Big Idea

Expertise vs. Opportunity

Before investing significant time and money in an opportunity, distance yourself from your industry and read it with the highest possible level of objectivity. Reflect on your possible biases: Are you overestimating your own knowledge and expertise? Are you overestimating or misinterpreting signals that the opportunity exists?

Industry Dependencies

Speak with other emerging companies that are already working with your target industry. Ask them about their experience and inquire about the length of the sales cycle and the reasons behind it. Then, decide whether you are ready to enter that industry or not.

Barriers to Entries

Homework is, once again, the key here. Establish the barriers to entry in your industry and evaluate the cost of making your way in. Make sure to understand the internal operations and commercial aspects of your target customers to determine their liabilities towards their established vendors.

Company Naming

Spend the time required to come up with a company or brand name that people will remember. Use any of the GenAI tool to help you with this process. Check a few online resources to learn the basics of brand development and test it extensively with your network. If you realize that people have a tough time referring to your brand correctly, change it immediately.

Founding Team

Founder Profiles

If your venture requires a founding team, seek out individuals who possess a unique combination of domain expertise, communication skills, and organizational abilities. Be demanding in your search. If one of these skills is missing, it is better to pass and look for another individual with a more suitable profile.

Mindset

Do not make anyone a founder until you are completely sure that you can work with them. Reach an agreement with them on all key aspects of the venture before spending the first euros or dollars. If you are unable to do so, it is better to work alone at first. Seriously.

Capital Ownership

When creating a company, it's important to keep, at first, the majority of shares and voting rights for yourself. Don't compromise on this. You need to maintain control of the key decisions that will impact the venture, particularly if you are the driving force behind it and bring the network and domain expertise needed to put the company on the map.

CEO Priorities

During the first few years, it's essential to get your hands dirty by delving into the nitty-gritty of your product and taking ownership of the product roadmap. Spend the remainder of your time building the foundations for growth and the discipline that comes with it.

Company

Country

Don't be fooled by your perceptions of a particular tech hub. It's important to do your homework and evaluate the extent to which the country facilitates entrepreneurship. Understand the cost of building and, more importantly, retaining a team there.

Law Firm

Choosing established, experienced law firms or small shops to set up your business and assist with funding raises may not be the best choice. Instead, search for mid-size firms that have experience with venture capital and international exposure. Seek advice and learn from other early stage companies about their recommendations and experiences.

Taxes

To protect yourself from unexpected tax situations, it is important to set up a legal entity to own your shares in your venture. Depending on your location, this may cost a few hundred euros per year to maintain. However, it will save you headaches and ultimately be key to a successful funding raise.

Funding

Don't feel compelled to jump on the well-publicized, venture capital-driven funding bandwagon if it's not necessary. Fundraising efforts can be a major distraction and often overrated. Instead, consider alternative financing options that will allow you to focus on your business while securing the necessary funds.

Technology

Your technology stack choice significantly impacts your venture's growth, product quality, and team building. Dedicate ample time to this decision with a suitable technical co-founder, as it's one of the most crucial after defining your big idea.

Fundraising

Homework

When it's time for you to negotiate the first term sheet, make sure you allocate enough hours to learn about funding. By doing so, you will be well-prepared to secure the best possible deal as a founder. Additionally, you will save on legal fees that can be invested elsewhere.

Timing

One golden rule is to never, ever rush to seek external funding until the time is right. Instead, focus on building a small product, shipping it, and acquiring your first customers. This approach will provide you with more options and a stronger negotiation position when you're ready to raise your seed round.

Investors

If you are unable to convince multiple investment firms to discuss a term sheet with you, it indicates that your venture is not attractive enough. In such a case, you may want to reconsider your big idea and potentially end the journey. The worst outcome would be to have the wrong investors with unfavorable terms, which will inevitably lead to an even worse situation down the road.

Terms

When reviewing your first term sheet, focus on three critical elements: pre-money valuation, vesting, and liquidation preference clauses. Investor-friendly, standard terms that protect founders suggest you've found the right partner. If the terms are unfavorable, continue your search for a more aligned lead investor.

Amount

When choosing between large or small funding rounds, consider your desired company structure. Do you want a lean team of versatile individuals working under pressure, or a larger, more traditional organization with diverse profiles? Your funding choice will significantly shape your early-stage company culture.

Use of Funds

Office Space

After securing funding, resist splurging on office space. Instead, invest in robust virtual infrastructure and tools for effective remote collaboration. Organize regular in-person meetups to foster team spirit and culture and to collaborate on key design work.

Team

When building your initial team, prioritize the most critical roles that will enable you to go to market quickly and validate your big idea with real customers. Additionally, hire an HR professional right away to avoid costly hiring mistakes in the early stages.

Salaries

With limited funding, prioritize achieving the highest return on investment. Pay your team members at market rate, but clearly communicate that improved compensation hinges on more solid financials (e.g., new funding rounds or large customer contracts). If a team member receives a better, above-market offer elsewhere, don't try to match it at that point.

Perks

Wait to introduce perks until your company's future is more secure. Gradually expand benefits as customer contracts and revenue grow. Make this approach clear to your team from the start. If your finances permit, consider investing in sending your tech team to their annual developer conference—the return on investment tends to be immediate.

Travel

Travel is crucial for building relationships and brand awareness in a startup. Budget wisely and embrace cheaper accommodations to maximize networking opportunities. One well-timed trip can lead to significant business breakthroughs, justifying the investment in travel.

Day-To-Day

Human Resources

Your early investment in HR will set your venture on the right path. By prioritizing a professional recruitment approach and fostering an open, transparent culture from the start, you'll attract better talent and retain them long-term—even when times get tough.

Product & Tech

Lead product definition initially, especially for digital experience-focused products. For API-first products, share responsibility with your technical lead. In both scenarios, strong collaboration is crucial. Maintain product leadership and avoid outsourcing to a CPO or Product Manager too early.

Sales & Marketing

Prioritize product-market fit before hiring sales and marketing people . Focus on building your product, attracting customers, and crafting a compelling story. As the founder, you're the best salesperson to initially drive growth.

Objective Setting

Implement a process for setting, monitoring, and communicating objectives from day one, with OKRs (Objectives and Key Results) being highly recommended. This framework organizes priorities and ensures team alignment, proving invaluable as the company grows.

Customers

Commercial Strategy

A successful commercial strategy often requires taking a contrarian approach, targeting new markets or customers. While the overall strategy should be clear, execution may be chaotic, so remain flexible and open to pivoting based on feedback from select potential customers.

Business Model

A clear business model is crucial even in early stages, as it's essential for onboarding partners, customers, and investors. Develop a clear, understandable business model that aligns with your marketing proposition, but be prepared to offer initial discounts or free trials.

