Unsexy Entrepreneurship

The 5 Questions Every New Founder Asks (And We Finally Answer)

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 [https://tinyurl.com/6fwvem3v].

How to Pivot Smart—Not Desperate | 021

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 [https://tinyurl.com/6fwvem3v].

Finding Your First Customers | 020

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 [https://tinyurl.com/6fwvem3v].

The Mentorship Myth: Why No One Mentor Can Save Your Business | 019

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 [https://tinyurl.com/6fwvem3v].

The Lean Startup Playbook: Launch Ugly, Learn Fast | 018

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. 💡 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 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 [https://tinyurl.com/6fwvem3v].