Podcast
Unsexy Entrepreneurship
Hosted by Charles Harris · EN
Want to quit your job and build real financial freedom—but not sure where to start?
This podcast is for millennial entrepreneurs who are ready to take control of their future through business ownership. Whether you’re looking to start a business, buy an existing business, or grow a side hustle into a full-time gig, we give you the real-world playbook that actually works.
Hosted by Charles Harris, a CPA turned business owner, and Dr. Seth Jenson, director of The Entrepreneurship Institute and an Oxford PhD in Business Strategy who’s helped thousands launch companies, this show cuts through the noise and gives you straight talk on:
• How to start a business from scratch
• What to look for when buying a small business
• The mindset shift from employee to entrepreneur
• How to avoid beginner mistakes that cost you time and money
• Proven strategies to grow your small business
No fluff. No hype. Just the unsexy truth about building a business that works—so you can build a life you actually want.
Subscribe now if you’re ready to stop dreaming and start doing.
Got questions? Contact us here: https://tinyurl.com/6fwvem3v
10episodes
Episodes
Newest firstAll episodes
The 5 Questions Every New Founder Asks (And We Finally Answer)
Dec 2300:45:56Tap to summarizeIn 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:Should I be an LLC or an S-Corp?When is the right time to start paying myself?What percentage of revenue should go toward salary?When should I hire someone—and when should I contract instead?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.
Transcribe →How to Pivot Smart—Not Desperate | 021
Dec 1600:21:20Tap to summarizeThinking 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 marginWhy chasing easy money often leads to shallow expertiseThe sunk-cost trap: why people stay too long in a dying business modelHow to spot real market signals vs. ego-driven decisionsWhy “following your passion” sometimes isn’t enough—and when it isHow to test hypotheses like a strategist, not a floundering founderThe 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’tThe 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.
Transcribe →Finding Your First Customers | 020
Dec 900:26:05Tap to summarizeYou 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 entrepreneurThe difference between wantrepreneurs and real founders (and how to cross the line)How to find your first 5 clients using your existing social capitalWhy building a product before selling is a recipe for wasted timeWhen to use Facebook Marketplace, Meta ads, or just walk into businessesThe power of hand-to-hand combat (aka: doing what doesn’t scale)How to ask better questions and get real customer feedbackWhen to discount your early customers—and when it’ll cost you in the long runWhy your first customers should be obsessed with youOrganic growth strategies better than throwing money at adsHow to piggyback off influencers and niche groups—for freeWhether 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.
Transcribe →The Mentorship Myth: Why No One Mentor Can Save Your Business | 019
Nov 2500:24:02Tap to summarizeIf 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 processWhether 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.
Transcribe →The Lean Startup Playbook: Launch Ugly, Learn Fast | 018
Nov 1800:28:00Tap to summarizeYou 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.💡 You’ll Learn:Why “building is fun, but it’s not entrepreneurship”What a Minimum Viable Product (MVP) actually is—and why it’s NOT just for softwareHow to avoid building a product that only you wantWhy it’s better to get paid for a janky product than to perfect one no one buysThe “Build → Measure → Learn” loop, explained with real examplesHow to launch a plumbing business (or any service biz) using the lean methodThe power of testing with Google Forms, PDFs, and fake workflowsWhy your customers don’t always know what they want—and what to do about itHow Charles upgraded his accounting firm by listening to feedback (and ignoring some of it)The difference between feedback-driven and vision-driven entrepreneurshipHow to make small bets and iterate toward product-market fitWhether 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.
Transcribe →Stop Guessing Your Tax Bill: Here’s What Smart Founders Do Instead | 017
Nov 1100:08:37Tap to summarizeThink 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.💡 You’ll Learn:What “tax planning season” really means—and why now is the timeThe actual process Charles uses with clients to estimate tax billsWhy waiting until April is too late to do anything usefulThe #1 mistake people make with S-Corp elections (and how to avoid it)Why “go buy a truck” isn’t a smart tax strategyThe real cost of being an S-Corp (hint: it’s not just taxes)The difference between saving money and spending moneyThe best long-term way to reduce your tax bill (spoiler: retirement accounts)Why accurate bookkeeping NOW could save you thousands laterHow to use your tax rate as a “discount rate” when making business purchasesWhy peace of mind is the best return on investment you’ll get from tax planningWhether 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.
Transcribe →Hiring Smart: Avoid These Costly First-Time Founder Mistakes | Ep 016
Oct 2800:40:57Tap to summarizeYou’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.💡 You’ll Learn:Why your first few team decisions shape the future of your businessWhen to hire vs. outsource vs. figure it out yourselfThe “value multiplicative” test for bringing on a co-founderWhy many startup partnerships fail (and how to avoid that fate)How to avoid giving away expensive equity when a simple contractor will doThe real cost of your first hire (it’s not just salary!)How to future-proof your business by building around your bottlenecksWhen to trust your long-term vision—and when to just listen to your businessWhether 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.
Transcribe →Why You Only Need 40 Clients (Zero to One pt. 3) | 015
Oct 1400:28:56Tap to summarizeYou’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 yoursThe difference between TAM, SAM, and SOM (yes, these matter)How to market-size local service businesses with free toolsWhy market size matters less than you thinkHow small numbers can still build a big businessThe overlooked power of niche dominationReal examples from law firms, music schools, and high-end porch decoratorsHow to back-calculate revenue goals based on client countWhy 40 clients could be all you ever needWhether 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.
Transcribe →Validation: Will Your Business Idea Will Actually Work? Zero to One pt.2 | 014
Oct 700:34:44Tap to summarizeYou’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.💡 You’ll Learn:What validation really means (and what it’s not)The two biggest risks every founder must test: demand and channelsHow to identify and break down your value proposition assumptionsWhy being scientific (not emotional) about your idea leads to revenueReal-world examples of testing assumptions with free tools like ChatGPTHow to use AI to research trends, competition, and market sizeWhat Airbnb, Kickstarter, and farmers markets have in commonThe role of MVPs—and when to go pro vs. scrappyWhy a “soft launch” is often smarter than a grand openingThis 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.
Transcribe →Salary or Distribution? How Business Owners Really Get Paid | 013
Sep 3000:23:29Tap to summarizeSo 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.💡 You’ll Learn:The difference between revenue and profit (and why it matters)How to know when you can start paying yourselfThe difference between a salary and a distributionHow much to set aside for taxes (hint: 20–30%)When to open a business bank accountHow to avoid cash flow panicThe value of consistent, responsible payWhy you can’t wait until April to think about taxesWhether 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.
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