keenly to advisors and employees, and deliberately build processes for collective decision-making. They reserve their opinions in meetings, choosing instead to solicit diverse viewpoints before weighing in; a counterintuitive move that leads to more honest conversations and smarter strategy. The inability to adapt, on the other hand, is lethal. Data from Hagberg’s cohorts shows that unsuccessful founders are consistently more egotistical and stubborn, craving to be right over being successful and cultivating environments where disagreement is stifled. This leads to what Hagberg terms “sunflower bias”; teams that simply turn to follow the founder, rather than challenging assumptions or uncovering blind spots.   Building Teams, Accountability, and the Myth of the Asshole Genius

On this episode of Christopher Lochhead: Follow Your Different, in an unfiltered and deeply human conversation with Christopher Lochhead and Eddie Yoon on their Creator Capitalist Conversation, Monroe Jones traces his journey from the experimental studios of Alabama and Nashville to working alongside icons like U2, Stevie Nicks, and David Crosby. Through stories of uncertainty, obsession, and unlikely breakthroughs, Monroe offers a blueprint for building a life and career powered by authentic passion and “slow dopamine.” If you’ve ever wondered what it takes to create a meaningful, enduring legacy in the music business, or any creative field, legendary Grammy-winning producer Monroe Jones offers a masterclass in the transformative power of obsession, generosity, and self-forgetfulness. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   The Art of Serendipity: Building a Life Through Obsession and Generosity From the earliest moments of the conversation, it’s clear Monroe Jones’ career wasn’t pursued with a perfect plan, but rather, navigated by an intense pull, what he calls “the disease” of creativity. Growing up in the South, Monroe was steeped in family, tradition, and, crucially, music; a world that intersected unexpectedly with architecture, marketing, and the showmanship of the British pop invasion. By his teens, Monroe was constructing makeshift studios, experimenting with reel-to-reel tape machines, and hustling his way through the yellow pages of Nashville’s Music Row. Resourcefulness was his secret weapon. For nearly a decade before his breakthrough, Monroe lived on a writer’s stipend, stacking thousands of “unseen reps” in the studio, all the while feeling compelled to create, regardless of circumstance. But perhaps what truly sets Monroe apart is not just the hustle or even the technical prowess, but his commitment to generosity and openness within creative communities. He recounts transformative moments: in dimly lit control rooms at A&M Studios or impromptu sessions with future legends, where serendipity and relationships created leaps of opportunity. “A lot of it is in a Forrest Gump sort of way,” Monroe laughs, describing chance encounters with the likes of Bono and Jimmy Iovine. Yet these “lucky breaks” were only possible because Monroe had prepared meticulously for a decade, learned every piece of new technology, and was always willing to show up for others, both as a collaborator and behind the scenes. “Creativity is freedom for me,” he declares. “If I can make something, boy oh boy. That’s it.”   Design, Songwriting, and the Architecture of Lasting Craft One of the most insightful threads running through the conversation is Monroe’s unique perspective on the parallels between songwriting, architecture, and marketing. He attributes much of his creative worldview to both his father, a celebrated architect, and a college professor who urged him to pursue his true passion. The insight? Structure underpins all acts of creation, whether building a cathedral or crafting a pop anthem. Monroe sees songs as buildings, each with their own rooms (verses, choruses, bridges) and design principles, a blend of logic, beauty, and flow. This architect’s eye carries over to his work with artists at every stage, from the earliest demos to Grammy-caliber productions. Monroe’s obsession with “stacking reps”, hours spent learning, iterating, and failing, is the invisible scaffolding behind creative legends. He reflects on years in the studio as both exhilarating and grueling, emphasizing that the foundational investments of time and curiosity yield not just technical mastery, but an enduring inner capital of confidence, relationships, and creative assets.   Slow Dopamine: The Bliss of Self-Forgetfulness and the True Creative Edge Perhaps the richest takeaway from Monroe’s journey is hi...

