Friends

Who are your closest friends?

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.