Pilot Customers

Onboarding pilot customers early is key to validate your product vision and shape your roadmap, but securing agreement isn't enough. It's essential to ensure all key stakeholders within the pilot customer's organization are fully on board to avoid potential sabotage. If you have a choice, select those who more closely align with your target market.

Suppliers

Onboarding suppliers is essential for the success of a marketplace venture and resembles the fundraising process. It requires a compelling vision to create a fear of missing out among your target suppliers. Success hinges on demonstrating your marketplace's potential—through prototypes for consumer-facing marketplace or pilot customers for B2B platforms.

Life

Family

Starting a tech venture requires abandoning romantic ideals of entrepreneurship, as it demands heavy financial sacrifices with no guaranteed success. The constant pressure of running the business can severely strain family relationships, making it crucial to prepare your loved ones for this challenging journey.

Hobbies

While being obsessed with your first startup is natural, it's crucial to maintain a healthy work-life balance by protecting time for hobbies and activities away from screens. These moments, especially when shared with family, allow your mind to regenerate and ultimately contribute to both your well-being and your venture's success.

Friends

Close friends are essential companions on the entrepreneurial journey, offering unique value through their unbiased perspectives and emotional support that differs from family involvement. Their distance from the entrepreneurial world allows them to provide fresh insights and create a safe space for expressing doubts without judgment.

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.

Another thing that made my chaotic entrepreneur journey manageable was the presence of friends. Just a few close friends who truly care about you can make a world of difference. While friends can't replace the unique affection, moral support, and physical presence that family provides, they offer these forms of support in their own way. What sets them apart from family members, however, is that they're not emotionally or financially impacted by your entrepreneurial missteps (or successes, for that matter).

These few close friends can serve as invaluable sounding boards. Actually, they're most helpful precisely because they're unfamiliar with entrepreneurship and work in different fields. Their distance from your professional world allows them to offer fresh, unbiased perspectives—especially when you're uncertain about decisions, caught in an emotional rollercoaster, or when your self-confidence has dropped to the level of your socks.

Often, they bring clarity to issues you're facing. Because they know you well, they can spot internal conflicts in your behavior and statements—even ones you're not aware of. They'll suggest paths you either didn't see or chose to ignore, and they'll help you face difficult realities. Even when your final decisions differ from their suggestions, they've helped by bringing new options to your attention. Most importantly, they provide a safe space where you can express all your doubts, concerns, fears, and hesitations without facing judgment, disinterest or their own fears.

Two friends of mine showed exceptional presence during my six-year Flyiin journey. They were there from day one until April 29, 2021, when Priceline completed the acquisition of the company. One of them was (and still is) completely removed from my professional world. Despite dealing with his own s… (pardon my French), he would check in every month to see how I was handling what was personally a difficult situation—especially during those first three and a half years when I wasn't earning anything.

While he couldn't help with specific work issues (funding, co-founders, etc.) given how different our professional worlds were, his constant presence and attention reminded me that I wasn't alone. And that matters, because entrepreneurship, especially in those early years, can feel incredibly lonely.

Another dear friend played an even more crucial role during those years. Having worked together early in our careers, he was closer to my professional world. He later became a professional coach and developed deep insight into the human side of business and organizations (and we all know how messy that can be). His contribution to my journey as a founder proved invaluable—he helped me see realities I was unconsciously avoiding.

For example, after our failed term sheet in 2017, he helped me recognize my sunk cost fallacy bias. Though I ultimately chose to persevere and continue investing rather than cut my losses, I made that decision fully aware of this bias. He also helped me understand the tensions that arose from running a company with a cofounder from different cultural and professional backgrounds. While these challenges persisted, having someone to discuss them with rationally was invaluable.

Key Takeaway #34

Close friends are essential companions on the entrepreneurial journey, offering unique value through their unbiased perspectives and emotional support that differs from family involvement. Their distance from the entrepreneurial world allows them to provide fresh insights and create a safe space for expressing doubts without judgment.

Being obsessed with your first company is, I guess, natural. That was certainly my case. You've been thinking about your big ideas for possibly many years. You've chosen to sacrifice a certain lifestyle to bring this idea to life. If your idea is sensible, you will have assembled your founding team and brought early investors on board. You may even have made your first hires.

Every step in the initial phase of your journey brings more responsibilities, more decisions to make, and more doubts to address. Your entire life then revolves around this new baby of yours. If you can't find even a little time when your mind isn't focused on it, you'll burn out. The result? You won't be able to think clearly, you'll make more mistakes than usual, and you'll make your family's life even harder.

This is where having solid hobbies plays a crucial role in your well-being—and ultimately in the early successes of your venture. Make sure you protect time for these activities at all costs. These moments allow your mind to wander elsewhere. My personal advice is to choose activities that take you away from screens. Whether it's sports, arts, music or cooking or even learning a new language—through group conversations, the goal is to disconnect from your venture. Like any other muscle, your mind needs time to regenerate to perform efficiently.

If these hobbies involve family members, even better. They create precious moments to reconnect with loved ones, shifting your focus from the company to what truly matters. These moments are invaluable.

For those who know me, they're aware of my addiction to (free) skiing. Just like my focus on knowledge sharing and structured information at work, it borders on obsession. Skiing was one thing I refused to give up all those years. We did it on a budget—even venturing to the Czech Republic, which I never imagined visiting with skis but turned out to be surprisingly excellent for backcountry. Those weekends and weeks with the family were absolutely essential for my mental health because once on skis, all worries disappeared. The same would happen when mountain biking in summer.

Obviously, there aren't many mountains in Berlin or its surroundings. So here comes my other stress relief: running. At my most disciplined, I would run through the woods or along the Havel three or four times a week. Running doesn't take your mind off your company—at least it didn't for me. However, it does allow you to think quietly and calmly about it, sometimes leading to clearer decisions.

Living in Berlin means having access to abundant arts and music events. While I rarely went to concerts, I frequently explored galleries and museum exhibitions. These spaces were perfect for filling your mind with beauty instead of... emails to write and pitch decks to produce. My wife and I would often end such days at our favorite cocktail bar, sipping a negroni or old fashioned—though on the day of our successful seed raise, I traded my usual old fashioned for a cocktail called "millionaire".

Key Takeaway #33

While being obsessed with your first startup is natural, it's crucial to maintain a healthy work-life balance by protecting time for hobbies and activities away from screens. These moments, especially when shared with family, allow your mind to regenerate and ultimately contribute to both your well-being and your venture's success.

Here's another million-dollar question: are you ready for such a demanding and stressful journey? We often have a romantic view of entrepreneurship, imagining it will bring freedom, control, and success to our lives. However, the reality is quite different: you'll have little to no (financial) freedom, your venture will control your life, and success is far from guaranteed.