On this episode of Christopher Lochhead: Follow Your Different, we welcome back Ray Wang, principal analyst and CEO of Constellation Research, for a dynamic discussion on technology’s future. We explore the explosive rise of AI-native companies, the shifting global tech landscape, and the urgent need for U.S. manufacturing revitalization. Ray also highlights NVIDIA’s dominance in AI, the U.S.-China tech rivalry, and challenges facing Western innovation. The conversation addresses local governance, inefficiencies in public spending, and the importance of community-focused leadership. Insightful and timely, the episode offers a candid look at the opportunities and risks shaping tomorrow’s tech-driven world. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Ray Wang on the Rise of AI Exponential Companies: Redefining Tech’s Competitive Landscape The tech industry is undergoing a radical shift as “AI exponentials” redefine how companies launch, scale, and compete. Coined by Christopher Lochhead and analyst Ray Wang, these ultra-lean ventures harness artificial intelligence to achieve extraordinary efficiency, often generating tens of millions in annual recurring revenue with only a few employees. ServiceNow’s rise to a $180 billion market cap illustrates the long arc of cloud innovation, but today’s startups push the model further. Sites like tinyteams.xyz track firms posting up to $20 million ARR per employee, while projects such as Turbo Learn AI, built by college dropouts using only ChatGPT, AWS, and Perplexity, show how minimal capital can now create high-impact software. This “atomization” of business echoes biotech’s disruption of big pharma: innovation emerges outside legacy giants, who increasingly serve merely as distribution channels. The next frontier may be one-person, billion-dollar enterprises, unleashing vast creative potential while reshaping society. Ray Wang on the White Collar Recession and the AI-Driven Future of Work Ray Wang warns that the world is entering the largest White-Collar Recession yet, driven by rapid automation and AI. Tech giants like Microsoft and Nvidia expect to double revenue without adding comparable headcount, transforming the workplace from a broad pyramid into a narrow diamond. This shift threatens entry-level and managerial roles, leaving young workers with limited opportunities and older professionals facing displacement despite valuable expertise. Rather than simple layoffs, Ray sees an evolution of work. Experienced knowledge workers, equipped with affordable, scalable tools, are more likely to launch their own ventures than climb shrinking corporate ladders. Venture capital, built for slower, capital-heavy startups, struggles to keep pace as AI founders can bootstrap to profitability. The next two years, he predicts, will usher in a golden age of AI entrepreneurship. Yet this transformation raises urgent questions about mentorship, economic mobility, and how society will adapt alongside technological progress. Geopolitical AI, the US-China Cold War, and the Battle for Humanity’s Future Ray Wang casts the US–China tech rivalry as a defining struggle for humanity’s future: one fought with chips, algorithms, and influence rather than weapons. He contrasts China’s centralized, surveillance-driven AI model with the West’s ideal of decentralized abundance and freedom. This conflict, simmering for over a decade, now plays out in debates over chip exports, data sovereignty, and social-media persuasion wars. America currently holds a three-year chip advantage through companies like Nvidia, which dominate both hardware and AI software ecosystems. But Wang warns this lead is fragile: Chinese engineers are skilled, manufacturing capacity is world-class, and Europe risks irrelevance unless it chooses a side.

On this episode of Christopher Lochhead: Follow Your Different, we welcome back marketing leader and author Laura Ries for the conclusion of their two-part conversation. If you haven't listened to part 1 or would like to remind yourself where we left off, you can check it out here for a quick recap (FYD 405).  Laura shares insights from her new book, The Strategic Enemy, emphasizing the importance of defining what your brand stands against. The discussion covers lessons from her father Jack Trout’s legacy, the power of positioning, and the role of visual storytelling in marketing. Laura has been on the frontlines of marketing for decades, carrying on the legacy of her father, Al Ries, and pushing the boundaries of positioning with her own punchy perspective. So what’s the real difference-maker in a market crowding with noise, AI, and everyone vying for a sliver of attention? It’s not merely being seen. It’s being distinct, thanks to the power of strategic opposition. Join us as we get into it and more with Laura Ries. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Opposition over Superiority Laura puts it in plain English: “The mind understands opposition faster than superiority.” Translation? If you want people to quickly get why they should care, you have to tell them what you’re not. Chick-fil-A isn’t just for chicken lovers, it’s for people who are tired of burgers. In-N-Out doesn’t bother with chicken or vegan burgers; they double down on a simple, hyper-focused menu that stakes out clear territory against the bells and whistles of modern fast food. When brands define WHO or WHAT they’re battling, it’s easier for us to pick sides. Defining an “enemy” isn’t about trash talk, it’s about clarity. It sharpens what your business stands for, attracts loyal fans, and carves out space the competition can’t touch.   Laura Ries on Finding Your Horse & Riding It This goes deeper than companies. The idea holds for personal brands, careers, even college choices. Laura recalls her father’s (now out-of-print) classic “Horse Sense”: don’t desperately try to do everything yourself; align yourself with the right “horse” (be it a category, a company, a person) and let synergy do the work. In a world of endless new tech and shifting industries, picking the right vehicle can be everything.   Stop Chasing Attention. Start Picking Fights (the Smart Way) At the end of the day, nobody cares about your journey just for the sake of it. They care about how you make THEM matter, how you help them win THEIR battles, or fight an enemy they find worth taking down. So, next time you’re tempted to “go viral,” ask yourself: Are you actually useful, or just noisy? Have you defined your enemy? Because if your brand (or your career) doesn’t stand against something, it’s just floating in the middle… and nobody roots for the middle. Laura’s full-throttle approach: get clear, get focused, and don’t be shy about drawing a line in the sand. To hear more from Laura Ries and her thoughts on Strategic Opposition, download and listen to this episode.    Bio Laura Ries is a leading marketing strategist, best-selling author, and global keynote speaker. She is the co-author of several influential books on branding, including The 22 Immutable Laws of Branding and The Fall of Advertising & the Rise of PR written with her late father and legendary positioning pioneer, Al Ries. Her new book The Strategic Enemy: How to Build & Position a Brand Worth Fighting For will be published in September 2025 by Wiley. As chairwoman of RIES, the consulting firm she founded with Al, Laura has advised Fortune 500 companies and startups alike on building powerful, enduring brands. Her expertise lies in positioning, brand focus, and creating category dominance in competitive markets.   Links Connect with Laura Ries!

If you’re fascinated by the intersection of deep human connection and legendary entrepreneurship, this episode of Christopher Lochhead: Follow Your Different with Brad Feld is a masterclass. Brad Feld, co-founder of Techstars and Foundry Group, unpacks the profound philosophy at the heart of his new book, "Give First: The Power of Mentorship," offering both tactical wisdom and hard-won personal perspective. This is not the typical “give-back” story, but a look at how true mentorship and generosity fuel the careers and lives of those willing to embrace a different approach. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Brad Feld on Mentorship: More Than the “Guru on the Mountaintop” Myth Brad Feld’s journey with mentorship began in his youth, encountering influential figures before “mentoring” was even part of the social lexicon. Like many from the 1970s and 1980s, he didn’t realize the people shaping his trajectory were mentors, but the relationships he had changed everything. Critically, Feld draws a distinction between mentors and gurus: the former guide, question, and encourage self-discovery; the latter simply impart answers from a higher level. He notes that over time, truly powerful mentorship evolves: “There’s a magic trick where mentors become peers." - Brad Feld Real mentoring relationships become two-way streets—everyone learns, everyone grows.   Give First: Non-Transactional Generosity as a Superpower At the heart of his philosophy is a core principle: "Give First" means putting energy into a system without a required transactional expectation of return. This, Feld insists, is not simple altruism nor traditional “pay it forward,” which often feels obligatory or limited to later stages of a career. Instead, giving first is a chosen mindset, accessible at any stage and open to anyone: students, new grads, and seasoned executives alike. A key insight: “Pay it forward is obligatory," Feld explains, "Give First is non-transactional. There’s no obligation.” This liberation from expectation creates space for unexpected returns in relationships and opportunities, often arriving from unrelated directions and on unpredictable timelines.   Brad Feld on the Art (and Challenge) of Being Accessible: Random Days and “Assignments” As an influential figure in the startup world, Feld faces a deluge of requests from aspiring entrepreneurs and peers alike. Balancing generosity and boundaries is an evolving practice. His solution was to create “Random Day”: a designated day each month packed with 15-minute meetings open to anyone interested. This provided structure, scale, and protection from being overwhelmed, while also ensuring he could still make a meaningful impact and learn from every encounter. Equally important is Feld’s email “assignment” technique. Rather than simply agreeing to every meeting, he requests more specificity from senders, an effortful response that immediately filters for genuine intent. Feld’s data is telling: about 50% of people simply never reply to the assignment, allowing him to focus energy on the truly motivated, engaged few. To hear more from Brad Feld and how Giving First is a Superpower, download and listen to this episode. Bio Brad Feld is a venture capitalist, entrepreneur, and author with more than three decades of experience in investing and building startups. He is a co-founder of Foundry Group, a Boulder-based venture capital firm focused on early-stage technology companies. In addition to his work with Foundry Group, Brad co-founded Techstars, one of the world’s most successful startup accelerators, helping thousands of entrepreneurs launch and scale their businesses. He is also deeply involved in fostering entrepreneurial communities worldwide. An avid writer, Brad has authored several books on startups and venture capital.

On this episode of Christopher Lochhead: Follow Your Different, we sit down with marketing royalty Laura Ries, the daughter of Al Ries and Chairwoman of RIES, to unpack what makes for truly powerful brand building. The discussion, sparked by American Eagle's controversial Sydney Sweeney campaign, offers a masterclass in cutting through the noise and making brands that dominate for decades, not just news cycles. In a world obsessed with fleeting attention spans, viral TikToks, and celebrity partnerships, the rules for building a lasting brand have never been more confusing, or more misunderstood. When “attention” has become the trending currency, too many marketers forget the fundamental principles that separate overnight sensations from category-defining legends. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Chasing Attention Versus Owning a Strategic Position Laura Ries doesn’t mince words. Right from the start, she asks, “Are we just going out for attention’s sake?” In the American Eagle campaign, the retailer had Sydney Sweeney, a star adored by a young demographic. front and center with the tagline “Sydney Sweeney has great jeans.” The resulting hullabaloo proved attention-grabbing, but Laura and Christopher quickly zero in on the flaw: it was a win for Sweeney’s personal brand, maybe the category of jeans, but not for American Eagle. Compare this to the iconic Brooke Shields for Calvin Klein moment, seared into pop culture by its taboo-breaking line: “Nothing comes between me and my Calvins.” Everyone still remembers it. And Shields herself, now in her 50s and 60s, gets asked about it to this day. Why did it stick when so many celebrity-driven campaigns fade fast? Laura argues the difference is clear: Calvin Klein tied a provocative moment to a real, ownable positioning idea. It wasn’t just attention; it was differentiation, and it transformed the brand. The Leader, the Challenger, and the Power of Contrasts Christopher then adds, “The category king of jeans is Levi Strauss”. If you’re not the leader, you can’t just market the category; you must establish a well-defined, opposite position. Calvin Klein’s campaign worked because it created a contrast in the market: there’s an implied competitor, a reason to choose Calvin’s over everything else. American Eagle, on the other hand, failed to anchor its campaign in any clear difference or strategic enemy. Christopher asks, “If you’re American Eagle, what the fuck are you doing?” To this, they both agree: at the very least, American Eagle, given its patriotic name, should have leaned into American-made authenticity rather than a generic celebrity endorsement disconnected from any unique brand promise. Category Design: The True Differentiator Brands like Dude Wipes and Liquid Death exemplify the playbook for building new categories, and thus, legendary brands. Dude Wipes didn’t invent wipes, just as Liquid Death didn’t invent water. But they staked out a radically different, memorable position: “Dude” wipes for men, and canned water that resembles a beer or energy drink and brands itself as death to plastics. This isn’t attention for attention’s sake; it’s strategic, memorable, and deeply anchored to a big idea: a core enemy, a new experience, a bold promise. To hear more from Laura Ries and her thoughts on why virality isn't enough to build a legendary brand, download and listen to this episode. Bio Laura Ries is a leading marketing strategist, best-selling author, and global keynote speaker. She is the co-author of several influential books on branding, including The 22 Immutable Laws of Branding and The Fall of Advertising & the Rise of PR written with her late father and legendary positioning pioneer, Al Ries. Her new book The Strategic Enemy: How to Build & Position a Brand Worth Fighting For will be published in S...

In a special episode from the DisrupTV studios, marketing visionaries Christopher Lochhead, Ray Wang, Vala Afshar, and guest Sunil Karkera dive deep into the themes of Christopher Lochhead’s latest book, The Existing Market Trap. The conversation is a masterclass in modern marketing strategy, category design, and the seismic impact of artificial intelligence (AI) on business. If you’re a marketer, entrepreneur, or executive looking to future-proof your company and career, this episode is a must-listen. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Understanding the Existing Market Trap Most companies fail not because their products are bad, but because they compare their innovations to old market standards. This “existing market trap” forces them to compete in crowded, established categories, dooming them to incremental improvements and eventual irrelevance. Lochhead warns that trillions in investment will be lost if companies keep chasing existing markets instead of creating new ones, and much of the 90%+ startup failure rate is due to the trap of incrementalism, trying to be “better” rather than “different.” The key is to stop benchmarking new products against legacy solutions and instead ask: What new problem are we solving, and how can we define a new category around it? The Power of Category Design Category design is the discipline of creating and dominating new market categories. It’s not just a marketing tactic, it’s a strategic mindset shift. Markets are groups of people with a shared problem, while categories are defined by what people believe can solve that problem. Companies like OpenAI and Nvidia didn’t chase existing demand, they created it. Legendary category designers start with a vision of a radically different future and work backward, understanding that the language used to describe a product and category shapes what people believe is possible. Ultimately, the most powerful thing you can “ship” is a new belief about what’s possible. Rather than out-featuring competitors, the goal is to redefine the game and build the aisle, not just fight for shelf space. AI as a Co-Founder, Not a Copilot Treating AI as a mere “assistant” or “copilot” is a massive missed opportunity. AI should be the core foundation of your business and career. When AI is just an add-on, it leads to incremental change, but when it is treated as a co-founder, it enables exponential, net-new value creation. The next generation will be “native AI”; they’ll expect AI to be at the center of everything. To take advantage of this, businesses should integrate AI deeply, building processes, products, and even company culture around AI from the ground up, and reimagine roles so that AI is seen as a creative partner, not just a tool. To hear more of this amazing dialogue between marketing geniuses, download and listen to this episode.  Links If you wish to check out more episodes from DisrupTV, you can do so on these links: LinkedIn | X (formerly Twitter) | Youtube | Apple Podcast | Website We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, X (formerly Twitter), Instagram, and subscribe on Apple Podcast / Spotify!

