The Aspiring Solopreneur

If the holidays feel like a chaotic mash-up of family gatherings, last-minute tasks, and pressure to magically “figure out next year,” this episode is your breath of fresh air. Carly and Joe break down why December is actually the perfect time to prep your business, without overhauling your life, and how reconnecting with your why can completely change the way you enter 2026. They’ll walk you through mini-detox habits that clear mental clutter, lifestyle-first planning that puts joy back on the calendar, and small routines you can start now to build real momentum before January even arrives.FAQs From The EpisodeHow early should I start planning for the new year?Earlier than you think, but not in an overwhelming way. December is a great month to ease into planning by reconnecting with your personal and professional “why,” cleaning up digital clutter, and building tiny habits you want to bring into 2026. You don’t need a full-year plan, focus on your first 90 days, because it’s specific enough to take action but flexible enough to pivot as things change.What should I prioritize during a December “business detox”?Stick to high-impact clean-ups that reduce mental load: unsubscribe from emails you never read, unfollow accounts that drain your energy, organize your workspace, clear your desktop, and gather scattered to-dos into one place. These small resets set the stage for clearer thinking and a calmer January, without requiring hours of work.How do I build new habits for 2026 without burning out before the year even starts?Start practicing them now in micro-form. If you want to wake up earlier, try doing it one or two days a week in December. If you want to spend 10 minutes engaging on LinkedIn every morning, start this week. If you want to guard your deep-work hours, experiment with checking email later in the day. You’re not aiming for perfection, just building familiarity so January doesn’t feel like a hard reset. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

In this episode, Will Simpson gets honest about the moment he realized he didn’t want a boss. He breaks down the identity crisis that hit after leaving decades of COO/CTO life, the surprising advantage founders over 40 actually have, why solopreneurs must unlearn corporate thinking, and how embracing “good enough” is the key to launching anything. If you’ve ever wondered whether you’re too late, too structured, too corporate, or too unsure to build something of your own…this conversation is the permission slip you’ve been waiting for.FAQs From The EpisodeWhat makes this episode valuable for solopreneurs who come from the corporate world?Will explains exactly why corporate experience does translate, just not in the ways you think. He talks through the mindset traps, the “ambient stress” you leave behind, and how to rewire yourself for small-ball thinking, fast execution, and building something that actually energizes you.Does Will think it’s harder to become a founder after 40?Not at all, he argues the opposite. According to Will, founders over 40 bring unmatched domain expertise, resilience, and clarity. The data supports it, and he shares why experience gives mid-career professionals an overlooked edge that younger founders simply can’t replicate.What’s Will’s top advice for solopreneurs who want to use AI or no-code tools?He stresses that AI can help you build prototypes fast, but not without structure, constraints, and actual expertise guiding it. He breaks down why you can’t “speak” a fully functional app into existence, how to think like a builder instead of a coder, and why you should ship an MVP that’s slightly embarrassing. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

If you’re ready to create a business that supports your life instead of running it, this is the episode you need.Carly and Joe dive into Step Zero of the Solopreneur Success Cycle: Defining Your Goals, and spoiler alert: it’s way deeper than “make money” or “gain freedom.”You’ll learn how to uncover your true why, build goals that actually guide your decisions, and avoid creating a business you secretly resent. From toddler-style questioning to "change charts" and accountability hacks, this episode is your blueprint for building a business you actually like.Whether you're dreaming, pivoting, or feeling stuck, press play before you plan another move. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

Okay friends, buckle up, because today’s episode is one of those “wait… why has no one explained success like THIS before?” moments. We’re talking with Kyle Austin Young who breaks down success not as a magical personality trait, but as something you can literally math your way into.Kyle takes us into the world of probability hacking, a shockingly simple way to figure out your real chances of success in anything (launching a business, writing a book, running a marathon) and then shows you how to change those odds in your favor.If you’ve ever wondered why some goals finally click, and others fall apart even when you want them just as much…this conversation is going to change how you think forever.FAQs from the EpisodeWhat exactly is probability hacking, and do I need to be good at math to use it?Nope! Probability hacking is simply listing out everything that has to go right for your goal to succeed…then calculating your actual chances instead of relying on vibes and wishful thinking. Kyle walks through it using basic numbers you can do on your phone, no spreadsheets, and no formulas that look like they escaped from NASA.How does this help me as a solopreneur?Because solopreneurs love goals…but often underestimate how many things have to align to actually hit them. Kyle’s framework helps you see where your plan is fragile, what’s likely to derail it, and, most importantly, how to systematically remove risk so your odds of success jump dramatically. How do I know whether to keep pushing or quit a goal?Kyle doesn’t believe in quitting, he believes in pausing strategically. If your odds still look terrible even after removing risk, he suggests exploring alternate paths that may get you to your real underlying goal more efficiently. It’s not giving up; it’s probability-based pivoting. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

