
Loading summary
A
How long have you been sitting on that online course idea because you think the market is too saturated? My mentor, Amy Porterfield is teaching the new way to create courses that actually sell because the old way is dead. This is her only free live masterclass all year and you can grab your seat right now@jennaplusamy.com her masterclass is called the New and Better Way to Create and Sell a Profitable digital course in 2025. And while everyone's panicking about AI and saturation, Amy's 100,000 plus students are quietly building online courses that sell because they know what others don't. Amy's five step framework shows you how to validate your idea before you build it, position yourself as the guide people desperately need and launch with what works today. Not 2019 strategies. No tech nightmares, no fancy teams. Just proven strategy that you can execute while having a life. Every day you wait, someone with half your expertise is serving your people. Hit pause right now. Jennaplusamy.com I'll be there live taking notes because even I need to learn the new way. Jennaplusamy.com I'll see you there. Huge savings on Dell AIPCs are here and it's a big deal. Why? Because. Because Dell AI PCs with Intel Core Ultra processors are newly designed to help you do more faster. It's pretty amazing what they can do in a day's work. They can generate code, edit images, multitask without leg draft emails, summarize documents, create live translations. They can even extend your battery life so you never have to worry about forgetting your charger. It's like having a personal assistant built right into your PC to cover the menial tasks so that you can focus on what matters. That's the power of Dell AI. With intel inside with deals on Dell AI PCs like the Dell 16 plus starting at $749.99, it is the perfect time to refresh your tech and take back your time. Upgrade your AI PC today by visiting Dell.com deals that's Dell.com deals Can we talk about business regrets for a second? Because while everyone loves to say they'd never change anything, I'm over here thinking about five things I definitely would have done differently in my first few years. The plot twist I'm actually grateful for every single misstep. I'm Jenna Kutcher and I help you trade hustle for purpose and build a business that gives you the life you actually want to live. From a 300 Craigslist camera to a seven figure business I run from home. I've learned that success isn't just about what you do, it's about how you live. Here, you'll get strategies that work, systems that give you your time back, and steps that turn your effort into results and impact. If you're ready for clarity, confidence, and a business that feels as good as it looks, you're in the right place. This is the Goal Digger podcast. There is something so beautiful about looking back at the versions of ourselves who were just in that, like, figuring it out stage. You know, like, when I think about those first few years as an entrepreneur, I see this woman who was so full of fire and so filled with determination, but honestly had no clue what she was walking into. And I love her for that. She was making decisions from a place of pure intuition mixed with hustle without having the wisdom that only comes from actually living through the mistakes, stakes and the burnout and the breakthrough moments. She was someone who was doing her absolute best with the information she had. And there is something so sacred about that season of not knowing what you don't know. Now, from this vantage point, after years of growth, evolution, and yes, plenty of beautiful and public failures, I can see the patterns so clearly. The places where a little more strategy could have saved me months of spinning my wheels, where better boundaries could have prevented that inevitable crash, where more courage to be seen could have accelerated probably everything. This episode originally aired a while back, but I'm bringing it back because these lessons feel so relevant right now as we're in this season of analyzing our goals and chasing down our biggest dreams and maybe feeling that familiar pressure to figure it all out. Right now, I think that we need this reminder that growth is not linear and that every version of ourselves is exactly who we needed to be. Because here's what I've ultimately learned. We don't get to skip steps. Every single fumble, every pivot, every moment of not having a clue was preparing us for what's next. And if sharing these lessons can help you honor your own journey while maybe sidestepping a few more of the painful detours, that feels like the most beautiful full circle moment for me. So whether you're in your own figuring it out era or you're revisiting this with fresh eyes, let's dive in with so much love for the versions of ourselves who are brave to begin.
