Brilliantly Wrong: Marketing. Creativity. Startups.

In a world where AI can churn out one hundred blog posts before lunch, content alone is no longer a competitive advantage. What you say, and what you stand for, matters more than ever.

Lindsay King, Head of Integrated Marketing and Brand Strategy at Sifflet, shares insights from 14 years in marketing, spanning early-stage startups to IPOs, Uber to AI-first SaaS. In this conversation, we unpack how brand is making a comeback, why messaging with conviction beats content volume, and how taste is the new moat.

We cover:

• Why the pendulum is swinging back toward brand, away from performance marketing

• The underrated power of a strong editorial and brand point of view

• How AI is accelerating the need for human authenticity

• Brand as a “revenue shield," and why founders can’t ignore it

• The rise of marketers as the founders of the future

  
  

If you’re a founder, startup marketer, or creative leader trying to navigate the noisy, AI-saturated world we’re in, this episode is for you.

Agentic AI and the End of Busywork

In this episode of Brilliantly Wrong, I sit down with Aubriana Alvarez Lopez, Co-Founder and COO of Agnitio, to talk about what it really means to build with agentic AI, and why it might just be the operating system the media and marketing world has been missing.

We get into the weeds on startup life, moving fast without breaking everything, and how Agnitio’s platform is transforming media operations that used to take weeks into workflows that take just minutes.

Key Takeaways:

• Why agentic AI is different from the AI tools you're used to

• The biggest time-wasting tasks in ad ops (and how to automate them)

• Fundraising and building with clarity in the early-stage chaos

• What explainable and responsible AI actually looks like in practice

• Why “fail fast” is more than a motto—it’s a survival tactic

• The mindset shift required to lead in an AI-powered future

  
  

Aubriana brings insight, honesty, and vision to a conversation that cuts through the hype. Whether you're a founder, marketer, or just trying to keep up with the pace of innovation, this episode will challenge how you think about AI, and about your own time.

What if your industry’s most “inclusive” networking events were actually leaving people out?

In this episode, I’m joined by The Kay Prince — Director of Growth Marketing at Extreme Reach (XR) and founder of Buzz-Free Network (BFN) — the first sober community for the ad tech industry.

We talk about:

• Why so much of ad world culture revolves around alcohol

• The rise of the “sober-curious” Gen Z executive

• How to build inclusive events without killing the vibe

• The future of professional communities built around values, not vodka

Kay shares her personal story, how BFN is gaining traction at major conferences, and why the time for change is now.

If you’ve ever felt out of place at a happy hour, or want to build more inclusive communities in your industry, this one’s for you.

Toni Collis is on a mission to change the tech industry by building better leaders. As the host of Leading Women in Tech and an executive coach for women in the C-suite, Toni shares what she's learned from working with hundreds of brilliant, ambitious leaders who are often the only woman in the room.

In this conversation, we unpack the hidden costs of people-pleasing and the power of authentic leadership. If you've ever struggled to balance assertiveness with likability, or felt like leadership requires a tradeoff with your personal life, this episode is for you.

Key Takeaways:
– Why people-pleasing leads to burnout, underperformance, and lost respect
– The real reason women are still underrepresented in tech leadership
– How to set boundaries without sacrificing career growth
– Why good confrontation builds better teams and better technology
– The difference between mentorship and coaching—and why it matters
– What executives can learn from transparency
– How to stop waiting to be noticed and start leading on your own terms

Whether you're climbing the ladder or building one for others, Toni’s insights will help you lead more powerfully, sustainably, and authentically.

What do most startup partnerships get wrong? Tim Condon, Chief Revenue Officer at Clutch, joins the show to break down what actually drives partnership success, and why the best deals are built by putting the other party first.

Drawing on lessons from his time at The Washington Post and now leading the revenue and client functions at Clutch, Tim shares a no-BS look at how partnerships scale, where they stall, and what it means to create something truly valuable in B2B.

In this episode, we cover:

• Why most partnerships fail, and how to avoid common traps

• The surprising difference between big-name partners and scrappy ones

• How Clutch is helping B2B influencers build monetized directories

• The power of clear structure, defined roles, and aligned incentives

• Why Google isn’t the only growth channel that matters anymore

• How to think like an entrepreneur inside your organization

Whether you're in growth, sales, marketing, or partnerships, this one’s packed with hard-earned wisdom and fresh ideas.

What happens when you embed a creative agency inside a private equity firm? Brian Wakabayashi, Head of Brand at CōLab, joins Alexander to explore this unique model and share hard-won insights about startup marketing. CōLab creative studio reimagined for startups and built inside WestCap, a private equity investor. 

