The Aspiring Solopreneur

You’ve worked hard to get your solopreneur business off the ground, but what happens when things start to stall, or worse, head in the wrong direction? In this episode of The Aspiring Solopreneur, Carly and Joe dig into the “improving” phase of the Solopreneur Success Cycle. They uncover the seven most common failure modes that can quietly sabotage your progress, from burnout and stagnation to external threats and even your own mindset. Whether your business is thriving or just surviving, these insights will help you spot trouble early, course-correct with confidence, and keep your business aligned with the life you want to live.Popular Questions and Answers From The EpisodeWhat’s the first thing solopreneurs should address when improving their business?If there’s an existential threat, that has to come first. These are big, business-ending issues—like a major competitor undercutting your prices, new technology disrupting your industry, or a business model that simply isn’t working. Before worrying about tweaks or small improvements, solopreneurs need to tackle these threats head-on to ensure survival.What are the “seven failure modes” solopreneurs should watch out for?Joe outlined seven common failure modes:Misalignment – your business no longer matches your goals or interests.Overload – you’re working too much and burning out.Money problems – not enough revenue or profit to sustain you.External risks – outside forces like platform changes or new competitors.Stagnation – growth stalls or customers start slipping away.Execution failure – not delivering quality results to clients.Psychological barriers – mindset issues like fear, procrastination, or undercharging.Recognizing which one you’re facing is the first step toward fixing it.How do solopreneurs know when it’s time to reimagine their business?It’s time to reimagine when your business stops serving your life. Even if it’s profitable and running smoothly, if you’ve lost enthusiasm, feel misaligned, or your personal goals have shifted, that’s a signal to step back. Sometimes improving your business isn’t about fixing broken systems—it’s about reshaping it so it supports the life you want today, not the one you wanted years ago. 🌟 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

After spending so much time laying the groundwork in the planning phase, it’s finally time to take action. In this episode, Carly and Joe step into the doing phase of the Solopreneur Success Cycle, where strategies move from paper to practice. They share how to run your business with intention, capture issues before they slip through the cracks, and decide what deserves your immediate attention versus what can wait. From simple fixes to documenting big-picture improvements, this is the phase where solopreneurs turn ideas into execution and momentum into results.Important Questions From The Episode:Why is it important to document issues instead of just fixing them right away?Because not every problem is urgent. Writing issues down helps you pause, evaluate the impact, and decide whether it needs immediate attention or can wait until you’re in the improvement phase. It also preserves the insights you have in the moment or ideas you might forget months later when you finally revisit the problem.What framework can solopreneurs use to prioritize what to work on?The Eisenhower Matrix is a powerful tool. It helps you separate tasks into four categories: urgent and important, urgent but not important, important but not urgent, and neither urgent nor important. Doing this allows solopreneurs to focus on what truly drives the business forward rather than just reacting to whatever feels pressing in the moment.How can writing things down reduce stress for solopreneurs?Carrying everything in your head creates mental clutter and even sleepless nights. By getting issues, tasks, and ideas out of your brain and into a trusted system, whether that’s a notebook, worksheet, or an app, you free up mental space. You’ll rest easier knowing nothing important will slip through the cracks. 🌟 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

Ever wonder which tools and services you actually need as a solopreneur, and which ones are just shiny distractions? In this episode of The Aspiring Solopreneur, Carly and Joe revisit one of the most debated sections of their book, Solopreneur Business For Dummies: setting up your company’s tools and services. From creating rock-solid SOPs to knowing when to outsource, to avoiding the dreaded “tool overload,” they break down how to make smarter choices that actually save you time. Plus, they share how AI can help today (and where it still falls short). If you’ve ever felt stuck between doing it all yourself, hiring help, or buying yet another app, you won’t want to miss this conversation.Three Episode TakeawaysShould I outsource tasks as a solopreneur or keep doing everything myself? You don’t need employees to be a solopreneur, but you also don’t have to do everything alone. Outsourcing to contractors or companies for specific tasks can save time and prevent burnout. The key is to outsource before you’re desperate. This way, you have time to properly train someone and set up processes that work.How do I know which tools are worth paying for? Start by identifying the specific problem you want to solve, then choose tools that are simple, affordable, and easy to integrate with your current setup. Avoid chasing “shiny objects” that solve problems you don’t even have yet. Use free trials strategically and actually test them on a real task during the trial period, and start with monthly payments until you’re confident it’s a good fit.What should come first: documenting processes or finding tools and services? Always start with documenting your processes in the form of standard operating procedures (SOPs). If you try to outsource or automate a broken process, you’ll only make the problems bigger. SOPs give you a clear, repeatable checklist that works whether you do it yourself, hand it off to someone else, or use a tool to automate 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

Think of onboarding like a marriage: you don’t stop showing up once the vows (or the sale) are made. In this episode, they unpack why onboarding is the delight phase of the buyer’s journey, how to prevent buyer’s remorse, and the small but powerful touches that turn customers into lifelong fans (and evangelists). If you’ve ever wondered how to make sure your clients feel like they “married the right business,” this one’s for you.A Few Q&As From The EpisodeWhy is onboarding such a critical step after a sale? Answer: Because the sale isn’t the finish line, it’s the starting point of the customer relationship. Onboarding reassures buyers they made the right decision, prevents buyer’s remorse, sets clear expectations, and begins building long-term trust.What are some simple ways solopreneurs can make onboarding effective?Answer: Start with a warm welcome, whether it’s a personalized email, a short video, or even a handwritten note. Follow up with clear next steps, resources, or tutorials to help customers get value quickly. The key is making clients feel seen, supported, and confident right away.How does great onboarding impact future sales and referrals?Answer: Thoughtful onboarding turns new customers into fans and fans into evangelists. When clients feel cared for and successful with your product or service, they’re far more likely to renew, upgrade, or tell their friends about you, which makes lead generation and sales much easier down the line. 🌟 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

Sales doesn’t have to feel slimy or stressful. In fact, when you treat it as service, selling becomes a natural extension of helping people. In this episode, Carly and Joe break down the planning side of sales for solopreneurs, from understanding levels of touch to qualifying leads and nailing your quick pitch. If the thought of selling makes you cringe, this conversation will help you rethink the process and build a sales plan that actually feels good.Important Questions Answered In This EpisodeHow can solopreneurs approach sales without feeling sleazy? By reframing sales as service. Instead of trying to push a product, focus on finding people who have problems you can genuinely solve. When you approach conversations with the goal of helping rather than selling, it becomes natural, authentic, and far less intimidating, even for introverts.What does “level of touch” mean in sales planning? The level of touch refers to how much interaction you have with a potential customer. High-touch sales involve more personal engagement, like coaching calls or consultations, while low-touch or no-touch sales rely on things like websites, emails, or quick transactions for lower-priced products. Solopreneurs need to match their sales process to both their offering and the time they can realistically invest.Why is qualifying leads so important? Not every prospect is worth your time. By qualifying leads, making sure they have a problem you can solve, the authority to make a decision, and the budget to buy, you avoid wasting hours chasing “tire kickers.” A simple system for filtering leads upfront saves time, energy, and frustration later on. 🌟 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

After nine years of collaborating virtually, Carly and Joe finally met face-to-face at the INBOUND conference in San Francisco. The sessions were buzzing with AI talk, but Carly and Joe zeroed in on what really matters for solopreneurs: marketing strategy that puts people first. In this episode, they unpack why human connection is more powerful than any algorithm, how trust fuels business growth, and why a solid strategy beats chasing every shiny new tactic. Whether it’s AI Engine Optimization or grassroots networking, you’ll learn how to cut through the noise and build marketing that actually works for solopreneurs.Important Takeaways From The EpisodeWhy is marketing strategy more important than tactics for solopreneurs? Because tactics change constantly. New platforms, AI tools, and algorithms come and go, but if you have a clear strategy, knowing who you serve, what your brand stands for, and how you build trust, you can adapt to any trend. Strategy is your foundation, tactics are just the tools you plug in along the way.How does AI impact solopreneur marketing? AI is creating noise in the marketplace, making it harder for people to know what’s authentic. The good news? That actually gives solopreneurs an edge. Solopreneurs have always relied on real human connection and trust to grow their businesses, and those skills are now more valuable than ever. AI can support your work by handling repetitive tasks, but it should never replace your strategy or your voice.What are the key steps to building an effective solopreneur marketing strategy? It comes down to five essentials:Build trust.Create resonance.Establish desire.Inspire action.Repeat the process.This loop ensures your marketing always stays people-centered, no matter the trends. 🌟 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 light of the INBOUND conference taking place right now, we decided to re-release the biggest takeaways from the 2024 event. While this episode was originally released last year, the information is still very relevant to solopreneurs now, so be sure to tune in! *HubSpot hosted their massive annual conference that covered the latest trends and tactics in marketing, sales, and AI…and we had two people attend who are ready to give you the biggest takeaways from the event that apply specifically to solopreneurs. Co-host of this podcast and founder of LifeStarr, Joe Rondo attended, and our very own George B. Thomas not only attended, but presented multiple times. So you have some very credible sources sharing their insights today.From groundbreaking strategies to fresh perspectives on automation, AI, and scaling small businesses, this episode is packed with golden nuggets for solopreneurs who want to stay ahead of the curve.Whether you're looking for new ways to generate leads, streamline your processes, or take your customer experience to the next level, this episode has you covered. 🌟 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

Now that we're halfway through the Solopreneur Success Cycles series we're doing leading up to the launch of our book, Solopreneur Business For Dummies, we wanted to re-release the first episode in the series that gives an overview of what it is, so that new listeners can be brought up to speed. It also serves as a good refresher for those who are following along!Ever feel like you're building your solo business one guess at a time?In this episode, Carly and Joe pull back the curtain on the Solopreneur Success Cycle, the foundational framework behind their new book Solopreneur Business for Dummies. From defining your goals (hello, Step Zero!) to tweaking, refining, and reimagining your business as it grows, they break down the entire cycle designed specifically for one-person businesses.It's not a lecture, it’s a roadmap with a healthy side of real talk, laughs, and lessons you can apply right away. Whether you buy the book or not (but, like, you should), this series is your shortcut to building a business that actually works for you. 🌟 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

Your brand is so much more than a logo and some colors—it’s your personality, your values, and the story you tell the world. In this episode of The Aspiring Solopreneur, Carly and Joe dive into what it really means to build a brand as a one-person business. From defining who you are (and who you aren’t) to crafting messaging that resonates, they’ll show you how storytelling becomes the foundation for every marketing move you make. If you’ve ever wondered how to stand out authentically without feeling “salesy,” this one’s for you. 🌟 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

Most solopreneurs make the mistake of trying to serve everyone and end up standing out to no one. In this short and punchy episode of The Aspiring Solopreneur, Carly and Joe dive into one of the most overlooked steps in building a successful solo business: positioning. They break down why niching down isn’t limiting, but rather the key to charging more, marketing smarter, and actually getting noticed. If you’ve ever said, “My product is for anybody,” this episode will make you rethink everything.