As entrepreneurs, creatives, and business leaders, we’re constantly making decisions — about strategies, budgets, and even where to focus our energy. But how often do we pause to ask: "Do I need this, or do I just want it?" In a world filled with tempting new tools, trends, and shiny distractions, knowing the difference can be the key to growth — or the reason we stay stuck.

In this episode, we put that question to the test with a mix of lighthearted and thought-provoking scenarios. From the practical to the absurd, we explore the gray areas of what truly counts as a necessity. Tune in for an entertaining and insightful conversation that just might change how you prioritize what really matters.

Lightning Round: What's Important

No one likes a boss breathing down their neck — but when you're the one in charge, knowing how much oversight is too much can be tricky. In this episode, we dig into the blurry line between healthy control and full-blown micromanagement. From trust issues to outcome-based leadership, we explore how leaders can maintain structure and accountability without disempowering their team.

Drawing on insights from Harvard Business Review's “The Anxious Micromanager,” we look at how anxiety and lack of preparation often fuel micromanaging behaviors — and what you can do instead. Whether you're a seasoned leader or just stepping into a management role, this episode offers a thoughtful and practical take on how to lead without smothering.

Read "The Anxious Micromanager" here: https://hbr.org/2023/09/the-anxious-micromanager

#growth #micromanging #lettinggo #smallbusiness #creativeindustry #podcast #midwestpodcast #michiganpodcast #workpodcast #marketing #videography #career #cocktail

Micromanaging and Control: When To Let Things Go

Every brand has its own unique challenges — but not every brand should be approached the same way. In this episode, Jen shares four brand categories she and her team at Redhead work with most often: corporate, place-based, boutique, and entrepreneurial. From the layers of stakeholder input in corporate branding to the emotional nuance of placemaking, we break down how each type calls for a tailored approach to strategy, voice, and visual identity.

We talk about how understanding your brand’s category can help you choose the right creative partner, avoid costly missteps, and ultimately build something that resonates with the people who matter most — whether that’s leadership, customers, peers, or influencers. Inspired by Redhead’s blog post “The 4 Types of Brands We Build (and Why the Distinction Matters)”, this episode is a must-listen for anyone navigating the world of brand strategy or rebranding.

For more on this topic, read the blog post here: https://redhead.studio/blog/4-types-brands-we-build-and-why-distinction-matters

What Type of Brand Are You? (And Why the Distinction Matters)

In our latest episode, we talk about why social media ads might not be delivering, when they can be effective (hint: brand-building > promotion), and why it’s critical to stop thinking of social media as your only marketing plan. We also challenge you to consider how you’d communicate your message if social media didn’t exist at all. From Super Bowl spots to smart, scrappy strategies — this one’s full of tough love and practical insight.



It Doesn't Work!

Color isn’t just a finishing touch — it’s a strategic tool that influences perception, emotion, and behavior. In marketing and branding, it’s one of the first things people notice and one of the most powerful ways to communicate without saying a word. But great color doesn’t happen by accident. It takes intention, skill, and an understanding of how color really works across mediums.

In this episode, we share real-life client stories, break down color theory, and explore how things like lighting, wardrobe, and even shadows can influence your final product. Whether you’re building a brand, producing content, or just trying to make your stuff look better, understanding color helps you get the most out of your creative investment.

Color: Why Hue Matters in Marketing, Design & Video

If you’ve ever launched a website or video and walked away, this one’s for you. No worries, we’re not judging! It’s a common trap to fall into, and when you ignore it, it quickly becomes a pain to update. But in today’s world, where your brand story is always in motion, marketing needs to be treated as an ongoing, strategic effort. In this episode, we’re making the case for retainer-style budgets and maintenance models that reflect how content actually works: continuously, iteratively, and in partnership.

We explore how consistent investment leads to better outcomes, more efficient use of time and resources, and greater flexibility when the unexpected happens. Planning for ongoing care keeps your tools from becoming outdated, your messaging fresh, and your brand infrastructure responsive. It’s not just about having a polished launch — it’s about keeping things healthy, aligned, and ready for what’s next.

Why Ongoing Budgets Beat One-Off Projects

If you've ever felt like you need to have it all together before you can lead effectively, this episode is for you. No judgment here — we've all been there! In this candid conversation, we're sharing our own messy truths, from Jen's permanently grimy oven and abandoned Christmas card habit to Karen's perfectionism paralysis and lone wolf tendencies.

This isn't just therapeutic oversharing — there's strategic value in recognizing where you fall short. When you stop apologizing for things that make you who you are and understand that your personal standards don't apply to everyone else, you free up mental energy for what actually matters. We explore how self-awareness translates to better leadership and more authentic connections. It's about working with your natural tendencies rather than against them and building systems that account for your actual human limitations. Because people don't follow perfect leaders — they follow authentic ones.

The Bad and the Ugly

Here's what we know: People don't like surprises, especially unpleasant ones, and when information is missing, they'll fill in the gaps — rarely with generous assumptions. We break down why proactive communication with clients, your team, and even in your personal life feels harder than it should be, then share strategies for getting ahead of the narrative. From understanding why we avoid these conversations (spoiler: we assume people know more than they do) to crafting that perfectly timed heads-up email, we explore how transparent communication builds trust and prevents those awkward moments when everyone's caught off guard. It's not about having everything perfect; it's about communicating with intention before situations spiral out of control.

Quick, Send the Heads-Up Email

Brand marketing vs. performance marketing. It's not about picking sides — it's about understanding the dance. Performance marketing drives the clicks and the sales, but brand marketing? That's the reason anyone cares in the first place.

Here's what most people miss: these two approaches work better together than apart. Drawing insights from Nielsen research showing that 71% of people say they’re more likely to buy from a brand they recognize, we explore how brand marketing creates the conditions where your performance marketing can actually work. Tune in as we break down the difference between transactional and relational marketing, why consistent storytelling matters more than you think, and how values-driven messaging builds the kind of loyalty that turns into long-term business growth.

Case Study: Brand Marketing with Redhead

We've all seen internet trolls who jump straight to outrage without understanding the full story. But here's the uncomfortable truth: We all do this sometimes. In our everyday work and relationships, we jump to conclusions, assign motives, or make decisions based on half the story. It's human nature to want to find an explanation and solve problems quickly, but that instinct can backfire spectacularly.

In this episode, we dig into why our brains are so quick to fill in the gaps with assumptions — often wrong ones. Sharing real examples from our work-lives, we explore what's really happening when we assume the worst and talk about practical ways to slow down, ask better questions, and let curiosity lead instead of assumptions. Because when you take the time to get the full picture, you'll find better outcomes every time.

The Danger of Jumping to Conclusions

Hi. Jen Estill and Karen Stefl here. In The Speak Easy Podcast, we share years of expertise in marketing, branding, video production, strategy—not to mention management, employee development, mentoring, sales, creativity, maintaining life balance, managing money, and.. you get the idea. It takes a lot to keep a couple of creative studios thriving. 

We developed this podcast after years of "how do you..." boss lady conversations. It was clear that if we were both in such similar places with regard to business growth, and personal growth, and work/life/motherhood/bossland balance, then other women may be, too. We'd been sharing confessions over cocktails for quite a while—solving problems, asking for advice, and whispering the secret fears and disappointments that successful women are never supposed to have. (You've had those, right? It's not just us?)

Thus, Speak Easy was born. Our goal and our promise is to speak with honesty about the challenges that experienced women in the creative industry face. To create a community where we can support one another and abandon the mantra that we put on a good face and make it look like we have it all together, even when we don't. You can expect honesty, complete vulnerability and even a good laugh.

And cocktails. You can expect cocktails.