What I Learned Mentoring Founders
The Ego Trap and the Learning Paradox
After mentoring hundreds of founders, I’ve learned a painful truth: you can’t save a founder from themselves. No matter how much guidance you give, some lessons only sink in after a dose of reality.
In startup mentorship, I’ve observed two recurring themes: what I call the Ego Trap and the Learning Paradox.
Understanding these can help both mentors and founders navigate the journey more effectively.
The Ego Trap: “That Won’t Happen to Me”
Every founder — new or experienced — tends to fall into what I dub the Ego Trap. This trap is the little voice that says, “My situation is different. I’m the exception to the rule. That advice doesn’t apply to me.” It’s human nature to believe we’re unique, but in startups this mindset can be costly.
What Founders Say vs. What They Mean: Founders often sincerely say things like:
“I want your honest feedback.”
“I need your expertise.”
“I value your experience.”
However, what they actually want (usually subconsciously) can be different: they’re looking for validation of their ideas, quick fixes for complex problems, or even a cheerleader rather than a critic. Admitting this isn’t easy, but it’s the truth I’ve seen repeatedly. This disconnect isn’t about dishonesty — it’s about optimism and ego. Founders truly believe their startup won’t face the same hurdles others did. It’s different for me. And that belief can blind them to hard truths.
Recognizing the Ego Trap is crucial. If you’re a founder, ask yourself: have you ever nodded through a mentor’s advice while thinking, “We’ve got it handled”? It’s okay if you have — most of us have been there. The key is to catch yourself in that moment of overconfidence. The sooner you do, the quicker you can avoid expensive mistakes others have already made.
The Learning Paradox: Wisdom Hurts (Until It Doesn’t)
So what happens when a founder falls into the Ego Trap? That’s where the Learning Paradox comes in. Simply put, some lessons can’t be taught — they must be learned through experience. I call it a paradox because founders often do seek advice, yet don’t truly absorb it until they feel its importance firsthand.
Here’s the painful cycle I’ve watched repeat over the years:
A founder eagerly asks for guidance — coffee meetings, calls, mentorship sessions.
They listen and nod politely… but mentally, a part of them is dismissing the advice (“We’ll be fine, that won’t happen to us”).
A few months later, they encounter the very problem we discussed — and the solution that was suggested suddenly clicks, only now it’s accompanied by real consequences.
They come back and acknowledge, “We should have listened.” The lesson finally sticks, but via a costly trial by fire.
Every experienced founder reading this is probably nodding — we’ve all learned at least one lesson the hard way. As we say in Turkey, “Only someone who has fallen from the roof understands the pain of the fall.” In other words, you cannot fully comprehend certain lessons until you’ve personally experienced them. This is the Learning Paradox: advice often makes sense in theory, but it becomes truly meaningful only after reality validates it.
For mentors, this paradox is both frustrating and oddly reassuring. Frustrating, because you wish you could save the founders from the pain you see coming. Reassuring, because it’s a reminder that you’re not a bad mentor — it’s just that experience is the best teacher. The founder will learn; it just might not be on the first try.
Changing My Approach to Mentorship
Facing these patterns, I had to change how I mentor. I realized I can’t force-feed wisdom to someone who isn’t ready to digest it. So, I’ve evolved my approach in a few important ways:
Mentor by Choice, Not Obligation: Now I only mentor when I genuinely want to and when I sense the founder is open. Instead of trying to save every ship from sinking, I focus on founders who truly value the guidance. This way, our conversations are meaningful and not just box-ticking exercises.
Embrace the Inevitable Lessons: I’ve made peace with the fact that some lessons require personal pain to sink in. I no longer feel guilty when a founder doesn’t take my advice and stumbles — I expect it might happen. My role is to be there to help them interpret the failure, not prevent it outright.
Repeat the Important Stuff: If I find myself giving the same piece of advice over and over, I take it as a sign. As the saying goes, “If the same advice keeps finding you, it’s trying to tell you something.” I’ll gently point this out to founders: if multiple mentors (or multiple experiences) are delivering the same message, pay attention!
Let Founders Own Their Mistakes: Perhaps the hardest change has been learning to step back. I let founders make their own decisions, even if I suspect a mistake. Of course I warn them, but I’ve stopped trying to drive for them. Sometimes the most helpful thing you can do is let someone fail fast and cheap — and then be there to help them up, dust off, and analyze what happened.
This shift in mindset has made mentorship more rewarding and less draining. By accepting the Ego Trap and Learning Paradox as natural parts of the journey, I’ve become a more patient mentor. Paradoxically, founders seem to benefit more from our sessions now — perhaps because there’s no pressure, just honesty and understanding.
Parting Thoughts: Advice for Founders (and Mentors)
If you’re a founder, remember this: the advice you resist most is usually the advice you need most. That uncomfortable feedback, that mentor suggestion that made you think “nah, not us” — don’t discard it so quickly. It might save you a world of hurt to revisit it with an open mind. Being a founder requires confidence, but it also requires humility to know you’re not an exception to the laws of business and growth.
For fellow mentors, my advice is to embrace your limited role. You’re a guide, not a savior. Share your experience and perspective, but understand that founders may need to learn by doing. And that’s okay. Your wisdom isn’t wasted — it’s just deferred until the founder is ready to use it.
What do you think? Founders, have you ever learned a lesson the hard way that, in hindsight, someone tried to warn you about? Mentors, how do you handle the Ego Trap in those you guide? I’d love to hear your stories. Let’s discuss in the comments – your experiences might just save someone else from a fall off the roof.
Thanks for your wisdom!