Learned the Hard Way: 5 Costly Founder Mistakes

Founding a startup is one of the most challenging experiences one can go through. No matter how much you study, research, and prepare, there are mistakes that only practice – and pain – will teach. Throughout my journey as a founder, I made decisions that cost money, time, and energy. Some of these choices could have been avoided if I had listened to those who had already been through it. That’s why I’m sharing five lessons that deeply marked me and might help you avoid the same missteps.

The Early Bet on Inbound Marketing

In the early days of the company, I chose to heavily invest in inbound marketing strategies. I created content, bought traffic, implemented automations – all to attract leads in a scalable way. On paper, the strategy made sense. However, in practice, I realized that in my segment, the cost of acquisition through paid traffic was extremely high, and the return was uncertain. What really worked was direct contact with potential customers through outbound approaches and sales made by myself, as the founder.

It was a reality check. It wasn’t the time to build a sophisticated funnel or generate leads passively. It was the time to fight, talk to the market, validate hypotheses, understand pain points, and adjust the product. More than that: I understood that, in the early stages, sales need to come from the founder themselves. If you can’t sell your solution, it’s unlikely someone else will. Inbound can be powerful, but it requires time, investment, and business maturity. For those seeking their first sales, it’s better to stay grounded and prioritize direct and controllable strategies.

Bringing on a Co-Founder Without Vesting

Another significant mistake was how I handled the entry of an operational co-founder. With the goal of sharing responsibilities and accelerating growth, I integrated the co-founder directly into the company’s equity, formalizing the partnership from the start without any vesting agreement.

Over time, plans changed, and this co-founder decided to leave. That’s when the lack of predictability became a problem. Lengthy negotiations, changes to the articles of incorporation at the commercial registry, discussions about equity values… a bureaucratic and draining process that could have been avoided with a simple vesting agreement with a cliff clause. This would have protected the company, allowed for a smoother exit, and reduced the legal and financial impact. Today, I understand that formalizing the relationship from the beginning, with clear rules for entry and exit, isn’t distrust – it’s responsibility.

Excessive Caution in Fundraising

When the market looked at our company and showed interest in investing, I found myself facing multiple proposals. It was the chance to raise a larger amount of capital, but I chose to be conservative. I raised little, thinking about preserving equity and raising more in a future round.

This was one of the moments that taught me the most about fundraising timing. The best time to raise capital is when you don’t need it. It’s when there’s demand for your business, when you have options and can negotiate from a position of strength. Unused capital can be applied intelligently, generating returns until the need arises. Opportunities don’t knock twice. Waiting to raise “later” can mean seeking resources in a less favorable scenario, with less negotiating power.

A Scalable Product with Non-Scalable Services

When developing the product, I focused on building something robust that would meet the market’s needs well. However, for it to truly work, I needed to offer services that complemented the solution. This created an imbalance. While the product was scalable, the services weren’t. The dependence on these services hindered growth and, worse, masked the real value of the technology I was offering.

I learned that it’s essential to develop a product that stands on its own, especially if the goal is to scale. The focus needs to be on completely solving the pain of a specific niche with a product so well-tuned that it doesn’t require external support or complementary services. Otherwise, the customer buys for the service, not the technological solution, which compromises the business model in the long run.

Ignoring Alternative Sources of Capital

For a long time, I associated growth with bringing in investors. Venture capital seemed like the only viable path to accelerate operations. Only later did I realize that’s not always the case. Often, what the company needs is working capital – something that can be obtained through credit lines, such as Pronampe, with low interest rates and simple conditions.

Seeking investment from funds brings along complex clauses, demands in the articles of incorporation, a seat on the board, and obligations that don’t always make sense for the business’s stage. In some situations, bank capital may be the best solution: fewer constraints, more autonomy. It’s important to evaluate each moment of the company with clarity and not follow ready-made formulas. Not all growth needs to come from diluted equity.

Conclusion

Every mistake I made brought valuable learning. Some were costly, others draining, but all contributed to making me a more conscious and prepared founder. I share these experiences with those who are starting out or already on the journey, with the intention of sparking reflection and, perhaps, avoiding some bumpy roads.

The entrepreneurial journey is made of choices, and the more information and shared experiences we have, the better those choices will be. If you’ve been through something similar or are facing a decisive moment in your startup, share your story in the comments. Let’s exchange experiences and grow together.