On this episode of Christopher Lochhead: Follow Your Different, we sit down with Chris Happ, co-founder and CEO of Virtuous AI, to discuss the urgent need for businesses to embrace AI. We explore how companies have a narrow two-year window to integrate AI deeply or risk being left behind. Chris shares real-world insights on closing the “execution gap” with AI, treating AI as a true business partner, and why curiosity is now the top skill for leaders. This episode is essential listening for marketing professionals and executives navigating the AI-driven future. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Chris Happ on the AI Tipping Point for Business If you’re a business leader, entrepreneur, or marketer, you’re standing at a crossroads. The AI revolution isn’t coming—it’s already here. Christopher sat down with Chris Happ, CEO of Virtuous AI, to tackle a critical question: Do businesses have just two years to embrace AI, or risk being overtaken by it? This is not just another tech hype cycle. As Chris Happ puts it, companies will either become AI-first or become fossils. The pace of change is relentless, and the window to act is closing fast. The Urgency: Why the Next Two Years Matter Chris Happ and Christopher Lochhead draw a powerful parallel between today’s AI moment and the dawn of the commercial internet in the late 1990s. Back then, the fear was being “Amazoned”—disrupted by a digital-first competitor. Today, the risk is being left behind by AI-native businesses. Chris estimates that businesses have about a two-year window—maybe less—to make AI a core part of their operations before the competitive gap becomes insurmountable. The pace of AI development is exponential. What seemed impossible last year is table stakes today. And this isn’t just a tech problem; it’s a business survival issue. Every industry, from butchers to billion-dollar enterprises, is at risk. The advice is clear: start now. Don’t wait for AI to “mature.” The companies that experiment, learn, and iterate today will dominate tomorrow. Look at how leading companies are using AI—not just in Silicon Valley, but in your own industry. The Execution Gap: The Real Barrier to Growth Most successful companies already have solid strategies. The real challenge is execution. Chris Happ calls this the “execution gap”—the chasm between what you plan and what you actually deliver. As companies grow, executing on strategy becomes exponentially harder. Critical information is often locked away in different departments or systems, and too much time is spent on repetitive, low-value tasks. AI can close this gap by analyzing data and generating insights in seconds, not weeks. AI-driven processes reduce human error and ensure best practices are followed every time, enabling you to do more with less and scale your operations without scaling your headcount. Chris Happ shared a story where Virtuous AI’s “Violet” answered a complex business question in just 26 seconds—a task that would have taken a traditional data team two weeks. The lesson: map out where your strategy breaks down in execution, identify the bottlenecks, and pilot AI solutions in high-impact areas like sales forecasting, customer segmentation, or process automation. To hear more from Chris Happ and how you can turn AI into a valuable business partner, download and listen to this episode. Bio Chris Happ has served as Chief Executive Officer of Virtuous AI since June 1, 2024, leading the company’s move from beta into enterprise-ready deployments of its “AI in a Box” platform. An experienced tech executive and entrepreneur, he previously co‑founded blueSolutions (exiting to Hubwoo), led Goby through growth to exit via Conservice, and scaled MarketTime to 780 % revenue growth and Inc. 5000 recognition. A graduate in Economics from Miami University,

On this episode of Follow Your Different, Christopher Lochhead welcomes “IRON” Mike Steadman, a former Marine officer, national boxing champion, and entrepreneur into another installment of Creator Capitalist Conversations. Together, they explore Mike’s inspiring journey from military service to empowering Black veteran entrepreneurs. The conversation highlights the importance of identity, resilience, and mindset in overcoming challenges and reinventing oneself. This episode is a must-listen for anyone seeking inspiration and actionable advice on personal growth and entrepreneurial success. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Embracing Identity Transformation In the world of entrepreneurship, few stories are as compelling as that of “IRON” Mike Steadman: a former Marine officer, three-time national boxing champion, and now a category designer and advocate for Black veteran entrepreneurs. Mike’s identity was deeply rooted in his military service. Transitioning to civilian life, he faced the challenge of being seen as "just a boxing coach" rather than the multifaceted leader he knew himself to be. Working with performance psychologists and entrepreneurial mental health coaches, Mike learned to step back and view himself from a broader perspective, a process he calls "psychological distancing.” By intentionally shaping his identity, Mike was able to move from being defined by his past roles to actively designing his future as an entrepreneur and advocate.   Resilience Through "Time Under Tension" Just as boxers build strength and skill through grueling training, entrepreneurs develop their instincts and capacity by enduring the pressures of business. When COVID-19 shut down Mike’s in-person boxing business, he faced a moment of defeat. Instead of giving up, he used the crisis as a catalyst to pivot—launching a podcast and building a new business model from scratch.   Motivation Beyond Money Financial goals are important, but lasting motivation comes from deeper sources—purpose, impact, and community. Mike found that helping others succeed (as a ghostwriter and editor) was more fulfilling than chasing personal accolades. Inspired by a business coach’s analogy, Mike emphasizes nurturing the "soil" of your life—health, relationships, and mentorship—so your business can thrive. Mike also noticed that as he hit financial milestones, the excitement faded. He began to set new, personal challenges—like running a marathon or reaching Everest Base Camp—to keep himself engaged and fulfilled. To hear more from “IRON” Mike Steadman and his thoughts on reinventing oneself and looking at things from different POVs, download and listen to this episode.   Bio “IRON” Mike Steadman is a Marine Corps Infantry Officer turned entrepreneur, author, and boxing coach. As the founder of IRONBOUND Boxing, he empowers youth in Newark through boxing, mentorship, and enrichment programs. Mike also leads IRONBOUND Media, helping veteran-owned businesses build impactful brands through podcasting. A U.S. Naval Academy graduate and combat veteran, his leadership philosophy integrates discipline, resilience, and service. Mike hosts the “Confessions of a Native Son” podcast, exploring race, business, and personal growth. Passionate about social impact, he continues to create opportunities for underserved communities, embodying his mission to fight for those without champions in their corner.   Links Connect with “IRON” Mike Steadman! Website: IronboundBoxing.org | IronboundMedia.com | DogWhistleBranding.com Linkedin: in/Iron-Mike-Steadman Instagram: @IronMikeSteadman   We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, X (formerly Twitter), Instagram,