B
Okay, I honestly can't shake the thought of this meme that I saw where someone had gotten a no Regrets tattoo but they accidentally spelled regrets wrong and it reads no regerts and I just keep laughing to myself as I think about that. So if I start chuckling during this episode, that's literally what I'm envisioning. But real quick, before we talk about the wrongs, I do want to make quick mention of the things that I felt went right early on that allowed me to grow quickly and reach the right people and lay a foundation for a solid business. I'm sorry, but my mom always taught me to seek out the positive in things, so I can't help myself. Before we talk about what I did wrong, let's talk about what we did right. Some of those right things include hiring an accountant to handle the tax and finance side of things, becoming legit legally right away by opening an LLC before I was even making money, sharing my work loudly and consistently on social media to attract more of my target audience, being bold and direct enough to send people direct messages or land in their inboxes asking if they might need my services. And I even made small financial investments into my business early on, like taking out a paid ad that ended up paying for itself within a week to promote the start of my new business. While some of those methods and the advice I offer around them might have shifted in the last decade, I'm honestly quite proud that I took a chance on myself by doing all of that while working a full time job at the same time. Okay, so enough with the good stuff. Let's talk about the messy mistakes. That's why you're here. It is time I get to the juicy stuff. Those mistakes, those missteps, and looking back now, just plain silly things that I did early on in business that I've learned buckets of lessons from and that I hope will help you learn and make better decisions too. So first, I wish I had understood that I should create with a purpose, not just for the sake of creating. So have you ever heard the advice if you build it, they will come? Well, I took that a little too literally early on in my business, and I see new entrepreneurs do this all of the time. Just like you wouldn't build a house without a plan or a blueprint, it's important that anything you're creating for your business is tied to an end result. So if you're spending time, energy or money on something, it's important to tie every action to this deeper purpose. So get this. When I first started out, I blogged five times a week for years. Like literally years. I never missed a single day. I honestly don't even know how I came up with enough content to push out that many posts, and none of them really did anything for me beyond giving me an excuse to share a Facebook post directing people to my blog before moving on to the next day. The posts didn't grow an email list. They didn't lead to another destination on my website. They didn't include strategic calls to action or set me up as an authority. Those daily blog posts were just content pieces created for the sake of creating. Essentially, they were like my online journal, the space to occasionally share my work without any information about how to work with me, book my services, or stay in touch. If I had either approached writing with this end result in mind and with more strategy, or if I had reallocated that already limited time to create and promote just one piece a week, it would have served me so much better. Throwing a little strategy behind my creation process could have totally shifted my approach and the response to my work. So nowadays I create less content per week, even though I have a team helping with the creation and the promotion of that content. Because we make sure each and every single piece that we push out is tied to this deeper goal and includes clear opportunities for my audience to take action, whether that's downloading a freebie or using an affiliate link for a product or service, or joining my email list or signing up for a training. It's less work all around, and it's a more thoughtful, strategic approach to creating that I totally wish I would have had in those early days. It is wild to me when I log into my WordPress and see that I have published thousands of blog posts. And when I think about how I literally posted Monday through Friday, it didn't matter if it was Christmas or New Year's or Labor Day. I was literally just creating for the sake of creating. I want for you to hear this. It is not always about creating more. It's about the strategy behind the creation. So remember that. Don't make the same mistake I did. Don't put yourself on this hamster wheel of creation without tying it to something deeper, a greater end result. Number two, I wish that I had set boundaries that would save me from burnout. So this is one of those things that I know in hindsight would have saved me a lot of exhaustion and kept me from overworking myself. Like, if I could actually go back in