The Bold Biz Podcast

Send us Fan Mail The faceless vs face forward question every midlife woman asks before starting a side business 👉 Grab the free Claude Quick Start Guide here: https://www.theboldbiz.com/claude If the thought of putting your face on the internet makes you want to disappear, you are absolutely not alone. The faceless versus face forward question is one of the biggest blocks midlife women hit when t...

Send us Fan Mail How midlife women are using AI to build side businesses faster than ever, plus a personal announcement you won't want to miss 👉 Grab the free Claude Quick Start Guide here: https://www.theboldbiz.com/claude If you've been quietly watching everyone talk about AI and feeling like you've somehow missed the boat, this episode is going to change that. Jenny breaks down...

Send us Fan Mail You Don't Need More Ideas. You Need a Way to Filter the Ones You Have. This episode picks up right where Episode 27 left off — once you've named the fears, it's time to actually do something about them, and the Four-Filter Framework is where that starts. The Four Filters: Filter 1: Skills — Does this idea build on something you already know, or would you be starting...

Send us Fan Mail Are you too scared to start? Here are the 7 fears holding midlife women back from building a side business If you have been thinking about starting a side business but something keeps talking you out of it, this episode is for you. Jenny gets honest about the 7 most common fears women over 40 have before they take the leap — and what to actually do about each one. She has felt eve...

Send us Fan Mail Do you have a graveyard of half-built businesses, abandoned Etsy shops, and courses you never finished? You are not alone, and more importantly, you are not broken. In this episode, Jenny gets really honest about her own side business journey – from a $3,000 course she never completed, to Entrepreneurial Gals (a beautiful website with absolutely nothing to sell), to an Etsy jewelr...

Send us Fan Mail Have you ever looked at your business and thought… what is the point? Like you’ve been showing up, trying, creating, learning, and still not seeing enough movement to prove it’s working? In this episode of The Bold Biz Podcast , Jenny talks honestly about the part of building a side business that almost nobody shares online, the valley. The slow season. The invisible progress. The...

Send us Fan Mail Do you feel curious about AI… but also a little intimidated, behind, or convinced it’s “for younger people” or more tech-savvy entrepreneurs? In this episode of The Bold Biz Podcast , Jenny explains why women over 40 cannot afford to ignore AI, especially if you want to build a side business with limited time, limited energy, and no desire to do everything the hard way. This is no...

Send us Fan Mail Do you ever feel like you’ve missed your moment… like everyone else is already ahead, already building, already figuring it out? In this episode of The Bold Biz Podcast , Jenny dives deep into one of the most persistent and quietly limiting beliefs that keeps women stuck, the feeling of being too late, too behind, or too far removed from where they “should” be. This is not just a...

Send us Fan Mail What if the business you start today… isn’t the one you stick with forever? In this episode of The Bold Biz Podcast , Jenny challenges one of the biggest fears that keeps women stuck before they even begin, the pressure to choose the “perfect” idea that will work long term. Because when every decision feels permanent, it’s easy to stay stuck in overthinking, waiting, and not start...

Send us Fan Mail Do you have too many ideas… and still feel completely stuck? In this episode of The Bold Biz Podcast , Jenny dives into one of the most frustrating and confusing phases of building a side business, having multiple ideas, all of them with potential, and not knowing which one to choose. Because here’s the truth.  Having too many ideas can feel just as paralyzing as having none. Jenn...

Send us Fan Mail Have you ever felt like you need to do everything to make your business work… and then end up overwhelmed, exhausted, and stuck? In this episode of The Bold Biz Podcast , Jenny shares a very honest look at one of the biggest mistakes she made over and over again when trying to build her side business, doing too much, too fast, and burning out before anything had the chance to work...

Send us Fan Mail Comfort feels safe. Familiar. Predictable. But what if the very thing that feels safe is quietly holding you back from the life you actually want? In this episode of The Bold Biz Podcast , Jenny talks about the hidden cost of staying inside your comfort zone and why so many women settle into routines that feel stable but slowly disconnect them from their bigger dreams. Jenny share...