In this episode:

Startup Marketing Reality Check: From seed stage to near-IPO, Brian shares what actually works at different company stages, why founders don't understand brand strategy, and how to train boards to measure more than just short-term metrics.

The Dating Analogy: Brian's memorable framework for balancing brand and performance: "Performance is going out and asking for a date. Brand is working on yourself to become someone worthy of a relationship." Both matter, but the balance is everything.

Beyond CAC and LTV: Why relying solely on Meta and Google for customer acquisition makes you "essentially a subsidiary" of those platforms. Brian explains the hidden costs of performance-only marketing and how rising ad rates are crushing profit margins.

The CōLab Experiment: How WestCap built an internal creative studio to actually do the work for portfolio companies, not just give advice. Brian breaks down why most PE/VC "operating platforms" fall short and how their embedded model creates real value for startups.

Key takeaways:

• Why diversifying beyond Meta/Google isn't just smart—it's survival

• How to sell long-term brand investments to numbers-focused boards

• The three-tier framework: business strategy → marketing strategy → brand strategy

• Why startup marketing leaders need to think like consultants, not just tacticians

• How to build for your company's next growth stage, not just where you are today

  
  

About Brian:

Brian Wakabayashi is Head of Brand at CōLab, WestCap's internal creative studio. Before joining the private equity world, he spent over a decade at major agencies including McCann and BBDO, working on brands like Xbox, LinkedIn, Taco Bell, and Mars Petcare. He's passionate about helping startups build lasting marketing strategies and memorable brands. 

About Brilliantly Wrong:

Brilliantly Wrong is part of The StartUp Marketer podcast network for marketers, founders, creatives, and anyone willing to embrace risk for extraordinary outcomes. Alex Stonehouse and his guests regularly dive deep into the art and science of marketing, startup growth, creativity, and mastery from a perspective that challenges the conventional.

Visit https://thestartupmarketer.com to learn more and be part of the community.

Ever feel like you're drowning in marketing tasks as a solo marketer or small team? David Cardiel knows exactly how that feels. As a fractional marketing leader, he found himself managing everything from SDR teams to executive reporting while keeping the marketing engine running, all while still being responsible for the overall marketing strategy and execution.

His solution? Building an entire AI marketing team with custom assistants for every discipline. Discover how David created specialized AI assistants for product marketing, content creation, competitive analysis, and more - each with their own personality and expertise.

In this conversation, David shares his practical approach to AI automation, including his favorite tools beyond ChatGPT, how to start small and build up, and why he treats AI implementation like jazz - iterative, creative, and uniquely yours.

Whether you're a team of one or leading a small marketing department, you'll walk away with actionable strategies to automate the busywork so you can focus on what really moves the needle.

Key Topics:

• Building custom AI assistants for different marketing functions
• Essential AI tools for solo marketers and small teams
• Transitioning from traditional marketing to AI-powered workflows
• Fractional marketing leadership insights
• Starting your AI journey without waiting for perfection

Guest: David Cardiel is a fractional marketing leader who has built and scaled marketing engines at multiple high-growth startups. He specializes in helping companies navigate tough market conditions with limited resources and smart AI implementation.

What happens when you're crushing it on paper but feel completely disconnected from your work?

Kelly Ramirez, Founder of Elemental Leadership, knows exactly what that feels like. In this transformative conversation, she shares her journey from Google executive to seven-figure agency owner to executive coach—and the pivotal moment that changed everything.

Kelly's story begins in the early days of digital marketing at Google, where she worked with massive travel clients like Expedia, managing hundreds of millions in ad spend. After nearly a decade riding the Google rocket ship, she took the leap to start her own growth agency and scaled it to seven figures.

But success on paper doesn't always equal fulfillment. Kelly describes the defining moment when she was pitching a $70 million company and suddenly felt like she was watching herself from outside her body. That's when she looked up and said the words that would change her life: "I don't want to do this anymore."

In this episode, Kelly gives listeners the tools to:

Question your currency - Success isn't just about salary, equity, or status. Ask yourself what you're actually trading in and whether it aligns with your values.

Create space to listen - High achievers often measure themselves against external benchmarks for decades. You need intentional space away from execution mode to hear your inner voice.

Stop blindly charging ahead - The biggest thing holding leaders back is the inability to slow down and gain perspective on how they're showing up.

Identify hidden fears and limiting beliefs - Kelly discovered her hidden fear was being "a spineless mediocre failure," which drove her to take over situations instead of truly leading.

Leadership is about nervous system regulation - People don't remember what you said, they remember how you made them feel. Creating psychological safety enables creativity and better problem-solving.

