The Aspiring Solopreneur

Joe Rando, Carly Ries
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You didn't become a solopreneur to build a business that runs your life. You did it so your business could serve it. The Aspiring Solopreneur is the twice-weekly podcast at the heart of the Life-First Movement. It's for solopreneurs who believe the business should be designed around life, not the other way around. Hosts Joe Rando and Carly Ries, co-authors of Solopreneur Business for Dummies, sit down each week with solopreneurs who are building Life-First Businesses and experts who are helping others do the same. Every episode explores what it really takes to design, run, and evolve a one-person business with your life at the center. Basically, what we're trying to say is: Life First. Then Business.

  1. 7H AGO

    Stop Overpaying Taxes: The Real Rules for Location-Independent Solopreneurs

    Most solopreneurs spend zero time thinking about taxes until April 14th. Bobby Casey has spent decades thinking about almost nothing else, for his own businesses and for the hundreds of location-independent entrepreneurs he's helped restructure, relocate, and legally stop overpaying. Bobby has lived in 10 countries, started and sold companies across multiple continents, and currently runs two businesses: a high-end consulting practice for entrepreneurs with complex international structures, and Business Anywhere, a platform that automates the compliance and administrative backend of running a business. In this episode, we discuss: His own origin story. A near-fatal motorcycle crash led Bobby to a solo camping trip where he worked out exactly what he wanted his life to look like. The dartboard analogy he came up with that week  (lifestyle as the bullseye, business as one of the rings) is one of the clearest articulations of the Life-First Business philosophy we've heard from a guest. The most expensive mistake nomadic solopreneurs make. Bobby shares the story of a Canadian client who spent 10 years outside Canada without restructuring her business, and ended up paying $5 million in taxes she didn't legally owe. The fix existed from day one. She just didn't know to ask. The 183-day myth. Almost everyone in the digital nomad space believes that staying under 183 days in a country keeps you safe. Bobby has read the tax residency laws of roughly 140-150 countries. He says only one actually uses a clean 183-day rule. Every other country has its own criteria, and assuming otherwise is how people get caught. What U.S. solopreneurs can actually do. The Foreign Earned Income Exclusion (Form 2555) allows qualifying Americans abroad to shield up to $130,000 of earned income from federal taxes. Yes, even if your clients are all in the U.S. Bobby explains how it works, who qualifies, and how to maximize it with a spouse. The South Dakota move. One night's stay. A mailing address. And you can move your driver's license and your state tax residency, to a state with zero income tax. Bobby explains why this works for solopreneurs and why it doesn't work for remote employees. This is a rare episode: genuinely practical, not theoretical, from someone who has lived it in 10 countries and helped hundreds of others do the same. Connect with Bobby: Global Wealth Protection: globalwealthprotection.comBusiness Anywhere: businessanywhere.ioLife First. Then Business. 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    49 min

  2. 5D AGO

    Life First. Then Business. Here's What That Actually Means For Solopreneurs.

    In this episode, Joe Rando and Carly Ries officially draw a line in the sand. After nearly 300 episodes and hundreds of conversations with solopreneurs, they name the single insight that keeps showing up in every episode that lands differently: the Life-First Business. Joe and Carly explain why most solopreneurs unintentionally build a business that ends up owning them, why that happens by default and not by choice, and why the forces reshaping work right now make this the right moment to name it, claim it, and build a movement around it. Key Points Most solopreneurs start by asking "what can I sell?" but the better starting point is designing the life you want the business to serve.Falling into The Ownership Trap isn't a character flaw. It happens by default when you say yes to revenue before you've designed the life around it.A Life-First Business is not about working less, it's about making conscious tradeoffs so the business gives you the freedom that actually matters to you.AI is reshaping the solopreneur landscape in two directions at once: pushing people out of traditional employment and empowering them to run a real business solo.The Life-First Movement is bigger than LifeStarr. If you're helping solopreneurs build businesses that serve their lives, Joe and Carly want to hear from you.FAQs What is a Life-First Business? A Life-First Business is one designed from the start to serve the life you want, not the other way around. Instead of building around your skills and seeing what life fits around the business, you begin with Step 0: defining what you want your life to look like. The business is then designed to support that. Does Life-First mean working less or only part-time? No. A Life-First Business is not about working fewer hours or generating passive income from a beach. It's about making intentional tradeoffs, choosing the freedoms that matter most to you, and building a business that protects them, whatever that looks like for your life. Why is this conversation happening now? Two forces are converging: AI is displacing or reshaping traditional jobs, pushing more people toward solopreneurship as a real option. At the same time, AI is giving solopreneurs the capability to run a serious business without a team. That combination makes this the right moment to define what a well-designed solo business actually looks like. What is The Ownership Trap? The Ownership Trap is what happens when a solopreneur builds without a life plan (saying yes to whatever pays, running everything on memory and email, with no system and no plan to evolve). The business grows, but it starts running the person instead of the other way around. What is the Life-First Movement? The Life-First Movement is the category of people, businesses, and ideas organized around one belief: the business exists to serve the life. Joe and Carly are building this movement at LifeStarr, but they're clear it's bigger than any one company. If you're working to help solopreneurs build businesses on their own terms, they want to connect. Life First. Then Business. 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    11 min