Are you still up to it? If so, that's great—but is your family on board? Have you thoroughly discussed what building a tech venture means with your life partner? Have you explained to your loved ones that holidays, nice restaurants, major purchases, and even gifts won't be as frequent as they were with your secure corporate job? And once you've had that conversation, remember this: whatever timeframe you've estimated for financial constraints, multiply it by two, at least.

Then there's the emotional pressure of running your own business. Your mind will be constantly focused on your venture—day and night. You'll sleep poorly, waking up in the middle of the night thinking about things you've done, haven't done, or done wrong. When you're with your loved ones, you'll only hear half of what they say (and I'm being optimistic here). Your family will understand at first and be flexible. But how will they feel after three years of this? Don't take this aspect of entrepreneurship lightly. Your marriage and family relationships could be the biggest collateral damage of your decision if you don't pay enough attention.

When I started working on flyiin, I was fully aware of what it would mean for us as a family. Having left my corporate job seven years earlier, we were already accustomed to a less comfortable lifestyle. When I decided to fully commit to flyiin, we relocated to Berlin due to its manageable cost of living at the time (though Berlin has changed significantly since then). Rents were cheaper than in most other European tech hubs, the French school was free, and we could go out without breaking the bank. While my business plan projected two years without a salary, this "transitional" period stretched to three and a half years, with my first paycheck finally arriving in January 2019.

Those years were, indeed, tough on everyone. I became obsessed with flyiin—perhaps inevitable for a first-time founder. My thoughts revolved around nothing else. I'd wake up at night to check responses from US-based investors and spend a couple of hours writing replies. Even during family weekends, my mind stayed locked on flyiin. My son would often stop mid-story and say, "papa, tu m'écoutes pas là" (dad, you're not listening to me now). It wasn't a healthy way to live.

The situation intensified as the company grew, bringing investors, staff, and objectives into the mix. The situation reached its peak during negotiations with our acquirer in 2021. We encountered last-minute surprises that threatened to unravel the entire deal—a key employee threatening to leave, and an investor demanding changes to deal terms just days before the signing date.

Key Takeaway #32

Starting a tech venture requires abandoning romantic ideals of entrepreneurship, as it demands heavy financial sacrifices with no guaranteed success. The constant pressure of running the business can severely strain family relationships, making it crucial to prepare your loved ones for this challenging journey.

I've spent most of my career dealing with the airline side of the flight sales business. Because of this, I naturally assumed that the supply side is the starting point of a marketplace or distribution business. To a certain extent, this is true. In a standard, healthy business model, suppliers pay to participate in your marketplace—and therefore pay your bills. The content they provide makes your marketplace attractive to your customers, whether those are end-consumers or other businesses. Moreover, the supply side offers a path for you and your team to gain industry expertise, ultimately maximizing the value of your venture in the long run.

How do you onboard suppliers when your product is still in development? Well, the supplier game closely resembles the fundraising game. If your suppliers are large, established businesses—like airlines—you need to pitch them a vision and product so compelling that they'll want to be first in. Essentially, you want to create a fear of missing out.

Easier said than done. The key is demonstrating that your marketplace will outperform others or open doors to untapped markets for your supply partners. In a consumer-facing environment, a well-thought-out prototype showing how users can purchase products more efficiently can do the trick. If your platform targets other businesses, it's trickier. You're making a promise they must believe you can deliver. Having signed-up pilot customers already will make your job significantly easier.

At flyiin, we actually did a good job of bringing airlines on board with our Air Travel Marketplace concept. There were several reasons for this success. First, I had a strong network within airline organizations, bolstered by the presence of a former airline CEO in our venture as our early angel investor. His association with flyiin opened doors and gave us instant credibility with many airlines. Second, some of the largest European and US airlines had made significant investments in building sales and distribution APIs, and they were eagerly seeking partners to use them. Finally, our product concept was refreshing, relevant, and incredibly appealing (I might be a bit biased here).

In about two years, we had secured the participation of more than ten airlines in our Air Travel Marketplace, with numerous ongoing discussions with others. At that time, airlines viewed us as an exciting newcomer and the ideal platform to test their sales and distribution APIs as soon as they were ready to expose them to third-party sales channels. We were on a roll.

In 2018, when we pivoted, it was a whole different game. Our traction with airlines slowed down. Sure, those already on board stayed on. Our strategy to serve channels outside the traditional travel agencies space was still appealing and sensible to them. However, we didn't have any platform customers yet to demonstrate the validity of our strategy. The signatures of two pilot customers didn't really change this—as they weren't representative of our claimed strategy.

Our story would have been completely different if we had secured either Airbnb or Capital One (both companies we were in discussions with). However, two major obstacles stood in our way. First, the Covid pandemic hit. Second, even without such crisis, these players wouldn't have partnered with such an early-stage company as flyiin.

Key Takeaway #31

Onboarding suppliers is essential for the success of a marketplace venture and resembles the fundraising process. It requires a compelling vision to create a fear of missing out among your target suppliers. Success hinges on demonstrating your marketplace's potential—through prototypes for consumer-facing marketplace or pilot customers for B2B platforms.

They do matter a lot, especially in a business-to-business environment. Involving pilot customers at an early stage is the best way to validate your vision and product concept. Moreover, it will help shape your product roadmap, maximizing your chances of reaching product-market fit quickly. This principle also applies to consumer-facing products, where you'll want beta users to test your product early on to confirm you're heading in the right direction.

Product development involves many critical decisions when creating your initial version. Consider a marketplace product, for example. You'll need to choose between a vertical or horizontal approach. Should you integrate a few suppliers with a broad range of capabilities? Or should you onboard many suppliers but limit the feature set? Pilot customers or beta users are invaluable in helping you make these crucial choices.

An important consideration, though: securing a company's agreement to pilot your product doesn't necessarily mean you're in the clear. All key people in this company need to be fans of your product concept and must perceive it as critical for their future growth. You may have convinced the CEO, but others in management might not be on board and could potentially sabotage the pilot phase (again, I have learnt this the hard way). Therefore, don't celebrate such a win too early. Instead, spend time developing relationships with all key stakeholders within your pilot customer's organization.

For reasons I've highlighted earlier, flyiin's consumer-facing Air Travel Marketplace never went live. Consequently, we couldn't determine if our new approach to marketing flight products was on the right track. Our approach was clearly contrarian to existing online travel agencies and flight search engines. It could have been either a tremendous success or a complete disaster—I'll never know.

When we pivoted to focus on developing our Airline DirectConnect Platform, we were fortunate to onboard a pilot customer just a couple of months after raising our only financing round. It was a good start, as it would allow us to go live within months. Unfortunately, two issues arose: the customer went out of business six months after we launched with them, and in the interim, we developed features that were possibly too specific to their needs as a consumer-facing product, and not entirely applicable to our wider market. Another crucial lesson: if you have the choice, select pilot customers whose needs align closely with your target market to avoid veering off course.