True transformation comes from within - Tactical solutions don't fix deeper issues. Real change happens when you generate your own answers through powerful questions.

The power of purposeful stillness - Kelly and Alex discuss his artist father who would sit in his rocking chair to study his work, taking creative pauses is essential for breakthrough insights.

Embrace the uncomfortable conversations - Sometimes the most productive thing you can do is create pause and ask "What's going on with me?" before reacting.

Kelly is an executive coach who works with founders and business leaders in six-month intensives, helping them identify what's truly holding them back from having the impact they want to have. After 15+ years building and scaling businesses, she now focuses on unlocking human potential and supporting transformational change.

This episode is perfect for anyone feeling successful on paper but unfulfilled in reality, leaders who want to understand what's really driving their behavior, or anyone considering a major career transition.

Brilliantly Wrong is part of The StartUp Marketer podcast network for marketers, founders, creatives, and anyone willing to embrace risk for extraordinary outcomes. Alex Stonehouse and his guests regularly dive deep into the art and science of marketing, startup growth, creativity, and mastery from a perspective that challenges the conventional.

Visit https://thestartupmarketer.com to learn more and be part of the community.

In this enlightening conversation, host Alex Stonehouse sits down with Ashley Hernandez, a product marketing leader and entrepreneur with an impressive career in the cybersecurity and tech space. Ashley shares her journey from marketing generalist to finding her true calling in product marketing, where she discovered "all the things I've liked is the product marketing piece of being the generalist."

Ashley takes us through her career evolution, including how she first recognized product marketing as her ideal path after seeing a job description that perfectly aligned with her passions for writing, strategy, and collaboration. She discusses the meaningful mission she found in cybersecurity, particularly in her current role helping smaller companies with DoD contracts achieve compliance and security.

Beyond her full-time career, Ashley offers valuable insights into building her business, October Dreams Studios. She shares practical wisdom about carving out dedicated time for entrepreneurial pursuits while balancing family life with two young children.

The conversation touches on creativity both in marketing and personal life, the importance of surrounding yourself with supportive people who understand your goals, and setting boundaries to protect what matters most. Ashley's approach to building a multifaceted career while staying true to her priorities offers inspiration for marketers at any stage of their professional journey.

Whether you're looking to specialize in a marketing niche, start a side business, or simply find more balance between work and personal growth, Ashley's thoughtful perspective provides a roadmap for finding your own marketing home.

Brilliantly Wrong is part of The StartUp Marketer podcast network for marketers, founders, creatives, and anyone willing to embrace risk for extraordinary outcomes. Alex Stonehouse and his guests regularly dive deep into the art and science of marketing, startup growth, creativity, and mastery from a perspective that challenges the conventional.

Visit www.thestartupmarketer.com to learn more and be part of the community.

In this insightful conversation, Alexander Stonehouse sits down with Nathalie Pramanik, the founder and CEO of Little Chompions, a company dedicated to making feeding babies fun and stress-free.

Nathalie shares her journey from successful marketing executive to passionate entrepreneur, discussing how motherhood inspired her career pivot and the challenges of building a business from the ground up.

Episode highlights include:

Self-funding strategy: Nathalie's deliberate decision to bootstrap her business rather than seeking outside investment

The Little Chompions mission: How Nathalie and her business partner Monica are creating expert-backed solutions to make mealtime less stressful for parents and more enjoyable for babies

The power of expertise: How Nathalie partnered with a speech language pathologist and feeding therapist to create products with solid professional backing

Finding a gap in the market: Why the transition to solid foods catches many parents off guard and how limited guidance from pediatricians creates confusion

Education first approach: Why Little Chompions focuses on knowledge and guidance as their primary product, with physical items supporting their educational mission

The Good Housekeeping seal: Winning the 2024 Parenting Award and using it as a strategic tool to build consumer trust

The engineering mindset: How her Dartmouth engineering background helps her break down complex problems and approach product design

Entrepreneurial challenges: The surprising loneliness of decision-making and the difficulties of wearing every hat in the company

The connection to Next Day: The unexpected way Nathalie met her business partner through advising an alcohol recovery beverage company

Future plans: Expanding Little Chompions' educational resources and developing one-on-one support options for parents.

Brilliantly Wrong is part of The StartUp Marketer podcast network for marketers, founders, creatives, and anyone willing to embrace risk for extraordinary outcomes. Alex Stonehouse and his guests regularly dive deep into the art and science of marketing, startup growth, creativity, and mastery from a perspective that challenges the conventional.

Visit www.thestartupmarketer.com to learn more and be part of the community.