How startups lose millions: founder failures at TrustMe, Delever, and Smartestprep

Mistakes in the early stages often don’t seem critical at the time, but they ultimately determine the company’s future growth rate. Founders shared cases where incorrect decisions in negotiations, financial management, and hiring led to long-term consequences and significant financial losses.

Chingiz Dauletbayev, CEO of TrustMe

The most memorable failure was related to securing investment from Tim Draper.

In November, we made it into the top 10 startups in Silicon Valley, and at one of the dinners, he said he wanted to invest in us. At that time, we were convinced that the investment was practically already in our pocket.

However, it turned out that he had everything planned six months in advance. After that, we exchanged emails, and he scheduled the next meeting only for September. Meanwhile, our product was primarily working for Kazakhstan and was poorly adapted for the US market, while we were urgently starting to adapt everything for the American market.

Two weeks before the meeting, he moved it to an earlier date, and the team simply didn’t have time to fully stabilize the product for the US. But by September 11, we managed to prepare and held the call.

I presented the product, metrics, and explained how the platform worked. He liked everything and said he wanted to invest. I suggested signing the agreement through our platform to immediately demonstrate how it works.

He agreed. I sent the link for signing, but it didn’t open. The team started urgently fixing everything, while I kept him distracted to maintain contact.

On the second attempt, the link opened, but the interface was in Cyrillic, and he simply didn’t understand where to click. We tried to explain, switched the language, and manually forwarded links, which took about half an hour.

As a result, his mood dropped significantly because he had spent a lot of time, and his schedule is packed every hour. He was ready to invest, but at some point, he said, “Everything is clear,” and informed the team that he would not proceed with the deal.

Thus, we lost a potential investment of about $1 million — simply because we failed to set up the signing process in time and properly.

After that, I continued traveling and meeting with investors around the world, but this story remains one of the most illustrative for me.

Fakhridin Yusupov, CEO and founder of Delever.uz

We had a failure that didn’t directly affect money in the short term but had a significant long-term impact on the company’s growth and financial results.

At the very beginning, thinking that we had a strong product and a great app, we didn’t sufficiently understand the client’s infrastructure. We approached the client and started talking about how awesome we were. The client was generally willing to consider us but immediately asked, “How much does it cost?”

I stated the price, and in response, I heard, “Why is it so expensive?” Being confident in ourselves, we said it was a great price, instead of considering that this was a major client with whom we could build a long-term partnership. We offer an infrastructure solution, and clients usually work with us for three to four years, but we didn’t take that into account then.

As a result, in the following stages, this client simply stopped talking to us and refused meetings. To return to dialogue, it took us about four years and a lot of work: we re-entered through other major brands, presented case studies, and proved the value of the product.

Only after that were we able to resume negotiations with them. Moreover, the client’s attitude was already different, more cautious. If we had better understood the client and built the right strategy back then, we would have become their partner much faster and more easily.

This case showed that a lack of understanding of major brands and their logic significantly affects not only revenue but also the company’s growth rate. Because when you have major clients in your portfolio, other companies trust you faster and quickly understand the value of your product.

Laura Vaygorova, CEO of Smartestprep

If we talk about major drawbacks, an example from last year. In 2025, we had a significant cash flow gap — approximately 60 million tenge. We couldn’t understand why it had occurred. We trusted our director — operations and academic — too much and placed many hopes and responsibilities on him to accurately calculate the cost of products with the financier.

It turned out that many things were not passed on to the financier for verification, and processes were launched without this information. As a result, we missed out on nearly 4% of net profit. We lacked funds to cover basic costs for the team and so on. We only noticed this after three months because the company had savings and reserves. When this was discovered, it was painful: we ended up in significant debt and had to cover this gap.

There were also moments in 2023 when our co-founder left without signing a non-compete agreement. I advise all founders to do this, because he immediately created a competing company and took part of the team. As it later turned out, he had been preparing for this in advance. Consequently, we lost a lot of money because we had to buy out his share, and we had given him the share in the existing company — just like that, without a vesting period and so on. In the end, the loss was $50,000–$60,000.

This is also an important lesson: founders must conclude clear partnership agreements so that all conditions are spelled out. You cannot just give away a share in the company, even if it is at an early stage. If you are a founder, always issue shares through vesting so that the person first proves themselves and then gradually receives their share.

The third example, where we also lost money repeatedly, is hiring star specialists. We hired a marketer from Kaspi, then from Yandex — with a high fixed salary of several million tenge. At that time, we were still inexperienced and relied on their expertise. But it turned out that the person didn’t know how to deliver results and didn’t deliver any.

We simply lost a lot of time, money, and nerves. In the end, 7–10 million tenge was wasted depending on the case: the large fixed salary consumed the budget, but there was almost no result.