Twelve months later, just before COVID-19 hit, we secured another pilot customer—a travel tech company that chose to outsource their partner airline integrations to us rather than handling them in-house. Although not our target profile, we desperately needed to process live transactions to validate our platform. However, we faced a significant challenge (besides the pandemic resulting in zero flight bookings): we couldn't progress beyond implementing a single airline integration on their behalf, despite our initial agreement to integrate 4–5 airlines at minimum. This experience taught me another two valuable lessons: having the CEO's support alone isn't always enough and… don’t celebrate too early.

Key Takeaway #30

Onboarding pilot customers early is key to validate your product vision and shape your roadmap, but securing agreement isn't enough. It's essential to ensure all key stakeholders within the pilot customer's organization are fully on board to avoid potential sabotage. If you have a choice, select those who more closely align with your target market.

It does indeed. In fact, you won't have a chance to onboard supply partners, pilot customers, or investors if you don't have a basic idea of how you plan to generate revenue. Even some of your early employees will want to know this before committing to work for you. At a minimum, you should know who will contribute to your revenue: supply partners, users, bookers, advertisers, or a combination of these. While you likely can't precisely define fee levels yet, early discussions with your target revenue contributors will give you a clearer picture of what's achievable and when.

In a business-to-business context, establishing business model elements is crucial for onboarding supply partners and customers. Even when they're convinced of your product or solution's value, they'll need clarity on costs to secure the investment in their next budget cycle. That's why you should ensure your business model and pricing are easily understandable and aligns with your overall marketing proposition. Avoid the trap that many larger organizations fall into—pricing models with too many variables and fee levels. As always, do your homework and research the models that have succeeded and failed in your market.

A clear business model doesn't necessarily mean you can apply it from day one. You'll likely need to compromise, offering your product at a discount—or even for free—initially. Your pilot customers and partners will expect this concession. It allows them to validate their expectations of the product and support before committing to a longer collaboration with your venture.

When I first envisioned flyiin as a consumer-facing Air Travel Marketplace, I was confident that partner airlines would pay to participate. Our plan was to eliminate key players from the value chain, saving airlines significant distribution costs. We aimed to merchandise their products in a way that would reinforce, not commoditize them, while giving airlines ownership of travelers purchasing flights through our marketplace.

In reality, convincing airlines to accept our proposed model proved challenging (that’s an understatement). Many categorized us as just another online travel agency—albeit a refreshing and more innovative one—and consequently wanted to impose the same conditions: no commissions. Nevertheless, I proceeded because we needed these supply partnerships to bring our marketplace product to life. I remained confident that once operational, they would recognize the value of our sales channel and accept new terms beyond the pilot phase (that’s the eternal optimist in me).

The position of our partner airlines remained unchanged when we pivoted to a pure tech vendor role in 2019. In all honesty, I didn't reopen discussions with them and simply leveraged the previously signed pilot agreements. However, I managed to implement the demand side of our business model with customers who would use our Airline DirectConnect Platform to power their own flight products. While our fees were low compared to our competition (here is another understatement), the intent was to secure a foothold in our target market and generate live transactions through our platform. Unfortunately, we didn't fully achieve this goal. One of our pilot customers went out of business less than six months after signing the agreement—just our luck—and the other joined during the COVID-19 pandemic, resulting in zero transactions.

Key Takeaway #29

A clear business model is crucial even in early stages, as it's essential for onboarding partners, customers, and investors. Develop a clear, understandable business model that aligns with your marketing proposition, but be prepared to offer initial discounts or free trials.

A basic commercial strategy is crucial for a strong start. No question about this. Defining your target market and how to reach it will guide which product features to develop first. It will also help prioritize supply partners to onboard, if your business relies on them.

Unless your venture addresses an industry that's yet to be digitalized (are there any left?) or focuses on a geography without established players, your best chance for commercial success is to take a contrarian approach. Whatever path the incumbents in your market follow, take a different—possibly opposite—one. If the barriers to entry are high, expand your market's boundaries. Consider potential customers who aren't on the incumbents' radar. Think about how your product will improve consumers' lives or enhance other businesses’ operations and revenues.

Commercial strategy isn't the same as commercial planning, especially in a business-to-business context. As you pursue your first pilot customers, opportunities may vanish as quickly as they appear. Discussions with early customers will likely influence—sometimes significantly—your product development roadmap. This will put pressure on your team (and yourself). Make it clear to them that while the strategy may be set, the execution will probably be chaotic.

When we started working on our concept of a consumer-facing Air Travel Marketplace, I'll be honest: I didn't have a specific segment of travelers in mind. I simply knew that online travel agencies were twenty years old and flight search engines were ten years old—neither of which, in my view, were meeting the expectations of both travelers and airlines anymore. We did speak to and present our prototype to our partner airlines. All were excited about it because it provided an opportunity to test the APIs they were building. However, we didn't speak to many travelers before starting to design and build our prototype. That was a mistake, one which could have been costly if we had proceeded with our original vision and got it wrong.

When we pivoted to become a tech partner for consumer-facing brands, I realized our success hinged on looking beyond traditional online travel sellers These established players were locked into their historical tech partners (known as GDS) due to technical, functional, and—as importantly—financial reasons. With no viable business model in this market, we couldn't compete. Instead, I targeted other online players who weren't yet selling flights but could use our technology to enhance their existing customer offerings. My vision was to break open the flight sales market and expand it beyond traditional travel agencies—a strategy our main competitor quickly replicated.

We built an Airline DirectConnect Platform that conceals the complexity of flight products, allowing new players to sell flights and associated services as easily as they would sell a pair of pants and a matching sweater. We had several promising discussions (including with Airbnb), but the reality is that this strategy was probably too bold and certainly too visionary (story of my life). Then COVID hit, and the whole thing became history. Ironically, it was one of the traditional online travel players that ended up buying us.

Key Takeaway #28

A successful commercial strategy often requires taking a contrarian approach, targeting new markets or customers. While the overall strategy should be clear, execution may be chaotic, so remain flexible and open to pivoting based on feedback from select potential customers.

Those who know me would say I'm extremely (excessively might be a better word) organized—start by asking my wife. My obsession with knowledge sharing and structured information might even be seen as borderline obsessive. There is a reason for this. My experience in larger companies has shown me, time and again, how much time and productivity is wasted when information isn't widely available or easily accessible. This creates inefficiencies, duplications, and misalignments that early-stage companies with limited funding simply can't afford.

Even if process and structure aren't your cup of tea, I advise establishing at least one process as early as possible. This process should help create, monitor, measure, and communicate objectives for yourself and your team. Your first investors will expect quick progress on key milestones. Without a process to efficiently prioritize the many competing priorities within your company, you'll likely fail.

