Have you ever heard a story so raw, so real, that it physically stopped you in your tracks? The kind of story that makes you put down your to-do list, take a deep breath, and remember why you started this journey in the first place?

May is National Small Business Month, and while I LOVE hearing from the headline-makers and household names, today is about something even more special: real stories from real listeners of this podcast. 

These are the kind of women who tune in while they’re juggling kids and client calls, who build their dreams during nap time or after their 9-to-5. They may not have gone viral, but what they’ve built? It’s powerful. It’s personal. And it matters.

Tonbra, Maris, and Chelle didn’t just build businesses… They built something beautiful from heartbreak, identity shifts, and unimaginable challenges. From cancer diagnoses to grief to reinvention, these women turned their hardest chapters into platforms that now help others.

If you’re walking through your own hard chapter, or even just need a reminder of what’s possible on the other side of pain, this one’s for you.

And hey, if you want to be part of this kind of community I’d love to invite you into the Goal Digger Podcast Insiders Group: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

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Goal Digger Show Notes: https://www.jennakutcherblog.com/national-small-business-month-stories 

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In a world that celebrates big milestones, loud announcements, and curated perfection, it’s easy to forget that some of the most meaningful wins don’t make it to the feed. 

They happen behind closed doors. They don’t come with applause. They aren’t always photogenic… but they are real. And they are enough.

Today’s episode is a deeply personal one. I’m pulling back the curtain on how my definition of success has changed over the years… How I’m still digging my biggest goals, but now it’s in a way that aligns more with how I want to feel, not just how it all looks.

Whether you’re in a season of quiet growth, private healing, or just choosing to build a life that prioritizes peace over performance, I hope this episode feels like a soft place to land.

Let’s redefine what it means to win… even when no one else is watching. Ready? Click play!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/choosing-peace-over-performative-success

Thanks to our Goal Digger Sponsors:

Get $25 off your first purchase at http://therealreal.com/goaldigger.

Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. 

For a limited time, get $25 in Shippo credit when you spend your first $25. Claim your offer now at http://shippo.com/goaldigger! 

Find a co-host today at http://airbnb.com/host. 

Deposit or spend $5,000 in 90 days to earn up to $500 in rewards at ⁠mercury.com/goal⁠. Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC. The IO Card is issued by Patriot Bank, Member FDIC, pursuant to a license from Mastercard. Working capital loans provided by Mercury Lending, LLC NMLS ID: 2606284.

For years, Amy Porterfield has been my unofficial business mentor turned best friend, and let’s just say, there’s no one I talk shop with more. 

We have DAILY convos about what’s working, what’s changing, and how we’re navigating the shifts in online business. And in 2025? It’s all about agility, strategy, and getting creative with how we show up.

In this episode, Amy and I are diving into the biggest trends we’re noticing, the shifts we’re making in our businesses, and why Pinterest is having a MAJOR moment right now. 

If you’re looking for a way to drive more traffic without constantly creating new content, I’ve got you covered! My free training Create Once, Traffic for Months: My 1-Hour Pinterest Strategy to 120x Your Content’s Life is ready for you!

Click play now and let’s dive into this conversation that originally aired on The Amy Porterfield Show. 

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/lead-generation-strategies-that-still-work 

Thanks to our Goal Digger Sponsors:

Get $25 off your first purchase at http://therealreal.com/goaldigger.

Sign up for your $1/month Shopify trial period at http://shopify.com/goaldigger. 

For a limited time, get $25 in Shippo credit when you spend your first $25. Claim your offer now at http://shippo.com/goaldigger! 

Find a co-host today at http://airbnb.com/host. 

Deposit or spend $5,000 in 90 days to earn up to $500 in rewards at ⁠mercury.com/goal⁠. Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC. The IO Card is issued by Patriot Bank, Member FDIC, pursuant to a license from Mastercard. Working capital loans provided by Mercury Lending, LLC NMLS ID: 2606284.

For most of us, creating content is the part that feels natural, but promotion feels more vulnerable. So we do what we’ve always done… we make something new. We stay busy. We stay in motion.

But what if the real power isn’t in making more, but in letting what you’ve already made breathe a little longer? What if the magic isn’t in more content, but in more intention behind how it’s shared?

Visit http://www.teachmetopin.com to learn about the platform I’ve been teaching about for over eight years, one I’ve helped over 25,000 people use in their business to create content systems that actually last!

In this episode, I’m walking you through a simple mindset shift that changed everything for me. If you're feeling burned out, tired of feeding the algorithm, or wondering why your content doesn’t seem to carry the weight it should, this one’s for you.

We’ll explore what it looks like to shift from short-term content bursts to long-term, strategic sharing. I'm talking about ways to make your creations live longer, reach further, and work harder without requiring more from you every single day.

If you’re ready to get off the content hamster wheel and start building a business where your work keeps working, even while you rest, this is your permission slip. Press play now!

And don’t forget: save your seat for my free class: Create Once, Traffic for Months: The Pinterest Plan That Extends Your Content’s Lifespan in Just One Hour a Week at http://www.teachmetopin.com!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes:https://www.jennakutcherblog.com/content-repurposing-strategies-to-beat-burnout

Thanks to our Goal Digger Sponsors:

What if I told you there’s a way to make that same piece of content live longer, work harder, and drive traffic for months, without creating more, more, more?

Head to http://www.teachmetopin.com and I’ll show you how!

Today’s episode is a roundtable with two of my favorite women in the Pinterest world: Kate Ahl of Simple Pin Media and Heather Farris of Heather Farris & Co. We’re all Pinterest Educators, and we’re pulling back the curtain on how we use Pinterest in 2025 to give our content new life.

