Jen Estill and Karen Stefl — creative studio entrepreneurs, brand and video experts, boss ladies, moms

The Speak Easy Podcast

Business EN ↓ 251 episodes

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 wome...

Author

Jen Estill and Karen Stefl — creative studio entrepreneurs, brand and video experts, boss ladies, moms

Category

Business

Podcast website

thespeakeasypodcast.com

Latest episode

Jul 2, 2026

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Episodes

49: Relevance And The Mid-Career-ness Of It All 18.06.2019

When you hit that mid-career mark, it can feel as though you've seen it all. You've got a solid grasp of who you are: your leadership style, your values, your purpose. You've learned how your team gets into a groove, and what it takes for you all to produce your best work. Why mess with a good thing? To stay relevant, that's why. Having a solid sense of who you are and where your skills lie is gre...

48: Recognizing Our Faults (Almost To A Fault) 04.06.2019

It's the quintessential interview question: What's your biggest weakness? While the savvy interviewee might try to spin the topic in their favor, there's no denying that we all have personal and professional faults. From lack of patience to not wanting to ask for help, we can admit that we (and most entrepreneurs) come up short in certain areas. So why does it feel downright unnatural for us to ad...

47: The Fine Line Between Critique And Criticism 21.05.2019

We know, we know; at the end of the day, critique and criticism are beneficial. They help drive us forward. Push us out of our comfort zones. Make us the best versions of ourselves. Then why are critique and criticism sometimes difficult to give and receive? Turns out, there's a world of difference between criticism and critique. And in a world where criticism comes a dime a dozen (especially in t...

46: Entrepreneurial Hindsight is 20/20–Featuring Guest Kelly Rossman-McKinney 07.05.2019

As we look back on our careers, it becomes clear that there's no way to forecast every change that will come our way. Industries shift, trends come and go and we can't pretend to know it all. How can we identify our blind spots and fill the gaps of what we don't know? This episode's guest, Kelly Rossman-McKinney, is an experienced communicator with more than a few notches in her belt. From former...

45: Change Is Always In Season 23.04.2019

It's been said many times before, but we'll say it again: Change is inevitable. Personally, professionally and regardless of the season, change chugs along whether we think we're ready or not. Truth is, even if we might not know it at the time, we're usually more prepared than we think. For entrepreneurs, business is like a Michigan season. Everything can change in the blink of an eye, with snow o...

44: Defining Success And Getting Our Priorities Straight 09.04.2019

Defining success is difficult. It's like trying to analyze how far we've come by comparing miles to kilometers or tiny, baby footsteps–everyone's measuring stick is different, which is why we simply can't compare our successes to others. As tempting as it may be. For us, definitions of success vary day-to-day. Some days we're thinking big picture and looking at the long-term, and other days we jus...

43: Hitting Reset After Hitting The Brink 26.03.2019

For entrepreneurs, the candle is usually burning at both ends. We're leading our businesses by day, leading our families (and often still our businesses, thanks to technology) by night and on the weekend. It's this constant engagement, mentally and physically, that excites us. And it's also this constant engagement that taxes us the most. Don't get us wrong–as entrepreneurs, we seek this sense of...

42: Making And Breaking The Rules 12.03.2019

Sure, some (okay, a lot) of rules are necessary. Like rules backed by data, or rules that keep us from dying. As much as our punk-rock alter egos would like to disagree, we need rules to keep it all together and create a safe environment. The tricky part is determining which rules are solid, and which are kind of BS. One thing most entrepreneurs have in common is the tendency to sidestep rules. Tr...

41: Show Up, Follow Through And Don't Be A Dick 26.02.2019

Yes, it would be nice to claim that we don't care what other people think about us and go about our lives rebellious and free. But let's get real: As business owners and professionals, we simply cannot ignore the importance of a solid reputation. Our reputations are the lifeblood of our businesses; they drive leads, satisfy current clients, set the tone, help us produce great work and put bread on...

40: Is 'Fake It Till You Make It' Bullsh*t? 12.02.2019

Sure, faking it can get you to the point of making it. (Whatever "making it" implies.) But once you've wowed that boss, hiring manager or team with your quick-thinking wit (read: bullshit), what's next? You suddenly get a sinking feeling in your soul when it hits you: you actually have to deliver on your promises. Don't get us wrong, faking it isn't always a bad thing. For those just starting out...

39: Why ‘Entrepreneurial Rigor’ Isn’t An Oxymoron 29.01.2019

We normally see rigor associated with scientists or academics, but what does it look like for entrepreneurs in the creative industry? We may not like to admit it, but nothing sets the foundation for success like entrepreneurial rigor. We can have infinite creative ideas floating around in our heads–still, at the end of the day, we need rigor to get the job done. Whether through heavy critique, det...

