Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

By Jen Howat and Erica BollingerBusinessEntrepreneurshipMarketing
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Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business episodes

  • Why Every Entrepreneur Needs Community (And How It Led to This Podcast)

    In their very first episode together, Jen and Erica tell the story of how they met — and why two business owners who could easily see each other as competitors chose collaboration instead. It's a conversation that gets right to the heart of why this podcast exists in the first place: community.

    They talk honestly about the isolation that so often comes with entrepreneurship, what changed for each of them once they got intentional about finding their people, and how showing up consistently for a mastermind and a co-working community reshaped the way they run their businesses, manage their time, and think about their own limitations.

    In this episode, we talk about:

    • Why business owners often see people in similar industries as competitors instead of collaborators

    • The story of how Jen and Erica met and how their friendship turned into this podcast

    • Why entrepreneurial isolation is so common

    • How joining a co-working community and a mastermind group changed the way Jen and Erica each ran their businesses

    • Why accountability helps you follow through on what matters

    • The difference between a "gap" mindset and a "gain" mindset

    • Why margin matters for creativity and decision-making, and how each of them builds it into a deadline

    • Reframing limitations as a gift and a protection, rather than a flaw to push through

    • Why it's better to commit fully to one community than to spread yourself thin across many

    Resources Mentioned in this episode:

    • The E-Myth Revisited by Michael Gerber

    • The Gap and the Gain by Benjamin Hardy and Dan Sullivan

    • Find Your People by Jennie Allen

    • Emotionally Healthy Spirituality and The Emotionally Healthy Church by Pete Scazzero

    • The Ideal Week concept, popularized by Michael Hyatt

    Listener takeaway:

    If you don't currently have a community of fellow business owners, take one small step toward finding one this week — tour a co-working space, go to a networking event, or reach out to another entrepreneur. And if you already have your people, don't let summer be the season you drift: send a text, show up in small ways, and stay connected. Community is an investment of time, but it pays back in momentum you can't create alone.

    A reflection from Jen and Erica:

    This episode is proof of its own point. Jen and Erica met inside the very community they're describing, and what started as two women offering similar services in the same small market — who easily could have kept their distance — grew, through consistently showing up, into a real friendship and now a shared podcast. It didn't happen overnight, and it wasn't the plan when they first met. It happened because they kept showing up.

    Connect:

    Take one step toward community this week — reach out to someone in your industry, show up to a networking event, or check in on someone in your circle. Let Jen and Erica know what step you took; they'd love to cheer you on.

    We'd love to hear from you. You can connect with us at [email protected].

    35 min
  • You Weren't Thinking About Me

    Have you been wondering where I've been? Spoiler: you probably weren't. In this bridge episode, I'm calling myself out for the pressure I put on myself to produce content constantly—and giving you permission to do the same. Because here's the truth: you can't do it all, and that's okay.

    Plus, a heads up that we are launching our new show Our Entrepreneurial Lives in just a few days! New title, new co-host, same RSS feed so you don't have to update anything!

    3 min
  • Letting Go of What's Working So Something Better Can Take Its Place

    The hardest kind of change isn't letting go of something bad or broken. It's letting go of something that's working. When things are good, they're comfortable. They're familiar. And that comfort can become the very thing keeping you from something so much better.

    In this episode, we're talking about how you've sometimes got to let go of something good in order to make room for something better.

    If there's something in your business or your life that you want to let go of but you're holding onto because it works, this one is for you.

    Get Your Build it Better Blueprint

    If you're in a season of evaluating what's next for your business — if you're wondering what to hold onto and what to let go of in order to grow — I would love to have that conversation with you. I offer a free strategy call where we take a deep dive into your business and you'll walk away with a personalized Build it Better Blueprint — a clear, prioritized action plan for your business, yours to keep. Schedule yours today!

    18 min
  • How to Keep Moving Forward When Your Motivation Has Completely Disappeared

    Every entrepreneur knows the feeling. You start a new project full of excitement and energy, and then suddenly you're stuck. You're not at the beginning anymore, but you're nowhere near the end either. You've hit what I call "the muddy middle" and most of us will do everything we can to get out as quickly as possible!

    In this episode, you'll discover why the muddy middle is actually a sign that you're on the right track and how you can start pressing through to the other side.

    Free Strategy Call & Build it Better Blueprint

    You've done incredible work building your business and helping clients get results. Now let's create a plan to help you expand your reach and work with more people, all in less time. Book your call today!

    Connect With Jen

    Let's connect on Instagram or LinkedIn or visit Build it Better Communications HERE.

    17 min
  • You Are An Original

    A few weeks ago I was a guest on the MindHER podcast with Mandi Casey, and at the end of our conversation she asked me what one piece of leadership advice I've received that I still follow today. My answer was immediate — a quote attributed to Abraham Lincoln that I first found nearly ten years ago while preparing a sermon, and that has stayed with me ever since:

    "All men are born originals. Sadly, most die copies."