  3. APR 21

    You Still Have to Run the Business: The Truth About AI for Solopreneurs

    Most solopreneurs think AI is the answer to their chaos. It isn't. It's an amplifier. And if what it's amplifying is a broken system, a vague product, or a business built without a life plan, AI just makes the mess louder, faster. In this episode, Carly and Joe sit down with data scientist and AI educator Ben Tasker to cut through the noise around artificial intelligence and get to what actually matters for solopreneurs. Ben has spent over a decade in data science and now leads AI upskilling programs that reach tens of thousands of people. He's seen every flavor of AI mistake, and he's refreshingly blunt about which ones are most expensive. The conversation covers why chasing AI tools is the wrong strategy (and what to do instead), which skills will remain valuable as tools keep changing, how to use AI in a way that amplifies your voice rather than flattening it, the ethical gray areas solopreneurs are stumbling into without realizing it, and why agentic AI is exciting and dangerous in equal measure. The bottom line Ben keeps coming back to: AI cannot fix a bad business. You still need a proven system. You still need a real product. You still need to be the one at the helm. Guest: Ben Tasker | bentaskerai.com | LinkedIn Key Points AI cannot fix a bad system or a bad product. It amplifies what already exists, including what isn't working.The right question isn't "which AI tool should I use?" It's "which skills do I need to build so I stay relevant as tools keep changing?"The most durable AI skills for solopreneurs are prompt engineering, systems thinking, and responsible evaluation of AI outputs.Using AI to amplify your voice is smart. Using it to replace your voice is a liability, legally and relationally.Human in the loop is not optional. Draft, don't send. Suggest, don't decide. Assist, don't replace.Episode FAQs What's the biggest AI mistake solopreneurs make? Believing AI will fix a broken business. AI is an amplifier. If your system is unclear, your offer is vague, or you haven't closed deals yet, AI won't change that. It takes what you give it and makes more of it. The work of building a real business still belongs to you. Which AI skills should solopreneurs focus on right now? Ben identifies four: prompt engineering (how to get useful outputs), systems thinking (where AI fits in your workflows), responsible evaluation (knowing when the output is wrong or problematic), and creativity (how to use AI in ways that are genuinely useful, not just technically possible). How do solopreneurs use AI without sounding generic? Train the AI on your voice, your product, and your specific context. If you treat it as a generic input-output machine, you'll get generic output. Give it your style, your examples, and your constraints. Then review and edit everything before it touches a client. Is it ethical to use AI without disclosing it? It's a gray area that depends on how much human input shaped the final product. Ben's rule of thumb: human in the loop, with genuine editing and revision, makes disclosure less critical. Fully automated output with no human shaping is a different story. When in doubt, mention it briefly. It doesn't need to be a disclaimer, just a passing acknowledgment. What should solopreneurs know about agentic AI? AI agents are more powerful than a simple chat prompt, but they require more setup and more guardrails. If an agent has access to your data, your clients, or your communications, it needs human review at the end of every action. The use cases that work well are ones where the agent drafts or prioritizes, and a human approves before anything goes out. 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    30 min
  4. [Re-Release] The Psychology Behind Pricing For Solopreneurs That Actually Converts

