Unsexy Entrepreneurship

In this Ask-Me-Anything episode of The Unsexy Entrepreneurship Podcast, Charles Harris and Seth Jenson tackle the most common (and most confusing) questions new founders face. Whether you’re starting a bookkeeping business, a marketing agency, or any professional service, this episode is your tactical crash course.

We answer:

1. Should I be an LLC or an S-Corp?
2. When is the right time to start paying myself?
3. What percentage of revenue should go toward salary?
4. When should I hire someone—and when should I contract instead?
5. What’s the best tech stack for a service-based business?

Charles also shares insider tips on accounting platforms, invoicing tools (like Anchor), and why Google Workspace is still underrated. Seth gets real about the opportunity cost of your time and how to think like a founder when it comes to delegation and growth.

Whether you’re freelancing, scaling, or just figuring out what to do next, this episode is packed with unfiltered, practical advice to help you make smarter decisions, avoid costly mistakes, and grow with confidence.

📦 Plus: A sneak peek at a new business launch—Postcards from the Parks!

Got questions for Charles and Seth? Submit them HERE.

Thinking about pivoting your business? Hold up.

In this episode of Unsexy Entrepreneur, Charles Harris (CPA & founder) and Dr. Seth Jenson (PhD in strategy) unpack the messy middle of entrepreneurship—when your idea isn’t quite working and you’re not sure whether to double down or ditch it.

From Noah Kagan’s taco-to-t-shirt pivot to accountants rebranding themselves as CFOs, this episode is packed with honest, nuanced takes on how to listen to the market without losing your soul.

💡 You’ll Learn:

• What a “pivot” actually means (hint: it’s not just changing your mind)
• The 3 pillars that determine if your business is viable: demand, channels, and margin
• Why chasing easy money often leads to shallow expertise
• The sunk-cost trap: why people stay too long in a dying business model
• How to spot real market signals vs. ego-driven decisions
• Why “following your passion” sometimes isn’t enough—and when it is
• How to test hypotheses like a strategist, not a floundering founder
• The ethics of positioning: should you call yourself a CFO if you’re not one?
• When a micro-pivot (like rebranding your role) makes sense—and when it doesn’t
• The niche goldmine example of a friend who pivoted into audits for lawyers (and crushed it)

This episode will help you clarify if your business needs a bold new direction, a subtle tweak, or just a little more time. Perfect for solo founders, consultants, creatives, and operators navigating the tension between vision and validation.

Got questions for Charles and Seth? Submit them HERE.

You can’t call it a business if no one’s buying.

In this episode of Unsexy Entrepreneur, Charles Harris and Dr. Seth Jenson get real about one of the most important (and most avoided) moments in your entrepreneurial journey: getting your first customer.

If you’re stuck in “planning mode,” endlessly building, tweaking, and perfecting your product—but haven’t made your first sale—this episode is the kick in the pants you need.

🎯 You’ll Learn:

• Why getting your first customer is the true moment you become an entrepreneur
• The difference between wantrepreneurs and real founders (and how to cross the line)
• How to find your first 5 clients using your existing social capital
• Why building a product before selling is a recipe for wasted time
• When to use Facebook Marketplace, Meta ads, or just walk into businesses
• The power of hand-to-hand combat (aka: doing what doesn’t scale)
• How to ask better questions and get real customer feedback
• When to discount your early customers—and when it’ll cost you in the long run
• Why your first customers should be obsessed with you
• Organic growth strategies better than throwing money at ads
• How to piggyback off influencers and niche groups—for free

Whether you’re starting a cleaning business or building SaaS, this episode is packed with practical, real-world advice to get your first sale and build momentum—without hype, jargon, or startup theater.

Got questions for Charles and Seth? Submit them HERE.

If you’re an entrepreneur stuck trying to find the perfect mentor—someone two steps ahead who will take you under their wing, give you the playbook, and stick with you through thick and thin—this episode is a must-listen.

