The Aspiring Solopreneur

Joe Rando, Carly Ries
  • 5.0 (51)
  • ENTREPRENEURSHIP
  • UPDATED SEMIWEEKLY

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. 5D AGO

    Why Saying Yes Is Costing You the Solo Life You Designed

    This episode tackles one of the biggest struggles solopreneurs face: the guilt that comes with saying no. Carly and Joe dig into why so many solopreneurs feel overwhelmed, not because they lack time, but because they keep saying yes to things that don't serve the life they've designed. They introduce a simple but powerful filter for every opportunity that comes your way: Does this serve the life I designed? Not "is this a good opportunity?" or "can I handle this?" They walk through three common scenarios where solopreneurs are tempted to say yes when they shouldn't: the exciting exposure opportunity that eats your time and energy, the high-paying client who drains you with every interaction, and the favor for a friend or peer that chips away at your boundaries. Joe shares a real example of turning down a speaking invitation in Boston, and offers a practical alternative for difficult client situations, adjusting the relationship until the client self-selects out. Carly shares a communication tactic she's learned for declining without inviting negotiation: simply say "I can't right now" and stop there. The episode wraps with a weekly challenge: the next time something lands on your desk that you'd normally say yes to out of habit, pause and run it through the filter first. 🌟 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

    17 min

  2. MAY 19

    How to Build a Solo Business Without Losing Your Peace in the Process

    Alyssa Rogers is a certified life coach, burnout coach, military wife, and mom who is building her coaching business while still working a 9-to-5. After losing her childhood nanny at just 72, Alyssa realized that waiting until retirement to start living wasn't an option. She decided to create her own path toward freedom and fulfillment rather than settling for the "one day" mindset that keeps so many people stuck. In this episode, Alyssa shares how she accidentally discovered her calling as a burnout coach when her employer required her to get certified as a life coach. She breaks down the three types of burnout (career/financial, relationship, and personal), explains why comparison culture is destroying aspiring entrepreneurs, and reveals what she tells clients to do this week when they're overwhelmed. Alyssa also opens up about the online programs that overpromised and underdelivered, which ultimately pushed her to co-create her own digital marketing program with a built-in AI module that personalizes the experience based on who you actually are, not a cookie-cutter template. In this episode, you'll learn: The three types of burnout and how to identify which one is affecting youWhy your "why" matters more than the business model you chooseHow to do a personal and business audit when you're feeling stuckWhat most online business programs get wrong about mentorship and communityHow to use AI tools authentically without losing your voiceWhy building around your values instead of trending skills leads to sustainable successThe first steps to take when burnout hits before your business even gets off the groundConnect with Alyssa Rogers: TikTok: @freedombeyondburnout Resources mentioned: Henry Ford quote: "Whether you think you can or you cannot, you're right."Cody Johnson's song "Human."Connect with us: Subscribe on your favorite podcast platform and YouTube. Leave a five-star review to help us reach more solopreneurs building a life-first business. 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

    35 min

  3. MAY 14

    Ditch the 9-to-5 Mindset: How Solopreneurs Should Really Structure Their Day

    You left your 9-to-5 for freedom, so why does your calendar still run your life? In this episode of The Aspiring Solopreneur, Carly and Joe tackle a habit most solopreneurs don't even realize they have: building their business around the clock instead of around themselves. If you've ever filled an open time slot with whatever felt urgent (hello, inbox), this one's for you. Carly introduces a simple 3-step energy audit framework you can start using today: Step 1 – Identify Your High-Energy Windows Track your energy (not your schedule) for one full week. Rate each block of time as sharp, steady, or dragging. Don't judge it, just observe. You'll likely discover two to three genuine peak windows per day, and they may be shorter than you think. Step 2 – Match Peak Energy to High-Value Work Once you know your windows, protect them for the work that actually moves your business forward — strategy, revenue-generating tasks, relationship building. Stop spending your best hours on email, Slack, and admin. Step 3 – Structure Your Operations Around Your Rhythms Move recurring meetings, client calls, and contractor check-ins outside your peak windows. Batch low-energy tasks together. Communicate your availability to clients; it's a boundary, not an inconvenience. Build a daily template and default to it. Joe adds a power tactic: use Calendly (or similar tools) to create separate meeting types with different available time slots, one for high-energy meetings, one for everything else, so your schedule enforces your energy plan automatically. Whether you're a morning person or a night owl, this episode gives you a concrete system to stop optimizing your schedule and start optimizing your output. Challenge: Start your energy audit this week. One week of honest observation can reshape how you run your entire business. Key Topics: energy management for solopreneurs, life-first business, the ownership trap, productivity without burnout, scheduling strategies, solopreneur time management, peak performance windows 🌟 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

