Christopher Lochhead Follow Your Different™

Vala Afshar, Chief Evangelist at Salesforce and an insightful author, joins a dynamic discussion on the transformative power of AI in business. They delve into the concept of the 'existing market trap' and its pitfalls, highlighting the importance of creating new categories instead of simply improving existing ones. Afshar emphasizes the role of agentic AI as a co-founder in innovation and how it can shift SaaS models, urging businesses to adapt and engage with the community to thrive in an evolving landscape.

Chris Happ, Co-founder and CEO of Virtuous AI, shares his insights on the urgent need for businesses to embrace AI to avoid extinction. He emphasizes that companies have just two years to integrate AI or risk falling behind. Chris discusses the role of AI as a co-founder in operations and the importance of curiosity in leadership. He highlights the transformative potential of AI in enhancing productivity and innovation, urging businesses to rethink their strategies and adopt new technologies to stay competitive in a rapidly changing environment.

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, and subscribe on Apple Podcast / Spotify!  

Anna Furmanov, host of Building with Buyers, dives into customer obsession and the crucial role of 'super consumers' in startups. She emphasizes the need for empathy and collaboration within teams to foster innovation and drive growth. The discussion highlights how businesses should create demand by deeply understanding customer needs rather than conforming to existing market trends. Insights from passionate super consumers can guide product development, and the power of gifting in consumer behavior is explored as a vital marketing tool.

Al Ramadan, co-founding partner of Play Bigger Advisors and coauthor of 'Play Bigger,' joins to discuss the 'Existing Market Trap.' He highlights the dangers of fitting new ideas into outdated categories, which stifles true innovation. Al dives into the '13 deadly sins' that entrepreneurs commit that can sabotage their visions. He argues for the necessity of category design to create new markets. The conversation also touches on the rapid evolution of AI and the importance of establishing belief in a problem before seeking solutions.

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)    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!

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. Investments include Twitter, Lyft, Bazaarvoice, Sparefoot, Ayasdi, Xamarin, Doubledutch, Twitch.tv, Playdom, Chegg, Demandforce, Rappi, Smule, and Outreach. Link Connect with Mike Maples Jr.! Floodgate | Twitter | LinkedIn | Starting Greatness Podcast Check out Mike’s new book, Pattern Breakers! Amazon Books | Porchlight Books | Starting Greatness | Pattern Breakers Newsletter 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 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 Before venture capital, Steve spent five years as a design engineer at IDEO, developing products for clients like Nike, Cisco, and McDonald’s. He later served as Director of Engineering at Immersion and VP of Product and Engineering at Ning, a social platform he helped launch. His design work has earned him over 77 patents and accolades including the Business Week Design of the Decade Award and Red Dot Award.​ Steve holds degrees from Worcester Polytechnic Institute (B.S.), Stanford University (M.S.), and Stanford Graduate School of Business (M.B.A.). He is the author of The Way to Design and hosts Product Minds, a dinner series exploring the art and science of building great products.​ Links Connect with Steve Vassallo!   Website | LinkedIn | X (Formerly Twitter) 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!

Eddie Yoon and Katrina Collier, both Category Pirates, shake up conventional views on work and retirement. Eddie sees retirement as a runway for growth, not an end point, while Katrina emphasizes designing a fulfilling life where the urge to retire disappears. They unpack the 'big retirement lie,' highlighting that work can be meaningful and joyful. Their inspiring tales encourage listeners to rethink their careers as ongoing journeys filled with purpose, community, and continuous engagement rather than mere financial pursuits.