Brilliantly Wrong: Marketing. Creativity. Startups.

Jen Perry has spent her career on both sides of the creative table.

She came up as a creative at big network agencies, then moved client-side, before going on to build and lead creative teams at smaller shops.

At the time we recorded, she was executive creative director at Vagrants, and has since taken on a creative role with BJ's Wholesale.

In this episode, we talk about what makes creative work good no matter the format, and why she banned finished designs until her team could show her the idea behind them.

We also get into how bringing clients closer to the creative process builds the trust you need for bigger, bolder work.

We also get into the less glamorous side of creative leadership.

Jen explains why creatives rarely admit they're overloaded, and how her partners changed once she moved into leadership.

She also shares how she handles the loneliness that comes with being the boss, including building a personal board of directors.

In this episode:

• Jen's path from big-agency creative to client side to building creative teams
• Why "that's not my job" doesn't exist on a small team
• How to define good work when a 15-second spot and a feature film are so different
• AI, the backlash against generic content, and the pull back toward analog
• "Words on a page," or why the idea has to come before the layout
• Getting clients comfortable with risk through incremental trust, and always bringing a range
• Pulling back the curtain on the creative process to reduce anxiety and build ownership
• Why creatives need to understand the pressures their clients face
• Finding what a client actually needs, which is rarely the first thing they say
• Teaching both sides how to give and receive feedback
• A voiceover story about how the way you ask a question shapes the answer
• Creatives don't raise their hand, so tracking workload becomes a way to prevent burnout
• How your partners change when you step into creative leadership
• Loneliness at the top and building a personal board of directors
• What's next: branded content that lives in culture instead of feeling like an ad

Most startup leaders hear “PR” and immediately think two things:

1. Write a press release.
2. Get us in the Wall Street Journal.

But according to Pete Voss, that’s missing the point entirely.

In this episode, Pete talks about what PR actually looks like when you do it well, and why the best PR is really about bridging audiences and building trust.

We get into how startups can create stories that journalists actually care about (even when you don't have some massive revenue number or headline-grabbing funding round), why trends are often more interesting than statistics, and how to build relationships with reporters before you need something from them.

We also talk about the other side of PR: what happens when things go wrong. From bad press to angry customers to a CEO saying something they probably shouldn't have said, Pete explains why the best crisis response starts long before the crisis happens.

Pete has spent his career working in PR across some of the biggest tech companies in the world, as well as on the startup side.

He's also the author of PR Does Not Mean Press Release: A Public Relations Handbook for Tech Startups, which is exactly what we’re talking about in this episode.

Find Pete Voss on LinkedIn and check out his new book, PR Does Not Mean Press Release, on Amazon.

In this episode of Brilliantly Wrong, Alex Stonehouse sits down with Tim Bradley, Founder of Pennant Video, a mid-funnel video agency behind some of the most emotionally resonant and strategically sharp videos in B2B.

Tim’s story is one of clarity, craft, and conviction. From answering a Craigslist job post in 2011 to building one of the most recognizable creative brands in B2B video today, Tim breaks down how the industry evolved, why video is the most misunderstood medium in the marketing toolkit, and why the “messy middle” of a buyer’s journey is where trust is truly won.

Together, Alex and Tim unpack:

• Why top-of-funnel ads sell the click, but mid-funnel video earns the belief
• The Video Marketing Trifecta: Differentiation, Demonstration, and Validation
• How Anthem, Explainer, and Customer Story videos work together to build momentum
• Why care, craft, and creative risk outperform shortcuts and AI-driven sameness
• How to use video to strengthen sales, sharpen positioning, and unify a go-to-market engine
• The mindset behind Pennant’s powerful tagline: “Raise the Banner”

Whether you're a founder, a marketer, a creative, or someone realizing your brand needs to earn trust long before a demo request, this episode will change how you think about video, strategy, and storytelling.

In this episode, Alex Stonehouse sits down with Megan Whitehouse, a freelance designer and endurance athlete based in Seattle, to discuss her unconventional journey from Wisconsin to the Pacific Northwest. Megan shares how she transitioned from studying consumer behavior to pursuing design full-time

The conversation explores Megan's approach to creative work, including her philosophy that great design goes beyond aesthetics to tell compelling stories that resonate with audiences. She opens up about the challenges and rewards of freelancing, her process for working with clients, and how she's working to align her career with her passion for cycling and the outdoors.

