Urban Challenger: Why many investors like repeat founders #DHDL

For most early-stage founders, it is super impressive when they hear that someone has sold their startup for a large sum. But is someone like that still suitably motivated for their next start-up? The opinions of the TV lions are not the only ones that differ.


In the current episode of “Die Höhle der Löwen”, brothers Daniel and Simon Heitz dare to face the often very critical investors. With their start-up Urban Challenger, they set out to establish the coolest and most exciting city guide in Germany. In doing so, they are primarily addressing groups that not only want to gather knowledge on joint trips or at team events, but also want to have a lot of fun interacting with each other and their environment there.

The lions are then allowed to try out one of the many challenges and are supposed to pose one of their most outstanding characteristics or qualities and take a group photo of it, which everyone obviously enjoys.

The concept receives a lot of praise, but opinions differ about the founders, which is sometimes difficult to understand as a viewer. Perhaps a few crucial sentences and events are missing from the final cut, which of course leaves a lot of room for speculation.

However, one topic is very present and seems to have been hotly debated: do the two founders have the right attitude? Carsten Maschmeyer, for example, doesn’t like the answers to the numerical questions and concludes that the brothers don’t have the right “spirit” and therefore drops out. Nils Glagau will also list this as the main reason for leaving, but also says that he thinks the two are a cool team. Is this contradictory or what distinguishes a “cool team” from one with the right “spirit”?

You can’t really get a grip on it, but what becomes clear relatively quickly is the lions’ dissatisfaction with the founding brothers’ answers to the questions about planned turnover and customers. But even if you find them a little uncertain, because they often don’t come straight from the gun, they seem to have prepared themselves and answer the questions very well. Here, of course, it is also a lot of an investor’s subjective impression, whether one simply blames such an impression on nervousness or directly draws conclusions from it on a real lack of numerical certainty. The excitement factor is certainly even stronger in the cave, but it cannot be completely disregarded outside of it either; after all, a lot of money is at stake and not all founders already have plenty of experience as investors.

So were the lions perhaps a bit strict with Urban Challenger, or was there something else at play?

Tillmann Schulz also asked an important question in this context, namely whether both were already working 100% for their start-up. It came out that Urban Challenger ran as a side project for a while, as one of the brothers was studying while the other had another startup that was sold in 2021. Here you can directly feel the interest of the lions, especially Janna Ensthaler wants to know more. The founders speak of a “life-changing sum” and it at least resonates that both now want to focus fully on Urban Challenger.

In fact, it is always an exciting question among investors whether such “repeat founders” are to be judged unapologetically positive or not. In any case, they are very popular with many financiers, and for a long time it was the case that a team member who had already had a successful exit was almost a guarantee for a well-rated financing round, even in the early stages.

This is certainly understandable, after all, one can assume that such people possess the rare combination of professional skills and entrepreneurial qualities that is indispensable for the success of a start-up. But does that include the famous “spirit”? There are indeed some funders who believe that this is precisely what is lost when there is no more financial pressure. Others, on the other hand, believe that such founders will then look for fields of activity that they are passionate about and also welcome the fact that their start-ups have a longer runway due to less financial pressure of their own.

For Janna Ensthaler, at least, the positive arguments seem to prevail, she contradicts her fellow jurors and finally offers the founders the 60,000 euros they want – but for 25% instead of the 15% offered. She gets an immediate commitment, and in the later interview the founders emphasise that they were concerned with the partnership and not with the pure evaluation. In fact, it is often observed among repeat founders that they haggle less over the last percentages, but instead check investors more for their other added values. And Janna Ensthaler seems to be the perfect choice, especially with her platform Event Inc.

Carsten Maschmeyer remarks afterwards that she would be more enthusiastic about the company than the founders themselves, but the investor disagrees. The viewers can also see that the joy at Urban Challenger is great. So are the other four lions guilty of misjudgement? At the very least, this case illustrates once again how different the perceptions of different investors and thus their feedback can be, especially when it comes to rather fuzzy factors like “spirit”. Because less extroverted people may not always be able to demonstrate their spirit so clearly, so as an investor you could easily miss a great opportunity.

However, Urban Challenger was able to bring his spirit closer to all five lions, at least at the beginning of the challenge. It remains to be hoped that, together with their lioness, they will now take this spirit to many more cities.

Photo (above): TVNOW / Bernd-Michael Maurer

Ruth Cremer

Ruth Cremer is a mathematician and consultant as well as a university lecturer in the field of business models, key figures and financial planning. As a former investment manager, she knows what investors look for and also helps with pitch and document preparation in the investment or acquisition process. Since 2017, she is involved as an external consultant in the selection and preparation of the candidates in "Die Höhle der Löwen".