The Aspiring Solopreneur

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...

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...

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...

Setting boundaries is one thing. Setting them without feeling like a jerk is another. In this follow-up to their popular boundary-setting episode, Carly and Joe tackle the discomfort head-on and reframe boundaries not as confrontation, but as filters that let the right work through and keep the chaos out.

They dig into the boundaries you already have but never formalized, why being available around the clock actually makes you look less valuable, and how to handle the big three: response times, working hours, and scope creep. Joe shares a war story about working until 2 a.m. for...

Ashley Stahl, career strategist, founder of Wise Whisper Agency, and speaker of one of the most-watched TED Talks of all time, joins the show to break down exactly how solopreneurs can build a powerful personal brand through speaking, without burning out or constantly performing online.

In this episode, Ashley shares why "do what you love" is the wrong advice, how to identify your core values as a career filter, and why most people confuse credibility with authority (and which one actually gets you clients).

What you'll learn:

Ever open your inbox on a Monday morning, spend two hours responding to everything, and realize you haven't actually moved your business forward? You're not alone.

In this episode, Carly and Joe break down the crucial difference between communication and commitments, and why confusing the two is quietly killing your productivity as a solopreneur.

You'll learn the simple three-part structure (What + Who + When) that turns vague promises buried in email threads into trackable, actionable commitments. Joe shares his own journey from losing entire mornings to his inbox to building a paper-based system inspired by David...

Think forming an LLC protects your business name? Think again.

In this episode of The Aspiring Solopreneur, trademark attorney Joey Vitale, founder of Indie Law, breaks down why trademarks are the number one legal risk facing every small business and why most solopreneurs don't realize it until it's too late.

Joey shares real stories of entrepreneurs blindsided by cease and desist letters (including one who had to rebrand her podcast in 14 days while on vacation in Hawaii), explains the critical difference between LLC protection and trademark protection, and walks through exactly what you need to...

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...

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...

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 bl...

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...

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...

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...

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:

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...

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 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...

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...

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 i...

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...

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 rea...

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:

If you've ever felt like you're doing all the things in your business but still not landing consistent clients, this episode is for you.

Carly sits down with business strategist and marketing expert Jaime Ellithorpe of 540 Strategies to break down her proven Steps to Stability system, a no-fluff framework that helps solopreneurs stop spinning their wheels and start building a business that actually grows.

In this episode, you'll learn:

What if scaling your solopreneur business didn’t mean hiring a team or working 80-hour weeks?

In this episode, we’re diving into creative, cost-effective ways to grow, without giving up the freedom that made you go solo in the first place.

From automating tasks and outsourcing smartly to using AI to customize your messaging and repurposing content like a pro, we’re sharing real strategies that actually work. Whether you're a one-person powerhouse or just getting started, this episode is your blueprint for doing more with less.

Being a solopreneur is awesome but it...

What if mindset isn’t “woo”… but the strategy your business is missing?

In this episode of The Aspiring Solopreneur, we sit down with mindset expert Lee Baucom to break down how the way you think is quietly shaping your success (or holding you back).

From working with high-profile clients to helping everyday entrepreneurs thrive, Lee shares practical, real-world strategies that solopreneurs can apply immediately, without adding more to their already packed to-do list.

We unpack:

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...

Can artists really make money without underpricing themselves, chasing likes, or falling for the starving artist myth?

In this episode of The Aspiring Solopreneur, we sit down with Miriam Schulman, author of the Artpreneur, to talk about what it really takes for artists and creatives to build sustainable one-person businesses. From her leap out of Wall Street after 9/11 to building a successful career as an artist and business coach, Miriam shares the mindset shifts, pricing lessons, and marketing strategies that help creatives stop thinking small and start selling for real transformation.

We get into why...

Many professionals leave corporate to start a solopreneur business because they want more freedom, more control over their time, and the chance to focus on work they actually enjoy. But a few months in, many realize something surprising: they’re busier than ever.

In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando unpack the hidden force quietly draining solopreneurs’ time and energy...admin creep. 