You know that electric rush when you finally build the business you’ve been dreaming about? And then, right as you’re about to tell people… you freeze?In this episode, Carly and Joe dive into one of the least discussed but most universal solopreneur struggles: the fear of actually putting yourself out there. Why do so many solopreneurs, yes, even the wildly successful ones, get stuck right at the moment visibility matters most?From perfectionism to vulnerability to the dread of “seeming salesy,” we break down why this happens, the hidden costs of staying quiet, and the powerful mindset shifts that help you move forward with confidence (including why “I’m not selling-I’m helping” changes everything).If you’ve ever hesitated to hit publish, announce your business, or send that first promo email, this conversation is going to feel like a giant exhale. You’re not alone, and after this episode, you won’t stay stuck.FAQs From The EpisodeHow do I promote my business without feeling salesy or annoying?Absolutely, this comes up constantly. The key is reframing. Promotion isn’t about pushing; it’s about helping. Share stories, tips, and solutions that genuinely support your audience. If your intent is to serve, people won’t experience your message as “salesy," they’ll experience it as valuable. And the people who aren’t your ideal clients? They’ll self-select out. That’s a good thing.What if my work isn’t perfect yet? Should I wait until it’s ready?Short answer: No. Long answer: still no. Perfectionism is fear wearing a fancy outfit. Your audience can’t benefit from what they can’t see. Put the version out that is good enough to help someone right now. Then improve it based on real feedback instead of imagined critique. Visibility creates clarity.How do I get comfortable being visible if it feels so vulnerable?Start in your comfort zone and expand outward. If video feels like jumping off a cliff, start with written posts. If posting publicly feels overwhelming, start by sharing with a small circle. Momentum comes from micro-bravery. And remember: every solopreneur you admire felt this same discomfort. It’s not a sign you’re doing it wrong; it’s a sign you’re doing it. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

If you’ve been getting hammered with “AI income hacks” on Instagram and TikTok, you are not alone. Carly has been targeted so aggressively that she’s starting to suspect her phone can hear her thoughts, so today, she and Joe sit down with Becky Beach, a solopreneur who actually does this stuff successfully. From AI-powered funnels to Instagram chatbots to wildly profitable printable products, Becky breaks down exactly how she built a decade-long business that lets her make real money while still having time for her family. She shares the mistakes she made early, the systems she relies on now, and what solopreneurs need to know before diving into digital products or automations. If you’ve ever wondered, “Can this AI-funnel thing actually work?”...this episode is your answer.FAQs From The EpisodeCan I actually start with zero list and zero social media following?Yes, but not overnight. Becky makes it clear this is not a get-rich-quick play. She recommends picking a niche you genuinely care about, creating small pieces of free value, and using those to build your list through lead magnets. Social media helps, but email is what converts.Do I need design skills to sell printables or digital products?Nope. Becky happens to be a trained designer, but plenty of sellers rely on Canva, templates, or affiliate programs to get started. You can promote other creators’ printables while you learn, then create your own later.Are AI funnels and chatbots too saturated now to work?Not if you bring something unique. Becky explains that even though AI is everywhere, most people execute poorly. Your edge is: – niching down – making user-friendly products – offering consistent free content – using your story and personality as your differentiator AI tools help automate and scale, but they only work if your foundation is solid. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

If you've ever wondered how Joe somehow whips up a custom GPT for literally everything, from content creation to arguing with him when ChatGPT gets too agreeable, this is the episode you’ve been waiting for. Carly finally asks the question the whole community’s been thinking: “How is Joe doing that?” And this time, he actually shows us.Step-by-step.On-screen.In real time.Whether you want a GPT that writes in your brand voice, handles your workflows, or just keeps you honest (looking at you, You’re Wrong GPT), Joe breaks down exactly how he builds them: what’s easy, what you need to prepare, and what most solopreneurs totally overlook.If you’ve ever said, “I wish a GPT could do this for me…” Good news: after this episode, it can.FAQs From The EpisodeDo I actually need a paid ChatGPT plan to create my own GPTs?Yes. As Joe explains, GPT creation isn’t available on the free plan. You’ll need the $20/month subscription to access the “Create” option. The good news? If you use even a handful of AI-powered tasks in your business, you’ll easily make that cost back in saved time.What kind of “training material” do I need to upload to build a useful GPT?Think brand voice guides, examples of past content, frameworks you use, instructions you follow, or any assets that show how you want your GPT to think and write. More clarity = better output. You don’t need a huge pack of documents, just a few strong examples go a long way.How do I know what kind of GPT I should create for my business?Start with the tasks you repeat constantly or the ones that drain the most time: content creation, email drafts, lead gen messages, customer onboarding, proposals, social captions, etc. If you’ve ever said, “I wish someone could just do this for me,” that’s the perfect candidate for a custom GPT. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