time and change my mindset knowing what I know now, things might have looked wildly different. And I honestly struggle with this one because sometimes burnout leads to the breakthrough, but when it hits, it can be so hard and tricky to navigate. The truth about burnout is that it never should be the goal or the destination, but it happens to a lot of entrepreneurs and usually leads to things like better boundaries and more balance. If we pay attention and we use that burnout as a signal that something's got to change. I honestly don't think there was any other way for me to learn that hard lesson of realizing that I was pushing myself way too hard and that I had to find a better solution to care for my time, my energy, my health, and to really create actual work and life boundaries. From working a set amount of hours and not giving out my phone number, to taking every Sunday off and turning down double header wedding weekends, I had to learn the hard way that boundaries aren't selfish. They actually protect you. They protect your creativity, they protect your passion, they protect your longevity in a career. There are so many ways to incorporate your own necessary boundaries that can keep you from overworking yourself or hitting burnout. Because the truth is, when you start a business, you're usually so passionate and on fire that you find yourself becoming obsessed with the work and that feeling of progress. It's like once you get momentum, you simply cannot stop. You're also busy balancing the pressure of doing your own thing and proving people wrong, which is kind of what my neighbor found. And you're trying to make it. And so when you take a bet on yourself, you're likely going to work even harder. You know that that end result is a reflection of you. And so it's really not shocking that we often hit burnout. The first three years I was on this upward trajectory as a wedding photographer, I was saying yes to just about everything. I did a ton of crazy things. Like, one time I shot two weddings in one weekend in different states. I literally finished a wedding in Milwaukee and drove all the way to Minneapolis hours and hours and hours, only to get a few hours of rest and recharge my gear before the next day. Like, I did not necessarily understand how to say no, and I did not really know how to look at what my time was worth. I drove all over the place. I was always available. I said yes to everything. I slept with my computer on my freaking nightstand. Like, I spent hours responding to inquiries and answering questions. I even missed some of my best friends weddings because of client work. And I never, ever preserved or saved weekends to be spent with family or for time off. Like, when I look back at that, it's like, honestly, soul crushing because I'm like, I was so pumped to be doing what I loved, but I also took on so much responsibility And I struggled to say no. I was the yes girl. Like, my overzealousness led me to be someone who didn't know how to say no. And I chased more until I was so burnt out that I had totally squashed any passion I had started out with. Like, I hit this point where I just wanted to walk away. And, like, my windowless office suddenly became appealing again. I didn't realize at the time that all of those yeses to work meant equal no's to living my life, to being present with the ones that I loved. And for me, it took hitting total burnout and exhaustion to really recognize that more money wasn't making me happy and that I started all of this in order to get my life back, not to sign it away. Well, I eventually, quote, got it and made the decision that I'd rather live on less money to get back my time. It's a decision that absolutely shifted everything for me. Like that decision of saying, you know what? I am willing to say no to 6 figures. I'm willing to work for 50k again, just to have a life again, actually change the trajectory of my business. And it would have been nice to have learned this one a little bit quicker. But if you can get out ahead of it, my best advice is this. Try even small ways to protect and value your time and allow for rest to be a part of your workflow by scheduling breaks into your day and allowing at least one full day a week off of work. Like, literally, if you're not taking a day off each week. Holy Hannah, start there. But please take this advice to just protect yourself from the rock bottom that burnout can be, and do it so that you don't end up burning the candle at both ends and ultimately resenting what you do for a living. Like, I look at how I went from this, like, passionate person who wanted to bring her camera everywhere, who just loved the art of photography, to somebody who was so burnt out and exhausted that I was like, man, like, checking myself into a hospital for exhaustion. Sounds like a vacation. That is not okay. That does not have to be what entrepreneurship looks like, and that should not be the vision you are pursuing right now.