From constant email checking to Slack notifications, scheduling logistics, CRM updates, and endless small tasks, these seemingly minor responsibilities can quickly take over your week if you’re not car...

Most solopreneurs start their business for freedom, but many end up overwhelmed by the financial side of running a company. Taxes, retirement planning, business structure, and investment decisions can feel intimidating, which often leads to what today’s guest calls the “Paralysis Penalty.”

In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando sit down with financial strategist Mike Milligan to unpack practical financial strategies every solopreneur should understand. Mike shares how delaying financial decisions can quietly cost entrepreneurs thousands, and explains simple systems that can help solopreneurs keep more of what they earn.

You’...

Most solopreneurs think their marketing problem is their offer, pricing, or marketing channel. But often the real issue is much quieter, and far more damaging.

They’re speaking to the wrong version of their audience.

In this episode of The Aspiring Solopreneur, Carly and Joe unpack a powerful marketing framework that can instantly improve how solopreneurs communicate with potential clients: Problem Identity, Process Identity, and Product Identity.

Many solopreneurs stop their messaging at the problem stage, constantly reinforcing pain points like overwhelm, inconsistency, or burnout. While this may grab attention, it ra...

Think you need thousands of followers to make money online? Think again.

In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando sit down with creator and educator Megan Spencer, who built a thriving business helping everyday people earn online, without chasing viral fame or building massive audiences.

Megan shares how user-generated content (UGC), freelancing, and other creator economy opportunities allow solopreneurs and side-hustlers to start earning quickly, sometimes within their first week. Even better? Many of these opportunities are introvert-friendly, require no followers, and can be done quietly from home.

...

What do branding yourself, redefining freedom, and learning how to actually sell have in common? Solopreneur coach Moe Choice breaks it all down in this wildly refreshing episode. From bouncing back after burnout and bankruptcy to building 15K+ months, Moe shares the mindset shifts and practical skills that truly move the needle.

If you're tired of vague advice and ready to get real about positioning, marketing, and building a business on your terms, this one’s a must-listen.

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advi...

In this episode, Carly and Joe sit down with Bobby Klinck, Harvard Law grad and founder of Plainly Legal, to break down the legal basics every solopreneur should handle early without getting scared, overwhelmed, or spending $5,000 on day one. Bobby explains the “prevention vs cure” approach to legal protection, the fast checks that can save you from a painful rebrand, and the biggest copyright mistakes that trigger expensive demand letters.

You’ll learn what to prioritize first, what you can safely DIY, and how to avoid the most common traps (like using a brand name without a tradem...

Most solopreneurs don’t fail because they lack skill. They stall because they stay private.

In this episode, Carly shares a powerful takeaway from a women’s solopreneur retreat in Colorado Springs: the moment you say your business idea out loud is the moment it becomes real.

Because when no one knows what you're building, no one can help you build it.

You’ll learn the three essential types of community every solopreneur needs, not just for emotional support, but for growth, opportunity, and momentum.

If you’ve ever felt stuck, invisibl...

What separates solopreneurs who stay stuck from those who scale into something bigger?

In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando sit down with attorney and business strategist Brandon Williams, whose experience working with major brands like Steve Harvey Global gives him a unique perspective on what it really takes to grow a business from a single idea into a lasting legacy.

Brandon breaks down one of the biggest myths about solopreneurship: that doing it alone means building it alone. He explains why the most successful solopreneurs actively build networks, leverage...

In this episode of The Aspiring Solopreneur, Carly and Joe get real about how to future-proof your business (and yourself) for the inevitable changes ahead. From spotting shifts in your industry to using AI and automation wisely, diversifying income streams, and planning for the long haul, this episode is your blueprint for staying resilient no matter what tomorrow throws your way.

It’s not about predicting the future, it’s about being ready for it.

Episode FAQs

What does it mean to future-proof your business as a solopreneur?
Future-proofing is all about buil...

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 bes...

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...

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 FAQs

How 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...

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...