38: Plans, Endgames And Questions We Didn't Know Existed—Featuring Special Guest Gabrielle Lawrence 15.01.2019

"Planning ahead" means different things to different people. Whether you're a small business owner or an estate planner, it's all about identifying your endgame. Sometimes you just need a kick in the pants to sit down and identify what that endgame is, exactly. This episode's guest, Gabrielle Lawrence, is an attorney specializing in business, probate and estate planning (all while writing restaura...

37: Creative Muscles Need Training, Too 04.01.2019

For some reason unbeknownst to us, there seems to be a common misconception that creativity is a natural-born talent. That creatives just wake up in the morning and flawlessly complete seamless, innovative projects without breaking a sweat. We're here to break it to you: creativity requires a lot of hard work. You can't run a 5k with just ten minutes of training, and you can't execute a record-bre...

36: Resilience 18.12.2018

We like to think successful entrepreneurs, in general, are significantly more resilient than the average person. Nothing is guaranteed in our work, and there's no safety net. The ability to bounce back from failure or critique is a necessity in order to keep things running and lead our teams forward. But, turns out, resilience is more complex than you might think. It's not just about getting back...

35: Maintaining Virtual Relationships 04.12.2018

We'll be honest—if we had it our way, every new relationship would start with a meaningful face-to-face chat. But in today's business environment, one needs to master virtual relationships in order to adequately scale an organization. While there's a slew of impressive technology designed solely to connect teams across the country (and the globe), remote work is easier said than done. Virtual rela...

34: When Things Go Wrong 20.11.2018

Responsibility is inherent in leadership. When something goes wrong on your team, all roads lead to your desk. People look to you to boost morale, patch the mistakes and devise a plan to move forward. This can be stressful, or this can be empowering. Usually it's both. Chances are, every entrepreneur has more than a few memories of a time when everything fell apart. Someone dropped the ball, misse...

33: Following Creative Trends 06.11.2018

Creative ideas are not to be underestimated; a lot of critical inventions we couldn't see ourselves living without today started as simple trends. Someone, somewhere comes up with an innovative idea that's fresh and unique—but only a few trends truly stick. It's not always clear whether something will stand the test of time or lose its thunder. After all, there was a time when an entire corporatio...

32: The Inevitability of Busy 23.10.2018

It's inevitable that there are more demands on your time than you can realistically handle. If your business, projects and family schedules are anything like ours, your calendar is often full to the brim. But you can either complain about it, or accept it and move on.

31: Vulnerability in Leadership 09.10.2018

Why do we treat vulnerability like it's a negative thing? Saying "I don't know" and "I need help" seems like the purview of our young kids, not grown-up women in leadership. But let's be honest: sometimes even when you feel at risk of being emotionally exposed, you can find the courage to be yourself. So, maybe vulnerability isn't such a bad thing?

30: Who Left Me In Charge?—Featuring Special Guest Sarah Anthony 25.09.2018

This episode, we're welcoming a special guest: Democratic nominee from House District 68 Sarah Anthony. As District 3 Ingham County Commissioner, Sarah was the youngest African-American woman to serve as County Commissioner in in the nation. She's also Deputy Director of Partnerships and Advocacy at the Michigan College Access Network. Impressive resume aside, Sarah's a woman with an inspiring bac...

29: Difficult Decisions 12.09.2018

Hiring an employee. Expanding your office. Choosing a Bloody Mary garnish. As entrepreneurs, our lives are full of decisions (big and small). But the big, difficult decisions that truly impact people's lives can be hard pills to swallow. Challenging decisions are inherent in leadership. It's pretty much a part of the job description. In times or trouble or uncertainty, it's our responsibility to b...

28: Impatience is a Virtue 28.08.2018

Impatience gets a bad rap. In the professional world, we often forget that is that impatience is the driving force behind getting any project off the ground. If a business leader is too patient, they could overthink the situation, brainstorm for weeks, and never actually roll up their sleeves to get things started. We all need a little impatience to drive our ideas forward. Still, there needs to b...

27: We Hate Sales and Prospecting, Too. 14.08.2018

It’s true: entrepreneurs don't go into business to do sales and prospecting. They want to focus on the things they love, and sometimes it can feel like sales are getting in the way. That’s why it’s is a tricky subject to talk about in creative services. We're not simply putting objects on shelves with price tags; our services are largely relationship-based. And a relationship is more challenging t...

26: Staying Organized and Keeping Our S*** Together 31.07.2018

There's a lot more to organizing your life than buying a new planner and a label maker. Aside from the obvious, there are a myriad of factors that can help us stay organized: professionally, personally, and mentally. As entrepreneurs and creatives, staying organized can be especially difficult. Creative people sometimes get a bad rap when it comes to organization; but "creative" and "organized" ar...

Bloopers: Our Birthday Gift to You 24.07.2018

We turned one! To commemorate our anniversary, we're giving you a listen behind the mic with a quick bloopers reel. We usually try to keep our episodes short. Which means our audio engineer, Scott, has to edit out quite a bit of foolishness. Since our podcast is about pulling the curtain back on our lives as creatives, we thought we’d show some of the silliness that goes on in the recording booth.

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