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Hey Fearless Friend!

Today on Stay Fearless or Die Trying:

1. Solutions to the struggle of making money and losing money with a startup.

2. Listen to tips from the co-creator of the celebrity endorsed gym Rumble Boxing.

3. I spoke at ECSU on Thursday and it was so incredible to meet so many aspiring and current startup founders. Thank you for coming!

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“I can’t stay out of the red!”

If I had a dollar for every time a startup founder said that, I wouldn’t need a startup—I’d be rich. I get it. Money struggles are real, and they can make or break your business. After working with tons of startups, I’ve realized that financial struggles fall into three categories:

1. Concept Problems: Your business model, strategy, or finances are all over the place.

2. Product Problems: Your pricing is off, or your execution is messy.

3. Market Problems: You’re either selling to the wrong crowd or marketing like it’s 2005.

4. The amount of founders I interact with who are marketing like they’re still in 2005 is crazy. You can find someone so cheap to hire to help you on Fiverr or Upwork, or invest in a coaching call for one or two hours with someone who is advanced in the field to walk you through the process.

Chances are, you’re dealing with a messy mix of these. But don’t worry—I’ve got you. Let’s break it down and fix it so your startup can actually make (and keep) money.

1. Fix Your Business Model

If your startup is a money pit, the problem could be at the core: your business model, strategy, or financial management.

🚨 Weak Business Model – If you can’t clearly explain how your business makes money, that’s a problem. Influencers and content creators be warned: this is not a reliable source of income until years into your career. Don’t stop hustling and maintaining a full-time job or side hustle until your dreams come to fruition.

💸 Poor Financial Management – Track every dollar! Profitability should be the goal—not just growth. I have a Google sheet I attempt to update weekly with how much Chief Swag Officer has made, any refunds, and what our margins are. It’s a lifesaver.

⚔️ Tough Competition – If you’re up against big players, find your edge. Niche down, improve customer experience, or offer something they can’t.

🏦 Over-Reliance on Funding – Investors are cool, but relying too much on funding instead of actual sales is risky. Focus on building a profitable business, not just raising capital. Keep interviewing customers about they like and don’t like to ensure you’re keeping expectations for your customer base in check.

✅ Fix It: Streamline expenses, validate your revenue model, and don’t scale too fast without a solid foundation. Just because people go viral and become famous overnight doesn’t mean that has to happen to your brand.

2. Fix Your Offering & Pricing

Your product might be amazing… in your head. But if the execution is off, so is the cash flow.

💰 Poor Pricing Strategy – Underpricing devalues your brand, and overpricing scares off customers. Use competitor research and A/B testing to find that sweet spot. Ask GPT how to set up A/B testing for your brand if you don’t know how to.

⚙️ Operational Inefficiencies – If your overhead is eating up profits, simplify. Automate where you can and cut unnecessary costs. Your business should run lean. You do not need to hire a full-time social media team off of the bat! I’ve been running Chief Swag Officer since August and JUST hired a social media gal.

✅ Fix It: Get real customer feedback, refine your pricing strategy, and make operations as smooth as possible.

3. Sell to the Right People the Right Way

Even the best product will flop if you can’t sell it right. Marketing mistakes and a weak customer connection can drain your revenue fast.

🚫 Lack of Product-Market Fit – If nobody needs your product, they won’t buy it. Talk to potential customers before you launch. Pivot if needed.

🐌 Slow Sales Cycle – If deals are dragging, shorten your sales funnel. Offer limited-time deals or simplify the buying process.

📢 Inadequate Marketing & Sales – If no one knows you exist, they can’t buy from you. Invest in social media, SEO, and partnerships. Don’t ever rely on ads. You are the best person to sell your product and sell it lean.

✅ Fix It: Make sure your product is actually needed, improve your marketing, and focus on cost-effective customer acquisition.

The hardest part in all of this is trying to do it from the bottom of the ocean. That’s why it’s so important to identify where you’re leaking money and fix it before it sinks your business. Stay smart, stay lean, and keep testing what works. You got this! 🚀

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