In this episode, we sit down with David Lee, Chief Creative Officer at Squarespace, to trace his journey from a restless teenager in suburban Montreal to leading one of the most design-forward companies in the world.

David shares how skate culture and DIY design first opened his eyes to creativity, what he learned at the Rhode Island School of Design (including the life-changing lesson of drawing with his left hand), and how he carved his path through some of the world’s top creative agencies like Sid Lee, AKQA, and Wieden+Kennedy, before making the bold leap into tech.

He also reflects on building Squarespace’s in-house creative team, embracing risk, and the role of self-awareness as the most valuable career investment. From navigating imposter syndrome to leading creative teams through technological disruption, David’s story is a masterclass in staying curious, adaptive, and human in a rapidly changing world.

In this episode, we explore the unconventional path of Jeremy Jones, who transformed his passion for punk rock, skateboarding, and counter-culture creativity into a thriving advertising and marketing career. Jeremy shares how making band flyers and touring with musicians became his informal MBA in marketing, teaching him branding, promotion, and creative problem-solving long before he understood what advertising actually was.

Discover how Jeremy's creative partnership—formed through both bandmate chemistry and advertising collaboration—propelled him through agency ranks, culminating in representing Team USA at Cannes Young Lions. His journey spans radio promotion, boutique agencies, and eventually a global role at J. Walter Thompson before making the pivotal leap to building MailChimp's acclaimed in-house creative team, Wink.

Jeremy reveals the philosophy behind MailChimp's distinctive "expert absurdist" brand voice and shares insights from memorable campaigns like "Email Is Dead" and "The Customer." He emphasizes the importance of bringing organization and belief to creative teams, understanding client businesses deeply, and marketing to marketers in ways that inspire rather than bore.

The conversation offers invaluable guidance for creatives at every stage: students should lead with passion over perfection, early-career professionals must raise their hands for opportunities, and new leaders need to stay connected to the work while investing in relationships outside their industry. Jeremy's advice on "fishing in other rivers" and maintaining hobbies for creative rejuvenation provides a refreshing perspective on sustainable creative leadership.

Whether you're an aspiring creative, agency professional, or in-house marketing leader, this episode delivers authentic wisdom from someone who built his career on curiosity, relentless work ethic, and never forgetting the scrappy, DIY spirit that started it all.

In this episode, we sit down with Emma Donelan, Marketing and Communications Director at Data.org, to explore how data and artificial intelligence are being harnessed to address some of the world's most pressing social challenges. Emma shares the powerful work Data.org is doing through global innovation challenges and capacity-building initiatives that bridge technology and humanitarian impact.

Discover how Data.org partners with philanthropic organizations and corporate entities to scale transformative data and AI solutions across five global hubs, including India and Africa. Emma highlights their focus on critical intersections between climate and health, along with innovative approaches to interdisciplinary training and workforce development that are creating new opportunities in underserved communities.

The conversation features compelling success stories, including an AI-powered platform in Mumbai revolutionizing access to sexual and reproductive health information. Emma emphasizes the crucial importance of localism in technology deployment, ensuring solutions are culturally relevant and community-driven rather than imposed from outside.

Emma also shares her fascinating personal journey from studying art history to venture capital and ultimately to leading communications for social impact technology. She reveals how her great-aunt's influence sparked her enduring passion for creativity and meaningful work, demonstrating that unconventional paths can lead to profound impact.

Whether you're interested in AI for social good, international development, or building a purpose-driven career, this episode offers valuable insights into how technology can be deployed ethically and effectively to create positive global change while generating economic opportunity.

For more marketing resources, check out nativedigital.com.

Join us for a fascinating conversation with David Boyle, Director at Audience Strategies, a data company that builds capabilities that merge traditional audience research with AI-powered analysis. David shares how his love for mathematics' predictability became the foundation for a diverse career spanning AI, data analytics, strategy consulting, philanthropy, politics, and even the music industry.

Listeners will gain valuable insights into David's strategic framework, including his innovative "now, next, and never" audience segmentation approach that drives effective strategy development. He emphasizes the critical importance of deep audience insights in shaping business decisions and shares practical wisdom on focusing skills development, building meaningful professional relationships, and understanding the inherent limitations of data-driven decision making.

Throughout the conversation, David underscores a key career principle that has guided his success: the transformative power of working alongside talented people. His perspective offers a refreshing take on how analytical skills can be applied creatively across industries while maintaining intellectual honesty about what data can and cannot tell us.

Whether you're interested in data science, strategic consulting, or simply curious about building a non-linear career path, this episode provides compelling insights from someone who has successfully brought mathematical rigor to wildly diverse professional challenges.

For more marketing resources, check out nativedigital.com.

In this engaging episode, we follow Andrew McKechnie's remarkable career trajectory from his early days as a marketing student at Auckland University of Technology to becoming a strategic marketing leader driving innovation in climate technology. Andrew's journey showcases the power of adaptability and continuous learning in building a truly global marketing career.

