• 406 The Give First Playbook: Brad Feld’s Tactics for Building a Legendary Life
    Aug 25 2025
    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.
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    1 hr and 12 mins
  • 405 The Enduring Power of Positioning with Laura Ries (Part 1)
    Aug 18 2025
    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...
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    1 hr and 2 mins
  • 404 Is Agentic AI the End of SaaS as We Know It? | DisrupTV
    Jul 21 2025
    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!
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    46 mins
  • 403 Closing the Execution Gap: Chris Happ on Vibe Creating and the Future of Business
    Jul 14 2025
    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,
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    1 hr and 40 mins
  • 402 Why Your Identity Is A Choice (Not A Label) with “IRON” Mike Steadman
    Jul 7 2025
    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,
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    58 mins
  • 401 Listen To Your Top 3% Superconsumers And Find What’s Weird | Building with Buyers
    Jun 2 2025
    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!
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    1 hr
  • 400 The Existing Market Trap with Al Ramadan
    May 26 2025
    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...
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    1 hr and 33 mins
  • 399 How DUDE Wipes Flushed The Competition And Became A $219M Category King | Creator Capitalist Conversations
    May 19 2025
    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!
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    54 mins