On this episode of Christopher Lochhead: Follow Your Different, the script is flipped and we listen to Christopher Lochhead explore the critical theme of customer obsession, especially within startups on the Building with Buyers podcast, hosted by Anna Furmanov. This conversation focuses on the importance of empathy, both for customers and within teams, and advocates for breaking down departmental silos to foster collaboration and drive sustainable growth. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Christopher Lochhead on Understanding the "Existing Market Trap" Christopher Lochhead explains that many startups fall into the "existing market trap," where they build something new but compare it to existing products. This approach stifles innovation and fails to create new demand. Instead, startups should focus on understanding their customers deeply and innovating based on their needs. Christopher introduces the concept of "super consumers," who are passionate individuals at the edges of the bell curve. These customers are not just users; they are evangelists who can help shape and define categories. He suggests that you look for customers who are highly engaged with your product and vocal about their experiences. You then create exclusive communities or programs for these super consumers to gather feedback and encourage them to spread the word about your product.   The Importance of Authentic Dialogue Christopher discusses the decay of civil discourse in society and its impact on authentic dialogue. He believes that healthy debate and the exchange of differing viewpoints are essential for a functioning society and fostering innovation in business. Christopher also shares his personal experiences with being de-platformed on social media for promoting free speech. He argues that the ability to engage in civil discourse is crucial for personal expression and fostering innovation.   Challenges in Startups Anna and Christopher discuss the common pitfalls startups face as they grow, such as shifting focus from customer feedback to product development and sales. Christopher shares examples of companies that have thrived by prioritizing customer relationships and adapting their offerings based on customer needs. Some of the things they could do are to analyze how successful companies maintain their customer focus and apply similar strategies to your business. They should also be willing to pivot your strategies based on customer feedback and market changes. To hear more from Christopher Lochhead and Anna Furmanov, download and listen to this episode.   Links Like what you hear? You can check out Anna Furmanov’s podcast, Building with Buyers.   We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, X (formerly Twitter), Instagram, and subscribe on Apple Podcast / Spotify!

On this special 400th episode of Christopher Lochhead: Follow Your Different, Christopher and guest Al Ramadan discuss their new book, "The Existing Market Trap." They explore the pitfalls businesses face when trying to innovate within established market categories, emphasizing that fitting new ideas into old frameworks stifles innovation. They advocate for category design, which involves creating new market categories rather than competing within existing ones. They also introduce the "13 deadly sins" that entrepreneurs often commit, offering insights to help avoid these common mistakes. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Al Ramadan on Understanding the Existing Market Trap The "existing market trap" refers to the tendency of businesses to try to fit new ideas into old categories. This approach often stifles innovation and growth, as companies focus on competing for market share rather than creating entirely new markets. Al and Christopher argue that this mindset is fundamentally flawed and that true innovation comes from redefining problems and opportunities rather than fitting new solutions into outdated categories. Some of the consequences of the market trap include financial loses, Constantly competing in saturated markets can lead to exhaustion and disillusionment among founders, and loss of strategic direction by the company.    Al Ramadan on The Power of Category Design Category design is a business strategy that focuses on creating new market categories rather than competing within existing ones. This approach allows businesses to escape the constraints of established market definitions and pursue groundbreaking innovations. Why is Category Design Important? Category design is essential because it empowers companies to reshape the market landscape rather than simply compete within it. Instead of fitting into existing frameworks, successful businesses create entirely new categories that address previously unmet needs, unlocking fresh opportunities for innovation and growth. This strategic approach also plays a critical role in building belief, both internally and externally, in a company’s vision. By shaping perception and defining a unique space, category design helps generate demand, positioning the business as a leader rather than a follower.   The 13 Deadly Sins of Category Design Al and Christopher introduce the concept of the "13 deadly sins" that entrepreneurs often commit when scaling their businesses. These sins serve as cautionary tales for founders who may be tempted to chase after existing market demand rather than focusing on creating new opportunities. Several common pitfalls can hinder a company's success in the market. One is the Engineer’s Dilemma, where teams become overly focused on technical features instead of addressing broader market needs. Another is the Obviously Better Fallacy—the mistaken belief that having a superior product alone guarantees market success. Finally, the Horizontal Tool Illusion occurs when a company tries to serve everyone, rather than honing in on a specific market segment. These missteps can dilute value, confuse customers, and ultimately prevent a product from gaining traction. To hear more from Christopher and Al Ramadan about the existing Market Trap, download and listen to this episode.    Bio Al Ramadan is a co-founding partner of Play Bigger Advisors and coauthor of the book, Play Bigger. He also co-founded Quokka Sports, which revolutionized the way people experience sport online. Al then joined Macromedia and Adobe, where he spent almost ten years changing the way people think about great digital experiences. At Adobe, Al led teams that created the Rich Internet Applications category and helped develop the discipline of experience design. In the early ‘90s he applied data science to Australia’s Americas C...