In this episode of the Unsexy Entrepreneurship Podcast, co-hosts Charles Harris and Dr. Seth Jenson debunk the myth of the “mega mentor” and reveal a smarter, more realistic path to growth: building a portfolio of micro-mentors. This isn’t about chasing gurus—it’s about curating your own board of advisors who can help you with real-time, tactical decisions in the trenches of business.

We cover:

• 👎 Why the idea of a “forever mentor” is outdated—and potentially harmful
• 🔍 How to identify and approach the right people with the right questions
• 🛠️ Why a mentor is more like a contractor than a guru
• 🤝 How to build relationships with mini-mentors without feeling awkward
• 💬 Why mastermind groups, DMs, and 15-min Zoom calls are more powerful than you think
• 🧠 How to use social capital to get answers when you don’t even know the right question
• 🚫 Why even Mark Cuban can’t answer all your questions (and why that’s okay)
• 👣 Why your journey to expertise can’t be skipped—and how every “failed” convo is part of the process

Whether you’re just getting started or looking to scale, this conversation will help you reframe how you think about mentorship, connection, and building your business support system.

Got questions for Charles and Seth? Submit them HERE.

You don’t need a team. You don’t need a logo. You don’t even need your product to be perfect.

You just need something janky that gets the job done.

In this episode of The Unsexy Entrepreneur, Charles Harris and Dr. Seth Jenson break down the Lean Startup Method—the strategy used by companies like Airbnb to validate their ideas and build real momentum before spending big.

If you’re stuck waiting until everything is “ready,” this episode will get you moving.

• Why “building is fun, but it’s not entrepreneurship”
• What a Minimum Viable Product (MVP) actually is—and why it’s NOT just for software
• How to avoid building a product that only you want
• Why it’s better to get paid for a janky product than to perfect one no one buys
• The “Build → Measure → Learn” loop, explained with real examples
• How to launch a plumbing business (or any service biz) using the lean method
• The power of testing with Google Forms, PDFs, and fake workflows
• Why your customers don’t always know what they want—and what to do about it
• How Charles upgraded his accounting firm by listening to feedback (and ignoring some of it)
• The difference between feedback-driven and vision-driven entrepreneurship
• How to make small bets and iterate toward product-market fit

Whether you’re starting a side hustle, tech product, or service business, this is your permission to build ugly, learn fast, and start now.

Got questions for Charles and Seth? Submit them HERE.

Think tax planning is boring? Think again.

Because the difference between winging it and planning it could mean $30,000 in unexpected taxes (true story from this episode).

In this solo episode of The Unsexy Entrepreneur, Charles Harris (CPA and small business owner) walks you through the exact playbook he uses with his clients to reduce tax bills, avoid nasty surprises, and make smart, long-term moves before year-end.

If you’re a solopreneur, freelancer, or small business owner, this episode will help you stop procrastinating and start preparing.

• What “tax planning season” really means—and why now is the time
• The actual process Charles uses with clients to estimate tax bills
• Why waiting until April is too late to do anything useful
• The #1 mistake people make with S-Corp elections (and how to avoid it)
• Why “go buy a truck” isn’t a smart tax strategy
• The real cost of being an S-Corp (hint: it’s not just taxes)
• The difference between saving money and spending money
• The best long-term way to reduce your tax bill (spoiler: retirement accounts)
• Why accurate bookkeeping NOW could save you thousands later
• How to use your tax rate as a “discount rate” when making business purchases
• Why peace of mind is the best return on investment you’ll get from tax planning

Whether you owe $3K or $30K, this episode will help you take control of your business finances—so you can walk into tax season with clarity and confidence.

You’ve got the idea. The hustle. The vision.

Now the question is—who do you need to build it?

In this episode of The Unsexy Entrepreneur, hosts Charles Harris (CPA, firm owner) and Dr. Seth Jenson (business strategist) dive into one of the most high-stakes decisions every founder must face:

👉 Should you go solo? Bring on a co-founder? Hire employees? Or just outsource?