A
This podcast is brought to you by Mercury Banking that helps entrepreneurs do more with their money. When I first started taking my business seriously, I remember feeling stretched thin. I was juggling invoices, tracking payments, and managing cash flow across different tools. It was messy and I thought banking had to be that way. That's why I was impressed with Mercury. Unlike traditional banking, that feels clunky and outdated. Mercury is designed to make managing money effortless so that you can focus on what actually grows your business. Everything you need is in one intuitive product. Banking cards, spend management, invoicing and more all in one place. Plus, Mercury flexes to fit all types of businesses, so whether you're a funded startup agency or e commerce brand, it can be tailored to you. Visit mercury.com to join over 200,000 entrepreneurs who use Mercury. Mercury is a financial technology company, not a bank. For important details, check the show notes. You know that sinking feeling when you see your latest campaign report? 87% of your budget went to people who would never buy from you. Random scrollers clicking your business course ad students engaging with your entrepreneur Content your perfect ad creative about building sustainable income shown to people who aren't even trying to build a business. That's why LinkedIn ads exists. While other platforms guess who might be interested? LinkedIn knows who your buyers are. Target the exact job titles making purchasing decisions. Reach VPs of marketing at Growing Companies. Find HR directors at mid sized firms. Target entrepreneurs ready to invest in their growth. Zero waste, maximum impact. Stop hemorrhaging, budget on random audiences and start reaching actual decision makers who can write the checks only with LinkedIn ads. Spend $250 on your first campaign on LinkedIn ads and get a free $250 credit for the next one. Just go to LinkedIn.com goal that's LinkedIn.com G O A L Terms and conditions apply. Running a business means wearing every hat, creating content one minute, handling customer service the next, then trying to figure out shipping logistics. It can get overwhelming fast when you're building your dreams. Finding the right tool that not only helps but simplifies everything is a game changer for millions of businesses. That tool is Shopify. Shopify powers millions of businesses worldwide and 10% of all all e commerce in the US from Gymshark and Mattel to brands just starting out. With hundreds of ready to use templates, you can create a store that matches your brand. Shopify's AI tools write product descriptions and even headlines so you can create content faster. Plus, with their built in email and social tools, it's like having a marketing team in your back pocket. From inventory to shipping to returns, Shopify is the partner every entrepreneur needs. If you're ready to sell, you're ready for Shopify. Turn your business idea into With Shopify on your side, sign up for your $1 per month trial and start selling today at shopify.com golddigger go to shopify.com goaldigger shopify.com golddigger.
B
Number three I wish that I had thought beyond my signature service. So we're switching gears here, but since we're going back in time, I want to paint the full picture for you. So I was all in as a wedding photographer and I honestly was in this stage of life where like, I couldn't believe that I could get paid to photograph people's weddings. It was such a surreal experience and all I could think of was, wow, like I'm really doing this. Starting out as a photographer, it was pretty natural to think I only had one thing to offer, which was my photography services. And let's be real, it is wise to master the art of the one thing you want to be known for before expanding into a zillion other offers. I was actually really proud of myself for hitting this point where I was turning down the random family sessions or puppy portrait sessions and telling people I am a wedding photographer, I specialize in wedding photography. Frankly, that was a really good first step. But now looking back, I also realized that there were ways that I could have focused on my one thing, which was photography, while also at least thinking through ways that I could potentially create additional opportunities for revenue around that one thing. Now that I know so much about passive income digital products, upsells and affiliate sales, I wish I had been thinking just slightly bigger at the very beginning to give me a taste of what it'd be like and feel like to make some money without I was having to trade my time. I mean, at the beginning, most of us are more than willing to trade our time for money. In fact, most times it's the necessary place to begin when starting a business and getting it going from the ground up. But there does come a time of recognizing that the time for money game isn't as freeing as what you had envisioned for entrepreneurship. I mean, where are my fellow service based friends at? You guys understand the struggle of wanting to show up and serve with your skills, but also wanting to take time off of work occasionally without worrying that the income is just going to completely stop. For me, this reality sunk in when I was actually experiencing our second pregnancy loss and I actually had to show up to shoot a wedding knowing what was going on inside of my body. Like the reality that I had built something that meant that if I didn't show up, I wouldn't get paid hit me like a ton of bricks. So even if you're not ready to expand your offerings or you're not 100% sure what additional ways you want to incorporate more passive income. It's important to think about these things even from the early days to help you take action faster than I did. Now, while I eventually figured it out, it took me a few years and I wish I would have at least thought about ways to incorporate and add in extra revenue streams even if I didn't implement them right away. Again, it's great to be a master at one thing to get known for that thing, but don't limit your thinking or your dreaming of other ways that you can bring in revenue, specifically ways that aren't trading your time for money. Number four is this. This is my number one business regret. Okay, let's walk through it. I wish I would have started my email list sooner. Now hear me out. When people ask me like what is your number one regret? It is this. And I know it sounds so silly and it sounds not really a shiny thing, but seriously you guys, your email list is the number one indicator of your business's health and longevity. And it is something I have been talking about literally for years. Even before it was cool or people understood why they needed an email list or what they'd send to one if they even had it. I have had so much conviction on this topic that I could talk about it all day. You can literally scroll back and see that I've been talking about email list for years. So you might have heard the stat that for every $1 spent on email marketing an average of $42 is made. But did you know the global email marketing