Sheila Lirio Marcelo, Kathryn Finney, Daniella Pierson, and Sara Blakely
Let’s be real—starting a business can feel like stepping off a cliff with no parachute. 🪂 The challenges entrepreneurs face are always there, but taking that first step? That’s where most people freeze. Fear, uncertainty, and a million “what ifs” keep so many great ideas locked away.
I’ve been there. When Damon White and I co-founded ARCHTOCULTURE, the vision was crystal clear, but the path? Not so much. 😬Not by a long shot. There were a lot of moments of doubt, plenty of late-night strategy talks, and more than a few roadblocks. But every challenge taught me something that made the journey worthwhile.
So, if you’re standing at the edge, wondering what’s holding you back, let’s break it down. 🧐Here are the top five reasons aspiring entrepreneurs hesitate—and how you can move past them.
Sara Blakely in the early days of Spanx
1. Fear of Failure 😱
Failure is that shadow hanging over every big dream. The idea of investing your time, energy, and savings—only to fall flat? Yeah, that’s scary. So is being laid off or losing your 401k.
“The REALITY is there are NO safety nets”
Ways to Tackle It:
- Shift Your Perspective: Failure isn’t the end—it’s feedback. It’s where the best growth happens. 🌱
- Start Small: Launch with a minimal viable product (MVP). Test the waters without diving all the way in.✅
- Learn from Others: Every successful entrepreneur has faced failure. The difference? They didn’t stop. Google: Steve Jobs ✅
✨Here’s how one founder pushed through fear:
Sara Blakely, founder of Spanx, started with just $5,000 and faced rejection after rejection but didn’t quit. She learned from every “no,” and stayed scrappy. Her perseverance in the face of fear turned her into one of the youngest self-made billionaires.💰
👉 Fear didn’t stop her—it fueled her.
Daniella Pierson during the start-up days
2. Lack of Funding 💸
Let’s be honest—MONEY MATTERS. Turning an idea into reality without financial backing can feel impossible.
“We all need money, but how do you get it?”
How to Break Through:
- Bootstrap First: Use personal savings or small investments. Starting small isn’t a setback—it’s smart. 💡
- Tap Into Your Ecosystem: Think: Rich uncle or neighbor – no Seriously! Ask your network. You’d be surprised who’s willing to invest or support. 🤝
- Leverage Crowdfunding: Platforms like Kickstarter or Indiegogo are great for getting early support. 🚀
- Look for Grants & Competitions: Industry-specific grants like Hello Alice or pitch competitions can be game-changers. 🏆
- Join Accelerator Programs: Groups like Y Combinator, Techstars or retail specific programs like Target Accelerators can provide funding, mentorship, and resources to help you scale. 📈
“People invest in People” and “Proof of Concept”
✨How one founder navigated funding hurdles:
Daniella Pierson founded The Newsette in 2015 while still a student at Boston University. She started with just eight subscribers and zero outside funding. Instead of chasing investors, she doubled down on organic growth and smart partnerships. Today, her media company is valued at $200 million. Pierson achieved this remarkable growth without relying on venture capital funding. Her journey exemplifies how leveraging personal savings, reinvesting profits, and building a strong brand can overcome funding challenges.
Proof that you don’t need deep pockets—just a deep hustle.💡
Archtoculture founders Kyle Frazier and Damon White on a Google Meet call
3. Impostor Syndrome
That little voice saying, “You’re not good enough”? Yeah, we all hear it. When I launched Archtoculture, even with years of experience, I questioned myself. Starting from scratch was intimidating.
👉 Confidence isn’t a starting point—it’s something you build by showing up, learning, and doing the work.
How to Rise Above:
- Build a Support Network: Surround yourself with people who believe in you—mentors, peers, other entrepreneurs.
- Focus on Your Strengths: Own your expertise and unique perspective. You bring something valuable to the table.
- Keep Learning: No one knows it all. Stay curious. Take courses, read, and ask questions.
✨How I tackled impostor syndrome:
When ARCHTOCULTURE was just an idea, it felt daunting. But I leaned into my network, honed my craft, and stayed mission-focused. Now, we’ve helped numerous emerging brands grow through strategy, planning, and partnerships with corporations like Chan Zuckerberg Initiatives, Foot Locker LEED, and Target Accelerators. I’ve learned that building relationships through authenticity and connection is the cure for insecurities. 🙌
“You WILL grow into your shoes, you WILL become WORTHY.”
Sheila Lirio Marcelo before Care.com
4. Uncertainty About Market Demand 📉
What if no one wants what you’re selling? Not knowing if there’s a market for your idea can stop you cold.
“Is this an evergreen opportunity or just a trend?”
