
942: The Price of Entrepreneurship No One Talks About (And Why I'd Pay It Again)
24/12/2025 | 38 mins.
Becoming an entrepreneur is the most expensive personal development program you will ever pay for, and I'm not even talking about the money. I'm talking about the version of yourself that you have to let die: the people pleaser who waits for permission, the woman who apologizes before she speaks, that part of you who thinks staying ahead of everything will finally make you safe. I've watched the “girl boss” era rise and fall. I've witnessed hustle culture get worshipped and then finally questioned. I've been in rooms I thought I needed to be in only to realize those weren't my rooms at all. Here's what I know: entrepreneurship is not just about building a business. It's about becoming someone who can. For women especially, this journey will ask you to unlearn almost everything you've been taught: to stop making yourself small, to stop waiting for permission, to stop apologizing for wanting more. Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/entrepreneurship-costs-and-rewards Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Check out What Should I Do With My Money? from Morgan Stanley. Listen now at https://mgstnly.lnk.to/bqe8HiAC!GD. Visit http://www.spectrum.com/freeforlife to learn how you can get Business Internet Free Forever. Experience the power of a Dell PC with Intel Inside®, backed by Dell’s price match guarantee. Shop now at https://www.dell.com/deals. Your dream wardrobe’s one click away. Visit https://www.revolve.com/goaldigger for 15% off your first order with code GOALDIGGER.

941: How to Break Free From the System That Needs You to Doubt Yourself
22/12/2025 | 55 mins.
Anna Malaika Tubbs is a two-time New York Times bestselling author and a leading voice in gender, race, and equity. Her newest book Erased: What American Patriarchy Has Hidden From Us is a wake-up call, one that challenges us to rethink everything from who gets remembered to who gets rewarded. I met Anna recently at a retreat hosted by Onsite in Tennessee and she was magnetic. The best part about meeting her is I had no idea what she did for a career and didn't learn about her books until the very last day. Once I heard what she was writing about, I knew she would make the perfect guest for this show. Anna pulls back the curtain on the narratives that have quietly shaped how we see ourselves, our businesses, and our worth. What sets her apart is her ability to take complex systems and translate them into powerful stories that reveal what's been buried and show us how to reclaim what's ours. And trust me, you'll never see patriarchy, power, or your own story the same way again. So if you've ever felt like the rules of success weren't written for you, if you've struggled with visibility or making space for your full self in your business, if you've been playing small because it felt safer than being too much, this conversation is for you. Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/how-to-break-free-from-patriarchal-systems Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Check out What Should I Do With My Money? from Morgan Stanley. Listen now at https://mgstnly.lnk.to/bqe8HiAC!GD. Visit http://www.spectrum.com/freeforlife to learn how you can get Business Internet Free Forever. Experience the power of a Dell PC with Intel Inside®, backed by Dell’s price match guarantee. Shop now at https://www.dell.com/deals. Your dream wardrobe’s one click away. Visit https://www.revolve.com/goaldigger for 15% off your first order with code GOALDIGGER.

940: 10 Marketing Predictions for 2026 (That Won't Make You Want to Quit)
17/12/2025 | 51 mins.
When you read the title of this episode, you may have thought that I’m here to tell you about the next app you need to download or the algorithm hack you're already late to. But no… Goal Digger, I'm here to tell you what I'm seeing beneath the surface. The shifts that are happening whether we talk about them or not. The moves the sanest, smartest women I know are already making quietly. This isn't about keeping up. It's about seeing what's coming and deciding—on your terms—what you want to build toward. The future doesn't belong to the loudest or the busiest. It belongs to the women who built something they can actually sustain. Who chose presence over performance. Who said no to the parts of this that were slowly killing them. So let's talk about where we're headed. Not so you can add ten more things to your to-do list. But so you can exhale. So you can see what you've been feeling is not just you… It's the beginning of something new. Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/2026-marketing-predictions-for-small-business Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Check out What Should I Do With My Money? from Morgan Stanley. Listen now at https://mgstnly.lnk.to/bqe8HiAC!GD. Visit http://www.spectrum.com/freeforlife to learn how you can get Business Internet Free Forever. Experience the power of a Dell PC with Intel Inside®, backed by Dell’s price match guarantee. Shop now at https://www.dell.com/deals. Your dream wardrobe’s one click away. Visit https://www.revolve.com/goaldigger for 15% off your first order with code GOALDIGGER.

