What if the reason your business feels stressful isn’t more work, it’s how you’re handling your money?

In this episode, Megan Schwan pulls back the curtain on the financial mistakes almost every solopreneur makes (especially early on) and how to fix them without becoming a numbers nerd.

We’re talking pricing mistakes, scope creep, avoiding your books, fearing taxes, and why most solopreneurs are unknowingly treating themselves like underpaid employees. Megan breaks down bookkeeping systems, tax strategies, and the Profit First method in a way that actually makes sense, and helps you step fully into the CEO role.

If you’ve ever said, “I’ll look at my numbers next month,” this episode is for you.

Episode FAQs

What bookkeeping systems do solopreneurs really need to stay organized?

You don’t need complicated spreadsheets or expensive tools, but you do need structure. Megan recommends:

• A real accounting software (like Wave, QuickBooks Online, Zoho Books, or Xero)
• A mileage and receipt tracking system to capture deductions
• A cash flow management system like Profit First to prioritize paying yourself, saving for taxes, and stabilizing cash flow

These systems help you treat your business like a business, not a side project.

What’s the first step if finances feel overwhelming or intimidating?

Start doing your bookkeeping consistently. Megan emphasizes scheduling regular time to work on your business, not just in it. Reviewing your reports and understanding where your money is going builds confidence, clarity, and better decision-making. Avoiding the numbers only makes problems bigger later.

How can solopreneurs become more recession-proof?

Two big moves:

• Create a budget so you have a plan for your money and can ask smarter questions when numbers don’t match expectations.
• Save for taxes proactively (about 8–15% of sales) so tax bills don’t derail your cash flow or peace of mind.

Megan also explains how Profit First helps solopreneurs build “real profit” and spot issues before they become emergencies.

🌟 Featured Resource: LifeStarr Intro for 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

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If the holidays feel like a chaotic mash-up of family gatherings, last-minute tasks, and pressure to magically “figure out next year,” this episode is your breath of fresh air.

Carly and Joe break down why December is actually the perfect time to prep your business, without overhauling your life, and how reconnecting with your why can completely change the way you enter 2026. They’ll walk you through mini-detox habits that clear mental clutter, lifestyle-first planning that puts joy back on the calendar, and small routines you can start now to build real momentum before January even arrives.

FAQs From The Episode

How early should I start planning for the new year?

Earlier than you think, but not in an overwhelming way. December is a great month to ease into planning by reconnecting with your personal and professional “why,” cleaning up digital clutter, and building tiny habits you want to bring into 2026. You don’t need a full-year plan, focus on your first 90 days, because it’s specific enough to take action but flexible enough to pivot as things change.

What should I prioritize during a December “business detox”?

Stick to high-impact clean-ups that reduce mental load: unsubscribe from emails you never read, unfollow accounts that drain your energy, organize your workspace, clear your desktop, and gather scattered to-dos into one place. These small resets set the stage for clearer thinking and a calmer January, without requiring hours of work.

How do I build new habits for 2026 without burning out before the year even starts?

Start practicing them now in micro-form. If you want to wake up earlier, try doing it one or two days a week in December. If you want to spend 10 minutes engaging on LinkedIn every morning, start this week. If you want to guard your deep-work hours, experiment with checking email later in the day. You’re not aiming for perfection, just building familiarity so January doesn’t feel like a hard reset.

🌟 Featured Resource: LifeStarr Intro for 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

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In this episode, Will Simpson gets honest about the moment he realized he didn’t want a boss. He breaks down the identity crisis that hit after leaving decades of COO/CTO life, the surprising advantage founders over 40 actually have, why solopreneurs must unlearn corporate thinking, and how embracing “good enough” is the key to launching anything.

If you’ve ever wondered whether you’re too late, too structured, too corporate, or too unsure to build something of your own…this conversation is the permission slip you’ve been waiting for.

FAQs From The Episode

What makes this episode valuable for solopreneurs who come from the corporate world?

