I was halfway through my gym workout, catching two birds with one stone: training my body while feeding my mind with an interview. Peter Thiel — co-founder of PayPal and Palantir, and one of Silicon Valley's most influential investors — was talking with Mathias Döpfner right before receiving the 2026 Axel Springer Award [LINK TO VIDEO]. Then he said something that made me stop mid-set: “A lot of the founders of these tech companies, I think, are both insiders and outsiders.”

Wow. That's me. That's exactly me. All my life, I have been an insider-outsider.

Today, let me share what it feels like to live in and out — and why this in-between place is both a hidden advantage and a quiet burden. If you have ever felt that you are part of a group yet never fully belong to it, this article is for you.

“It's Both, Though”

What struck me most came a moment later. When the interviewer suggested that being an outsider can be an advantage, Thiel pushed back: "I want to say it's both, though. It's this outsider-insider combination. People always exaggerate the outsider piece."

He is right. The romantic story of the lone rebel storming the castle is only half the truth. The insider knows the rules, the language, and the people. The outsider sees what the insiders no longer see. The magic happens when one person carries both — close enough to understand the system, distant enough to question it.

A Life Lived In and Out

When I look back, I see the same pattern everywhere.

I grew up in a small village in Rhineland-Palatinate, Germany. I felt deeply connected to the people in my village, played on the local football team, and saw everyone as a friend or respected neighbor. Yet I also attended the Gymnasium, the academic high school, and some teammates sensed that I was different. A few may have found me a bit arrogant — and perhaps, at times, I came across that way.

When I was twenty, it was my age group's turn to host the village's big annual festival — shows, music, and long nights of celebration. My father had passed away just three months earlier. I felt I needed to get out. So instead, I joined a group of high school friends on a four-week trip through France, Spain, and Portugal. I know some of my hometown friends were disappointed — and I understand why. For me, it was the right decision.

In the army, I chose the reserve officer track. The regular soldiers saw me as a "traitor" aiming for something higher. The sergeants saw me as someone who would eventually outrank them — and the career officers saw me as someone who would soon be gone. I held the rank, yet never quite belonged to any of these groups.

At Deutsche Bank, the pattern became a rhythm. While studying at Saarland University, I worked at a Saarbrücken branch as a "floater," filling in wherever someone was sick or on vacation — always arriving, always leaving. I was also a semi-professional middle-distance runner: when my fellow students went for coffee, I went for training. During my Ph.D., I rotated between Saarbrücken and the head office in Frankfurt, and wrote my thesis in a quiet office inside the bank — joining colleagues for lunch, then returning to my desk alone. In my final year, I spent a couple of months at my doctoral advisor's institute to complete my statistical analyses more quickly, surrounded by fellow doctoral candidates and postdocs. Inside and outside once again.

After my Ph.D., I secured a rare spot in Deutsche Bank's international staff exchange program. When told I lacked experience, I replied: "Look at my career — everything about it is unusual. It's my risk. Send me out." From several offers, I chose the smallest Deutsche Bank branch in Asia: Ho Chi Minh City. Conventional wisdom said: go big. But the small one offered the most room to learn and grow fast — exactly the right decision.

A Collection of Labels

Over the years, I have collected quite a few labels. In the village: the one who was a bit different. In the army: a traitor to some, a passing guest to others. At regional offsites in Asia: too academic, too independent — although I saw myself as a doer with drive. After a few disappointments, it finally dawned on me: I am not a banker. I am an entrepreneur.

So I became both a founder and an academic. And the labels kept coming — only now, they contradict each other. At universities, colleagues saw me as unusually dynamic, entrepreneurial, and colorful. Among fellow entrepreneurs, I am the professor.

Too entrepreneurial for the academics. Too academic for the entrepreneurs. I have to smile about that paradox. Wherever I go, I am inside — and a little outside.

Perhaps this feeling is as old as creativity itself. In some ways, I can relate to Albert Einstein, who confessed: “I am truly a 'lone traveler' and have never belonged to my country, my home, my friends, or even my immediate family, with my whole heart.”

You Are Not Alone

Soon after that gym session, I shared Thiel's words with a good friend — a former company founder and academic with a Ph.D. who lives a free and independent life. He paused, then said: “I have felt like this all my life.”

