

Christopher Lochhead Follow Your Different™
Christopher Lochhead
Christopher Lochhead | Follow Your Different is pioneer in real dialogue podcasts. “The best business podcast” – Podcast Magazine “The worst business podcast” – Neil Pearlberg
Episodes
Mentioned books

Sep 8, 2025 • 44min
407 The Enduring Power of Positioning with Laura Ries (Part 2)
Laura Ries, a leading marketing strategist and chairwoman of RIES, returns for a deep dive into brand positioning. She discusses her new book, 'The Strategic Enemy,' emphasizing why brands should define what they stand against. Laura reveals how the mind quickly grasps opposition over superiority, making distinctiveness crucial in a noisy market filled with AI and competition. Drawing from her father's legacy, she explores the importance of clarity in positioning, collaboration, and the impact of visual storytelling in effective marketing.

Aug 25, 2025 • 1h 12min
406 The Give First Playbook: Brad Feld’s Tactics for Building a Legendary Life
In this engaging discussion, Brad Feld, a venture capitalist and co-founder of Techstars, reveals his unique 'give first' philosophy inspired by his new book. He challenges the traditional guru-mentorship model, advocating for genuine peer relationships that foster mutual growth. Brad shares his insights on the evolving job market shaped by AI, emphasizing the need for adaptability and tech-savviness. With a mix of humor and deep reflection, he dives into the significance of mentorship, kindness, and learning from setbacks in both personal and professional realms.

Aug 18, 2025 • 1h 2min
405 The Enduring Power of Positioning with Laura Ries (Part 1)
In a captivating conversation, marketing strategist Laura Ries, chairwoman of RIES and daughter of Al Ries, delves into the art of brand positioning. She critiques American Eagle's celebrity-driven campaigns, highlighting the pitfalls of chasing transient attention instead of strategic positioning. Laura emphasizes the crucial difference between fleeting trends and enduring brands, advocating for authenticity and a focus on product identity. Through insightful examples, she explores how comfort and clarity can redefine marketing strategies in today's competitive landscape.

26 snips
Jul 21, 2025 • 46min
404 Is Agentic AI the End of SaaS as We Know It? | DisrupTV
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.

40 snips
Jul 14, 2025 • 1h 40min
403 Closing the Execution Gap: Chris Happ on Vibe Creating and the Future of Business
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.

Jul 7, 2025 • 58min
402 Why Your Identity Is A Choice (Not A Label) with “IRON” Mike Steadman
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!

15 snips
Jun 2, 2025 • 1h
401 Listen To Your Top 3% Superconsumers And Find What’s Weird | Building with Buyers
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.

8 snips
May 26, 2025 • 1h 33min
400 The Existing Market Trap with Al Ramadan
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.

May 19, 2025 • 54min
399 How DUDE Wipes Flushed The Competition And Became A $219M Category King | Creator Capitalist Conversations
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!

May 12, 2025 • 52min
398 Why Quitting Isn’t As Risky As You Think with Carylyne Chan | Creator Capitalist Conversations
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!