The Aspiring Solopreneur

Hosted by Joe Rando, Carly Ries

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308

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Jun 2026

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About the show

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.

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July 9, 2026Episode 31312 min

Stop Benchmarking Your Solo Business Against Someone Else's Highlight Reel

You're having a great week. Clients are happy, work is steady, you took the afternoon off. Then you open your feed and see another solopreneur bragging about their 50K month and their brand-new contractor. Suddenly your good week feels like failure.In this episode, Carly and Joe unpack the comparison trap and why solopreneurs are uniquely vulnerable to it. With no colleagues, no performance reviews, and no external benchmarks, it's easy to measure your real life against someone else's highlight reel. Spoiler: a lot of what you see online is baloney nobody can fact-check a 50K month claim.Joe shares why trading his Lexus for a Hyundai changed his happiness level by exactly zero, and why "stuff" never delivers the fulfillment it promises. Together they lay out a practical detox: audit your inputs, define your own normal, build a personal scorecard, and find a comparison community optimizing for the life you actually want.In this episode:Why comparison is a distorted measuring stick, not jealousyHow hustle culture and the "four-hour work week" flex are both trapsThe lifestyle inflation trap and spending to signal success you don't feelJoe's Lexus-to-Hyundai reality check on material thingsA step-by-step feed detox to protect your mental well-beingHow to build success metrics rooted in your life first goalsIf you've ever let someone else's chapter 10 make you feel behind in your chapter 3, this one's for you.Enjoyed the episode? Leave a five-star review, share it with a fellow solopreneur, and subscribe on your favorite platform, including YouTube. 🌟 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

July 7, 2026Episode 31227 min

The 3-Step System That Buys Back 50 Hours a Month for Solopreneurs

Most solopreneurs think delegation is something you earn after hitting a revenue milestone. Claire Giovino, co-founder and CEO of 50hrs.com, says that belief is exactly what's keeping you buried in your inbox.In this episode, Claire breaks down "attention design," the practice of building your business around your energy, not just your time. She walks us through the energy audit you can start today (no budget required), why your inbox should be one of the FIRST things you delegate (even though it's usually the last), and the eliminate → automate → delegate framework that helped her hand off 90% of her business.We also dig into the difference between being busy and being productive, "sneaky procrastination" (looking productive while avoiding the one thing that actually grows your business), themed workdays, and why Claire hasn't needed an alarm clock in years.What you'll learn:How to run a 1–2 week energy audit and match your hardest work to your energy peaksWhy "only I can answer these emails" is a myth, and why fresh eyes often do it betterThe eliminate → automate → delegate framework for buying back your timeWhat to hand off first when you're doing sales, fulfillment, admin, AND contentHow themed days (social Mondays, SOP Tuesdays, call-only Wednesdays) kill context-switchingThe 6-month goal question that beats every 10-year planConnect with Claire:50hrs.com: book a free discovery call with Claire or her co-founderplaybook.50hrs.com: free playbook for hiring and training an assistant yourselfLove the show? Leave a 5-star review, share this episode with a fellow solopreneur, and subscribe on your favorite platform, including YouTube! 🌟 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

July 2, 2026Episode 31111 min

The Counterintuitive Key to a Life-First Solopreneur Business

We obsess over income minimums (rent, bills, the baseline we need to survive) but treat the top end as infinite. In this episode, Carly and Joe challenge the "always more" mentality and make the case for setting an income ceiling in your life-first business.They dig into why more money almost always comes with strings attached, and why "enough" isn't a number, it's a measure of what each next level of income will cost you in time, health, and relationships. Carly shares a practical way to calculate what a genuinely good life actually costs (vacations, retirement, the coffee shops and live music you love...no yacht required), and Joe tells the story of turning down a million-dollar deal at his last startup because it didn't fit the focus.You'll learn:Why an income ceiling matters as much as an income floorHow to define "enough" without picking an arbitrary numberA framework for weighing new income opportunities against what they'll cost your lifeHow a ceiling unlocks the freedom to say no, take risks, and choose meaningful workThe honest caveat: a life-first business still takes hard work and sacrifice to buildThis isn't anti-money; it's anti-earning-at-the-expense-of-everything-you-value. If your business exists to support your life (not the other way around), this episode is for you.If this resonated, share it with a fellow solopreneur, subscribe on your favorite podcast platform, and leave us a five-star review; it helps other life-first soulpreneurs find the show. 🌟 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