  4. MAY 12

    Why Your 40s and 50s May Be the Best Time To Become A Solopreneur

    He was fired from 39% of his entertainment industry jobs. Then he turned serial failure into a superpower. John Tarnoff spent decades as a Hollywood studio executive and film producer, getting hired, getting fired, and reinventing himself over and over again. After surviving the dot-com crash, a string of layoffs, and an identity crisis in his 40s, John made a radical move: he went back to school at 50, landed his dream job at DreamWorks Animation, and eventually built a thriving coaching practice helping mid-career professionals take control of their careers. In this episode, John joins Carly and Joe to break down exactly how solopreneurs can apply the same reinvention framework he used, even if they're starting from scratch, feeling unconfident, or struggling with the identity shift from corporate employee to business owner. What you'll learn in this episode: → Why your 40s and 50s are actually the ideal time to take big career risks → How to turn a messy career history into a compelling narrative that attracts clients → The three pillars every solopreneur needs: superpower clarity, a personal board of directors, and thought leadership → Why "if your market is everybody, your market is nobody," and how to find your niche → How to network authentically when you hate networking → Why confidence comes last (not first) and what to rely on instead → The one daily habit John recommends before anything else, and it's not what you'd expect → Why your identity is never your job title, and how to liberate yourself from that trap Whether you're mid-career and thinking about going solo, already running a one-person business, or stuck in the messy middle of a transition, this conversation will give you permission to stop waiting and start building. Find John: LinkedIn (search John Tarnoff Career Coach) 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

    38 min

  5. MAY 7

    The Life-First Business Framework: Pricing, Clients & Freedom

    Most solopreneurs think their biggest problem is getting more clients. But what if the real issue is that you built the wrong business in the first place? In this episode of The Aspiring Solopreneur, hosts Carly Ries and Joe Rando break down the #1 pattern they see after working with thousands of solopreneurs: people chase clients without first designing a business around the life they actually want to live. The result? Burnout, frustration, and a business that feels like a job you can't quit. Carly and Joe walk through the essential questions every solopreneur should answer before asking, "How do I get my next client?": → What do I want my days to actually look like? → How much do I really need to earn to fund the life I want? → What kind of work energizes me vs. drains me? → Who do I want to work with, and who are my "energy vampires"? They also tackle pricing strategy head-on. Joe shares a real example of someone who charged $500 for work that saved a company $400,000, and how value-based pricing can transform your income without adding hours. The conversation covers when to raise prices, when to outsource, and why charging by the hour might be keeping you stuck. Whether you're just starting your solopreneur journey or you're deep in the hustle wondering why it doesn't feel right, this episode gives you a practical framework for building a business that supports your life, not the other way around. Key topics covered: Designing your business model around your ideal lifestyleValue-based pricing vs. hourly billingHow to determine how many clients you actually needWhen to consider outsourcing, automation, and AISetting realistic income goals as a solopreneurWhy niching down matters more than you thinkThe difference between making a living and making "too much"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

    12 min

  6. MAY 5

    Stop Avoiding Your Numbers: Financial Confidence for Solopreneurs

    Most solopreneurs got into business to chase a passion, not to crunch numbers. But avoiding your financial data is one of the fastest ways to stay stuck, underpaid, and overwhelmed. In this episode, we sit down with Andy Weins, junk removal business owner, professional speaker, and fractional CFO, who spent 17 years learning (sometimes the hard way) that the answers to your biggest business problems are hiding in data you're probably not collecting. Andy breaks down why entrepreneurship is inherently emotional and illogical, and how that wiring makes business owners uniquely bad at tracking the numbers that actually matter. He shares the story of a graphic designer charging one client the equivalent of $9/hour without realizing it, explains why your "best-selling" product might be draining your profits, and walks through how to build a KPI scorecard, even if you're a one-person operation. He also introduces his 20-20-10 framework: 20 hours working in your business, 20 hours working on it, and 10 hours investing in yourself. Plus, a dead-simple formula to calculate your real billable rate starting today. What You'll Learn in This Episode: — The difference between accounting and financial leadership (and why your CPA isn't enough) — How to calculate customer acquisition cost in three different ways — Why you should start with many KPIs and whittle down to the vital few — The 20-20-10 weekly structure for solopreneurs — A quick formula to find your minimum billable rate using 48 weeks and 20 hours — Why "spite is a hell of a drug" but success is more sustainable Resources Mentioned: — Andy's book: Stop Avoiding Your Numbers: The Guide to Financial Confidence for Small Business Owners — Atomic Habits by James Clear — The 7 Habits of Highly Effective People by Stephen Covey — Connect with Andy on LinkedIn or at AndyWeins.com 🌟 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

    33 min

  7. APR 30

    Why Your Solo Business Isn't Giving You the Life You Wanted (And How to Fix It)

    If your solopreneur business feels like it's running you instead of the other way around, you've fallen into the Ownership Trap. In this episode, Carly and Joe break down the three root causes behind why so many solopreneurs end up building a business that controls their life rather than supports it. In this episode: What the "Ownership Trap" is and why almost every solopreneur falls into itWhy this is a design problem, not a motivation problemThe 3 causes: No Design, No System, and No Plan to EvolveHow to start viewing every business decision through a "Life First" lensReal stories from Joe and Carly about the mistakes they made, and what they learnedIf you've been grinding away wondering why you left your 9-to-5 only to end up right back in the same trap, this episode is for you. Life first. Then business. Subscribe to The Aspiring Solopreneur so you never miss an episode, and if this resonated, leave us a ⭐⭐⭐⭐⭐ review. It helps more solopreneurs find the show! 🌟 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

    15 min

  8. APR 28

    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
See All (300)

Trailer

5
out of 5
51 Ratings

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
    300
  • Rating
    Clean
  • Copyright
    © 2021-2024 WorkStarr, Inc.
  • Show Website
    The Aspiring Solopreneur

You Might Also Like