The episode takes an inspiring turn as Megan recounts her solo 2,000-mile bike-packing journey down the Pacific Coast—a 27-day adventure that took her from Seattle to the Mexican border. She discusses the profound moments of solitude, unexpected connections with strangers, and how endurance sports have become her form of therapy and creative problem-solving.

Megan also reflects on training for Ironman competitions, leading women's cycling groups in Seattle, and her philosophy of saying yes to challenges before knowing exactly how she'll accomplish them.

The conversation touches on the importance of disconnecting from constant stimulation, the value of life experiences in fueling creativity, and her goal to merge her professional work with her athletic pursuits in the outdoor industry.

In this episode, Alex Stonehouse sits down with David Somerville, Principal at Smrvl, to explore the philosophy behind great design and why the best work doesn’t just look good, it tells a story.

David shares lessons from his time leading creative direction at The Atlantic, Defense One, and beyond, before building his own design studio rooted in curiosity, play, and lateral thinking.

Together, they unpack how emotion, imperfection, and intuition bring design to life, and why every brand needs to make people feel something before asking them to do something.

You’ll hear:

- How design and storytelling work together

- Why flaws can make brands more human

- The tension between structure and spontaneity

- What brands can learn from the way we play games

This is a conversation about creativity, connection, and the messy, magical process of making design that feels alive.

What makes a marketing partner more than just another agency? Amanda Wallman, founder of Alpine Edge Marketing, joins Alex Stonehouse to share her journey from alpine ski racing to running a founder-led consultancy helping startups and small businesses grow.

We talk about:

• Why being founder-led creates deeper trust and stronger partnerships.

• How lessons from ski racing apply to marketing, growth, and testing strategies.

• The importance of clarity, consistency, and momentum in building brands.

• Why marketing is a business solution, not just campaigns.

• And how to bring back the fun, creativity, and energy that unlock better results.

Whether you’re a founder, a marketer, or somewhere in between, Amanda’s insights on building authentic, human-centered marketing strategies will leave you inspired.

In this episode of Brilliantly Wrong, Alex Stonehouse sits down with Sarah Schaffer, Founder & CEO of Bond Studios, to explore The Three Cs of Modern Marketing: Content, Communications, and Creative.

Sarah brings a journalist’s eye for truth and storytelling into the marketing world, building brands rooted in trust, clarity, and authenticity.

We talk about how journalistic ethics translate into communications strategy, why listening is the most underrated agency superpower, how to avoid the “hot take express” on LinkedIn, and why the future of marketing depends on both market savvy and storytelling substance.

Whether you’re a founder, marketer, or comms leader, Sarah’s perspective will sharpen the way you think about brand, trust, and how to connect with your audience in meaningful ways.

In this episode of Brilliantly Wrong, Alex Stonehouse sits down with Peyton Tackes, Director of Marketing and Communications at Ross • Scalise, to explore her journey through agency life, entrepreneurship, and in-house legal marketing.

Peyton shares how she balances data-driven marketing with authentic storytelling, why educating clients can be the most powerful form of marketing, and what it’s like to build a personal brand while being a military spouse who moves every two years.

We cover everything from navigating attorney buy-in and using data to drive change, to the importance of resilience shaped by athletics, and Peyton’s insights into the evolving role of marketing leaders.

Enjoy!

In this episode of Brilliantly Wrong, I sit down with Alyssa Olerud, Founder and CEO of Fearlyss Media, to talk about how service-based entrepreneurs and leaders can build powerful personal brands without overcomplicating social media.

Alyssa shares how she left her corporate career to start her own business, why she believes in “feeling the fear and doing it anyway,” and how she created her signature F.L.O.W. Framework (Foundation, Lifestyle, Offer, Wisdom) to help clients find their voice, tell their story, and attract business through authentic content.

Along with host, Alex Stonehouse, they discuss:

• What it takes to start a business without a safety net
• Why mindset matters more than a marketing plan
• The role of storytelling in turning social media into revenue
• How to balance authenticity with professionalism online
• The origin of the FLOW Framework, and how to implement it to improve your personal brand and presence online

Hope you enjoy! Don't forget to subscribe, share, and give us a 5-star rating if you enjoy this episode with Alyssa.

What does it take to build a career around storytelling in B2B SaaS while still keeping your own creative spark alive? In this episode, I sit down with Kerri Linsenbigler — writer, editor, marketer, and self-described content chameleon.

We talk about:

If you’ve ever wrestled with finding your voice as a marketer, or wondered how to create content that’s clear, human, and memorable, Kerri offers great advice that you can act on immediately.