On this episode of Christopher Lochhead: Follow Your Different, we have a Dude conversation with the chief Dudes of DUDE Wipes to talk about how they wiped their competition and became the leader in their category. This episode is part of the Creator Capitalist Conversations, a mini-series spotlighting real-life legends who have rejected traditional career paths and built lives around what makes them different. These are stories of people who didn’t wait to get picked. They picked themselves—and started building careers that pay them to be radically them. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Links Learn more about Dude Wipes! LinkedIn | Dude Wipes   We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram, and subscribe on Apple Podcast / Spotify!

On this episode of Christopher Lochhead: Follow Your Different, we are treated to an inspiring conversation with Carylyne Chan, a startup founder, investor, and advocate for autonomy and entrepreneurship. This episode is part of the "Creator Capitalist Conversations" miniseries, which emphasizes the importance of taking control of one’s career and life. Carylyne's journey from a challenging upbringing in Singapore to becoming a successful entrepreneur in various sectors, including AI and blockchain, offers valuable lessons for anyone looking to carve their own path. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Getting to know Carylyne Chan Carylyne's story is one of choosing herself rather than waiting to be chosen. As we go further into the episode, we dive into the emotional and psychological aspects of making significant life changes, particularly the leap from traditional employment to entrepreneurship. Carylyne begins her story by recounting her upbringing in Singapore, where she faced significant challenges, including a turbulent family life. At the age of 14, she took her first internship at the National Environment Agency, which sparked her interest in understanding how people work and the importance of teamwork. This early experience laid the foundation for her entrepreneurial spirit.   Carylyne Chan and her Leap to Entrepreneurship As Carylyne transitioned from high school to college, she continued to pursue her passion for entrepreneurship. She participated in hackathons and collaborated with friends who shared her interests. This led to the creation of a startup focused on AI chat summarization before it became a mainstream concept. Their journey took them to an accelerator program in Hawaii, where they worked tirelessly to grow their business. Carylyne then discuss the emotional challenges that accompany the entrepreneurial journey. She highlights the importance of recognizing when one has outgrown their current situation and the courage it takes to make a change. She believes that the biggest risk is not quitting a job that no longer serves you but rather staying in a life that feels unfulfilling.   Discovering Her Superpower The conversation shifts to the concept of identifying one’s unique strengths or "superpowers." Carylyne acknowledges that her path to self-discovery has been complex and filled with trial and error. Initially, she viewed herself as an operational person, someone who gets things done. However, as she navigated through her first formal startup, she realized that her skills extended beyond operations to include marketing, design, and leadership. Christopher and Eddie discuss the significance of emotional intelligence in Carylyne's success. They highlight her ability to remain calm amidst chaos, a skill that has been honed through her upbringing and experiences. Carylyne’s capacity for rapid synthesis—quickly learning and distilling complex information into actionable narratives—has been a cornerstone of her work as an advisor and entrepreneur. To hear more about Carylyne Chan and her entrepreneurial journey, download and listen to this episode. Subscribe to Category Pirates today and join the crew in our Category Design journey on the business seas!   Bio Carylyne Chan is a Singapore-based entrepreneur and the Co-Founder and former CEO of CoinGecko, a leading global cryptocurrency data platform. With a background in psychology and marketing from Carnegie Mellon University, she blends analytical thinking with strategic vision to drive innovation in Web3 and fintech. Carylyne is also a startup advisor and frequent speaker on blockchain, digital assets, and entrepreneurship, recognized for her role in advancing transparency in the crypto space.   Links Connect with Carylyne Chan!Website | LinkedIn | X (formerly Twitter)

On this episode of Christopher Lochhead: Follow Your Different, we engage in a riveting conversation with Mike Maples Jr., co-founder of Floodgate and a prominent venture capitalist. This episode, which is a part of the "Creator Capitalist Conversations" miniseries, goes into the themes of entrepreneurship, personal capital, and the transformative power of artificial intelligence (AI) in the ideation process. The dialogue offers a wealth of insights for aspiring entrepreneurs and seasoned business professionals alike. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.   Mike Maples Jr.'s Journey: From Entrepreneur to Venture Capitalist Christopher Lochhead sets the stage by introducing the miniseries "Creator Capitalist Conversations," which celebrates individuals who have carved their own paths in the business world. The episode features Mike Maples Jr., who shares his journey from a successful entrepreneur to a venture capitalist in Silicon Valley. This transition, marked by risk-taking and self-discovery, offers valuable lessons for anyone looking to forge their own path in business. Mike Maples Jr. recounts his significant career shift from being a well-respected founder and head of marketing for a successful software company in Texas to starting anew in Silicon Valley as a venture capitalist. This transition, he notes, is daunting for many, especially for someone who had already achieved a level of success and recognition. Mike's approach to risk-taking involves viewing new ventures as opportunities to explore interesting ideas rather than potential failures. This mindset allows him to gradually escalate his commitment as he gains confidence.   