    APR 16

    [Re-Release] The Psychology Behind Pricing For Solopreneurs That Actually Converts

    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 FAQs How 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 Solopreneurs Are 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

    14 min

  5. APR 14

    The Pricing Strategy That Doubled This Solopreneur's Income in Year One

    Are you stuck in the hourly billing trap, racing against the clock while your clients pressure you to go faster, cheaper, and more?  In this episode, Jonathan Stark, the "Ditching Hourly" guy, joins Carly and Joe to break down exactly how solopreneurs can escape time-for-money pricing and switch to a value-based model that benefits both you and your clients. Jonathan shares the surprising moment he realized hourly billing was the root cause of nearly every frustration in his business, from scope creep to client tension to capped income. After making the switch, he doubled his income in year one and watched his client relationships transform almost overnight. This isn't abstract theory. Jonathan walks through his exact process for determining what your work is worth to a client, including his "why conversation" framework, a series of strategic questions that uncover urgency, business value, and what a home run looks like before you ever quote a price.  He also explains how to structure a three-option proposal, why he defines scope last (not first), and how to handle scope creep without awkward confrontations. You'll also hear Jonathan's take on retainer pricing, why he doesn't send "rates are going up" letters, when hourly billing might still make sense for newer solopreneurs, and why he keeps contracts minimal even though any lawyer would call him crazy for it. In this episode, you'll learn: Why hourly billing creates a self-fulfilling cycle of scope creep and client tensionThe "why conversation" framework: three categories of questions that reveal what your work is actually worthHow to build a three-option value-based proposal that practically sells itselfWhy Jonathan prices first and defines scope last, and how that changes everythingHow to handle scope creep requests without damaging the client relationshipThe difference between project-based value pricing and retainer-based advisory pricingWhen hourly billing might still be appropriate (and when it's a trap)Why getting paid upfront changes the entire dynamic of client workHow to raise your prices over time without losing existing clientsResources mentioned: Jonathan Stark's free email course: valuepricingbootcamp.comJonathan's website: jonathanstark.comDitching Hourly podcastIf you found this episode helpful, share it with a solopreneur friend who's struggling with pricing. And don't forget to leave a five-star review and subscribe on your favorite podcast platform, including YouTube. 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    41 min

  6. APR 9

    How to Get Leads Without Social Media (For Solopreneurs Who Hate Posting)

    You've been told you need to become a full-time content creator to grow your business. Post every day. Fight the algorithm. Do the newest TikTok dance. But what if you hate social media, and still need leads? In this episode, Carly and Joe break down practical lead generation strategies for solopreneurs who don't want to build an audience on social media. From leveraging your existing network to borrowing other people's audiences to building a referral system that actually works, these are relationship-first approaches that replace the pressure to go viral with something that feels a lot more real. Whether you're leaving corporate and dreading the "you need to be on social media" advice, or you've been solo for a while and want alternatives to the content hamster wheel, this episode is for you. Key topics covered: Why solopreneurs don't need a massive social media following to generate leadsHow to use social media for relationship-building without posting or broadcastingUsing LinkedIn for direct outreach and genuine connection (not selling)Tapping your existing network (past coworkers, vendors, clients, friends, and family) as your first lead generation pipelineThe simple outreach message that lets people know what you do without being pushyBorrowing audiences through podcast guesting, webinars, guest articles, and PRHow to build a referral system instead of hoping word-of-mouth happens on its ownBook recommendation: The Referral Engine by John JantschMemorable Takeaway Relationships, reputation, referrals...everything you do should go back to human connection and trust. Resources & Links Mentioned The Referral Engine by John JantschLifeStarr Community Alex Hormozi's YouTube channel 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    13 min

  7. APR 7

    Your Phone Is Sabotaging Your Solopreneur Success (Here's the Fix)