What happens when the Wild West days of early internet marketing collide with the deeply human side of AI? In this episode, Steven Sakach from aiCMO joins Carly to talk about blending empathy with innovation (yes, even in a world that often feels robotic and copy-and-paste). From his outrageous early-career bidding wars to his BLISS framework (Build Love Into Scalable Systems), Steven shows solopreneurs how AI can actually make your business more human, not less.If you want to use AI without losing your voice, deepen emotional connection with your clients, and build systems infused with purpose (and love), this is your episode.FAQs From The EpisodeHow do I keep my marketing from sounding generic when using AI?The key is anchoring your AI-generated content in your purpose, values, and voice. Stephen’s platform (and the approach he recommends) starts with defining your higher purpose — what you actually care about, who you serve, and why you do what you do. When AI has that context, plus your differentiators and brand voice, it stops producing “same-same” results and starts sounding unmistakably like you.How do I use AI without losing authenticity or connection with my audience?You deepen authenticity before you generate content. Ask AI to help you understand your customers’ emotional journey — what fears they have, what delights them, what frustrations they experience. Once you understand the emotional landscape, AI can help you create “surprise and delight” moments, strengthen connection, and design experiences that feel personal and human. Authenticity comes from clarity, not from avoiding AI.What systems should I build first if I want to grow but stay true to my values?Stephen suggests starting with BLISS: Build Love Into Scalable Systems. That means creating processes that aren’t just efficient, but kind — onboarding steps that lower anxiety, feedback loops that keep you aligned with client needs, and systems that consider impact on people and planet, not just profit. When you systemize kindness and empathy, your values show up consistently, not just when you remember. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

AI isn’t coming for your solopreneur job, but it will happily take your tasks. In this episode, Carly and Joe break down how to turn AI into the world’s most over-eager intern: fast, enthusiastic, occasionally clueless, and totally coachable. From using AI without losing your voice…to avoiding “hallucination traps”… to building a GPT that actually remembers what you told it, this episode shows solopreneurs exactly how to manage AI, not get managed by it.FAQs From The Episode:How do I actually ‘train’ AI for my business?”Treat it like onboarding a new team member. Upload or paste your brand guidelines, audience description, business plan, examples of your writing, and list of do’s/don’ts into a custom GPT. Then, add instructions that reinforce your tone, values, target audience, and preferred outputs. Revisit the training regularly, because AI can “forget” if everything stays in one long chat thread.What tasks should I delegate to AI, and which ones should stay 100% mine?Delegate:Drafting (blogs, emails, social posts)Research summariesBrainstorming ideasRewriting in different tonesOrganizing messy textNever delegate:Strategic thinkingTopic selectionOpinions or point of viewFinal editsAny part of your brand voice that requires nuanceAI can assemble the pieces, but you must decide what the puzzle looks like.How do I keep AI from drifting, forgetting instructions, or making weird mistakes?Use a custom GPT (not just one long chat). Put your recurring instructions directly into the system prompt so they don’t fall out of the context window. Reinforce boundaries often (“never use profanity,” “don’t use dashes,” etc.), provide examples, and correct mistakes as they happen. Think of it as ongoing performance management. The more feedback and clarity you give, the better it performs. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free

In this episode, Luke Hessler gets radically real about losing everything and rebuilding faster using the only assets no one can take: mindset, skills, and relationships. We dig into personal branding for any personality (yes, introverts), the “one post a day for a year” muscle, turning your warm network into real leads (today), and scaling without employees by fixing fulfillment first and systemizing customer acquisition. It’s gritty, generous, and wildly practical.FAQs From The EpisodeI’m introverted. Can I really build a personal brand without being on camera all day? Yes. A personal brand is just your authentic offline reputation, online. If video drains you, lead with thoughtful written posts, frameworks, and slow-paced explanations. The people who think like you will prefer it. Pick one platform, post once daily for a year, and use simple content buckets (e.g., Expertise, Process, Personal). Watch engagement to see what lands, then iterate.I need leads fast on a tiny budget. What should I do this week? Start with your warm network. Make a handwritten (or spreadsheet) list of every relevant contact and call them. Offer a small “beta” program to a few ideal clients for free in exchange for a testimonial, a case study, and 1–2 introductions. Measure it like math: if 1 in 10 says “yes,” and you need 5 clients, make 50 quality outreaches. Don’t overcomplicate. Sort for the “ready now,” not convince the “not now.”How do I scale without hiring employees and avoid burning out? Fix fulfillment first. Ensure partners/vendors can handle increased volume so new sales don’t create churn. Then systemize customer acquisition (choose one core motion: landing page + traffic, affiliates, or cold outbound that sets appointments). Expect a short initial sprint (the jet uses 80% of fuel on takeoff), then automate/outsourcing what worked: repurpose posts, templatize outreach, use software or reliable vendors. Choose a sustainable cadence over heroics. 🌟 Featured Resource: LifeStarr Intro for SolopreneursAre you building a business on your own and feeling like you’re going it alone? That stops today. LifeStarr Intro is a free, forever membership built especially for solopreneurs who want real support, real resources, and real community.When you join LifeStarr Intro, you unlock:A vibrant community of like-minded solopreneurs for feedback, encouragement, and connectionThe LifeStarr productivity app (coming soon), built to support your workflow using GTD principles (that’s Tasks, Projects, Inbox that works)Live problem-solving meetups, expert sessions and strategies...and you don’t pay a thingTotal value: $65/month. Your cost? Zero.👉 Ready to stop struggling solo and build a business that works for you? Join LifeStarr Intro for Free