June 30, 2026Episode 31031 min

Why Betting On Yourself Is the Safest Career Move Now

Is your corporate job really safer than going solo? Hooman Radfar, co-founder of Collective and an early investor in Uber, SpaceX, Stripe, and OpenAI, argues the opposite. After living through a brutal 2008 layoff, he realized that "safety" at a big company is often an illusion, and that betting on yourself may be the smarter long-term move.In this episode, Hooman shares why he walked away from venture investing to focus on solopreneurs, what separates thriving solo businesses from struggling ones, and why AI is quietly creating a new class of high-earning, one-person companies. He also breaks down the unglamorous back-office work (bookkeeping, taxes, entity formation) that quietly derails most solopreneurs, and how to avoid it.In this episode, you'll learn:Why "corporate safety" is often a myth, even at companies like Google and MetaThe real reason most solo businesses fail (hint: it's not the work itself)How AI is changing the math on what one person can buildWhy extreme focus beats taking on every client who comes your wayThe simple daily habit Hooman credits for long-term entrepreneurial successConnect with Hooman Radfar: LinkedIn & X/ Website: collective.comEnjoyed this episode? Leave us a five-star review, share it with a friend who's thinking about going solo, and subscribe on Apple Podcasts, Spotify, or YouTube. 🌟 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

June 25, 2026Episode 30911 min

Work-From-Home Boundaries For Solopreneurs

Working from home blurs the line between "on the clock" and "off." In this episode, Carly and Joe dig into why work-life harmony still requires firm boundaries, especially in the summer when kids are home and your laptop lives in the kitchen.They cover the hidden guilt of "casually checking emails," why your kids and family can't tell focus mode from downtime, and the practical systems that protect both your business and your personal life.What you'll learn:Why work-life harmony beats work-life balance, and why it still needs boundariesHow to set spatial boundaries with a dedicated workspace (and the trap of hiding in it)The lost ritual of "signing on" and "signing off" each dayHard start/stop times (Joe works 8 to 6, no weekends)The "fake commute" trick to mentally shift into work modeCommunication boundaries: telling your family when you truly can't be interruptedHow Carly uses "the Brick" to block phone apps from 3–9 PM during kid timeWhy rest is a performance tool, not a betrayal of productivityWhether you're building a life-first business or just trying to stop answering emails at the dinner table, this episode gives you a practical framework for protecting your time and your mental space.Enjoying the show? Leave us a five-star review; it helps other life-first solopreneurs find us. Subscribe on your favorite platform, including YouTube. 🌟 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

June 23, 2026Episode 30828 min

The Clarity Problem Killing Solopreneur Search Rankings

Most service-based solopreneurs think they have a keyword problem. According to SEO and AI search specialist Julia Bocchese, what they actually have is a clarity problem.In this episode, Julia breaks down how wedding photographers, interior designers, brand designers, and other creative business owners can get discovered through AI search platforms like ChatGPT, traditional Google SEO, and Pinterest—without burning out or paying thousands for tools.She also shares how she accidentally built her business while studying Viking history in grad school (yes, really).What you'll learn:Why "clear is kind" applies to your website, not just your relationshipsThe difference between how Google ranks individual pages vs. how AI search reads your entire siteWhy ChatGPT pulls from Reddit, reviews, and podcasts, not just your homepageThe "top third of the page" rule that changes how you should write blog posts and FAQsWhy AI search favors small, specific businesses over big competitorsHow to treat Pinterest as a search engine (not social media) and rank pins on Google tooAffordable keyword tools under $20/month (Key Search, Ubersuggest)The one visibility fix to prioritize in the next 30 daysGuest: Julia Bocchese, founder of Julie Renee Consulting, specializes in SEO and AI search optimization for service-based and creative businesses.Connect with Julia:Website: JulieReneeConsulting.comInstagram: @juliereneeconsultingLinkedIn: Julia BoccheseFavorite success quote: "Clear is kind. Unclear is unkind." — Brené BrownLoved this episode? Leave a 5-star review, subscribe on your favorite platform, and share with a fellow solopreneur. 🌟 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

June 18, 2026Episode 30713 min

The Life-First Solopreneur Manifesto

You left corporate to gain freedom, so why does your business feel like the most demanding boss you've ever had?In this episode, Joe walks Carly through the brand-new Life-First Solopreneur Manifesto: a short, no-nonsense framework built from everything they've learned working with thousands of solopreneurs across 300+ episodes.They dig into "the ownership trap": what happens when you build a business around your skills instead of the life you actually want to live. The result? A business that consumes you instead of one you own.In this episode:Why 65% of people start businesses for freedom, but 80% end up losing sleep over themThe three root causes of the ownership trap: no life-first design, no commitment system, and no plan to evolveThe "accountability gap" and why running your business out of your inbox is quietly failing youThe one question that reframes everything: What does your Tuesday look like?How to build a business that serves your life instead of the other way aroundThis isn't a motivation problem. It's a design problem, and it's fixable.We want to hear from you: Carly@LifeStarr.com or Joe@LifeStarr.com (LifeStarr with two R's)Find the full manifesto here: https://www.lifestarr.com/life-first-manifestoIf this episode struck a chord, leave us a five-star review and share it with a fellow solopreneur who needs to hear 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

June 16, 2026Episode 30640 min

How She Made $100K in Her First 90 Days as a Coach

Andrea Engstrom did $2 million in sales for someone else before she ever bet on herself. When she finally launched her own coaching program, she generated over $134,000 in her first 90 days, and today she runs consistent six-figure months while working just three days a week and homeschooling her kids.In this episode, Andrea breaks down exactly how she did it, step by step: how she filled a workshop with 500 registrations using only organic social posts, the costly mistake she made on her first launch (and the free-call pivot that saved it), and the three-day "nail your niche" closing process that more than doubled her conversion rate.She also gets honest about the mindset shift that changed everything: why systems create happiness, why "preparation is a form of procrastination," and why your highest-value activity is the only thing you should protect.What you'll learn:The "bet on yourself" moment that launched her businessHow she got 500 workshop registrations with zero paid adsWhy her one-call close became a three-call close (and doubled sales)How $25K/month in payment plans removed all sales pressureThe simple math behind $25/hour work vs. $1,000/hour workWhat to outsource first (hint: it's not in your business)"Business is a tool that enables you to live the life you desire. Business is not life."Connect with Andrea at andreaengstrom.com and register for her free workshop, 100K in 90 Days.Enjoyed this episode? Leave a five-star review, share it with a fellow solopreneur, and subscribe wherever you listen, including YouTube.Life First. Then Business. 🌟 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

June 11, 2026Episode 30516 min

Why Solopreneur Vacations Feel Impossible and How to Fix That

Think you can't take a real vacation as a solopreneur? Carly and Joe are calling it what it is: a design flaw, not a workload problem.In this episode, they break down why time off feels impossible when you work for yourself, why solopreneur PTO is really UPTO (unpaid time off), and how the ownership trap convinces you that the business leaves when you do. Then they get practical with a step-by-step pre-vacation runway that starts four to six weeks out, not four to six days.You'll learn how to set client expectations from the start of every relationship, how to decide between going fully dark and scheduling limited check-ins, and why your re-entry plan matters just as much as your prep. Plus, Joe makes the case for the hybrid "have laptop, will travel" approach, and Carly shares the buffer day trick that protects your post-vacation glow from inbox overwhelm.What you'll learn in this episode:Why your business surviving a week without you is a design question, not an effort questionThe vacation readiness audit every solopreneur should run before booking a tripHow to build vacation boundaries into your scope of work from day oneGoing dark vs. scheduled availability, and how to choose what fits youThe hybrid vacation model for extending trips without losing incomeHow to design a re-entry plan with a buffer day so you don't kill your vacation highThis week's challenge: What is the one thing that would need to be true for you to take a full week off in the next six months? If it doesn't exist in your business yet, can you build it?If this isn't the worst episode you've ever heard, leave us a five-star review. It helps us reach more solopreneurs building a life-first business.Subscribe to The Aspiring Solopreneur on your favorite podcast platform, including YouTube.Life First. Then Business.Life F 🌟 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

June 9, 2026Episode 30447 min

How Solopreneurs Get Seen Without a Team or a Budget

What would you do with 90 days, $100, and zero credibility? Personal branding expert Alejandro Sanoja says forget everything else, go on a podcast tour.In this episode, Carly and Joe sit down with Alejandro Sanoja, founder and CEO of Latinpresarios, adjunct professor at the University of Houston, TEDx speaker, and one of the top six personal branding experts to follow. Alejandro shares how he went from an introverted immigrant who fled Venezuela's economic collapse to building a brand around authentic communication, and why podcasting is the single highest-leverage move a solopreneur can make right now.We dig into the storytelling framework that makes "selling" feel natural, the warmth-plus-competence formula that actually builds trust, and why introverts often outperform extroverts when they do the prep work. Alejandro also breaks down how he protects his time by "dripping" his visibility instead of burning out, and shares a real client result: 3–5 new clients and ~$30K in pipeline in 90 days from podcast appearances alone.In this episode, you'll learn:The $100 personal branding plan: podcast tour math (list, camera, AI tools) that actually fits the budgetHow to tell a story with an "inciting incident" so promotion never feels salesyThe warmth + competence formula behind real trustWhy introverts can make better salespeople, and the prep that gets them thereHow to set boundaries and run visibility as a "drip" to avoid burnoutWhy SEO content alone no longer cuts through in the age of AI overviewsThe asymmetry of value: ~2 hours of work that compounds into 30+ pieces of contentAbout our guest: Alejandro Sanoja is the founder and CEO of Latinpresarios, an adjunct professor at the University of Houston, a TEDx speaker, published author, and international speaker recognized as one of the top six personal branding experts to follow.Resource: Landing page mentioned in the episode: https://latinpresarios.com/the-aspiring-solopreneur/Find Alejandro on LinkedIn and at latinpresarios.com.Enjoyed this episode? Leave a 5-star review, share it with a friend, and subscribe on your favorite podcast platform, including YouTube.Life First. Then Business. 🌟 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