Discover how Andrew's foundation as a copywriter evolved through strategic roles across diverse markets, from Singapore's dynamic advertising scene to the competitive U.S. market. He shares insights from his tenure at tech giants like Apple, where he played a pivotal role in launching the company's first major environmental campaign, and Verizon, where he successfully built and led an innovative in-house marketing team.

The conversation explores Andrew's core philosophy of consistency, adaptability, and relentless skill development—principles that have enabled him to thrive across different cultures, industries, and marketing challenges. He reveals how these values have guided his career decisions and continued success.

Currently leading branding and storytelling efforts at AIRCO, a cutting-edge company converting CO2 into synthetic fuels, Andrew demonstrates how marketing expertise can drive innovation adoption in emerging industries. His perspective offers valuable insights into positioning breakthrough technologies and building compelling narratives around climate solutions.

Whether you're starting your marketing career, considering international opportunities, or looking to apply your skills to emerging industries, this episode provides inspiration and practical wisdom from a marketer who has successfully navigated global markets and technological transformation.

For more marketing resources, check out nativedigital.com.

In this fascinating episode, we explore the intersection of historical wisdom and modern business leadership with John Lewis Gaddis, Professor at Yale University and renowned author whose book, "On Grand Strategy," has unexpectedly captivated the business management community. Gaddis reveals how centuries-old strategic principles remain profoundly relevant for today's executives and entrepreneurs.

Discover Gaddis's elegant definition of strategic thinking as "the art of getting from where you are to where you want to go," emphasizing the crucial balance between ambitious aspirations and realistic capabilities. Through compelling historical examples—from Napoleon's catastrophic overreach to Lincoln's masterful long-term vision—he illustrates common strategic pitfalls that continue to plague leaders across industries.

The conversation delves into Gaddis's passionate advocacy for broad liberal education, particularly the study of history, as essential training for developing the common sense and adaptability that effective leadership demands. He argues that understanding historical patterns provides invaluable context for navigating today's complex business challenges.

Gaddis also offers sobering warnings about the dangers of overreliance on technology and the corrosive effects of social media on strategic thinking. His perspective challenges leaders to think beyond digital solutions and consider the enduring human elements of successful strategy.

Whether you're a CEO, entrepreneur, or aspiring leader, this episode offers timeless insights for developing strategic thinking skills that transcend technological trends and industry shifts.

For more marketing resources, check out nativedigital.com.

Join us for an inspiring conversation with Joel Grabenstein, VP of Sales, Brand, Product Marketing at Yakima Products, as he shares his dynamic career evolution from tourism and hospitality education to becoming a respected marketing leader in the outdoor industry. Joel's story demonstrates how unconventional educational backgrounds can become powerful assets when combined with strategic thinking and genuine passion.

In this episode, Joel takes us through his early hustle in the outdoor industry, from attending trade shows to landing his breakthrough role at Yakima. He details his impressive career progression within the company, climbing from trade show coordinator to brand director through strategic internal mobility and consistent value delivery.

Listeners will gain valuable insights into Joel's philosophy on the critical importance of teamwork and emotional connection in building successful business relationships. He shares practical advice on essential skills for modern marketers, particularly emphasizing financial literacy.

Whether you're starting your marketing career, considering a career pivot, or looking to advance within your current organization, this episode offers authentic wisdom from someone who has built lasting success through relationship-building and strategic skill development.

For more marketing resources, check out nativedigital.com.

In this thought-provoking episode, we dive deep with Alistair Croll, an entrepreneur, author, and conference innovator who has spent decades helping organizations make better data-driven decisions and understand the hidden systems that shape business and society. He authored the bestselling "Lean Analytics" and has helped launch seven major industry conferences including O'Reilly's Strata and the FWD50 digital government summit. His latest work, "Just Evil Enough," explores subversive marketing strategies for challenger brands, drawing from his extensive research into how underdogs disrupt established systems and change the status quo.

In this episode, he shares his unique journey from inventing games in boarding school to revolutionizing how we think about business success. Alistair challenges conventional wisdom by advocating for "solving for interesting" rather than chasing fame or wealth—a philosophy that has shaped his remarkable career.

The conversation explores Alistair's groundbreaking marketing theories, including medium-first marketing, where the communication channel becomes as important as the message itself. He also breaks down his innovative "long funnel" approach that extends beyond traditional marketing stages to include attention, interest, desire, action, and fluency—providing a more comprehensive view of customer engagement.

Throughout the episode, Alistair emphasizes the critical importance of system awareness and subversive thinking in modern marketing, offering fresh perspectives that challenge industry norms. Whether you're an entrepreneur, marketer, or simply someone seeking a more interesting approach to professional growth, this episode delivers unconventional wisdom for navigating today's complex business landscape.

For more marketing resources, check out nativedigital.com.