market was valued at $7.5 billion in 2020 and is projected to increase to 17.9 billion by 2027? And beyond those stats, there are 4 billion daily email use users. So basically there is ongoing and exponentially growing power and profitability in pointing your marketing efforts towards email. So much so that four out of five marketers say they would rather give up social media than email marketing and I would 100% fall into that camp. By the way, all of these mind blowing stats come from the marketing pros over at HubSpot. So my email list is my number one asset in my business. Business. It's my number one focus in my business. It's the number one thing I invest in when it comes to business and it's the number one way I drive sales in my business. If that doesn't prove how important this point is, well, I'm not sure what will. What happened is that I didn't start my email list until years into my photography business and right as I was in the process of starting my side hustle in teaching. It took that pivot for me to realize this and to take action on it because I'd been so distracted by all the other things that I thought I needed needed to be doing. When I finally knew that I wanted to do something beyond shooting weddings, it felt like I was playing catch up on starting and growing my list. And once I did get started, and I can see now, I was so focused on trying to win shiny social media points, points that don't actually lead to a ton of results or extended brand loyalty or conversions. Here's the other point I want to make. I wish I would have started my email list back when I was a wedding photographer because service providers can benefit insanely from the rewards of email marketing. So I wish I wouldn't have looked at it as like something necessary when I entered this digital education space. But I wish that I would have seen it as an asset that was worth pursuing and investing my time and energy and effort into as a service provider and that would have laid the foundation for my pivot. So when I look back and I was focused on all the shiny things, now I understand the power of a lead or a subscriber and how an email list allows you to thoughtfully serve someone before you ever go to sell to them. I also love the fact that much of email marketing can be automated, meaning when we're talking about trading our time for money or serving and showing up, it gives you this opportunity to know that you can work smarter and not harder, that people can be served while you're resting, that you can set up automations that do the work for you. So beyond being the biggest needle mover for my business, email marketing is also one of the most powerful ways that most small businesses communicate with their audience, keep them informed, and make the most sales. In fact, 64% of small businesses use email marketing to reach customers, and that number is growing as entrepreneurs recognize the role that email should hold in their business. It's important when we look at our marketing efforts to recognize that we don't actually own our social media channels and we can't control the experience experience we offer followers or the frequency our posts are delivered. But with email, we get this opportunity to show up one on one into our audience's inbox for this more tailored personal way of communicating and building trust. Okay, number five is this. I wish I hadn't hid behind my work for so long. It's my last regret. This one is a really easy regret because looking back, I can 100%. See, see and understand why it happened. When you jump into something new, imposter syndrome lurks around every corner. And our biggest desire is to simply blend in and try to fit into our industry so that no one can call us out or call our bluff. I mean, the truth is, as creators and creatives and entrepreneurs, unless you are the face of your brand, it is way too easy to hide your bright and shining face and your one of a kind personality behind your work and instead just push your products and your work into the feeds and hope that they can speak for themselves. Like I see it so often with artists and photographers and writers and VAs and social media managers and coaches. I mean, it happens to all of us. And I get it because I did the same thing early on in my photography business. I didn't post any photos of myself or my life until about year three. And truth was I thought people just wanted to see my work and my photos of clients because after all, that was what I could offer for them and the service that they'd be most interested in booking. But looking back now, I can see how I was playing small and trying to blend in. And I lived with this belief that my work would speak for itself. But what I failed to recognize was that if people connected with me, then they were far more likely to appreciate and want to invest in my work. By hiding who I was, I was actually doing my clients and my audience a disservice. Sprout Social shared that 70% of consumers feel more connected to brands with CEOs who are active on social media. Which honestly makes sense when we think about our own user habits. Like we like connecting with other people and real faces and personalities, not just logos or faceless graphics or products. So when I use a time machine to look at my early website, it was literally just like everyone else's. It was wildly generic, there was zero personality. And I thought it didn't matter that people just wanted to follow along for my services. But I failed to see that people wanted an experience from me if they were going to work intimately with me as their wedding photographer. And honestly, I failed to acknowledge that I wanted people to choose me for me, not just for the end product. We all talk about this no like and trust factor in business and why it's so important, especially as a small business. And it's undeniable that there needs to be this level of trust between your client and you, especially if you don't just want to get picked up because you're the cheapest or because your price is the lowest. The quickest way to grow trust is to be true to you, to show off who you are, to share more of the humans behind the offers. There's going to be a lot of people out there who do what you do, but there won't be anyone else who can do it the exact same way that you do it. You are the only person with your story and your outlook and your units, sharing pieces of your life, your personality, your heart, through images of you or stories about your life and your thoughts, beliefs or values. It allows people to connect not just with your business, but with the mission and the heartbeat behind that business. You want to build a true brand. And a true brand has a personality. And you as a human, as a founder, as a creative, has a personality. So don't just hide behind your business. Don't let yourself believe that your worth is found in your output, but really share about who you are and why you do what you do. Because people will respect you and your work so much more and they'll choose you simply because it's you. Trust me on this one.