Mike Maples Jr. on the Importance of Self-Awareness Mike shares that the journey to discovering one's superpowers is often a gradual realization rather than a single defining moment. He emphasizes the importance of honoring one's time and using it to share one's unique gifts with the world. This perspective aligns with the Japanese concept of "ikigai," which represents the intersection of what one loves, what the world needs, what one can be paid for, and what one is good at. Mike then discusses the distinction between deep work—discovering new knowledge—and harnessing pre-existing knowledge. He notes that many high-paying jobs rely on established knowledge, which may become commoditized in the age of AI. By integrating the insights of others with his unique perspective, Mike has developed a robust intellectual framework that guides his investment decisions.   Exploring Airbnb's Seed Deck: A Case Study in Innovation Mike Maples Jr. shares an intriguing case study involving Airbnb's original seed deck from 2008. Using a software tool he developed, the "Pattern Breakers Insight Stress Test," he analyzes Airbnb's business model. This analysis reveals that everyday people would rent their private homes to strangers, creating a new category of accommodation that transcends traditional hotels. This insight is underpinned by several inflection points, including the growing comfort with online transactions and the rising consumer preference for authentic experiences. Encouraged by the insights gained from Airbnb's seed deck, Mike explores further possibilities, including creating a business model canvas, potential logo designs, and a narrative framework for Airbnb. This exploration leads him to realize that similar analytical techniques can be applied to various mental models, facilitating ideation and refinement. To hear more from Mike Maples Jr. and his thoughts on careers that withstand the test of time and tech, download and listen to this episode.   Bio Mike Maples Jr. is an entrepreneur turned venture capitalist. He’s co-founder of Silicon Valley based, early-stage VC Floodgate. And the host of the popular “Starting Greatness” podcast.

On this episode of Christopher Lochhead: Follow Your Different, we have a dialogue with Steve Vassallo, a General Partner at Foundation Capital, to celebrate the firm's 30th anniversary and explore the evolution of venture capital (VC) in Silicon Valley. We discuss the shift of many traditional VC firms from early-stage investments to a more asset management-oriented approach. Steve Vassallo talks about the importance of maintaining a craft-oriented, personalized approach to VC, focusing on product excellence and effective distribution. He also highlights the current trends in AI and blockchain, urging founders to prioritize innovation and core product differentiation in a rapidly changing market. With nearly 18 years at Foundation Capital, Steve shares his unique insights into the changing landscape of venture capital, the importance of maintaining a craft-oriented approach, and the challenges faced by early-stage founders. You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go. Celebrating 30 Years of Foundation Capital Foundation Capital recently marked its 30th anniversary, a significant milestone in its journey. The firm has launched its 11th fund, a $600 million vehicle aimed at supporting extraordinary founders at the earliest stages of their ventures, particularly in the enterprise sector. Steve Vassallo adds that more than half of their investments focus on early-stage companies, including seed and Series A rounds, with a strong emphasis on technology, particularly in fintech and crypto. Steve Vassallo on the Changing VC Landscape Christopher and Steve Vassallo then discuss the evolution of VC firms, noting that many traditional firms have transformed into asset managers rather than remaining true venture capitalists. Steve points out that the percentage of capital raised by these firms for early-stage investments has dwindled significantly. He estimates that only about 20% of the capital raised by these larger firms is allocated to early-stage investments, with the majority directed towards growth-stage companies. In contrast, Foundation Capital dedicates approximately 70-80% of their recent fund to backing founders at the inception of their ideas. Steve humorously refers to these early-stage entrepreneurs as "pre-founders" or "pre-criminals," highlighting the raw potential and creativity that often characterize this stage of entrepreneurship. The Craft of Venture Capital Their conversation then moves to the notion that venture capital is fundamentally a craft business rather than a scalable factory-like operation. Christopher likens the venture capital process to crafting custom surfboards, where the quality and personal touch of the creator matter significantly. He argues that the best results come from a deep, personalized partnership with founders, rather than a one-size-fits-all approach. Reflecting on his own background in product design, Steve Vassallo adds that he initially believed that the best product would always win in the market. However, he quickly learned that effective distribution often trumps product quality. This realization was humbling for him, as he recognized the critical role that marketing and sales play in a product's success. He stresses that when extraordinary products are paired with exceptional distribution channels, remarkable outcomes can occur. To hear more from Steve Vassallo and the future of Venture Capital, download and listen to this episode. Bio ​Steve Vassallo is a General Partner at Foundation Capital, where he invests at the intersection of design, technology, and business. Since joining the firm in 2007, he has led investments in transformative companies such as Stripe, Sunrun, Cerebras Systems, and Solana. Steve co-leads Foundation's crypto practice and is known for backing product-first founders tackling consequential problems ...