    In this episode I'm sharing why that quote has come back to me again and again and why it became especially important as I was building the Build it Better Communications agency. I also share how this showed up in a conversation with a client and how it might show up looking like "strategy" in your mind as well.

    Here's the truth: the world doesn't need another version of the person you admire most. It needs you to be you. Your perspective, your vision, your way of showing up for the people you serve. That is your competitive edge.

    This episode is an encouragement and a challenge to stop trading in who you are for who you think you're supposed to be.

    Ready to build a business that reflects who you are and where you want to go?

    Let's have a strategy session! In this free call we'll dig into your business together: how you work with clients, what you already have in place, and where you want to go. I'll answer any questions you have and afterwards, I'll send you a personalized Build it Better Blueprint with recommendations customized for you, so you walk away with something tangible no matter what! Schedule your call now.

    Connect With Jen

    Let's connect on Instagram or LinkedIn or visit Build it Better Communications HERE.

    15 min
  • When the Problem Changes (And You Don't Notice)

    Something has shifted for coaches and consultants over the last couple of years — and if getting clients has started to feel harder than it used to, you're not imagining it.

    In this first episode of a brand new series, I share one of the most important lessons from my own transition from personal brand to agency: I still serve the same people, but the problem they are wresting with has changed. And I almost missed it entirely.

    In this episode you'll hear:

    • What the "old problem" was — and why it no longer tells the whole story
    • How the coaching and consulting landscape has shifted, and what it actually takes to grow in today's market
    • Why assuming you already know your people's problem might be the most costly mistake you're making right now
    • The one thing every listener needs to do to make sure you aren't making this mistake

    If your message feels like it's falling flat, your offers aren't landing the way they used to, or you just can't put your finger on what's gotten harder — this episode is for you.

    Ready to find out what's actually standing between you and your next level of growth? Book a free strategy call at https://builditbetterco.com/strategy-call and walk away with your personalized Build it Better Blueprint — a clear, prioritized action plan for your specific business, yours to keep whether you work with us or not.

    Connect With Jen

    Let's connect on Instagram or LinkedIn or visit Build it Better Communications HERE.

    15 min
  • Why AI Isn't Really Helping Your Business - Yet

    Have you ever found yourself arguing with ChatGPT, re-prompting the same request five times, and walking away with nothing to show for it? I get it! I got to a point where AI wasn't giving me time back. It was stealing it away from me.

    The fact is many entrepreneurs are struggling with the use of AI. It is more and more available, and yet it doesn't seem to be really helping us.

    In this episode, I dig into the three reasons so many entrepreneurs are still struggling with AI despite having access to powerful tools: it amplifies unclear thinking instead of fixing it, we automate things that were never ready to be automated, and, most critically, we're deploying AI in the wrong places while ignoring the ones where it could genuinely help.

    So, how do you know what you should do with AI and what you shouldn't? I'll share a simple two-part test you can apply to any task in your business right now to figure that out. This isn't about tools. This is about a clearer way to think about where this technology actually belongs.

    15 min
  • Have Online Courses Officially Died? Not Exactly.

    Over the course of 2025 people were asking, "are online courses still a thing?" And now that Amy Porterfield has announced she is closing her Digital Course Academy, people are wondering if, in fact, online courses have officially died.

    In this episode of the podcast, we talk about the perfect storm that helped inflate the success of self-paced courses and what people want in this new season. You'll have a better understanding of how we got here, why it doesn't mean your online program is dead, and what it will take to build it better.

    If you want to discover whether or not your framework would flourish in the online space, schedule your free discovery call with me and get clarity on what to do next.

    30 min
  • This Isn't Working Anymore: When A Dead End Becomes a New Direction

    There's very little in life or business that's truly permanent. Seasons change. Priorities evolve. What once felt right can quietly start to feel off, even heavy. Some things simply don't work anymore.

    In this episode, I share my story of my first business coming to an end and how that lead me to what I do now. It was a hard transition. Honestly, in some ways it still feels that way now, too. If you are in a place where you are having to shift and pivot, this episode is for you!

    You can get your copy of We Lead: Building Connection, Community, and Collaboration for Women in Business, Volume 3 HERE.

    24 min
  • Why I Won't Be Using AI to Write in 2026

    If you think your newsletters, blog posts, sales pages, and podcast recaps are all starting to sound the same, you're not imagining things. This is what I thought was happening to me, and after gathering research from the top industry experts in digital marketing, along with my own particular observations and experience, it's all starting to make sense.

    In this episode of My Entrepreneurial Life, I share why I won't be using AI to write in 2026.

    Connect With Jen

    Let's connect on Instagram or LinkedIn.

    Are you wondering if you should build an online course or membership? Schedule your free discovery call with me and get clarity on what to do next.

    19 min

About Our Entrepreneurial Lives | The Struggle and Strategy of Building a Business

From the publisher's feed

Go behind the scenes with agency owners and friends Jen Howat and Erica Bollinger as they have candid conversations about the struggle and strategy behind building and growing a business and life you love.