Best Story Wins

It’s a tough time to be a marketer. Teams are lean, expectations are high, and AI is everywhere—but automation can only take you so far if your brand voice gets lost in the shuffle. So how do you keep your storytelling sharp and human in a world that’s increasingly not?In this episode, we’re joined by Trish Seidel, Marketing Director at Teal and the voice behind “Marketing’s Big Sister.” Trish brings a thoughtful, grounded perspective on what it means to build real brand connection in a noisy landscape. From her experience bridging U.S. and European startup cultures to her experiments with AI-powered content, Trish shares what’s working, what’s broken, and why marketers deserve better.We also talk about:Teal’s unique approach to scaling content with AI agents (that still sound human)The cultural divide in startup marketing across continentsWhy ABM often misses the markThe emotional weight of proving your value in scrappy teams

Brand teams are obsessed with differentiation, but what if distinctiveness is the real power move? And while you're chasing loyalty, your competitors are winning with reach.In this episode, Matt Maynard, Asana’s Head of Brand and Advertising, joins the show to challenge the dogmas of B2B brand strategy. From calling out the cult of rebrands to exposing the limits of loyalty and the illusion of celebrity endorsements, Matt lays out a new playbook rooted in evidence. He unpacks how real brand growth comes from building mental availability, not just big ideas, and why most marketers still mistake folklore for fact.We dive into:Why most B2B brand teams are optimizing for creativity instead of outcomesThe distinctiveness vs. differentiation smackdown (and why it matters more than ever)How AI is the ultimate sparring partner—not just a creative sidekickWhy brand characters beat celebrities in the long game of memoryHow Asana is automating workflows to bring brand science into every touchpoint

Many go-to-market strategies sound good on paper but fall apart in practice. The issue isn’t the lack of talent, but rather the misalignment, timing, or wrong assumptions they’re founded on.In this episode, Brandon Redlinger, fractional marketing leader and co-founder of The Forge community, shares what he's learned from years in the trenches of B2B marketing, from building ABM categories to launching his own curated community for marketing leaders. He talks about why brand matters more than ever, what makes community-building actually work, and how to avoid the common pitfalls that derail go-to-market efforts.We also explore:Why category creation starts with clarity, not buzzwordsThe value of brand in speeding up pipeline and reducing CACHow community can elevate marketing leadership—not just audience engagementWhat early-stage companies must get right in their GTM motionHow marketing leaders can vet roles and align with CEOs from day one

The old agency model is broken, and smart brands aren’t waiting around to fix it. Instead, they’re building lean, strategic ecosystems where storytelling, rather than scale, is the engine that propels growth.In this episode, Harrison Iuliano, cofounder of Moving You to BCC, breaks down why the classic agency-client model is officially dead and what smart brands are doing to replace it. He shares how high-performing brands are creating modern marketing machines by blending fractional talent, curated creative partnerships, and brand-first thinking. We dive into:Why brand, not performance, is your most defensible assetHow to structure your team for speed, quality, and creative outputWhat most companies get wrong about agency selectionWhy great products don’t save bad brands—and vice versa

The brands that move first on human connection build an edge no algorithm can touch. The question is: Will you move fast enough to matter?In this episode, Allison Stadd of Shipt lays out why brands that lead with care, and not only convenience, are the ones winning now and leading the human-centric revolution in marketing. She breaks down how human connection is becoming the real growth engine, how collapsing old brand and performance silos is unlocking smarter strategies, and why micro-communities are the future of loyalty.We also discuss:Why cultural activation is the new brand foundation.How customer anecdotes can turn into an untapped growth channel.Why every brand needs a drummer mindset to lead from the back and still own the stage.

Most B2B marketers are stuck proving short-term wins. Not because it drives the best results, but because it’s the only story the numbers can tell. Could this be why long-term growth, brand equity, and strategic influence keep slipping through the cracks?In this episode, Victoria Gamlen, CMO of Boundary Analytics, unpacks the disconnect between brand investment and how we measure success. She explains why traditional attribution models fall short in B2B, how correlation and time lag analysis offer a clearer view of pipeline impact, and what marketing leaders need to rethink to align with how buyers make decisions today.We also discuss:Why “brand vs. demand” is a false choice—and what to focus on insteadHow to use high-intent inbound as a bridge between brand activity and business outcomesWhat’s behind the recent shift in how leading companies approach brand marketingHow to advocate for brand investment with data that resonates with the C-suiteThe biggest gaps in B2B marketing measurement—and how to fix them

Michael Duda, a partner at Bullish and former agency leader, tackles the pressing challenges CMOs face in today’s market. He argues for marketing as an investment rather than a cost, emphasizing the need for a creative and financial strategy blend. Duda explores how to reclaim marketing power, the ROI of early storytelling, and the importance of customer-centric branding. He also discusses navigating market conditions, the dangers of 'safe' content, and how to build brands that withstand tough economic climates.

Marketers are pumping out more content than ever, yet consumers somehow trust it less than their own data. Impressions are meaningless if you’re not driving impact. In this episode, Chase Howell, VP of Marketing at InfoTrust, shares the formula of B2B marketing that builds trust, converts, and scales without losing its human touch. From launching bestselling books to ditching digital-only in favor of in-person events, Chase shares what it takes to make your brand unforgettable in a landscape obsessed with efficiency and drowning in AI-generated content.We also discuss:Why most "free reports" get ghosted (and what to do instead).How to turn your internal experts into legit thought leaders.Why authenticity will be the new conversion rate in the AI era.How philanthropy and brand are merging into one powerful differentiator.

Today, anyone can build an AI product on a weekend. To stand out in the market, you must rely on your story. In this episode, we are joined by Ben Parr, co-founder of Octane AI and Theory Forge Ventures to talk about what separates good companies from great ones: story and speed. Drawing from past experiences building AI products (before LLMs existed), Ben shares insights on how startup founders should think about brand, content, competition, fundraising, and the marketing industry post-ChatGPT. We also dive into:How AI is transforming marketing (and which jobs are disappearing first).The difference between pitching VCs vs. customers.How Octane AI built a loyal customer community.

Today, thinking about AI completely replacing humans is impossible. Why? Because it means replacing creativity, context, and more importantly, intuition. Hiten Shah, serial entrepreneur, investor, and now working on AI at Dropbox, joins Josh and Jason to discuss how smart marketers and builders are using AI as a thought partner rather than a content machine. Hiten also drops hard-earned wisdom on what marketing still gets wrong, why engineers still (and will likely always) lead the startup ecosystem , and the explanation of why “the best story wins” is more than just a nice phrase.We discuss:Why getting the best from AI starts with better prompting and pre-prompting conversations. Why the road to content quality often starts with content quantity. Augmenting vs replacing human task management with AI.The biggest myths about AI-generated content, and why it’s dangerous for your brand.