How to Push Through:
- Conduct Market Research: Use surveys, focus groups, and competitor analysis.🔍
- Test the Waters: Launch a beta version or a soft launch to gauge interest. 🌊
- Services That Can Help: Utilize platforms like SurveyMonkey for surveys, Typeform for feedback, and SEMrush for market analysis.
I’ve compiled a list just for you: CLICK or SCAN the QR below:
📄Psst.. Make A Copy 😄
✨Here’s how one founder validated her idea:
Sheila Lirio Marcelo, founder of Care.com, identified a gap in the caregiving market by leveraging data and personal experience. She noticed how challenging it was for families to find reliable care and used early research and surveys to validate her idea. Marcelo launched Care.com as an online marketplace, carefully analyzing user data to match families with caregivers effectively. This data-driven approach not only ensured trust and satisfaction but also allowed her to refine the platform based on real-time feedback. Her strategic use of data and community insights helped scale Care.com into a trusted resource for millions of families.
👉 The key takeaway? Start by understanding the problem deeply, listen to potential users, and let their feedback shape your solution.
Kathryn Finney in her college days at Yale University
5. Fear of Losing Financial Stability ⚖️
Walking away from a steady paycheck—In the 2020’s? That’s terrifying. Risking financial security isn’t easy when the stakes are high.
DeLaSoul Stakes is High – IYKYK
“How do you go ALL IN when everyone’s situation is different?”
Ways to Move Forward:
- Start Part-Time: Build your business on the side until it’s sustainable.
- Plan Your Exit: Know your “exit number”—the income you need from your business before making it full-time.
- Consult Experts: Financial planners can help craft a safety net. 🗣️
✨Here’s how one founder played it smart:
Kathryn Finney started The Budget Fashionista as a budget fashion blog — evolved into a media company — becoming one of the first Black women to achieve a seven-figure startup exit. She didn’t quit her day job until her business consistently brought in enough to sustain her. She later sold it in a seven-figure deal. She went on to launch another company Digitalundivided, empowering Black and Latina women entrepreneurs.
Her strategy: Once The Budget Fashionista’s revenue consistently surpassed her “exit number” (the amount needed to sustain her financially), Finney transitioned from treating it as a hobby to running it as a full-time business.
👉Get the business stable first, then take the leap.
🚀Resources for Small Business Owners
Going solo is tough—NGL. Here are some go-to resources that can actually make a difference in your entrepreneurial journey:
- SCORE: Think of this as free business coaching. SCORE pairs you with experienced mentors who’ve been in the trenches and can guide you through challenges—whether it’s refining your business plan, navigating funding, or marketing. Example: If you’re struggling with finding the right pricing model, a SCORE mentor can walk you through strategies that have worked in similar industries.
- SBA (U.S. Small Business Administration): This isn’t just a government site collecting dust. The SBA offers low-interest loans, business guides, and even local workshops to help you access funding and build your business the right way. Example: If you’re looking for startup capital but don’t know where to start, SBA-backed microloans or grants can be game-changers.
- Local Chambers of Commerce: Your local chamber isn’t just about networking happy hours (though those are a bonus). They can connect you with community programs, local business leaders, and initiatives that support small business growth. Example: They often host meetups where you can meet potential collaborators or even your first clients.
- Accelerator Programs: If you’re ready to scale fast, accelerators like Y Combinator, Techstars, or industry-specific programs like Target Accelerators can provide mentorship, funding, and access to investors. Example: Brands like Airbnb and Dropbox got their early boost from Y Combinator. These programs help refine your pitch, shape your growth strategy, and introduce you to the right people.
- Other Founders and Entrepreneurs: Never underestimate the power of connection. LinkedIn groups, industry events, or even casual coffee chats with fellow founders can spark game-changing ideas. Example: Daniella Pierson leaned into her network of fellow entrepreneurs to share strategies and navigate funding challenges—those real-world convos gave her insights you can’t find in a textbook.
If you know of any other really good resources please let me know in the comments!
Conclusion: Take the First Step – “JUST DO IT” ✅
Look, fear is valid—but it’s not a reason to stop. Every successful entrepreneur once stood exactly where you are now. The difference? They didn’t let fear win.🏆
When we started ARCHTOCULTURE, the path was uncertain. But leaning into small, calculated risks and focusing on our mission helped us build something impactful. We stayed curious, stayed connected, and kept learning. That’s what growth looks like. 🌱
Ask yourself:
✅ Does your business idea solve a real problem?
✅ Is your solution scalable?
If the answer is yes, ✅start small, ✅build smart, and ✅tap into the right resources.
And if you’re looking for more insights on overcoming challenges entrepreneurs face in building sustainable brands, let me know in the comments.