Send us Fan Mail Have you ever felt like you need to become an expert before you’re allowed to share what you know? In this episode of The Bold Biz Podcast , Jenny talks about one of the biggest mindset traps that keeps women from starting their side business, the belief that you need years of experience, certifications, or huge results before you can help anyone. The truth is much simpler. You do...

Send us Fan Mail Have you ever felt busy… but not actually moving forward? In this episode of The Bold Biz Podcast , Jenny unpacks why so many women stay in constant motion without real momentum, and why effort alone is not the answer. This is not about motivation. It’s not about discipline. And it’s definitely not about working harder. It’s about clarity, focus, and structure. Jenny dives into th...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny breaks down marketing in a way that finally feels human, doable, and not overwhelming. If the word marketing makes you tense up, feel behind, or instantly think of algorithms, funnels, and tech you “should” understand by now, this episode is for you. Jenny talks about why marketing often feels harder than it needs to be, especially w...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny dives into one of the most overlooked, and emotionally loaded, parts of building a side business: sales . For so many midlife women, sales feels awkward, heavy, or even shameful. Not because they’re doing it wrong, but because no one ever taught them the psychology behind why people buy . In this honest and grounding conversation, Je...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny explores one of the most powerful shifts you can make if you want to build confidence, momentum, and something truly your own, moving from being a constant consumer to becoming a creator. If you’re a woman who listens to podcasts, saves reels, bookmarks tools, buys courses, and is always “learning,” this episode is for you. Jenny gen...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny dives into a topic that completely changed how she thinks about money, business, and even her nervous system: recurring revenue . Not flashy income. Not viral income. Not one-hit-wonder months followed by stress and scrambling. But calm, predictable, repeatable income that builds over time ✨ This episode is especially for women in m...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny breaks down one of the biggest questions women ask when they start thinking about an online business: What could I actually sell? If you’ve ever felt stuck, overwhelmed, or unsure what your “thing” is, this episode is here to remind you that there isn’t one right path, and that you probably already have valuable skills you’re underes...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny dives into one of the most important, and least talked about, phases of building a side business, the dip . That uncomfortable, confusing middle stage where the initial excitement has worn off, results feel slow, and self doubt starts creeping in. The part where so many people quietly quit, not because they’re incapable, but because...

Send us Fan Mail In this episode of The Bold Biz Podcast, Jenny dives deep into manifestation, not the fluffy, wish-it-and-wait version, but the grounded, real-life way your thoughts, emotions, and actions quietly shape your future. Jenny shares personal stories from her own life, from visualizing her future partner years before meeting her husband, to manifesting a national morning TV appearance...

Send us Fan Mail In this episode of The Bold Biz Podcast , Jenny dives into what she believes is the most overlooked ingredient in building a successful side business, mindset. Not strategy. Not tools. Not AI. But the thoughts, beliefs, and inner dialogue that quietly determine whether you keep going or give up. Jenny opens up about her own mindset journey, from believing she was “just average” an...

Send us Fan Mail Why storytelling is the most powerful marketing tool for women over 40 In this episode of The Bold Biz Podcast, Jenny talks about storytelling and why sharing your real story is one of the most powerful ways to connect, build trust, and grow a business in midlife. She opens up about the fears that held her back for years, feeling “too old,” worrying her life was boring, protecting...

Send us Fan Mail The story behind my book and why your creative journey matters In this episode of The Bold Biz Podcast, Jenny takes you behind the scenes of one of the most meaningful chapters in her life, the journey of writing and self publishing her book Mitan & Moni . She shares the real, honest story of how a family tale from the late 60's turned into a book that would shape her con...

Send us Fan Mail In this episode of The Bold Biz Podcast, Jenny gets honest about the reality of today’s world and why women over 40 need their own source of income more than ever before . Job security is no longer guaranteed, retirement savings feel uncertain, and the rise of AI is changing the workplace faster than we expected. But instead of letting fear take over, this episode shows you the em...