    Are you grinding 18-hour days and still feeling like you're falling behind? The problem might not be your work ethic, it might be the device in your pocket. In this episode, Carly sits down with Justin Hai, author of Stress Nation and co-founder of Rebalance Health, to talk about the hidden way technology is hijacking your cortisol, wrecking your sleep, and making you a less effective business owner. Here's what you'll learn: → How notifications trick your body into a constant fight-or-flight state → Why multitasking might actually be slowing you down → The real reason willpower isn't enough to break your screen addiction → Simple sleep hygiene habits that can make you 10x more effective → How to set boundaries with clients without sacrificing customer service → Why isolation and loneliness are a hidden risk for solopreneurs, and what to do about it → Small changes you can make today to protect your sleep and lower stress Whether you're a solopreneur burning the candle at both ends or just someone who can't stop checking texts at 11 PM, this episode is your wake-up call. Episode FAQs Q: How does technology affect cortisol and sleep for solopreneurs? A: Every notification, buzz, and vibration from your phone triggers your body's fight-or-flight response by signaling to your brain that you may not be safe. This keeps cortisol levels elevated throughout the day and into the evening. When cortisol stays high at bedtime, your brain can't wind down, making it difficult to fall asleep or stay asleep. Since your body produces all of its essential hormones during uninterrupted sleep, consistently disrupted rest leads to fatigue, weight gain, anxiety, and diminished decision-making, all of which directly impact how effectively you can run your business. Q: Why is multitasking bad for solopreneur productivity? A: While some people can multitask effectively, many solopreneurs are actually less productive when they split their attention across multiple devices and tasks at once. Jumping between a meeting, social media, and a second screen fragments your focus and raises cortisol, which compounds stress over time. Instead of saving hours, multitasking often leads to lower-quality work and mental exhaustion. A more effective approach is to focus on one task at a time during your peak hours and protect your sleep so you can operate at full capacity rather than grinding through the day at 50 or 70 percent. Q: How can solopreneurs set boundaries with technology without losing clients? A: Start by recognizing that being available around the clock isn't great customer service; it's training your clients to expect 24/7 access at the expense of your health. Practical steps include removing social media apps from your phone so you only access them intentionally on a desktop, turning off all notifications except phone calls, and responding to texts and messages at scheduled times rather than in real time. Establishing a consistent sleep routine (going to bed and waking up at the same time every day) and avoiding screens, exercise, and heavy meals close to bedtime also help you recharge so that when you are on the clock, you're performing at your absolute best. 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    25 min

  8. APR 2

    From Corporate Salary to Solopreneur Pricing: The Mindset Shift Nobody Teaches You

    If you've left corporate, or you're thinking about it, there's one mistake almost every new solopreneur makes: pricing like an employee instead of a business owner. In this episode, Joe and Carly break down exactly why that happens and how to fix it. You'll hear the now-legendary "hammer story" that reframes everything you thought you knew about charging for your expertise, plus a practical framework borrowed from Alex Hormozi's $100M Offers to help you build an offer so valuable, pricing it high feels natural. In this episode: Why corporate conditioning makes solopreneurs chronically underprice their servicesThe single word that should anchor every pricing decision you makeThe hammer story, and what a ship engine teaches us about the value of experienceWhy "fear of the no" protects the conversation but destroys the businessHow higher pricing can actually increase your perceived valueA simple 3-step framework from $100M Offers to build and price a compelling offerResources mentioned: $100M Offers by Alex Hormozi 🌟 Featured Resource: LifeStarr Intro for Solopreneurs Are 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

    13 min
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About

You didn't become a solopreneur to build a business that runs your life. You did it so your business could serve it. The Aspiring Solopreneur is the twice-weekly podcast at the heart of the Life-First Movement. It's for solopreneurs who believe the business should be designed around life, not the other way around. Hosts Joe Rando and Carly Ries, co-authors of Solopreneur Business for Dummies, sit down each week with solopreneurs who are building Life-First Businesses and experts who are helping others do the same. Every episode explores what it really takes to design, run, and evolve a one-person business with your life at the center. Basically, what we're trying to say is: Life First. Then Business.

Information

  • Creator
    Joe Rando, Carly Ries
  • Years Active
    2021 - 2026
  • Episodes
    293
  • Rating
    Clean
  • Copyright
    © 2021-2024 WorkStarr, Inc.
  • Show Website
    The Aspiring Solopreneur

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