Navigating Success and Reinvention in the German Startup Ecosystem 

What you will learn:

• it seems like the key to a portfolio career lies in clarifying your “golden circle” – aka how the individual activities build mutual synergies. 

• There is a (rare) successful entrepreneurial archetype: emotionally resilient bordering on numb, extreme energy, always-on, great self-organization.

• Not all serial founders are returning to the VC game. They chart new paths in politics, bootstrapping, investing, succession.

⏲️ Reading time: 9 minutes

Germany’s startup scene is maturing. Between 2000 and 2015, many tech founders were building their first company. They are now returning as second and third generation entrepreneurs. Over the last years, I worked with many founders at the end of their cycle. This means they were exiting their business or leaving their roles. Their next moves made me curious: few are returning to build another VC-backed tech company. Some enter politics. Others take up teaching as professors. Many bootstrap fresh businesses. A few eye succession buy-outs from Mittelstand companies. Others build communities.

You may argue that venture-backed entrepreneurship doesn't work for founders over 35. They want time for their family. But I know from many personal conversations: they're not afraid of hard work, stress, or pressure. There are other reasons. I want to explore some of these stories, understand their life choices and what drives them.

Dominik Matyka was an enigma to me for the longest time. He arrived “on the scene” (the German founder & venture ecosystem) earlier than me. Dominik was already an established entrepreneur, angel investor and founding partner of Cavalry Ventures then. I had just begun working as a VC. Legit, I thought, and maybe a bit above my pay grade as a lowly investment manager. Over the years, his name popped up here and there. He started teaching at XU University and advising the marketing conference DMEXCO. 

In late 2023, we reconnected over dinner at the famous China Club, overlooking the Berlin Tiergarten. I realized then: he is doing all of these roles, the investing, teaching, advising, building, at the same time! That made me curious. Most entrepreneurs pick one thing and obsess about it. Dominik seems to be flourishing as a jack of all trades.

Once You’ve Made It, You’ll Lose your Edge

Many young-ish clients of mine begin coaching with a hesitation. They say “I don’t want to lose my edge. Maybe I don’t want to be fulfilled and happy in my life. After all, this anger and hustle is the rocket fuel that powered my career so far.” 

I reached out to some of my clients and friends about this, so here is it in their words:

• “I believe that the urge for financial wealth or being dependent on external validation mostly arises from one's own disorders or traumas. For many entrepreneurs, switching the 'fuel' for their own drive from a 'negative' to a 'positive' is certainly one of the greatest challenges.” (Agency CEO)

• “Yes, it heavily depends on why one is an entrepreneur. After my exit, I also temporarily lost the "hunger" because I was driven professionally by recognition and "making it." “ (VC-backed founder & serial entrepreneur)

This fear of losing one's edge after achieving success is common among founders. I asked Dominik one single question: What happened to your motivation once you “made it”? Metaphorically, can you still be “hungry” in hustle-culture-speak once you’ve earned enough money to feed generations?

Dominik is no – as we say in German – Kind der Traurigkeit, he is a bon vivant. He collects fast cars, enjoys fancy dinners and stands out with quotes such as “money is more important than purpose!” Yet, his response surprised me a little bit. (Maybe I gave him too much time to write out his answers?)

For me, "making it" is a concept that's constantly in flux, shaped by my evolving interests and life's changing seasons. It's more about the journey than any single destination, (...) the challenge of solving complex problems and the joy of fostering innovation that excites me.

Financial stability affords me the luxury to pursue projects that captivate me, rather than those dictated by prevailing trends or the allure of potential exits.

Moreover, my enthusiasm for fostering connections plays a significant role. I am naturally inclined towards initiatives that facilitate networking, learning, and knowledge exchange.

So I followed up with him and asked him to reflect about his failures, his conflicts of interests. I asked him to share it in a voice note, so I would get the unedited version.

Turns out, Dominik did land on his belly a couple of times during his career. He started a reference checking company but realized it would not work in the German market. In 2005, he founded a social network that failed because it was just too complex to build back then. 