Those who have worked with me in recent years know my passion for OKRs (Objectives and Key Results). I strongly recommend that founders implement OKRs in their company from day one—and read John Doerr's "Measure What Matters," which is truly eye-opening. Many of your team members might find this exercise premature or excessive at first. However, trust me—it will instill a discipline that will serve you well as your team and customer base grow tenfold. Even at this early stage, OKRs provide a framework to organize your management priorities and goals, and communicate them to the rest of the team. This transparency is key to achieving a level of alignment and efficiency that few companies manage to attain.

During flyiin's initial phase, I hadn't established a proper goal framework, as we had neither a team nor investors in place. I began using OKRs a few months after our successful—and only—funding round in 2019. I'd heard about OKRs and how they were incredibly helpful for founders managing numerous priorities and ensuring team alignment. I immediately bought the book I mentioned above and read it within a couple of weeks. Convinced by the model, I decided to implement it at flyiin right away, despite our team consisting of fewer than 10 people.

I presented the model to my co-founder and the team, starting by drafting annual, high-level OKRs that touched on all aspects of the venture. This gave them visibility into what we should achieve by the end of the year. Then, I asked the product and tech teams to produce quarterly OKRs, providing them with a framework to define and monitor their contribution to our yearly objectives. I would draft myself quarterly OKRs for the other areas (sales, funding, finance, operations, etc.).

The team wasn't sold on the necessity of going through this process at such an early stage. At first, they found it to be a complete waste of time because we were changing focus quite often, depending on the commercial opportunities that popped up. Despite their reluctance, I kept pushing for OKRs as they provided me with the best methodology to keep the team updated on how well or poorly we were doing against our objectives and on our overall progress. I believe the team ultimately recognized the value of OKRs as we approached our acquisition by Priceline.

Key Takeaway #27

Implement a process for setting, monitoring, and communicating objectives from day one, with OKRs (Objectives and Key Results) being highly recommended. This framework organizes priorities and ensures team alignment, proving invaluable as the company grows.

The short answer is: whenever you've demonstrated solid product-market fit. But when is that? Product-market fit happens when you're gaining real, sustained, repeatable traction from those who drive revenue. For example, if you build a marketplace, traction comes when you have many end-consumers or demand channels actively using your platform for transactions. While having the right supply base is crucial, it's customer demand that truly signals product-market fit.

Investing in any commercial role before reaching this milestone would be like throwing your hard-earned seed money out the window. This means, however, that you have another set of important tasks on your to-do list: attract and sign supply partners, convince demand customers (in a B2B environment) to take a leap of faith and try your product, build your brand, and develop a suitable yet scalable pricing strategy. The good news? You'll be the best person for these tasks. As the driving force behind the company, you're passionate about your big idea, which makes you the best salesperson—even if sales has never been your strong suit, like me.

Of course, you've got to find ways to do all this efficiently (meaning cheaply). In my experience, a successful commercial start hinges on two factors: a live product and an engaging story. With these in place, you'll be able to open doors to key supply partners, industry press, and pilot customers. Don’t travel around or make calls until you’ve got this in place.

Despite early challenges with product execution, the first flyiin was a marketing and sales success. Many major airlines embraced our vision of a new consumer-facing platform that would challenge traditional online travel agencies and flight search engines. Our timing was perfect—we offered airlines a way to justify their substantial investments in their new distribution APIs.

In less than 18 months, we had convinced over 10 major airlines to join our Air Travel Marketplace concept. The trade press was writing about us, and we had secured a large, founder-friendly investor to finance our live product development and go-to-market strategy. We achieved all this without a dedicated budget or role—our compelling story and prototype product did the trick.

After our failed seed investment and pivot to a pure tech solution, we had to start anew. While most airlines remained on board, some were less enthusiastic about the pivot. Our new challenge was finding "demand" customers—consumer-facing brands or tech players who would use our platform for booking transactions with our partner airlines. We signed two pilot customers in 2019–2020 (one of whom shut down just two months after going live with us). Yet, the reality was that our story lacked sufficient appeal, and our product wasn't quite ready to execute our strategy effectively.

I brought on board a more experienced commercial person in the middle of the COVID-19 pandemic. In denial of our reality—we were going nowhere—I wanted to establish the foundations of proper sales and account management early on. Not a very smart decision (to say the least). I had to let this person go just five months after she had joined our team.

Key Takeaway #26

Prioritize product-market fit before hiring sales and marketing people . Focus on building your product, attracting customers, and crafting a compelling story. As the founder, you're the best salesperson to initially drive growth.

Anyone who has worked in tech knows the challenges of collaboration between product and technical teams. How should these teams work together? Who has the final say? Who owns the roadmap and deadline accountability? These questions often arise in many tech companies, both young and mature. However, they shouldn't concern you in the early years of your entrepreneurial journey. Here's why.

In my view, the CEO of an early-stage venture should undoubtedly lead product definition. As the company's founder, you've cultivated the vision behind it, which is your responsibility to execute as quickly as possible. At this stage, there's no need for a CPO or product managers. If your product's success hinges primarily on digital experience, you should define these elements and prioritize their development —while naturally considering input from designers and developers who will help you bring your product to life.

If your venture is API-first, share product responsibility with your technical co-founder or lead. The product's success in this case depends primarily on the technical capabilities and developer-friendliness of your APIs. Nevertheless, stay as close to the product as possible. This proximity equips you with the knowledge to speak intelligently about it and make crucial decisions whenever needed. It also frees up time for your technical co-founder to focus on secondary but key aspects such as data privacy, security, and system reliability. Needless to say, maintaining a solid relationship with your technical counterpart is essential under this model.

One of my biggest regrets as CEO and founder of flyiin is not paying sufficient attention to our product—both our Air Travel Marketplace in 2016–2017 and our B2B Airline DirectConnect Platform from 2018 onward. The primary reason? As I wrote before, I was afraid to take on this role. I didn't feel I had the necessary skills, nor did I believe I could learn them quickly enough to do the job properly (ever heard of imposter syndrome?). A younger version of myself probably wouldn't have had these doubts.

This fear led me to make two crucial decisions. In 2015, when a contact in Berlin expressed interest in becoming a founder and CPO of flyiin, I saw it as a tremendous asset. I thought this would free me from worrying about developing our Air Travel Marketplace, allowing me to focus on fundraising, sales and marketing. Similarly, when we changed course in 2018, I let my final co-founder and CTO drive the definition of our Airline DirectConnect Platform.

The first decision was simply wrong. In an earlier chapter, I shared my views on why. The second was half-wrong. Our tech team did a great job designing and building a platform and API that I still consider superior to anything else built at the time, even five years later. However, I should have prioritized gaining a deeper understanding of these technologies, and managing the roadmap, and describing requirements or user stories. We didn't need to hire one—let alone two—product managers. I should have taken on these responsibilities myself and saved the salaries to extend our runway. Another lesson learned.