A
Can we talk about how bad underwear can ruin your entire day? Like I used to put on underwear and a bra knowing that I'd be adjusting it by 10am and completely over it by lunchtime. That is why I am obsessed with the Skims Fits Everybody collection. Now I bought skims for years, but I swear this line is a total game changer. The Fits Everybody Scoop Roulette has buttery soft fabric that literally feels like nothing and I mean that in the best way I can put it on and I forget that it exists. I'm so confident in these pieces that when I packed my grease suitcase it was basically all skims. I even wore their bodysuit for a recent branding photo shoot. Because when something fits this well, you just trust it. When your underwear actually works, you stop wasting precious mental energy on it and you can focus on any everything else that matters. If you're tired of uncomfortable intimates, this is your sign to try Fits Everybody Shop Skims Fits Everybody collection@skims.com Once you place your order, make sure to let them know we sent you. Just select podcast in the survey and choose the Gold Digger podcast in the drop down menu that follows. This message is sponsored by green light. My 6 year old woke up this morning asking if she could do chores to earn money. Why? Because she read a fancy Nancy book where Nancy worked to buy fabulous shoes and suddenly my daughter wanted to experience the same pride of buying something special with her own money. But here's what hit me. I had no good way to help her actually see and feel her money growing. Cash gets lost, piggy banks are abstract, and she can't really understand the connection between effort and reward. That's why we started using green light. Green light is the easy, convenient way for parents to raise financially smart kids and for families to navigate life together. And maybe that's why millions of parents trust and kids love learning about money on Greenlight, the number one family finance and safety app. Now when she does chores, I can instantly send her earnings to her card. She watches her balance grow in real time and feels genuine ownership over her money. And when she's ready for those fabulous shoes, she'll swipe her own card and experience that incredible feeling of Nancy had Don't wait to teach your kids real world money skills. Start your risk free Greenlight trial today@greenlight.com golddigger that's greenlight.com golddigger to get started. Greenlight.com golddigger Drew and I have been so lucky to travel to some amazing places over the years, and Airbnb has been at the center of so many of our best memories. We've stayed in some unforgettable places, like a house with an indoor pool in the Midwest where the girls practically turned into mermaids maids, and another with a hot tub that they refuse to leave even for dinner. We have celebrated holidays in these cozy homes away from home, gathering with families and creating new traditions and spaces that make us feel instantly welcome. And it got me thinking, if you've got a few trips on the calendar and your home's going to be empty anyways, you should be hosting. The best part is you don't have to do it all on your own. With Airbnb's co host network, you can team up with a local co host who handles the details of for you from guest messages, reservations, even on site support. So your home is cared for and your guests get that same kind of unforgettable experience you'd want for your own family. Find a co host@airbnb.com host so now.