Still, he recognizes this experience led him to start a video technology company or a global native advertising platform. Both turned into successful companies under his helm. No matter what, he says it is about staying in the entrepreneurial game. Deliberate practice of entrepreneurship will lead to new opportunities. Success will bring more wealth and requests. Even failures will give insights and new opportunities. They will also further build the practice of entrepreneurship. When pressed on his drive, Dominik responds: 

Actually, I am on the other end of the spectrum: I am too edgy, too pushy. I am constantly dissatisfied. Through my Bob-The-Builder-lens, I am inspecting my life and trying to fix things that could be solved in a better way. 

I need to comfort myself sometimes, when things don’t work out on one end of the spectrum. When I look at my life as a function of success, any given day might be volatile. But as long as the trend is upwards, I am fine. 

I need to remind myself of this truth every once in a while.

I find this an interesting shift in perspective. Away from reaching any specific outcome towards committing to the game itself. Focusing on the long game. Value investing.

I felt a sense of bewilderment when I listened to Dominik talk. How can he navigate the emotional turmoil of entrepreneurship with such simplicity but still successfully build multiple complex businesses? He would not be the first founder of this entrepreneurial archetype:

• They show emotional resilience and stoicism bordering on numbness to the daily volatility,

• they are focusing on the long game, the process of entrepreneurship, and

• They tirelessly generate energy. They are always-on, regardless of its impact on family and team. They are also excellent at self-organization.

There are a couple of elements in this archetype that I do not resonate with: I am absolutely not always-on, much to the contrary. Also, I pride myself in emotional sensitivity as the fuel of my creative and business pursuits. But I cannot help but notice the disproportionate share of this entrepreneur archetype among the successful founders. 

Focus & The Golden Circle

But isn’t there value in focus? Why not “double down”, as the tech lingo suggest, and drive outsized returns from one opportunity? Dominik admits that all these projects create an overwhelming workload. 

I am always online. My calendar is open from 6.30AM to midnight. Never in my life did I have an out of office reply - I think I just don’t want that. My teams know my working style extremely well, and combined with meticulous project management, it’s the only way I can make it work. 

But when he speaks about how all of these activities come together, I cannot ignore the striking parallels to our Career Sovereignty concept. 

Initiatives that facilitate networking, learning, and knowledge exchange align with what I consider my 'golden circle'—the core motivation that underpins my entrepreneurial endeavors.

He is referring to a mutually-reinforcing system of activities (“networking, learning, and knowledge exchange”) that fuels his motivation. This motivation is directed at “entrepreneurial endeavors” increasing the quality and quantity of those exact same activities. The flywheel spins faster and faster. Here is how the puzzle pieces make sense for him:

• I worked with DMEXCO because I thought there would be great synergies for the companies and investment funds I am engaged with,

• I co-founded Cavalry because I wanted to leverage my deal flow with external capital next to having a seed fund I would have loved to work with being a founder,

• I became a professor because I wanted to pass back knowledge and “help to nurture” new entrepreneurs, and now

• I’ve started “Better Call Dominik”, a mastermind group where entrepreneurs & investors share knowledge about money and business – especially personal finance. The initial idea was born out of a personal reflection on wealth, success, and the quest for more transparent and effective ways to secure my family's future. But then the curiosity kicked in, the joy of entrepreneurship.

Let's return to the core question of motivation. The paths to success are often entangled with strong beliefs about work. Many from my generation grew up under the mantra that success necessitates hardship. Yet, as we emerge from years of struggle, we cling to this mindset, perhaps out of habit more than necessity. My friends and clients added more nuance after reflecting:

• "I used to think progress required pain or significant effort. I've since learned this isn't mandatory and can actually impede." (C-Level exec at a CPG company)

• "Once financial stability and reputation are secured, the freedom to pursue genuine visions becomes unlimited. It prompts one to question the initial impetus behind their 'vision' – was it merely a stepping stone to 'success'?" (partner in a US venture firm)

These reflections highlight a key shift. It's a move from singular outcomes to a commitment to the journey itself. It's about embracing the long game. The focus is on lasting growth over quick gains.

Dominik Matyka's story exemplifies this ethos. Our understanding of motivation and success is ripe for reevaluation. The narratives we've explored invite us to consider not just how we achieve, but why we embark on these journeys in the first place. For Dominik and many like him, the answer lies in deliberate practice — in entrepreneurship as a craft.