Final Words

My biggest learnings and what I would do differently

That's it. My narration of my experience as a first-time entrepreneur, trying to get a travel tech venture off the ground, is coming to an end. The six years between 2015 and 2021 were exhausting yet incredibly inspiring. During this time, I learned things that an entire career in a large corporation would never expose you to—unless, I guess, you quickly reached the higher spheres of the corporate world.

This final section serves as a repository of my closing thoughts about the entire experience: my biggest learnings and what I would do differently. I also reflect on whether, given the chance, I would embark on such a journey again.

Do Your Homework

My biggest learning by far is that you shouldn't embark on such a radical endeavor without proper preparation. I did, and I paid the price numerous times. If, like me, you come from a corporate background, you have no experience with early-stage ventures. The only solution before starting your entrepreneurial journey is, therefore, to do thorough homework.

Don't skimp on the time you spend doing this preparation. Not only will it save you headaches down the line, but it will also increase your chances of success in the crucial first couple of years. Half of my struggles during my six years as founder of flyiin could have been avoided if I had taken time to investigate key topics before incorporating the company in Berlin with two people I barely knew.

Your top priority should be validating your Big Idea and all related topics—Expertise vs. Opportunity, Industry Dependencies, Barriers to Entry and Company Naming. If your Big Idea proves irrelevant, you'll hit a wall even with flawless execution.

Second in importance is choosing the right country and legal setup for your venture. Since European investors tend to be more conservative, if your Big Idea goes against local market “flavors”, your only funding options might be US-based investors. In such cases, you may need to establish a structure that allows for an easy flip to a US Delaware-based company, eventually.

If you're launching your venture with co-founders from day one, be crystal clear about the profiles and mindset that will maximize your effectiveness as CEO, and implement dynamics that set your venture up for success. Funding mechanisms and models are another crucial area to study and understand, though this can wait until you approach your first funding round.

What I Would Do Differently

Writing this blog or book has been primarily a therapeutic exercise. Even with my years of experience and accumulated “wisdom” (another big word here), there's always room for self-reflection. I've made numerous mistakes along the way. If you've read through every chapter, you'll have a clear picture of these missteps. Looking back on my entrepreneurial journey, there are five key things I would do differently.

Most importantly, I would have started solo, bringing in co-founders only after validating my Air Travel Marketplace concept. I would have leveraged my airline network to secure API access from a few carriers. Then, I would have hired contractors to help build a proof of concept, launch it, and test it with friends booking actual flights before seeking pre-seed funding. Only then would I have brought on a technical person full-time—testing our working relationship before potentially making them a co-founder during the next funding round.

Second, I would have structured the company differently—probably establishing a holding company in a country with a more flexible tax framework, like Ireland. At minimum, I would have created a personal holding company to own my shares in the German GmbH. I would have also avoided early expenses like office space and other non-essential costs, waiting to pursue them only once the venture was more established—which, in all honesty, it never achieved.

Regarding our Big Idea, I still believe that our concept of Air Travel Marketplace was—and remains—spot on. I should have fought harder against the pivot to a pure B2B vision. The transition to our Airline DirectConnect Platform forced us to secure deals on two fronts: airlines and resellers. Our failure to sign up resellers meant very few live transactions went through our platform. Had we stuck to our original vision, I'm convinced we would have processed far more transactions, making our product and technology significantly more valuable.

The final aspect I would change is my approach to product. As I've mentioned throughout this book, I should have taken ownership of the product from day one and maintained control until reaching product-market fit. This would have ensured that resources were spent on must-have features rather than nice-to-have ones. Most importantly, we could have launched in months instead of years.

Would I Go For It Again?

Without a doubt, yes. I have learned more during these six years than in my previous 20+ years working for large corporations or as a self-employed consultant. No other career path would have given me access to such constant decision-making, incredible insights into people management, and the opportunity for deep self-discovery. Even the negotiations and closure of Priceline's acquisition of flyiin were, in themselves, like completing a mini MBA.

As the originator of the Big Idea, especially in the early years, nearly every decision falls on your shoulders. Even after building a team, you'll still make most of the decisions since functions like finance, sales, marketing, and investor relations remain your responsibility. Though some of my decisions were wrong, late, or never made at all, I thrived under the pressure of being the master of our destiny—even when it came to trivial matters like choosing office snacks or picking a restaurant for our Christmas celebration.

Being based in one of Europe's most cosmopolitan cities, flyiin—like most startups—brought together people from diverse backgrounds. Our small team of ten to twelve people represented ten different countries across Europe, Asia, and Africa. Though they all shared technical expertise, each brought their unique cultural heritage. I found it fascinating to learn about these different perspectives and work to create an environment that respected everyone's background. Working with colleagues from a younger generation also taught me to adapt my management style — and maybe some aspects of my sense of humor too — to meet different workplace expectations.

Lastly, and most incredibly given that I was in my late forties, I discovered things about myself that few other journeys would have revealed. I discovered a resilience within myself that I had always suspected was there but had never fully put to the test. I also realized I lacked certain essential entrepreneurial traits—traits well described in Ben Horowitz's book "The Hard Thing About Hard Things." You must be ready to make tough decisions that sometimes (often) go against your personality. You need to make calls your co-founder might disagree with, even in their areas of expertise. And you must make these decisions quickly.

This self-discovery has been perhaps the greatest outcome of my experience as a "late first-time entrepreneur." Since I'm not planning to retire anytime soon, these insights will serve me well as I look for my next challenge.