This conversation is your blueprint for building your startup team the right way—without wasting time, money, or equity.

• Why your first few team decisions shape the future of your business
• When to hire vs. outsource vs. figure it out yourself
• The “value multiplicative” test for bringing on a co-founder
• Why many startup partnerships fail (and how to avoid that fate)
• How to avoid giving away expensive equity when a simple contractor will do
• The real cost of your first hire (it’s not just salary!)
• How to future-proof your business by building around your bottlenecks
• When to trust your long-term vision—and when to just listen to your business

Whether you’re in the Zero to One phase or scaling up your firm, this episode offers practical frameworks and personal stories to help you build smart from the ground up.

You’ve got an idea. Maybe it’s niche. Maybe it’s weird.

But can it actually make money?

In this episode of the Unsexy Entrepreneurship Podcast, Charles Harris (CPA, business owner) and Dr. Seth Jenson (PhD in business strategy) walk you through how to size your market—and how to think about scale, opportunity, and profitability in a practical, non-fluffy way.

They use a real example: a high school student who wants to launch a floral wreath and porch-decorating subscription business. What starts as a “cute” local idea turns into a potentially $24 billion market—and you’ll hear the logic behind every step.

💡 You’ll Learn:

• What “Total Addressable Market” (TAM) actually means—and how to find yours
• The difference between TAM, SAM, and SOM (yes, these matter)
• How to market-size local service businesses with free tools
• Why market size matters less than you think
• How small numbers can still build a big business
• The overlooked power of niche domination
• Real examples from law firms, music schools, and high-end porch decorators
• How to back-calculate revenue goals based on client count
• Why 40 clients could be all you ever need

Whether you’re planning a tech startup or a seasonal service hustle, this episode gives you the clarity you need to evaluate your idea like a strategist—and start building with confidence.

Got questions for Charles and Seth? Submit them HERE.

You’ve got a business idea. Now what?

In this episode of the Unsexy Entrepreneurship Podcast, Charles Harris (CPA and founder) and Dr. Seth Jenson (PhD in business strategy) dive into one of the most critical phases in the entrepreneurial journey: validation.

Whether you’re starting a new business, launching a product, or entering a new market, you must prove your idea works before you invest big time or money. And no—your gut isn’t enough.

• What validation really means (and what it’s not)
• The two biggest risks every founder must test: demand and channels
• How to identify and break down your value proposition assumptions
• Why being scientific (not emotional) about your idea leads to revenue
• Real-world examples of testing assumptions with free tools like ChatGPT
• How to use AI to research trends, competition, and market size
• What Airbnb, Kickstarter, and farmers markets have in common
• The role of MVPs—and when to go pro vs. scrappy
• Why a “soft launch” is often smarter than a grand opening

This episode gives you a concrete, step-by-step framework to test whether people want what you’re selling—and whether you can reach them consistently. You’ll walk away with the tools to become an expert in your customer, your product, and your market before you build anything big.

Got questions for Charles and Seth? Submit them HERE.

So you've started a business… but how do you actually pay yourself?

If you’ve ever felt confused, scared, or stuck about taking money out of your business, this Actionable Insights episode is for you. CPA and entrepreneur Charles Harris breaks down how to think about distributions, taxes, revenue vs. profit, and what your bank balance actually means — so you don’t starve yourself or screw up your cash flow.

Joined by Dr. Seth Jenson, Charles gives tactical, no-fluff advice for founders trying to build financially sound businesses — and actually get paid.

• The difference between revenue and profit (and why it matters)
• How to know when you can start paying yourself
• The difference between a salary and a distribution
• How much to set aside for taxes (hint: 20–30%)
• When to open a business bank account
• How to avoid cash flow panic
• The value of consistent, responsible pay
• Why you can’t wait until April to think about taxes

Whether you’re just making your first few sales or are sitting on $200K and still not sure if you can take a paycheck—this episode will give you clarity, peace of mind, and a real plan.

Got questions for Charles and Seth? Submit them HERE.