Key Takeaway #25

Lead product definition initially, especially for digital experience-focused products. For API-first products, share responsibility with your technical lead. In both scenarios, strong collaboration is crucial. Maintain product leadership and avoid outsourcing to a CPO or Product Manager too early.

I previously wrote that one of your first hires should be someone to help with recruitment, HR operations, and other aspects related to managing your company's most important asset: your team. At such an early stage, what matters most is how professional and credible you appear to the talent you're seeking to help build and roll out your product quickly. Since you won't have all the perks that larger or well-funded startups use to attract talent, the way you manage the people component of your venture will make the difference.

Once you've found the perfect match for your HR role, design and implement a solid recruitment process (and stick to it). This should include interview questionnaires and assessments that show you take recruitment seriously. Implement simple but efficient HR management software. Finally, ensure that you, your co-founders, and your HR partner craft job descriptions that best reflect the kind of company and brand you aspire to be.

Your early focus on HR shouldn't stop at recruitment. Once your first team members are in place, show that you care. Hold all-hands meetings from day one. Establish one-on-one meetings where every employee has a safe space to express concerns, issues, or sources of satisfaction directly with you and/or your co-founders. This will set you apart from many companies (who often fall short in this area). One last piece of advice, echoed by many: Don't hire too quickly just because you want to move fast. Hiring mistakes drain a lot of energy. If you don't find a good match, hold off on hiring for now.

At flyiin, we brought someone to help us with HR just two months after securing our first (and only) round of funding—which proved to be a good move. Actually, I had made her a first offer already in 2017 when I thought we had secured financing for our Air Travel Marketplace model. The term sheet fell through (as you know so well by now), so I had to tell her the position was no longer available—talk about credibility. Surprisingly, she still joined two years later when we pivoted and finally had cash in the bank (but I had to show her a bank statement).

We quickly assembled a team of eight engineers, including quite a few stars. We established a few principles to ensure this small but crucial team felt properly informed and motivated. We held monthly all-hands meetings to share transparent updates about our situation. We established monthly one-on-ones for every member to speak openly with my co-founder or myself. We also hosted regular team outings to foster a sense of community and team building—except for that one after-work bar gathering which resulted in a trainee being let go the next day. That much for team building.

I am convinced that our focus on building strong HR foundations and maintaining a high level of transparency enabled us to keep the team together even when things got complicated—ultimately leading to our way out with Priceline (rather than having to shut down the business).

Key Takeaway #24

Your early investment in HR will set your venture on the right path. By prioritizing a professional recruitment approach and fostering an open, transparent culture from the start, you'll attract better talent and retain them long-term—even when times get tough.

Yes, absolutely. When building a new company, brand awareness in your target market is a critical success factor. You'll begin by tapping into the usual channels: your industry networks, your advisors' connections, LinkedIn, and your industry's trade press.

Building relationships to reach your first commercial and product milestones is essential. You'll need to hit the road early to meet potential customers and partners, pitching your vision, roadmap and early wins. Find creative ways to attend key industry conferences affordably—for example, by securing speaking slots in breakout sessions or entering startup competitions. Connect with companies in your space, including your existing and potential competitors; these early relationships could become vital lifelines if plans don’t go as planned (as they did for flyiin).

Occasionally, you may need to fly out to meet with VC firms. However, before doing so, ensure you have solid numbers to present. Also, make sure you're meeting with the right people—not just junior analysts or associates who sometimes request meetings merely to appear busy. Otherwise, you'll waste both time and money.

You'll need to bid farewell to the corporate travel comforts of your previous life, though. Two-star hotels, Airbnbs, and budget airlines and basic economy fares will become your new normal. Fancy dinners? Forget about those (unless someone else is treating). Pizza, burgers, and ramen will be the norm. Funnily, the transition will feel natural. Your drive to bring your company's vision to life will far outweigh the loss of travel comfort.

Despite lacking a live product, flyiin’s Air Travel Marketplace concept garnered significant industry and press attention, establishing our brand early in the market. By 2017, we had built surprising momentum that exceeded my expectations from two years prior. Our success came from signing several major airlines for our beta phase. While our disruptive approach played a crucial role, the decisive factor was the personal relationships I built through multiple airline visits.

A few years later, as we pivoted to become a pure tech player, a single day trip to London to meet with a CEO resulted in our second—and ultimately only—pilot customer for our Airline DirectConnect Platform before our collaboration with Priceline. These one-day lunch meetings also opened doors to pitch our platform to Airbnb and discuss potential collaborations during their exploration of the transportation space—though they later abandoned that initiative.

I must admit that some of my accommodations severely tested my comfort levels. I vividly recall an Airbnb in Barcelona shared with three strangers attending the same conference—seriously challenging my sense of comfort at 46 years old. I also remember a rather shabby apartment rental in Fort Lauderdale and a basic hotel in Dubai for other industry conferences, while fellow attendees enjoyed the comfort of five-star hotels. That's when you become acutely aware of the difference between being a founder of a very early-stage venture and having long-term corporate employment.

Not to mention those long-haul flights at the very back of the aircraft or the one-hour commutes on the Berlin U-Bahn at 5 a.m. to catch a 7 a.m. budget flight.

Key Takeaway #23

Travel is crucial for building relationships and brand awareness in a startup. Budget wisely and embrace cheaper accommodations to maximize networking opportunities. One well-timed trip can lead to significant business breakthroughs, justifying the investment in travel.

I come from a generation where you'd be lucky to get free coffee, even within tech firms. Then, the Google and Meta of this world created a trend of "free everything," making it hard for emerging companies to compete. Younger generations working in tech became accustomed to these perks and now expect all tech companies to provide them.

If you are not investing in office space (like I suggested in a previous chapter), perks won't be an issue. However, if you decide to bring your team together in an office a few days a week, it will be. My advice is to resist the urge to jump on that train just yet. Sure, provide the basics like coffee, the ubiquitous Friday (or now Thursday) beers, and a few out-of-office lunches or dinners. These will help build a sense of community within the team and reveal sides of your team members that might not surface during work hours.

However, don't let perks—including training and language courses—become expected benefits too soon. They have a cost and can create a culture of entitlement, which isn't healthy at this stage of your venture. Just like with salaries, be disciplined about perks and expand benefits as your company develops and becomes more stable. Make this clear to any team members who choose to join your journey.

Truth be told, when flyiin became more than an entry in the local commercial register, I was all for perks. Just like the office space, it made me feel that we were real. A team, an office space, and perks: the dream was now reality. I immediately bought a fridge (which we'd give away two years later), stocked it with soft drinks and beers, and filled a few IKEA bowls with healthy and not-so-healthy snacks. I'd diligently restock these every week at the local supermarket (yes, that's also part of the early-stage startup gig). Our tenant provided this terrible coffee I spoke about before, and tea, at a cost.