Will explains exactly why corporate experience does translate, just not in the ways you think. He talks through the mindset traps, the “ambient stress” you leave behind, and how to rewire yourself for small-ball thinking, fast execution, and building something that actually energizes you.

Does Will think it’s harder to become a founder after 40?

Not at all, he argues the opposite. According to Will, founders over 40 bring unmatched domain expertise, resilience, and clarity. The data supports it, and he shares why experience gives mid-career professionals an overlooked edge that younger founders simply can’t replicate.

What’s Will’s top advice for solopreneurs who want to use AI or no-code tools?

He stresses that AI can help you build prototypes fast, but not without structure, constraints, and actual expertise guiding it. He breaks down why you can’t “speak” a fully functional app into existence, how to think like a builder instead of a coder, and why you should ship an MVP that’s slightly embarrassing.

🌟 Featured Resource: LifeStarr Intro for 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

If you’re ready to create a business that supports your life instead of running it, this is the episode you need.

Carly and Joe dive into Step Zero of the Solopreneur Success Cycle: Defining Your Goals, and spoiler alert: it’s way deeper than “make money” or “gain freedom.”

You’ll learn how to uncover your true why, build goals that actually guide your decisions, and avoid creating a business you secretly resent. From toddler-style questioning to "change charts" and accountability hacks, this episode is your blueprint for building a business you actually like.

Whether you're dreaming, pivoting, or feeling stuck, press play before you plan another move.

🌟 Featured Resource: LifeStarr Intro for 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

Okay friends, buckle up, because today’s episode is one of those “wait… why has no one explained success like THIS before?” moments. We’re talking with Kyle Austin Young who breaks down success not as a magical personality trait, but as something you can literally math your way into.

Kyle takes us into the world of probability hacking, a shockingly simple way to figure out your real chances of success in anything (launching a business, writing a book, running a marathon) and then shows you how to change those odds in your favor.

If you’ve ever wondered why some goals finally click, and others fall apart even when you want them just as much…this conversation is going to change how you think forever.

FAQs from the Episode
What exactly is probability hacking, and do I need to be good at math to use it?

Nope! Probability hacking is simply listing out everything that has to go right for your goal to succeed…then calculating your actual chances instead of relying on vibes and wishful thinking. Kyle walks through it using basic numbers you can do on your phone, no spreadsheets, and no formulas that look like they escaped from NASA.

How does this help me as a solopreneur?

Because solopreneurs love goals…but often underestimate how many things have to align to actually hit them. Kyle’s framework helps you see where your plan is fragile, what’s likely to derail it, and, most importantly, how to systematically remove risk so your odds of success jump dramatically.

How do I know whether to keep pushing or quit a goal?

Kyle doesn’t believe in quitting, he believes in pausing strategically. If your odds still look terrible even after removing risk, he suggests exploring alternate paths that may get you to your real underlying goal more efficiently. It’s not giving up; it’s probability-based pivoting.

🌟 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

You know that electric rush when you finally build the business you’ve been dreaming about? And then, right as you’re about to tell people… you freeze?

In this episode, Carly and Joe dive into one of the least discussed but most universal solopreneur struggles: the fear of actually putting yourself out there. Why do so many solopreneurs, yes, even the wildly successful ones, get stuck right at the moment visibility matters most?

From perfectionism to vulnerability to the dread of “seeming salesy,” we break down why this happens, the hidden costs of staying quiet, and the powerful mindset shifts that help you move forward with confidence (including why “I’m not selling-I’m helping” changes everything).

If you’ve ever hesitated to hit publish, announce your business, or send that first promo email, this conversation is going to feel like a giant exhale. You’re not alone, and after this episode, you won’t stay stuck.

FAQs From The Episode

How do I promote my business without feeling salesy or annoying?

Absolutely, this comes up constantly. The key is reframing. Promotion isn’t about pushing; it’s about helping. Share stories, tips, and solutions that genuinely support your audience. If your intent is to serve, people won’t experience your message as “salesy," they’ll experience it as valuable. And the people who aren’t your ideal clients? They’ll self-select out. That’s a good thing.

What if my work isn’t perfect yet? Should I wait until it’s ready?

Short answer: No. Long answer: still no. Perfectionism is fear wearing a fancy outfit. Your audience can’t benefit from what they can’t see. Put the version out that is good enough to help someone right now. Then improve it based on real feedback instead of imagined critique. Visibility creates clarity.

How do I get comfortable being visible if it feels so vulnerable?

Start in your comfort zone and expand outward. If video feels like jumping off a cliff, start with written posts. If posting publicly feels overwhelming, start by sharing with a small circle. Momentum comes from micro-bravery. And remember: every solopreneur you admire felt this same discomfort. It’s not a sign you’re doing it wrong; it’s a sign you’re doing it.

🌟 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

If you’ve been getting hammered with “AI income hacks” on Instagram and TikTok, you are not alone. Carly has been targeted so aggressively that she’s starting to suspect her phone can hear her thoughts, so today, she and Joe sit down with Becky Beach, a solopreneur who actually does this stuff successfully.

From AI-powered funnels to Instagram chatbots to wildly profitable printable products, Becky breaks down exactly how she built a decade-long business that lets her make real money while still having time for her family. She shares the mistakes she made early, the systems she relies on now, and what solopreneurs need to know before diving into digital products or automations.

If you’ve ever wondered, “Can this AI-funnel thing actually work?”...this episode is your answer.

FAQs From The Episode
Can I actually start with zero list and zero social media following?

Yes, but not overnight. Becky makes it clear this is not a get-rich-quick play. She recommends picking a niche you genuinely care about, creating small pieces of free value, and using those to build your list through lead magnets. Social media helps, but email is what converts.

Do I need design skills to sell printables or digital products?

Nope. Becky happens to be a trained designer, but plenty of sellers rely on Canva, templates, or affiliate programs to get started. You can promote other creators’ printables while you learn, then create your own later.

Are AI funnels and chatbots too saturated now to work?

Not if you bring something unique. Becky explains that even though AI is everywhere, most people execute poorly. Your edge is:
– niching down
– making user-friendly products
– offering consistent free content
– using your story and personality as your differentiator
AI tools help automate and scale, but they only work if your foundation is solid.

🌟 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free

If you've ever wondered how Joe somehow whips up a custom GPT for literally everything, from content creation to arguing with him when ChatGPT gets too agreeable, this is the episode you’ve been waiting for. Carly finally asks the question the whole community’s been thinking: “How is Joe doing that?” And this time, he actually shows us.

Step-by-step.

On-screen.

In real time.

Whether you want a GPT that writes in your brand voice, handles your workflows, or just keeps you honest (looking at you, You’re Wrong GPT), Joe breaks down exactly how he builds them: what’s easy, what you need to prepare, and what most solopreneurs totally overlook.

If you’ve ever said, “I wish a GPT could do this for me…” Good news: after this episode, it can.

FAQs From The Episode

Do I actually need a paid ChatGPT plan to create my own GPTs?

Yes. As Joe explains, GPT creation isn’t available on the free plan. You’ll need the $20/month subscription to access the “Create” option. The good news? If you use even a handful of AI-powered tasks in your business, you’ll easily make that cost back in saved time.

What kind of “training material” do I need to upload to build a useful GPT?

Think brand voice guides, examples of past content, frameworks you use, instructions you follow, or any assets that show how you want your GPT to think and write. More clarity = better output. You don’t need a huge pack of documents, just a few strong examples go a long way.

How do I know what kind of GPT I should create for my business?

Start with the tasks you repeat constantly or the ones that drain the most time: content creation, email drafts, lead gen messages, customer onboarding, proposals, social captions, etc. If you’ve ever said, “I wish someone could just do this for me,” that’s the perfect candidate for a custom GPT.

🌟 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 connection
• The 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 thing

Total value: $65/month. Your cost? Zero.

👉 Ready to stop struggling solo and build a business that works for you?

Join LifeStarr Intro for Free