This isn’t about trendy graphics or chasing viral pins. It’s about strategic, sustainable visibility in just ONE hour a week. If you’re tired of the content hamster wheel and you want to make your work work harder for you, this one’s for you!

And if you love this convo, save your seat for my free class: Create Once, Traffic for Months: The Pinterest Plan That Extends Your Content’s Lifespan in Just One Hour a Week at http://www.teachmetopin.com!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/pinterest-growth-strategy-2025 

Thanks to our Goal Digger Sponsors:

We’ve all been there—pouring time, energy, and maybe even money into an idea that felt like a winner, only to launch it and hear… crickets. It’s frustrating, it’s discouraging, and it can make you second-guess everything. 

But what if you could know before you create whether an idea is actually worth pursuing?

In this episode, I’m breaking down how to validate your ideas before you invest in them so you stop wasting time on offers, products, or projects that won’t sell. I’ll share the simple ways I test demand, get real audience feedback, and tweak ideas before they ever go to market. 

Whether you’re launching something new or refining what you already have, I want to help you save time, energy, and a whole lot of stress. Ready? Press play!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/what-products-actually-sell-and-how-to-validate-your-idea 

Thanks to our Goal Digger Sponsors:

Let’s be real: paid ads have changed a lot over the years, and keeping up with what actually works can feel like trying to hit a moving target. But lucky for me (and for you), I’ve had the same brilliant ads strategist in my corner for years, and she’s here today to break it all down for us!

Kerry Swetmon is a business strategist, a systems nerd, and a master of simplifying the complex world of online advertising. And she’s not just ANY expert in Facebook ads—she’s been MY personal go-to strategist for 8 and a half YEARS, helping me navigate the ever-changing digital landscape and making sure my ads are working for me, not against me. 

The last time Kerry was on Goal Digger was in 2017, so I think it’s safe to say we are over due for an updated look at the ads landscape in 2025!

In this episode, we’re diving into what’s actually working for Facebook ads in 2025—what strategies are performing best, what’s not worth your time or money anymore, and Kerry’s biggest tips for maximizing your ROI and there’s a shocking fact in this episode that I think will blow your mind when it comes to ads. Whether you’re running ads for the first time or looking to fine-tune your approach, this episode is packed with gold.

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/tips-for-building-a-paid-social-ads-strategy 

Thanks to our Goal Digger Sponsors:

You ever have one of those mornings where motivation feels... MIA? Like, the to-do list is waiting, your calendar is full, but the last thing you want to do is any of it? Yeah… same.

Whether it’s a weird funk you can’t shake or just one of those off seasons where inspiration feels so far away... I want you to know: you’re not broken, you’re not lazy, and you’re definitely not alone.

We all hit those low-energy, low-motivation stretches. 

In this episode, I’m sharing five things I come back to when I feel totally stuck. These aren’t hacks or hustle-y tips… Think gentle nudges, mindset resets, and simple practices to help you find your footing again.

I actually recorded this one during a time when I really needed these reminders myself. And honestly? I still revisit them anytime I’m feeling off or overwhelmed. So whether your spark just feels a little dim or you’re deep in the “blah” zone, press play. We’ll walk through this together!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/how-to-get-motivated-and-unstuck 

Thanks to our Goal Digger Sponsors:

Have you ever attended an event that completely changed the trajectory of your life? My guest today, Marina Middleton, certainly has. 

In 2021, she walked into her first Create & Cultivate event as an attendee, looking to make connections and gain insights for her own business. Fast forward to today—she’s the CEO and Partner of the very brand that inspired her.

Marina is a powerhouse when it comes to building communities, amplifying women’s voices, and helping them break barriers in business. Before stepping into her leadership at Create & Cultivate, she worked with Fortune 500 companies at Yahoo! and Tumblr, strategizing digital media campaigns. She has since coached and consulted hundreds of female founders, helping them grow their brands with confidence.

In this episode, Marina shares the defining moments that shaped her career—from navigating the corporate world as a woman of color to stepping into the CEO role of a major media and events brand. We’re diving into how mentorship, networking, and representation can accelerate career growth, plus the lessons she’s learned balancing leadership and motherhood.

If you’ve ever felt like an outsider in your industry or wondered how to cultivate the right connections to propel your career forward, 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://www.jennakutcherblog.com/women-in-leadership-tips-with-create-and-cultivate-ceo-marina-middleton 

Thanks to our Goal Digger Sponsors:

Today’s episode is one of my absolute favorites because it’s all about YOU. We’re diving into another Ask Me Anything—your real, unfiltered questions, straight from the Goal Digger community.

You left me the best voicemails—honest, thoughtful, and full of the kinds of questions we don’t talk about enough. In this episode, I’m answering some juicy ones: how to navigate major pivots, get out of content creation burnout, and yep… I’m even opening up about one of my biggest career flops and what it taught me!

These AMA episodes feel like a coffee chat with a side of business therapy, and I have a feeling something in here is going to hit right where you’re at—whether you’re just starting out or scaling up.

If you want to be part of a future episode, I’d love to hear from you! Simply call 218-203-9660, leave your name, where you’re calling from, and your question and YOU may be featured on a future episode of the Goal Digger Podcast!

Goal Digger Facebook Community: https://www.facebook.com/groups/goaldiggerpodcast/

Goal Digger Instagram: https://www.instagram.com/goaldiggerpodcast/

Goal Digger Show Notes: https://www.jennakutcherblog.com/ask-me-anything-jenna-kutcher-april-2025 

Thanks to our Goal Digger Sponsors: