The Aspiring Solopreneur

Everyone wants the shortcut. No one wants to hear the truth.In this episode of The Aspiring Solopreneur, filmmaker and media strategist Jake Isham delivers the reality most solopreneurs desperately need: you’re not failing, you’re just underestimating the volume it takes to succeed.From why real brands need thousands of reps, to how to think about content like the gym (without burning out), this conversation reframes success as a long-term, action-driven game. If you’ve ever felt behind, discouraged, or confused by “get rich quick” advice, this episode will reset your expectations in the best possible way.Episode FAQsHow much content do solopreneurs really need to be successful?Most solopreneurs dramatically underestimate the volume required to build trust, authority, and momentum. Success usually comes from hundreds (or thousands) of reps over time, not a handful of viral posts.Do solopreneurs really need to become a media company?Not at the beginning. Early on, solopreneurs should focus on one marketing channel that works. But to build a long-term brand, becoming a media company, gradually and sustainably, creates leverage, trust, and visibility.What’s the best content strategy for solopreneurs with limited time?A sustainable strategy focuses on consistency over perfection. Start with one format you can maintain, treat content like a workout routine, improve form over time, and measure progress by actions taken, not short-term results. 🌟 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

Standing out in a crowded market isn’t about being louder; it’s about being clearer.In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando break down why competition isn’t the real problem for most solopreneurs. The real issue? Vague positioning, hidden personalities, and businesses that look like everyone else.You’ll learn how to differentiate yourself even when your industry feels oversaturated, why your personal approach is often your biggest advantage, and how clarity around who you aren’t for can actually attract better clients. The conversation also tackles the role of AI and content overload, the importance of having a clear point of view, and why transparency, storytelling, and authenticity matter more than ever.If you’re a solopreneur struggling to stand out, attract the right clients, or feel lost in a sea of competitors, this episode offers a practical checklist to help you show up differently, and more effectively.EPISODE FAQSHow can solopreneurs stand out in a crowded market?Solopreneurs stand out by clearly communicating who they are, how they work, and who they’re best suited to help. Differentiation comes from personality, process, point of view, and transparency, not from trying to compete on volume or trends.Is competition really a problem for solopreneurs?For most solopreneurs, competition isn’t the issue. The bigger challenge is unclear positioning. Even in crowded markets, there is room for solopreneurs who clearly articulate their approach, values, and working style.What role does personal brand play in solopreneur success?Personal brand is a major advantage for solopreneurs because clients work directly with the individual, not a team or agency. Showing personality, preferences, boundaries, and transparency helps attract better-fit clients and build trust faster. 🌟 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 if working harder isn’t the answer, and never was?In this episode, Carly Ries and Joe Rando sit down with Lori Rogers to explore why mindset isn’t “woo,” it’s strategy. You’ll learn how small, science-backed shifts in thinking can reduce burnout, increase clarity, and unlock the kind of growth that actually feels sustainable.Episode FAQsHow does mindset impact success for solopreneurs?Mindset directly influences decision-making, resilience, productivity, and sales performance. Research shows that optimistic thinking improves problem-solving, increases productivity, and helps solopreneurs navigate challenges with more clarity and less burnout.What’s the difference between healthy mindset work and toxic positivity?Healthy mindset work acknowledges real challenges while choosing a productive perspective. Unlike toxic positivity, it doesn’t ignore stress or hardship; it helps solopreneurs respond with calm, clarity, and intentional action rather than overwhelm.What are simple daily habits that improve mindset and business results?Small daily practices like appreciation, brief mindfulness exercises, intentional movement, and conscious acts of kindness have been shown to increase optimism, focus, and long-term performance, without requiring more hours or hustle. 🌟 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 feel like you’re doing “all the right marketing things” but still not getting clients? This episode tackles that exact frustration head-on.If your posts are getting likes but not leads…if you’re busy with content but not booking calls…or if you’re wondering whether to pivot or quit altogether, this conversation cuts through the noise. We break down why niching down matters more than you think, how vanity metrics quietly sabotage your progress, why strategy must come before tactics, and what actually moves the needle for most solopreneurs: real human connection.This is your reminder that it’s not about doing more marketing, it’s about doing the right marketing.EPISODE FAQsWhy am I marketing consistently but still not getting clients? In most cases, the issue is not effort but alignment. Common problems include targeting an audience that is too broad, unclear positioning, focusing on vanity metrics instead of real conversations, and relying on tactics without a cohesive strategy. Effective marketing requires clear audience definition, strong messaging, and activities that lead directly to trust-building and sales conversations.What matters more than social media reach or engagement for solopreneurs? For most solopreneurs, direct conversations with ideal clients are more impactful than reach, impressions, or virality. One-on-one interactions, referrals, networking, and relationship-building consistently outperform high-volume content when it comes to generating qualified leads and clients.What’s the difference between marketing strategy and marketing tactics? Strategy defines the overall direction: who the target audience is, what positioning will resonate, and what outcome the marketing should achieve. Tactics are the specific actions used to execute that strategy, such as posting on LinkedIn, running ads, attending events, or sending emails. Without strategy, tactics become scattered and ineffective. 🌟 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 feel like traditional productivity advice just…doesn’t work for your brain?In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando sit down with ADHD coach and former academic Skye Waterson for a refreshing, practical conversation about overwhelm, focus, and building a business that actually works with your brain, not against it.Skye shares her wild origin story (including being recruited by the New Zealand government to train their intelligence services), why so many entrepreneurs experience ADHD traits, and how solopreneurs can prioritize, delegate, systematize, and scale without burning out. You’ll learn a simple prioritization filter that instantly reduces overwhelm, how to build a “map of your business,” smarter ways to delegate using AI, and one surprisingly powerful mindset shift that can help you start tasks more consistently.If you’ve ever struggled with focus, felt scattered, resisted rigid systems, or wondered why your motivation seems inconsistent, this episode will feel like someone finally put words (and tools) to your experience.EPISODE FAQsHow can solopreneurs with ADHD stay focused and reduce overwhelm? Solopreneurs with ADHD (or ADHD-like traits) benefit from externalizing their thoughts instead of trying to hold everything mentally. In this episode, Skye Waterson teaches a prioritization method that starts by writing down every task (work and personal), then filtering for true urgency and importance. This approach reduces cognitive overload, supports executive functioning, and helps overwhelmed solopreneurs focus on what actually matters instead of reacting to everything.What productivity systems work best for solopreneurs who hate rigid structure? Instead of complex planners or overly strict systems, Skye recommends starting with a “map of your business," a simple visual of how clients find you, how you sell, how you deliver, and how you retain or grow relationships. This gives solopreneurs clarity and control without requiring perfection. The goal isn’t rigid structure; it’s building flexible systems that support your energy, creativity, and attention.How can solopreneurs use AI to delegate and scale without hiring a team? Skye explains that many tasks can now be delegated to AI instead of people, such as turning a voice explanation into an SOP, organizing processes, drafting documentation, or clarifying workflows. For solopreneurs who feel overwhelmed by delegation or who aren’t ready to hire, using AI as a “thinking partner” can dramatically reduce workload, improve consistency, and support sustainable growth. 🌟 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 a solopreneur wondering “Am I charging enough?” or feeling awkward about raising your prices, this episode is for you.In this episode, Carly Ries and Joe Rando tackle one of the most common questions solopreneurs ask: How should I price my services or products? They unpack why pricing isn’t about greed, it’s about fairness, value, and respecting the years of expertise you bring to the table.You’ll hear why charging based only on time keeps you stuck, how underpricing attracts the wrong clients and leads to burnout, and why shifting toward value-based pricing can protect your energy while increasing your income. They also explore how niching down makes your work more valuable, why higher prices often signal greater credibility, and how your pricing can evolve as your business grows.If you struggle with imposter syndrome around pricing, worry you’re “too expensive,” or feel unsure how to confidently quote your work, this episode will help you rethink pricing with clarity and confidence.Episode FAQsHow should a solopreneur price their services?Solopreneurs should price based on value delivered, not just time spent. Your pricing should reflect the problem you solve, the outcomes you create, and the years of expertise behind your work, not simply an hourly rate. Value-based pricing attracts better clients and supports sustainable income.Why do solopreneurs struggle with charging higher prices?Many solopreneurs undercharge because of imposter syndrome, fear of seeming greedy, or wanting to be “nice.” But underpricing often leads to burnout, difficult clients, and income ceilings. Confident pricing helps attract clients who respect your work and your time.Is niching down really necessary to raise your prices?Yes. Niching down makes your expertise clearer and more valuable. When you specialize in a specific audience or problem, clients perceive you as the go-to expert, which makes it much easier to justify higher pricing and attract better-fit opportunities. 🌟 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 a solopreneur struggling with burnout, undercharging, or wondering how to build real income without sacrificing your energy, this episode is for you.Carly Ries and Joe Rando sit down with seven-figure solopreneur and writer Amy Suto to talk about what actually drives sustainable success as a one-person business owner. Amy shares why energy management matters more than time management, how she transitioned from Hollywood screenwriting to building multiple income streams, and what finally allowed her to charge premium rates with confidence.You’ll learn how to validate a side hustle before quitting your job, how positioning and portfolio matter more than credentials, why Substack is emerging as a powerful revenue stream for creators, and how to structure your content so clients can find you through Google and AI tools like ChatGPT. This conversation is packed with practical insights on pricing, identity shifts, inbound marketing, SEO, audience-building, and long-term business thinking for solopreneurs who want income and autonomy.Episode FAQsHow can solopreneurs avoid burnout when they’re responsible for everything?Burnout often comes from mismanaging energy, not just time. Amy recommends doing regular energy audits to identify which clients, projects, and tasks energize you versus drain you. Solopreneurs who build their workload around high-energy activities tend to stay consistent longer, make better decisions, and grow more sustainably.How can a solopreneur use Substack to build both community and income?Substack is a platform for free and paid newsletters that allows solopreneurs to grow an audience and monetize their ideas without upfront costs. Amy shared that Substack works well because:You can start for free and only pay a percentage once you earnIt supports organic discovery through Substack NotesIt allows creators to test ideas, build trust, and validate what people will pay forIt can become a long-term asset, not just another content channelHer key advice: be clear on who you serve, what pain point you solve, and what content belongs free versus behind the paywall.Why do so many solopreneurs undercharge, and how can they fix it?Amy emphasized that undercharging usually stems from an identity issue, not a strategy issue. Solopreneurs often struggle to see their work as valuable because they’ve been conditioned to believe legitimacy only comes from corporations or credentials. Her advice:Adopt the identity of a professional before you “feel ready”Price for the value you deliver, not just time spentIncrease rates gradually as experience growsRecognize that your energy, expertise, and problem-solving are premium assets 🌟 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.

What if building a business that supports your life actually isn’t about hustle…but about resilience, systems, and intention?In this episode of The Aspiring Solopreneur, Carly and Joe sit down with Mike Lynch, creator, RV-lifer, automation strategist, and founder of Flywheel Factory, for a refreshingly honest conversation about what solopreneurship really looks like behind the scenes.Mike shares the truth most people won’t say out loud: it’s harder than you think, it takes longer than you expect, and the path rarely looks the way you planned. But it’s also where creativity, freedom, and momentum can finally meet.You’ll hear how Mike and his family design RV travel around work (not the other way around), how he uses AI and automation to protect his creative energy instead of replacing it, and why building a “flywheel mindset” matters more than just staying busy.This is a grounded, practical, and motivating episode for solopreneurs who want to build smarter systems, reclaim their time, and design a business that truly supports their life.Episode FAQsHow can solopreneurs use AI and automation without losing their personal voice?Solopreneurs can use tools like Custom GPTs, content workflows, and automation platforms (like Make or Zapier) to streamline their work while still sounding like themselves. The key is starting with your own ideas and experiences first, then using AI to refine, organize, and scale your content, not replace your thinking. What’s the best way for overwhelmed solopreneurs to get started with automation?The best place to start is identifying one repetitive, frustrating task in your business and breaking it into smaller steps. From there, tools like Custom GPTs or simple automations can help eliminate bottlenecks. How can solopreneurs design a business that supports their lifestyle instead of causing burnout?It starts with defining non-negotiables (family time, flexibility, travel, health) and then building systems around those priorities.  🌟 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

Before you dive headfirst into your solopreneur journey, there are two things you absolutely need to nail down: your competition and your customers.In this episode of The Aspiring Solopreneur, Joe and Carly continue the series on the Solopreneur Success Cycle and break down why “everyone” is not your audience, how to spot opportunities your competitors are overlooking, and why creating personas (yes, even giving them names and backstories) can completely change how you connect with your market. Whether you’re refining your niche or just starting to sketch out your customer base, this episode will give you practical insights to avoid spinning your wheels and start building a business that truly resonates. 🌟 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

PR isn’t just for big brands with big budgets, and this episode proves it. In this conversation, PR experts Lydia Bagarozza & Bridget Sicsko,of Visibility on Purpose, break down exactly how solopreneurs can get featured in podcasts, publications, and major media without paying thousands or hiring an agency. They walk through a simple, repeatable PR framework that focuses on positioning, pitching, and consistency, plus why most solopreneurs are closer to press than they think.You’ll also hear why authenticity beats polish, how PR compounds over time (even when social media doesn’t), and how earned media helps you show up in Google results, AI search tools, and real buying decisions. If you’ve ever thought “PR isn’t for me,” this episode will change your mind.EPISODE FAQsIs PR actually worth it for solopreneurs without big budgets?Yes. PR is one of the most cost-effective long-term strategies for solopreneurs because it relies on earned media, not paid ads. You don’t need a publicist or a massive following, just clear positioning, a strong pitch, and consistent outreach. One good feature can keep working for your business for years. What do solopreneurs need before pitching themselves to media or podcasts?Before pitching, solopreneurs should have their digital foundations in place: a professional website, clear messaging, up-to-date social profiles, and strong positioning that explains what makes them different. Media isn’t looking for perfection. They’re looking for clarity and relevance. Does PR help with SEO, AI search, or discoverability?Yes. Earned media creates high-quality backlinks, credibility signals, and keyword relevance that help your business show up in Google and AI tools like ChatGPT. PR tells search engines (and AI) that you’re a trusted source, not just another website publishing content.  🌟 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

Everyone is busy planning what they’re bringing into 2026. New goals. New strategies. New habits.But what if the real progress comes from deciding what doesn’t make the cut?In this episode, we flip the usual New Year conversation on its head and talk about the things solopreneurs should seriously consider leaving behind. From creating content just because it’s “trending,” to chasing passive income fairy tales, to saying yes to clients and projects that quietly drain your energy, we break down what’s no longer serving your business (or your life).This is a practical, honest conversation about focusing on what actually works for your audience, your strengths, and your version of success. If you want to head into 2026 with more clarity, less noise, and a business that feels sustainable instead of exhausting, this episode is your permission slip to let some things go.Episode FAQsWhat should solopreneurs stop doing in 2026 to grow faster and feel less overwhelmed?Solopreneurs should stop doing activities that don’t directly support their audience, revenue, or energy. This includes creating content without a clear strategy, chasing “passive income” shortcuts, comparing their progress to others, managing every task themselves, and saying yes to clients or projects that don’t align with their core business. Letting go of these habits creates space for focus, clarity, and sustainable growth.Is passive income actually realistic for solopreneurs, or is it mostly hype?Passive income is possible for solopreneurs, but it is rarely instant or effortless. Sustainable passive income usually comes from productizing services, creating courses, books, or digital products after significant upfront work. Solopreneurs should avoid “get rich quick” promises and instead focus on building offers that reduce one-on-one time while still delivering real value and support to customers.How do solopreneurs know what to say no to without hurting their income?Solopreneurs should say no to projects that fall outside their core expertise, disrupt their workflow, or pull them away from their ideal clients even if the opportunity seems appealing in the moment. Long-term income stability comes from focus, consistency, and repeatable offers, not from taking on one-off or misaligned work that creates stress and inefficiency. 🌟 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 the word sales makes you tense up, this episode is about to change everything.In this conversation, sales expert Adam Cerra breaks down why most solopreneurs struggle with selling, and it’s not because they’re bad at it. It’s because they’ve been taught the wrong mindset. Instead of “closing,” Adam introduces inverse closing, a way to turn sales calls into guided conversations where prospects sell themselves without pressure, manipulation, or feeling salesy.You’ll learn how to stop pricing your time and start pricing your wisdom, how to run discovery calls that feel collaborative (not awkward), and how to follow up without chasing or feeling desperate. Whether you’re booking your first calls or already selling high-ticket services, this episode gives you practical, confidence-boosting shifts you can apply immediately.Episode FAQsWhat is inverse closing, and why does it work for solopreneurs?Inverse closing is a sales approach where the solopreneur acts as an assessor rather than a closer. Instead of pitching, you guide the prospect to articulate their own needs and reasons for buying. This works especially well for solopreneurs because it removes pressure, builds trust, and aligns sales with service, making conversations feel natural and collaborative.How can solopreneurs stop feeling “salesy” on discovery calls?Solopreneurs stop sounding salesy when they shift from trying to convince someone to helping them self-evaluate. By asking thoughtful, emotionally driven questions and listening deeply, the call becomes a guided conversation instead of a pitch. This approach positions the solopreneur as a trusted authority, not a persuader.What’s the best follow-up strategy if a prospect doesn’t buy on the first call?Most prospects don’t buy on the first call, and that’s normal. A strong follow-up strategy treats the second call as a continuation—not a chase. By maintaining leadership, referencing prior conversations, and removing urgency pressure, solopreneurs can increase conversions without sounding needy or desperate. 🌟 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.Episode FAQsShould 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

Why is it so hard to explain what you do, even when you’re really good at it? In this episode, messaging strategist Damian Vallelonga breaks down why solopreneurs struggle with clarity, confidence, and consistency in their messaging, and what to do about it.We talk about why referrals aren’t a strategy, how vague language quietly kills opportunities, and the exact framework Damian uses to help solopreneurs create elevator pitches, website headlines, and LinkedIn bios that actually make sense to other humans. If you’ve ever said, “I know what I do, I just don’t know how to explain it,” this episode is for you.Episode FAQsWhy do solopreneurs struggle to clearly explain what they do?Solopreneurs struggle to explain what they do because they know too much. Years of experience, details, and expertise live in their heads, making it hard to simplify their message for someone hearing it for the first time. Clear messaging requires stepping outside your own perspective and focusing on what your audience needs to understand, not everything you know.What is the simplest framework for creating an effective elevator pitch?An effective elevator pitch has three parts:The common problem your ideal client is struggling withWhat you do to help solve that problemThe outcome or transformation they experience as a resultThis structure keeps your message focused, relatable, and easy to remember, without turning it into a list of credentials or services.How often should solopreneurs update their messaging?Solopreneurs should revisit their messaging any time their business changes in a meaningful way. This includes adding or removing services, narrowing a niche, shifting strategy, or changing who they serve. Messaging should always follow business strategy, because outdated or unclear messaging creates confusion, and confusion is one of the biggest barriers to growth. 🌟 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 years of working alongside solopreneurs, 2025 finally gave us something new: real data, real patterns, and real lessons we couldn’t ignore. In this episode, Carly and Joe step back from the nonstop AI conversation to unpack what actually moved the needle for solopreneurs this year, and what didn’t. From why “human-first” marketing is outperforming polished automation, to the growing importance of personal brand, systems, community, diversified income, and mental health, this is a practical, honest look at what it truly takes to build a sustainable solo business.If you’re heading into the next year wanting less stress, more clarity, and a business that works with your life instead of against it, this episode breaks down the biggest solopreneur lessons of 2025, and how to apply them moving forward.Episode FAQsWhat were the biggest solopreneur lessons learned in 2025?The biggest solopreneur lessons from 2025 were that human-first marketing outperforms automation, strong personal brands build more trust than “company-style” positioning, and long-term success depends on systems, community, diversified income streams, and mental health. Solopreneurs who focused on authentic connection, clear processes, and sustainable work-life balance were more resilient and experienced less stress than those chasing trends or over-relying on a single client or revenue source. Why does a human-first approach matter more than ever for solopreneurs?A human-first approach matters because audiences are increasingly skeptical of overly automated, impersonal content. In 2025, solopreneurs saw stronger engagement and trust when they showed up as real people, sharing their perspective, personality, and lived experience instead of hiding behind polished brand language. Being authentic, transparent, and emotionally relatable helps solopreneurs stand out and build meaningful relationships, especially in an AI-saturated market. How can solopreneurs reduce stress while growing their business?Solopreneurs can reduce stress by building systems and processes, diversifying income streams, avoiding over-dependence on one or two clients, and intentionally protecting mental health and work-life balance. Investing time in documentation, automation, and community support creates long-term efficiency, while multiple revenue streams and customers reduce financial risk. Treating mental health as part of the business plan helps ensure the solopreneur, and the business, remain sustainable.  🌟 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 if the reason your business feels stressful isn’t more work, it’s how you’re handling your money?In this episode, Megan Schwan pulls back the curtain on the financial mistakes almost every solopreneur makes (especially early on) and how to fix them without becoming a numbers nerd.We’re talking pricing mistakes, scope creep, avoiding your books, fearing taxes, and why most solopreneurs are unknowingly treating themselves like underpaid employees. Megan breaks down bookkeeping systems, tax strategies, and the Profit First method in a way that actually makes sense, and helps you step fully into the CEO role.If you’ve ever said, “I’ll look at my numbers next month,” this episode is for you.Episode FAQsWhat bookkeeping systems do solopreneurs really need to stay organized?You don’t need complicated spreadsheets or expensive tools, but you do need structure. Megan recommends:A real accounting software (like Wave, QuickBooks Online, Zoho Books, or Xero)A mileage and receipt tracking system to capture deductionsA cash flow management system like Profit First to prioritize paying yourself, saving for taxes, and stabilizing cash flowThese systems help you treat your business like a business, not a side project.What’s the first step if finances feel overwhelming or intimidating?Start doing your bookkeeping consistently. Megan emphasizes scheduling regular time to work on your business, not just in it. Reviewing your reports and understanding where your money is going builds confidence, clarity, and better decision-making. Avoiding the numbers only makes problems bigger later.How can solopreneurs become more recession-proof?Two big moves:Create a budget so you have a plan for your money and can ask smarter questions when numbers don’t match expectations.Save for taxes proactively (about 8–15% of sales) so tax bills don’t derail your cash flow or peace of mind.Megan also explains how Profit First helps solopreneurs build “real profit” and spot issues before they become emergencies. 🌟 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 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