Mentor Magic

TL;DR

Hey, I’m Tim! ☕

When Odysseus left home to go to war, he asked his best friend, Mentor, to look after his son and to be responsible for his education. Thats where we get the word “mentor.”

I’d like to talk about my mentor, the late Alan Leong, who sadly passed away a year ago.

While this edition is more personal, the lessons he left behind are ones you can all learn from.

Here’s the one thing to remember: a good mentor teaches you how to look but not what to see.

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Let’s get into it ⤵

DEEP DIVE

“One looks back with appreciation to the brilliant teachers, but with gratitude to those who touched our feelings.” — Carl Jung, psychiatrist, psychologist, philosopher.

Alan's Advice

There’s a million stories I could share about Alan -we worked together for years, teaching 1,000 students across 30 courses- and I’m sure I’ll tell many of them over time.

But today I want to focus on one particular story about readiness.

There have been quite a few major changes in my life recently, and each time, I’ve felt a lingering sense of being unready. And when I do, this is the story I always think back to.

It's funny; I can’t even recall what was on my mind at the time, but I remember asking Alan “How do I know if I’m ready?”

I must’ve been preparing to make some big decision for my company. Or maybe I was just facing that existential founder dread that you’re probably also familiar with.

He looks at me (I could’ve sworn I caught a faint smirk), and in the most Master Oogway manner, says “You’ll know when you ask the question.”

Well, what’s the question?

TIM’S TAKE

Readiness Revealed

To understand why that’s funny, you have to know a bit more about Alan.

He held degrees in anthropology, languages, industrial engineering, and psychology. He served as an advisor to over 150 companies and was an award-winning professor.

But his way of teaching was, in his own words, quirky.

His PowerPoint slides often had nothing but pictures of alums or random graphics, like a cat wearing sunglasses, with no context whatsoever. His exams were notoriously ambiguous. He would answer your questions with even more questions.

As you can imagine, founder-type personalities gravitated towards his classes while others (who took his courses to fill credits) pulled their hair out.

His classes were obviously my favorite, yet in that moment, I was pretty frustrated.

What was the question? What do I need to ask to know if I’m ready? How does his answer help me deal with my situation in any way? Is he trolling me?

Did that mean I’m not ready?

I asked him repeatedly, that day and thereafter, but he never budged. He would simply look at me, smile, and say “You’ll know when you ask the question.”

I kind of gave up after a while. I figured it was one of those philosophical musings that didn’t necessitate an answer. In fact, thinking about it actually made me feel less ready.

But over time, as I matured as a founder, I voluntarily put myself in positions that I wasn’t totally ready for. I grew in proportion to the level of responsibility I took on.

Fast forward about four years since I first asked that question. We were at a retreat with our students and alumni. Everyone gathered in a circle to share questions they were pondering to get advice from the group.

Some were asking tactical questions about defining their ideal customers or improving user surveys, while others were talking about marketplace trends.

I decided to share the question about readiness.

I basically told the group what you just read, and subconsciously, without even thinking, added “Why does it matter if you’re ready?”

Alan’s eyes lit up. He pointed at me and said “There you go! That’s the question.”

And in that moment, I understood.

So, if you find yourself not feeling entirely prepared to face the challenges in your cofoundership, whether it’s a tough conversation, role ambiguity, scaling responsibilities, or setting boundaries, do it anyway.

If you wait until you’re fully prepared, you may find yourself waiting forever.

You’re more ready than you think.

From his obituary:

Alan found immense joy in opening his home (and heart) to his loved ones and was often seen gabbing the night away, hosting a steady rotation of students, friends, family and neighbors around his kitchen table.

It was at that kitchen table where I made some of my fondest memories.

Related Resources

• Sign up for GrowthMentor to get access to their database of vetted mentors and receive personalized advice so you can take out the guesswork.

• If you’re looking for a cofounder, check out StartHawk for an online platform and join LFC.DEV's in-person meet-ups in NYC for face-to-face connections.

• Missed a Cherrytree edition? Tsk tsk, but I’ll let it slide. Grab a coffee and hit the archive to get all caught up.

LAST LOOK

Make sure your cofounder sees this — either pass it along or get them to subscribe. A solid relationship takes everyone's effort.

Looking for a cofounder coach? Hit reply.

PS: Alan had a newsletter, so I guess I really am following in his footsteps. Bittersweet.

Tim He
Founder & CEO