939: A Conversation With My Mom About Time, Motherhood, and What Gets Passed Down
15/12/2025 | 55 mins.
Every time my mom comes on the show, you ask me to bring her back. You want her wisdom and her perspective, the way she sees straight through to what actually matters… and today, we’re giving the people what they want! My mom, Sue Shelerud, is intelligent, fierce, persuasive, empathetic, and deeply respected. Over the years, she built her impact face to face in classrooms and living rooms and hospital hallways. She shaped people and held space and asked the hard questions that made them think differently. I realized that as I've gotten older, we need collectively to learn from women like her, the ones who led in different ways than we do, the ones whose platform looked different, but whose influence was undeniable. The ones who remind us that impact isn't about how loud you are, it's about how deeply you show up. So today we're talking about motherhood and identity, about the differences between her generation and mine, about what it means to be a safe space for people, about what gets passed down when you lead with presence and not performance. This powerful conversation is for me, it's for my daughters, it's for anyone trying to learn from the women who came before us, the ones who did things differently, and the ones whose power showed up in ways we're only now learning to name. Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/motherhood-generational-wisdom-conversation-with-my-mom Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Check out What Should I Do With My Money? from Morgan Stanley. Listen now at https://mgstnly.lnk.to/bqe8HiAC!GD. Visit http://www.spectrum.com/freeforlife to learn how you can get Business Internet Free Forever. Experience the power of a Dell PC with Intel Inside®, backed by Dell’s price match guarantee. Shop now at https://www.dell.com/deals. Your dream wardrobe’s one click away. Visit https://www.revolve.com/goaldigger for 15% off your first order with code GOALDIGGER.

938: The Mic That Made Me: The Lessons I Never Expected to Learn from Podcasting
10/12/2025 | 47 mins.
When I started this show, I was working from home, building a business in isolation, and I felt like an imposter in every room I tried to enter. I thought maybe a podcast could help me feel less alone. Maybe it could help me prove I had something worth saying. And here's the part I never saw coming: I didn't think I could do solo episodes! I truly believed I needed a guest, a co-host, someone else to carry the conversation. But hundreds of episodes later, I can talk to a wall forever. I can hold space for an idea, unpack a framework, and connect with you, even though you're not responding in real time. That shift didn't happen overnight. It happened because I kept showing up. And along the way, this mic taught me more than any business course, any mentor, or any strategy ever could. Today, I want to share what I wish someone had told me about what's really possible when you start speaking your truth. Not the surface-level lessons about audio quality or interview techniques, but the deep, transformative shifts that happen when you give yourself permission to grow in public. Maybe you've felt that tug to use your voice, or you've been wondering if podcasting could be the thing that finally changes everything: I want you to understand what you're really signing up for… And why it might be the most important thing you ever do. Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/ Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/ Goal Digger Show Notes: https://jennakutcherblog.com/lessons-from-podcasting Thanks to our Goal Digger Sponsors: Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. Find a co-host today at http://airbnb.com/host. Check out What Should I Do With My Money? from Morgan Stanley. Listen now at https://mgstnly.lnk.to/bqe8HiAC!GD. Visit http://www.spectrum.com/freeforlife to learn how you can get Business Internet Free Forever. Experience the power of a Dell PC with Intel Inside®, backed by Dell’s price match guarantee. Shop now at https://www.dell.com/deals. Your dream wardrobe’s one click away. Visit https://www.revolve.com/goaldigger for 15% off your first order with code GOALDIGGER.



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