What quickly became clear was that perks would become a topic of discussion, and a recurring one: "Can we have other types of soft drinks?" "Can we get our own water cooler because the tenant's is too far away?" “What about a monthly gym subscription?” There was even a request for an ice cream machine (well, that one popped up in the retro notes as a joke because the team knew these perk discussions were driving me nuts).

Since our team consisted entirely of non-German employees, we offered German language courses. Although this perk was right, looking back, I believe it was premature. There was, however, another perk my co-founder introduced early on that proved to be a good decision. Each year, we'd send our tech team to the annual conference for developers using our tech stack. Our participation in ElixirConf EU not only enhanced our employer brand but also directly improved the quality of the platform we were building.

Key Takeaway #22

Wait to introduce perks until your company's future is more secure. Gradually expand benefits as customer contracts and revenue grow. Make this approach clear to your team from the start. If your finances permit, consider investing in sending your tech team to their annual developer conference—the return on investment tends to be immediate.

I didn't pay myself any salary for more than three and a half years. Here's the reality: until you secure your first significant round of funding, regular salaries are off the table. If you and your family aren't prepared—both mentally and financially—to go without a steady income for an extended period, entrepreneurship isn't for you.

This "no salary until proper financing" principle applies to co-founders too. Your priority should be conserving resources until you've validated your product with real customers. Yes, you'll face the challenge of finding founding team members who are hands-on and willing to work without immediate pay. That's, however, the only viable path forward. If you're working solo, you'll likely need to outsource tech and product work—but avoid giving equity to agencies, as this often creates messy situations later.

Salaries should become a focus only after securing funding. At this stage, be transparent with potential team members about your financial runway. Avoid making unrealistic promises just to attract talent. Make it crystal clear that salary reviews will only happen after your next funding round or once you've secured substantial recurring revenue from customers—this is an absolute must.

Those joining will likely do so for the nature of your project and the technical challenge, not (yet) the compensation. What about offering equity instead of competitive salaries? In my view, equity only makes sense once your venture is more solid. There's no need to invest time and legal fees into a compensation model that might ultimately prove worthless.

When we incorporated flyiin in Berlin in the summer of 2015, my original co-founders agreed to work without immediate compensation. However, one left almost immediately, and the other devoted only a fraction of his time to the project—which was problematic enough (even worse, we hired his own design and usability agency to create the prototype of our Air Travel Marketplace. Can you spot the glaring conflict of interest? Looking back, I still can’t believe that I allowed this to happen).

In the meantime, the back-end tech work was outsourced to a software development agency in Budapest. That turned out to be a good move for two reasons. First, the lead developer eventually became my final co-founder. Second, they built a prototype that landed us a very favorable term sheet with investors who would have been excellent partners. You already know how this ended.

When we were ready to pay salaries, we managed to strike the right balance. We needed to be attractive in a competitive market—the pool of talent in our chosen tech stack was scarce at the time—while also considering our monthly burn rate and return on investment. Though it went against my initial stance, I approved targeted and reasonable salary adjustments that helped us retain our entire team—which proved crucial for our eventual exit to Priceline.

As I highlighted in the previous chapter, our mistake wasn't spending too much on salaries. Instead, we made the mistake of investing in unnecessary roles like product managers and a sales person.

Key Takeaway #21

With limited funding, prioritize achieving the highest return on investment. Pay your team members at market rate, but clearly communicate that improved compensation hinges on more solid financials (e.g., new funding rounds or large customer contracts). If a team member receives a better, above-market offer elsewhere, don't try to match it at that point.

It's hard to say. When I started thinking of flyiin as a venture, I had grand plans for the organization's structure—all heavily documented, as you'd expect from someone who had spent (too) many years in large corporations. The reality is that there's no universal formula for structuring your team during the early stages. The ideal setup depends on your business's nature. With limited funds, you should focus on recruiting talented, committed individuals who can quickly drive significant progress in crucial areas.

When structuring your initial team, prioritize roles critical for developing and rolling out the first version of your product rapidly. This approach allows you to validate your vision efficiently while conserving resources. For tech ventures, investing in a core technical team is the natural path—but it does not necessarily have to be a large one. My experience with flyiin showed that a small, well-crafted, and talented technical team can take you far. As founder, handle all other functions yourselves.

One crucial exception though: invest in a top HR person from the beginning. This investment will not only prevent numerous headaches later on, but also play a vital role in implementing a proper hiring process. You must approach this key aspect with utmost diligence from the start. Write detailed job descriptions, develop comprehensive interview questionnaires and technical assessments, and implement a structured system for evaluating candidates. This way, you will increase your chances to select the most suitable individuals for your team. Remember, at this stage of your venture, you can't afford to make hiring mistakes.

During flyiin's first phase, our B2C focus led me to be persuaded that we should heavily invest in product design and usability. The goal was to showcase how our Air Travel Marketplace concept differed from existing online travel agencies and metasearch engines. In hindsight, that was a mistake - resulting partly from my decision to bring a a branding and design person onto the company’s founding team. A simple design and digital experience would have sufficed. The 80,000 euros we spent could have been used much more effectively elsewhere—for example, in developing further tech capabilities, ensuring we went live, and supporting a beta release with our early adopters.

After pivoting to B2B and securing proper financing, my new co-founder and I built our first team. In retrospect, we didn’t do badly. Our technical team became a superb asset, instrumental in finding our way out two years later. This success stemmed partly from hiring a head of talent as our third employee. Her expertise enabled us to effectively screen over 150+ candidates throughout our journey. In contrast, one of the two hires we made before she joined turned out to be a complete disaster, underscoring the importance of a structured and focus hiring process from the start.

Of course, we made some hiring missteps, such as bringing on product managers - and even a salesperson (what was I thinking, really?) - when our product-market fit wasn't established. However, overall, our hiring decisions were mostly successful, thanks to our structured approach designed by our head of talent and the technical assessments put together by the tech team.

Key Takeway #20

When building your initial team, prioritize the most critical roles that will enable you to go to market quickly and validate your big idea with real customers. Additionally, hire an HR professional right away to avoid costly hiring mistakes in the early stages.

Having grown up in an era when going to an office Monday through Friday was the norm, I initially thought securing office space was the immediate next step for any startup after landing its first round of funding. It seemed like the only way to foster community and, if I'm honest, to feel like a "real" entrepreneur (yes, that was my ego talking).

While I still believe face-to-face interactions are invaluable for understanding someone's personality, interests, and values, my experience—"helped" by the pandemic—has shifted my perspective. A physical office space isn't a necessity from day one. You can cultivate meaningful connections through regular all-hands and off-site meetings and by effectively using digital collaboration tools—something very few companies actually master. Ultimately, creating a sense of belonging rests primarily on the founders' shoulders.