B
You know all of my deepest, darkest regrets. Just kidding. But seriously, in reality, these are things that I'm actually really glad to be able to look back and say, well, now I know better and I can do better. And in that sense, they are all pieces of my entrepreneurial story and journey that I'm honestly proud of because they obviously led me to good things like creating better boundaries and learning to lean into my values and to understand who I am better and get creative with my strategies. So I want to know, what do you think? Like, I hope you can take my mistakes and use them for your own benefit. Please do that for the sake of this episode and maybe you can even cut a few years of your learning curves off while you're at it. It's always fun taking a walk down memory lane with you. So thank you for being here. And just like I told my neighbor, I want to tell you this. You are worth it. The visions you hold for yourself are worth is not your job to get anyone else to buy your vision. Your vision is yours and yours alone. If people want to be the naysayers, if they want to strike you down, if they want to make you doubt what you're doing, let them do that. It's usually a reflection of their own insecurity. But I promise you, if you bet on yourself, if you go all in, if you believe that you are worth betting on and that you can invest in yourself, man, I can't wait to see what you do. So I hope you enjoy today's episode. I hope you go for it. I hope you learn from my mistakes and I would love to hear from you. Hop on over to Instagram at Gold Digger Podcast and leave a little message. Tell me what your greatest regret is or what you learned. Like, I love reading and hearing from you about these episodes. And of course, until next time, keep on digging your biggest goals. Thank you so much for being a part of the Goal Digger movement.
A
Thanks for listening to the Goal Digger podcast. I hope today left you inspired and equipped with something you can put into action as you build a business that truly supports your life. If this episode resonated with you, here's how you can help the show reach even more entrepreneurs. Hit follow. Share it with a friend who's building something meaningful. And if you're feeling generous, leave us a review. Those reviews help other listeners discover these conversations when they need them the most. This show has become so much more than I ever imagined, and it's because of listeners like you who show up and share you are helping build something that will inspire entrepreneurs for years to come. For show notes, links and resources, head to gold diggerpodcast.com keep digging your biggest goals. The world needs what you're building.
Host: Jenna Kutcher
Air Date: September 17, 2025
In this insightful solo episode, Jenna Kutcher reflects on her entrepreneurial journey and shares the five major mistakes she made in the early years of building her business. Her mission is to help fellow entrepreneurs—especially creatives, women, and small business owners—learn from her missteps and bypass some of the pain points that come with starting and scaling a business. With her signature honesty and warmth, Jenna combines personal stories with actionable strategies and mindset shifts.
[Timestamps: 04:10–05:20]
[Timestamps: 05:20–06:30]
Before diving into regrets, Jenna shares a few foundational actions that set her up for long-term growth:
Quote:
“I’m honestly quite proud that I took a chance on myself by doing all of that while working a full time job at the same time.” [06:22]
[Timestamps: 06:33–08:50]
Quote:
“It is not always about creating more. It’s about the strategy behind the creation.” [08:30]
[Timestamps: 08:52–15:05]
Quote:
“Boundaries aren’t selfish. They actually protect you. They protect your creativity, they protect your passion, they protect your longevity.” [11:50]
[Timestamps: 18:26–20:30]
“For me, this reality sunk in when I was actually experiencing our second pregnancy loss and I actually had to show up to shoot a wedding…” [19:40]
[Timestamps: 20:31–25:00]
Quote:
“Your email list is your number one asset in your business… It’s the number one way I drive sales.” [21:30]
[Timestamps: 25:01–29:15]
“If people connected with me, then they were far more likely to appreciate and want to invest in my work.” [26:58]
“I drove all over the place. I was always available. I said yes to everything. I slept with my computer on my freaking nightstand.” [12:00]
“Now I know better and I can do better… they are all pieces of my entrepreneurial story and journey that I’m honestly proud of because they obviously led me to good things.” [32:40]
“The quickest way to grow trust is to be true to you, to show off who you are, to share more of the humans behind the offers.” [27:55]
“It is not your job to get anyone else to buy your vision. Your vision is yours and yours alone.” [33:06]
Connect:
Jenna encourages listeners to share their biggest business regrets or lessons on Instagram @goaldiggerpodcast.
For more, visit goaldiggerpodcast.com for show notes, tools, and resources.