Then I called two other founder friends. The first — a serial entrepreneur who is also an entrepreneurship professor — agreed right away: “It's sort of like a zoom in, zoom out.” Inside experience, he explained, lets you truly understand an industry. “But the idea to solve its problems doesn't come from inside the industry — it comes from how others see it in other worlds.”

And I noticed something else. My friends and I share the same profile in TIPS, Thinkergy’s Talent & Innovator Profiling System: we are all Ideators. And we all move easily between two worlds — at ease in a crowd, driving things with people, and equally at ease alone, creating things in solitude.

Six Traits of Insider-Outsiders

1. They think for themselves. Insider-outsiders are often mistaken for contrarians. Thiel rejects that: "I don't think the point is to be contrarian for its own sake — because then you just look at the consensus and put a minus sign in front of it. The real goal is always to try to think for oneself." Question: When did you last hold a view because you had thought it through, not because the group held it?

2. They say no when they carry a bigger yes. Saying no makes you unpopular. But when a deeper yes burns inside you, the no becomes possible. As Mahatma Gandhi observed: “A 'No' uttered from the deepest conviction is better than a 'Yes' merely uttered to please, or worse, to avoid trouble." Question: What bigger yes gives you the courage to say no?

3. They connect the dots across many fields. In a world that rewards narrow specialists, insider-outsiders roam widely — history, science, philosophy, psychology, the future. As Thiel put it: “There has to be room for at least one generalist in a world where everyone's hyper-specialized.” Lesson: Your many interests are not a distraction. They are your raw material for novel, original, and meaningful ideas.

4. They move between the crowd and solitude. They join, then withdraw; contribute, then create alone. This rhythm can puzzle others. Tip: Protect both halves — the time with people and the time without them.

5. They hold themselves — and others — to high standards. Insider-outsiders strive for excellence. When they meet people who are content with "good enough" — in a team, a company, or an institution — they grow restless, and sometimes say so. That rarely wins popularity contests. In the same interview, Thiel offered a provocative distinction: “The moral antonym is evil. The functional antonym is bad. A Ferrari is an evil car because it doesn't get many miles per gallon. A Trabby is a bad car.” 

Most of what goes wrong in organizations, he argued, comes not from malice but from mediocrity. My second founder friend, who runs a design agency, put it more bluntly: “When something is off standard, I can get extremely angry. But that's the magic sauce that got me where I am. I cannot compromise on that.” Question: Where have you settled for "good enough" when you know excellent was within reach?

6. They pay a price. Being in and out means being misunderstood, sometimes judged as arrogant or unsocial, and, at times, lonely. That is the cost of standing in the doorway. I wrote more about it in my reflection on twenty years as a black sheep.

Two Messages

To the insiders: If someone on your team keeps stepping in and out — joining lunch, then vanishing to work alone; skipping the party; asking odd questions — stop reading independence as arrogance. Start seeing it as a different way of contributing. That person may see what the group can't.

To my fellow insider-outsiders: Let me be clear — I am in no way comparing myself with Peter Thiel or the billionaire founders of the internet wave. A few insider-outsiders happen to be in the right place, at the right time, doing the right things — and they create extraordinary value for society. Many more of us are not there, and may never be. We are needed, too. Every system needs people standing in the doorway, looking both in and out. So walk your path, even when it feels lonely. And stay grateful to the insiders. Without them, there would be no house to step in and out of.

Where I Am at Home

So where do I belong? Partly in each of the places I have passed through — my village, the army, the bank, the faculty, the founders' club — and I carry something from all of them with me.

When I asked my design agency friend whether he feels like an insider-outsider, he didn't recognize himself at first. "I got out of what I didn't like, and I created my own space," he said. "So I don't feel like an outsider that much anymore."

His answer is mine, too. I feel at home when I work on a new innovation method or create a new creativity tool at Thinkergy, when I write, and when I stand in front of a group facilitating an innovation project or running a training workshop. In those moments, the question of belonging simply disappears.

As Henry David Thoreau knew: “If a man does not keep pace with his companions, perhaps it is because he hears a different drummer. Let him step to the music which he hears, however measured or far away.”

We may belong nowhere completely, but we can be at home in what we create.

© Dr. Detlef Reis 2026. 

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• Do you feel like an insider-outsider, too? Find out whether you're an Ideator — or which other talent type you are — with the TIPS test at tips-profile.com.
• Want to strengthen the mindsets that let insider-outsiders think for themselves and walk their own path? Discover Genius Journey, Thinkergy's creative leadership development and breakthrough creativity method.