So, here's my advice: don't rush to burn through your hard-earned investment capital on office space. Instead, focus on building a robust virtual communication infrastructure. Tools like Monday.com (I am a fan), Confluence, and the unavoidable Slack can help you collect, organize, and structure knowledge in a way that reflects your team's diverse personalities and strengths. Then, find inspiring venues to bring your team together periodically - be it bi-weekly, monthly, or quarterly - whatever rhythm works best for your team. As your company reaches new milestones, grows and makes cash, you can then—and only then—revisit your setup.

During flyiin's first three years, I operated without a formal office. My original co-founder generously allowed me to use his other company's (very cool) space at no cost while our contract design and technical teams worked together virtually. When I finally secured our first (and only) round of funding, my new co-founder and I immediately went hunting for our own office. I had this misguided notion that having our own space would somehow legitimize us as a company. We ended up with an okay space which, frankly speaking, didn't add much value. And the coffee—we were subletting from a communication agency—was terrible.

Fast forward ten months to December 2019. Feeling optimistic (or naive might actually be a more appropriate term) about my ability to raise a Series A round and expand the team, I decided to take over the adjacent space and invest in furniture. Big mistake. When the pandemic hit, those investments and fixed costs became an irrelevant burden overnight. Sure, I had a nice 90sq m office all to myself during the following twelve months, but was it worth the €4,800 monthly burn? Absolutely not. And since I was still subletting from the same agency, the coffee remained terrible.

Looking back, I realize that at that stage of our development, the office space made little difference. What truly mattered was fostering transparent communication, creating safe spaces for idea exchange, organizing regular team face-to-face gatherings, and establishing a well-thought-through virtual communication infrastructure. These are the elements that build a strong company culture, regardless of where your team sits. Our ability to keep the team together even as our situation grew increasingly uncertain suggests we didn’t do too badly in this area.

Key Takeaway #19

After securing funding, resist splurging on office space. Instead, invest in robust virtual infrastructure and tools for effective remote collaboration. Organize regular in-person meetups to foster team spirit and culture and to collaborate on key design work.

This question came up frequently in my discussions with our first investor (and advisor). Is it more beneficial to raise as much as possible to focus on building your team and business, rather than constantly being in fundraising mode? Or is it better to raise less, pushing yourself and your team to achieve milestones more quickly—potentially putting you in a stronger position for your next round?

I don't have a definitive stance on this. I used to believe that having a long runway was ideal. Devoting all your time and energy to shaping your team and business early on is incredibly valuable. Fundraising can become a full-time job, especially during early rounds, preventing you from dedicating enough time to building an A-Team and securing your first customers. It can also be emotionally draining, leaving you with less energy and clarity for the many daily decisions you face.

However, a shorter runway has its advantages. It forces you to make quick, decisive choices and invest wisely in what truly matters—like a functioning product, even if it's not perfect at first. It also pushes you to be transparent with potential hires and attract people who embrace the challenge. There’s no one-size-fits-all answer. The right approach depends on your business nature, product complexity, and capital availability in your region and target market.

During our first two years, we secured several hundred thousand from an angel investor. The goal was clear: this investment would fund our Air Travel Marketplace's MVP development. Given our lack of entrepreneurial track record, securing this initial investment and the involvement of this known airline figure was a significant success (I'm trying to stay humble, but I'm genuinely proud of this). While it helped us build a prototype, we should have reached the stage of capturing our first real bookings with that amount. But we didn’t. More on this in a future chapter.

Our first proper term sheet, signed with the US-based hedge fund in 2017, was for over two million dollars—peanuts for them but a fortune for us. At the time, this was also a decent seed round for a Berlin-based startup. My assumption was that they wanted to test our ability as a founding team to execute, with plans to invest much more once we delivered on our promise. I'll never know if that was truly their intention. Still, getting that term sheet signed remains one of the highlights of my journey—though the disappointment of not materializing the deal was equally intense (talk about an emotional roller coaster).

After pivoting to a business-to-business model in 2018, we secured an investment of a similar amount within a year. This amount seemed right at the time. However, it wasn't enough to establish ourselves, given the technical and commercial complexity of our endeavor. For perspective, our closest competitor raised more than €50m to build essentially the same thing (there is clearly some room for improvement in my pitching skills). And it certainly wasn't enough to survive the two-year Covid-19 crisis, when the travel industry ground to a halt.

Key Takeaway #18

When choosing between large or small funding rounds, consider your desired company structure. Do you want a lean team of versatile individuals working under pressure, or a larger, more traditional organization with diverse profiles? Your funding choice will significantly shape your early-stage company culture.

This chapter is not intended to introduce you to the intricacies of term sheets. There are far more knowledgeable and experienced people who have published very good books on the topic, including the one mentioned in the Homework chapter.

I am here, though, to share my experience with a number of critical terms you will be exposed to: valuation, share vesting and liquidation preference. The position of your investors on these terms will tell you whether they are committed to your venture and to you as founder(s), or simply looking for a quick return on investment.

Let’s start with valuation: if your lead investor accepts a valuation that does not dilute you as founders beyond the standard level of the raise you’re negotiating, it is a first sign that she or he has a genuine and long-term interest in your venture. Then, if their vesting clause lets you keep your vested shares in the event you decide to leave your company, she or he is genuinely interest in your well-being as a founder.

One other signal that your lead investor is not here to look for an early capital gain, is their stance in the event of a liquidation or a company sale. If they agree to a 1:1 ratio of their investment, you have the right investors on board. If they are looking to get twice their investment, it could be a sign that their primary driver is to exit as soon as the opportunity arises. Other control-related terms—such as drag-along rights, conversion, and protective provisions—will also reveal where your potential investors' true interests lie.

In 2017, we negotiated our first term sheet with the US-based hedge fund I mentioned in previous chapters. They were truly excited about our vision to create a new consumer model to purchase flights online and impressed by the work we had completed with a couple of hundred thousands euros. Their proposed term sheet reflected that enthusiasm with a very acceptable dilution for a solid seed raise (under 20%) and a 1:1 ratio in the event of a liquidation event.

Their vesting clause was more demanding on the founders since we would have had to sell our vested shares back to the company if any of us would want to leave the company. Not standard but fair given that the success of the venture depended on the long-term commitment of the founders. Interestingly, my original co-founder wanted to fight against this clause, giving me another clear signal that he wasn't fully committed to the venture.

The situation could have not been more different 18 months later. The terms pushed by the new investors were clearly intended to favor them in the event of an early exit or success. The founders dilution was out of line for a seed raise (over 40%). I won’t even go into details of the vesting and liquidation preference clauses we had to accept. Those will have any founders and respectable investors faint. However, we had no choice if we wanted to continue the journey.

Key Takeaway #17

When reviewing your first term sheet, focus on three critical elements: pre-money valuation, vesting, and liquidation preference clauses. Investor-friendly, standard terms that protect founders suggest you've found the right partner. If the terms are unfavorable, continue your search for a more aligned lead investor.